8 Days In Caribbean Itinerary & Caribbean Trip Planner

The Caribbean’s Hidden Treasure 

Sail – St. Martin, Anguilla, St. Barths

Not too long ago St. Martin was the sailing charter capital of the world! Recent history changed that, and the Virgin Islands became the place to go. The world of mega yachts and superyachts have discovered the charm and variety that St. Martin has to offer and it remains their playground of choice. We believe that it’s past time for charter guests on sailing yachts to rediscover all that this amazing charter destination has to offer.

The cruising area of St. Martin, Anguilla, and St. Barths islands are part Dutch, part French, and part British. Because of the uniqueness of this sailing destination, we highly recommend our guests to try a half-board or our local fare option so you can experience the culture of their fine cuisine! If you love wine, cheese, fancy desserts, or fluffy pastries – this is home to the greatest delicacies in the world. The supply of high-end ingredients also allows our chefs to provision for the best charter food during your trip and really show off their skills.

Not only does this area of the Caribbean have decadent food, they have multiple beach bars and secret coves to explore while you’re there. If you’re a beachcomber and love to mingle or if you tend to like quiet coves – there’s a spot for everyone to enjoy.

Day 1 – Arrive and Explore the Quaint Town of Marigot

Day One Arrive and Explore the Quaint Town of MarigotYour beautiful yacht serenely awaits your arrival in the French side capital of St. Martin – Marigot. After getting settled on your yacht, your Caribbean sailing party can wander the delightful streets of Marigot. Marigot is a quaint town dotted with multiple Paris style boutiques and delicious French cuisine.

Hike to the 18th century Fort Louis which is situated on top of a hill in Marigot with views stretching as far as Anguilla island 15 miles away.

If you have time go to Tijon to make your own custom cologne and perfume – it’s a must! Also, make a stop at Bacchus Bakery for fresh croissants and the best sweets in the Caribbean.

Day 2 – Your Pick of Snorkeling, Paddleboarding, or Kayaking in Anguilla



Day 2 of your Caribbean sailing vacation, you’ll sail to the British island of Anguilla and the stunning Crocus Bay. You and your group can enjoy snorkeling and cliff jumping in this pristine spot or a casual paddleboard or kayak through the blue waters. Your yacht provides snorkel gear, kayaks, and paddleboards so you have quick and easy access to start enjoying the Caribbean sea!


Another short ride away, you can find Shoal Bay, the world famous white sand beach that is regarded as a top 5 beach in the world! This beach will have you feeling relaxed and in vacation mode in no time! Nearby, the town of Sandy Ground has many great beachside restaurants and casual Caribbean nightlife.

Day 3 – Banky Banks: Savor the Tranquillity on Anguilla’s Surrounding Islets


On Day 3, you’ll set sail for one of the uninhabited islands surrounding Anguilla. Dog, Prickly Pear, Scrub Island, and Sandy Island are all beautiful island paradises where there’s no lack of sun, sand, or water activities.

Sandy island is home to what might be the perfect Caribbean beach bars on it’s solitary island with a 360 degree view of turquoise waters.  Prickly Pear has two amazing little rum joints for you to choose from.

After the beach bars, head to Banky Banks. Banky Banks is to the Leeward Islands as what Foxy’s is to the BVI’s. This amazing character sits in his funky treehouse bar playing his original tunes and entertaining his guests.

Anguilla hosts seven wreck dives around the island. If you’re a scuba diver wanting to venture into some of these wrecks this is your spot to find a myriad of tropical sea fish, sea fans, and coral!

Day 4 – Snorkel with Turtles in St. Barts

Snorkel with Turtles in St. Barts


Leave early on Day 4 and arrive in Gustavia, St. Barts three hours later. The gorgeous French colonial town is the jewel of this part of the Caribbean line with red roof houses and some of the world’s largest mega yachts.

With amazing restaurants and high-end duty-free shops, it has it all. You can explore the town or even jump on a scooter for a true island adventure. St. Barths is really a tale of two islands – you can choose to spend your day on isolated beaches and natural pools where few people go or party with the posh beachgoers on Nikki beach – coined the sexiest place on earth.

Your yacht will cruise the boat around to drop anchor at Anse de Colombier. This horseshoe-shaped bay provides you with one of the best snorkeling spots in St. Barts. Its steep hills which overlook the Caribbean Sea also host scenic hiking trails with views stretching all the way to Ile Fourche.

Day 5 – Escape light pollution and See the Milky Way Bright as Day on Ile Fourche

Ile FourcheDay 5 of your Caribbean sailing vacation, you’ll set sail to the nearby island of Ile Fourchue. This uninhabited island has some of the Caribbean’s best snorkeling. Part of St. Barth’s marine reserve, this island’s water houses an abundance of sharks, barracudas, stingrays, sea turtles, and lobster galore. Take a shot at navigating your way to the rock buttes of Ile Fourchue if you’re looking to get in a little day hike. You’ll reach the top for the panoramic view of St. Barths and St. Martin.

Watch as the Milky Way starts to appear right before your eyes this evening. Due to this island’s zero light pollution, the starry sky of Ile Fourche will give you another level of Caribbean tranquility.

Day 6 – Enjoy Local Cuisine and the Pristine Waters in Orient Bay

A couple hours sail brings you back to St. Martin. You’ll anchor in the windward side, off of Orient Bay. This 2-mile long white velvet beach hosts multiple beach clubs, watersports, kiteboarding, jet skiing, and more. Pop into the open-air eateries located near Orient for some delicious French cuisine.

Located in the heart of the marine park nearby, you can visit the little sandy island of Pinel, an alternate option for a day on the beach and a perfect lunch. Another great place to snorkel, Pinel offers a variety of marine life in the area, and this protected bay is great for a kayak and paddleboard! This island is a local favorite and one of St. Martin’s best kept secrets. They throw the best boat/beach parties on the weekends, and on the weekdays it’s typically quiet if you want a little more down time.

Day 7 – Snorkel, Cocktails, Tapas, Repeat in the Gourmet Capital of the Caribbean: Grand Case

After breakfast take a short sail to Tintamarre. This flat island was used as a secret submarine base in World War II. The island is your host for a perfect beach day and mud cliffs that provide a natural spa – when mixed with water it leaves your skin feeling soft as a baby!

Alternatively head off to Loterie Farm. Located in a rainforest, this secret hide-away oasis offers private cabanas, cascading waterfalls, private pools and even zip lines for those bolder souls.

Either way, later in the day, you’ll continue down St. Martin’s seductive northern coast for Grand Case. You can enjoy a snorkel at Creole Rock where you might see the elusive and beautiful Eagle Ray! End the day with one of the most idyllic places for a sunset stroll and enjoy one of Grand Case’s famous eateries on the beach. Grand Case is the gourmet capital of the Caribbean with multiple Michelen Star restaurants to choose from.

Rainbow Bar is St. Martin’s version of Nikki beach in St. Barths, and it’s the best beach bar here by far. This is where yachties and locals both hang out to bronze up on vacation and drink the best French Rose.

Day 8 – Get Your Last Caribbean Fix and Souvenirs & Hope for a Plane Delay!

Wake up to your last day with a delicious breakfast in Grand Case. We’ll then sail the final hour back to Marigot and prepare for your departure.

Don’t forget to stop at Bacchus Bakery on your way out to pick up your croissants and fresh bread for the plane ride home – you’ll be dreaming about them until your next charter here!

Since Kenny Chesney made the BVI famous and popular with his songs about those islands, people have been flooding to the BVI and US Virgin Islands.  And, if you’ve chartered in the virgin islands before (and even if you have not), St Martin and her surrounding islands may very well be the best charter destination in the Caribbean. The anchorages are less crowded, isolated beaches can still be found, and the food is out of this world. Add to all of this, the opportunity for amazing nightlife and extraordinary beach parties, and it is easy to see why we love this area as a superb choice for your next charter.

Top 3 Reasons to Book a US Virgin Islands Sailing Vacation

Here are top 3 Reasons to Book a US Virgin Islands Sailing Vacation

Not too many years ago, St. Thomas and the USVI were the number one destination for sailboat charters in the Caribbean.  Yacht vacations in St. Thomas were popular because the USVI is easy to get to, super safe, a US territory, and amazingly beautiful.  Caribbean sailing vacations from the USVI remained popular until marine laws charged in the 90s and the Moorings opened their large base in a little known place called the BVI.

Today, the winds of change have come again and the USVI is once again the top Caribbean sailboat charter vacation location.  Sailboat vacation clients are choosing the US Virgin Islands for their charter destination in record numbers and here is why!

  1. The beaches.I took my mom on a sailing vacation in the British Virgin Islands about 5 years ago.  We spent four or five days sailing in the Drake channel when she said “where are the beach”.  She was expecting beaches at every stop where she could sit at the ocean’s edge sipping a cocktail.  But most Caribbean charter destinations, particularly the BVI, fail to provide enough  amazing beaches for beach lovers.  Only St Martin/Anguilla and the Grenadines sailing vacation destinations can rival the USVI.  The beaches of St. Thomas, St. John and St. Croix truly stand out, and on a typical 7 night yacht vacation, you can easily make multiple stops per day with stunning long stretches of white sand. Read related article Top 10 beaches
  2. SnorkelingUS Virgin Islands Sailing VacationCompared to other sailboat vacation destination, the USVI is, by far, number one when it comes to snorkel sites, and I’d rank it very high in terms of dive sites.    Versus other popular sailing vacation areas, the US Virgin Island’s snorkel spots are actually under-utilized… particularly those not frequented by cruise ship clients.  There are more than 40 pristine snorkel spots in the National Park that surrounds St. John alone, and most of those are only assessable from a crewed charter yacht.  St. Croix’s Buck Island national park Is another amazing example of diverse and interesting, and mostly unvisited snorkel areas.  And finally, St. Thomas’s “out” islands, away from the mainland, provide exquisite options.  By contrast, the BVI sites are largely over used, St. Martin/Anquilla has limited options and the Grenadines exposure to large seas make snorkeling for beginners very difficult.  So, for snorkel lovers, there is no better place to book your next Caribbean sailing adventure.
  3. Beach Bars.  If beach bars, or bars in general plan a big role in your fun on a Caribbean sailing vacation, then look no further than the US Virgin Islands.  As you go around the USVI on your charter yacht, it is easy to find quiet and secluded beaches but high energy, fun beach bars abound.  My personal favorites, and ones that I think you should make mandatory stops at on your next sailing holiday include Bikinis, Skinny Legs, Miss Lucy’s and Lime Inn on St. John (and that does not included the amazing beach bars in quaint Cruz Bay.  On/around St. Thomas make sure to stop at Dingy’s and the new trending Latino bar on Honey Moon beach on Water Island, Sunset beach bar at secret harbor and the chicken shack bars on Coki Beach.  Finally, make sure you explore the funky bars along the boardwalk in St. Croix, including my favorite, the Scooter bar.   Most of the bars on my list are unknown to most people.  They were not made popular by country music songs, and you don’t see many people walking around wearing their shirts and hats.  But these amazing beach bars are rapidly catching on, and rival some of the coolest bars the Caribbean has to offer. Read related article Top 5 Beach Bars In The Caribbean 


US Virgin Island Sailing Vacations

Things To Know About US Virgin Island Sailing Vacations

US Virgin Island Sailing Vacations Gallery

When Covid-19 forced island nations like the BVI to close their borders, vacationers quickly found out that there was an amazing alternative.. for less money, and closer to home.  Caribbean sailing vacations focused on the US Virgin island became so popular this summer and fall that they might very well become a favorite sailing holiday destination long after the pandemic is just a memory.

The advantages of booking a US based yacht charter vacation include:

  1. They are easier to get to with direct flights from many US cities
  2. There are no customs/immigration fees
  3. No travel restrictions
  4. Less crowds
  5. And, due to less crowds, higher quality of reefs and marine life

iYachtClub ran more than 100 crewed sailing vacations this summer, all in the USVI and the response was amazing.  As with charters everywhere in the Caribbean, itineraries vary trip to trip, but our guests had trip of a lifetime experiences on their sailing vacations with 7 night itineraries that looked something like this.

Day 1  

Pick up at amazing Yacht Haven Grande in the heart of St. Thomas.    Make a short sail to historic Buck island for lunch and a swim in the natural turtle park.  After lunch, take a short sail to Honeymoon Beach on Water island, home of the “better than soggy dollar” Dingy’s Beach Bar.

Day 2

Take a short sail to Flat Key for the best snorkeling and diving in the Virgin Islands, followed by a trip to the north side of St. Thomas and perfect Megans Bay.  Finish day two at Coki Beach, a strip of sand filled with local eateries and bars.

Day 3

Head to St. John, and world famous Caneel Bay, home of the new Bikini Bar.  Once again, the new beach bar rivals the old standards set in the BVI and is a perfect place to forget your troubles J.  Take a late afternoon short sail down to Mahoe Bay, and another new beach bar, the Mahoe Crossroads Beach Bar.

Day 4

Start your day with a hike to the Anneburg Ruins and a snorkel at amazing Waterlemon Cey.  Take a nice sail in the afternoon around to funky Coral Bay and, in my opinion, St. John’s best new hot spot, the Lime Inn Taco Bar.

Day 5

Start your day with the longest sail of the week, and easy few hours down to St. Croix.  Spend two days exploring Buck Islands National Park, the cool Dutch town of Christiansted and, exploring the Virgin Islands only rain forest. 

Day 6

Sail back to St. Thomas for lunch at Christmas Cove and an amazing snorkel on the ledges off of Little St. James.  Take a short sail over to Secret Harbor, another amazing St. Thomas beach and beach bar scene.

Day 7

With the quality of new beach bars, amazing beaches and wildlife, and ease of access, the US Virgin Islands truly has become the new standard for Caribbean sailing vacations.  Vacationers with travel concerns will find that this trip will meet or exceed their expectations for what a great sailing holiday is and I believe that things will only improve as more and more people decide to choose the USVI over the BVI for their yacht vacations.

Virgin Island Charter Boats & Price Tips

What is the best charter boat to book, for each size and price category

When people call us to book their Caribbean Sailing Vacation, most of them do not have a good understanding of how much a yacht vacation really cost.  However, most of them do have a budget in mind for what they are willing to spend for their Caribbean sailing holiday.

Once we understand their budget, it is our job to maximize their budget, and to deliver the best sailboat trip possible. 

The yachts that deliver yacht holidays fall into different size categories.  And, within each size category, there are different types of sailing tours, like per cabin bookings, captain only bookings where you book the entire yacht, and all-inclusive vacations where you also book the entire yacht for your yacht charter vacation.  Below, for each budget range, I’m going to try to identify the best type of yacht, within each size category, to deliver the best Caribbean sailing holiday.  For each of these, prices are based on seven night yacht vacations.

If you are traveling alone, or as a couple and your budget is:

$2,000 to $3,000 each – the best yacht and value in this price range would be to book a cabin on a Sonoa 47 from Fountain Pajot.  You will most likely have 3 other couples on board with you and for just over $2,000 per person you can do an all-inclusive 7 night sailing vacation.  The Sonoa 47 is a new model of charter yacht, so your boat will be less than 2 years old.  They have a modern and bright look and feel and a second level fly bridge to spread out on.  For the money, for this type of traveler, you cant beat this model of charter yacht for a sailing holiday.

$5,000 to $6,000 each – the best charter yacht in this price range is, without a doubt, the Fountain Pajot Helia 44.  For under $12,000, two people can rent the entire yacht for a 7 night Caribbean sailing vacation that is all-inclusive.  The helia 44 charter yachts have a “honeymoon” suite that takes up ½ of the charter yacht.  Like the Sonoa 47, this is a very new model of boat, so your sailing holiday will be on a boat less than 3 years old.  The Helia 44 also has a fly bridget, and, a bright and airy look and feel.   These boats are fantastic choices for your Caribbean sailing adventure.

If you are bringing four to six people on your Caribbean sailing holiday, and your budget is:

$2,000 per person, then for sure, the best choices for your yacht holiday is a Leopard 46 or Lagoon 45.  These boats sleep up to six people easily and have been popular choices since their introduction into the yacht charter vacation industry back in 2008.  Six people can enjoy a 7 night all-inclusive sailing holiday for under $12,000 on either of these models, making them the perfect choice.

$2,500 to $3,000 per person… with this budget, for six people, the ideal choice is the new Fountain Pajot Elba 45.  These amazing charter yachts have been the “boat of the year” since introduced into the yacht vacation industry last year.  Your boat will be brand new, or less than one year old and will feature an amazing fly bridge.  Six guest can enjoy an all-inclusive, 7 night Caribbean sailing vacation for about $15,000 on one of these amazing boats.

If you are traveling with 8 to 10 people, and your budget is:

$2,500 to $3,000 per person… with this budget, the perfect yacht holiday should be on a Fountain Pajot Saba 50.  These elegant charter yachts are roomy enough to accommodate 8 to 10 people, depending on the layout and are perfect for larger groups that want to enjoy a Caribbean sailing holiday.  They have an oversized flybridge to spread out, and have a modern, contemporary feel.    Our clients that choose saba 50s for their sailboat trip typically spend between $18,000 and $20,000 for a seven night sailing holiday, making the saba 50 an excellent value.

$3,500 to $4,000 per person…. With this budget, 8 people should probably choose a Fountain Pajot Inpanema 58.  These large, elegant sailing yachts are ideal for high end clients who want to really spread out and relax on their Caribbean sailing holiday.  The Inpanema 58 has huge living spaces, including an oversized flybridge.  Our clients who book the Inpanema 58 for their sailboat trip typically spend just over $3,500 per person, or about $28,000 for an all-inclusive, 7 night Caribbean sailing vacation.

We work hard to have excellent options for every budget.  We are careful to only allow the very best options into our fleet, so that every client is happy and satisfied.  I often here “I could never afford that” when I tell people what I do for a living… but I think with these charter yacht options, and at these incredible prices, almost anyone can enjoy a Caribbean sailing adventure with their family and friends, or even alone!

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Top 10 Beaches To Visit On A Caribbean Sailing Vacation

What are the top 10 beaches to visit on a Caribbean Sailing Vacation?


Top 10 Beaches To Visit On A Caribbean Sailing VacationOn yacht vacations in the Virgin Islands, most of the trip is all about the boat.  And all about the crew.  But when you get to an island at the end of a day’s sail, the trip becomes all about the beaches.  Below is iyachtclub’s top 10 beaches to visit on your next Caribbean sailing charter.  Our top 10 list includes beaches from the Spanish Virgin Islands, U S Virgin Islands and British Virgin Islands.  So, in no particular order, but from west to east, here is our top 10 list for Caribbean Sailing Vacation:

1 Flamingo Beach, Culebra.  On a sailing tour, the entrance here is easy.  This beach is located on the north side of Culebra and is famous for its pink sand and amazing beach bars.  Oh, and there is an abandoned army tank on the beach… you don’t see that every day.

2 Playa Tortuga (Turtle beach) Little Culebrita (little snake island).  You will find yourself alone on this beach every day of the week except the weekends.  It is famous for its sea turtles, hense the name and its abandoned light house, a short walk away.  It is on the north side of the island and is one of my personal favorite places in the entire Caribbean.  A short walk to the north east corner of the beach takes you to a massive natural jacuzzi. 

  1. Bahia Salinas, Viegues. This small sweep of tan sand is located on the north side of viegues on the eastern tip. It is isolated and actually takes some skill to enter.  In all my visits, I’ve never seen another boat or person here.  You can snorkel around abandoned military equipment as this used to be a practice bombing range.  But, beside the pure beauty and isolation, the number one reason to come here is the star fish.  There are typically so many here, it is actually hard to walk!
  2. Honeymoon Beach, Water Island. No yacht charter vacation can be complete without a stop at this short, but well protected and amazing beach. Honeymoon is a west facing beach, so come for sun set, and if you are lucky enough to come on a Monday, stick around for moving night on the beach, facilitated by a sheet tied between two palm trees.  This jewel of a beach has two great beach bars, and the calmest water of any beach on the list.
  3. Little Cinnamon Beach, St. John. Almost everyone knows about Cinnamon Bay beach on St. John. Cinnamon Bay has always been a St. John favorite and was made popular by a Kenny Chesney Song.  But very few people know that just a short hike to the west takes you to the best St. John beach of them all, Little Cinnamon.  This small slice of heaven is pure romance. 
  4. Zihuatanejo, St. Croix Part of the Sandy Point National Wildlife Refuge, Zihuatanejo is the second longest beach on the list. This “can’t miss beach” is actually the furthest western point of the United States and was made famous by the final scene in the movie classic, Shawshank Redemption.  This is literally miles, and miles of untouched soft, white sand.
  5. White Bay, Jost Van Dyke No list of beaches in the Virgin Islands would be complete without White Bay. This short stretch of white sand is filled with fun beach bars and fun people.  Unlike the other beaches on the list, this is a party beach for sure, but early in the morning, and late in the afternoon, when are of the pain killers are gone, this is a stunningly beautiful combination of white sand and bath clear water.
  6. Smuggler’s Cove, Tortola

On Caribbean sailing charters, when approaching Tortola from the west, Smugglers Cove can be found just north of the western most point of the island.  There is nothing here but white sand, green trees and blue water, and that is hard to find on busy, busy Tortola.  That is why I love it!  Years ago,  before Hurricane Irma, two lovely ladies, Patritia and Ester use to setup a card table with a blender on it each day to create the beach’s only bar.  What a fantastic place to spend an afternoon!

  1. Savannah Bay, Virgin Gorda Difficult to get to, but worth the effort, is Savannah Bay beach on Virgin Gorga. This beach is also west facing, and, in my opinion, looking across the shallow blue water, then over the reefs protecting it, this beach offers the best sunsets in the Virgin Islands. 
  2. Anegada Beach. Well, number 10 is Anegada… the whole island of Anegada. There is no beach named “anegada beach” and people will argue that there are lots of beaches on Anegada.  But I say that the entire island is wrapped by one long, amazing beach.  My wife and I once walked for 5 hours on the beach on Anegada without seeing another human.  We were happy to end up at Cow Wreck Bar, because we were thirsty, but this is the only place in the world that I’ve found so far, where you can walk so long, on isolated white beaches!

On your next Caribbean sailing holiday, I’d recommend challenging yourself, or your captain, to the iyachtclub top 10 beach challenge.  See if you can visit all 10 beaches in one sailing holiday.  And, along the way, let me know if you find any great ones that I have not found!

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Is buying a boat a good business decision? Is it smart to buy a yacht?

Is It A Good Idea To Buy A Boat?

When our customers come down on Caribbean sailing vacations, often times they get a little “chrome fever” and start asking questions about buying a boat for themselves.  After the initial thrill runs out, and they start really thinking it through,  and looking at all of the wild promised on the internet, they usually come back to me and as a very good question… is buying a boat, as a business, and putting into a yacht charter vacation program, a good business decision?

Well.  It depends.  It depends on your tax/wealth situation.  It depends on how often, and for how long, you want to use your boat personally, it depends on market timing, it depends on where you want to put your boat, and, more than any other factor, it depends on who you choose to do business with.

I (Derek) could write a book on those topics and each one is so personal, that it would be impossible to really get to an answer.  So, instead of debating all of those points, I’d like to present a real life example.  Ours.  Because I really don’t know if buying a boat and running yacht holidays on it is a good idea, or a bad Idea, but I know how it worked out for me.

My wife and I had one too many glasses of wine at the Miami boat show in 2008 and purchased a leopard 4600 for $520,000.  She actually said to me “if we owned a catamaran, she would live on the water with me”.  It took me about 10 seconds after that to tell the sales lady that we were buying the boat.  We had just sold our small IT company in North Carolina, so we were at a cross roads in life anyway, so for us, it just felt right. 

Bella Vita

We picked up the catamaran in Tortola 9 months later and started running sailboat trips as an owner operator in the Caribbean sailing holidays industry.  We put $104,000 down and took a mortgage for the rest, on a 15 year amortization with a five year balloon.  Our payments were about $3,800.   We ran yacht vacations for paying passengers for about 5 years…. Running between 18 and 22 trips per year.  In that time, we were able to make our mortgage payments, accelerate the loan and, take 3 months off per year to go play on our boat… all paid for by the Caribbean sailing adventures that we were delivering. 

After 5 years, mostly because we were tired of having party animals on our boat, we put our Bella Vita in a managed crewed yacht program, and had her continue to deliver yacht holidays, but this time with a paid crew on her.  This was less profitable, but we were able to continue paying the mortgage, and accelerated the payments to a point that, after 9 years, the loan was paid off.

Now, 11 years after we purchased Bella Vita, we keep her on the Dutch side of St. Maarten.  She is completely paid for, remodeled and refit and is basically like brand new.  She is currently worth somewhere between $335,000 and $380,000, depending on who you ask.  We live on her 6 months out of the year.  At this point in time, the only cash I have in her is the $104,000 that I initially put down.  But, what money we put in the bank during the last few years of doing sailing trips was spent on upgrades and making her beautiful again, so moving forward, I’ll start going further in the hole to her. 

I think that $104,000 for what is essentially a 3 bedroom, 3 bath, floating winter home in the Caribbean is a great deal.  I don’t know what the $104,000 would have been worth in the stock market or real estate over the same period of time.  But, you also can’t measure the amount of joy that my wife and I have experienced while owning Bella Vita for the past decade.  So, was buying a boat a good business idea?  I’m not sure.  It depends J   But, looking back at the past 10 years, I would not have changed a thing.  I’m glad I bought the boat.  And, I’m very glad that I discovered and to part in the business of delivering Caribbean sailing vacations.

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iYachtClub Top 5 Beach Bars In The Caribbean

Top 5 Beach Bars In The Caribbean To Visit On Your Yacht Vacations

Every year, about this time, I endeavor to name the top beach bars in the BVI.  These are bars that everyone who has ever taken a Caribbean Sailing Vacation has been to.  They are in Kenny Chesney and Jimmy Buffet songs, and most people know them.

However, yacht vacations, and Caribbean sailing holidays in general, are about more than the BVI.  And, sadly, the BVI has decided to stay closed until September.  So, this year, I thought I’d broaden my scope a little.  And, it actually makes my list a LOT harder.  The Caribbean is full of amazing beach bars, so including the bars of the windward and leeward islands (all of our cruising areas) makes it nearly impossible to pick a top five.

First, my criteria for choosing the top 5 beach bars in the Caribbean when you are on Caribbean sailing adventure First, they have to be a “beach” bar.  I know that sounds funny, but there are great bars that are not on beaches that might otherwise make the list, like Saba Rock in the BVI, and Happy Island in the Grenadines.  Next, in order to be a great bar, you need atmosphere, and music in particular.  Then, we took into account the quality of the beach itself.  And finally, to make the list, we thought that great food was also important.  So, with that criteria in mind, here is iyachtclub’s 2020 top five beach bars in the Caribbean.  If you have not visited these, I’d suggest your rent an iyachtclub boat for Sailing Tours and check them out for yourself.

  1. Basil’s Bar, Mustique, Grenadines.  Basil’s comes in at number 5.  This is a bar for the rich and famous as well as for people like me!  It is a really cool place with great food and live entertainment.  As with the other bars in the list, it was difficult to pick just one bar in the Grenadines… the most amazing cruising area.
  2. Bankie Banx beach Bar, Anguilla.  Bankie Banx is to the rest of the Caribbean what Foxy is to the BVI.  His laid back bar is amazing, with a stunning beach, great food and live entertainment most days and nights. 
  3. Soggy Dollar Bar, Jost Van Dyke BVI.  Sorry Cow Wreck Bar….. I actually like Cow Wreck better, but there simply is no entertainment there.  Soggy Dollar wins, for me, out of the great BVI beach bars, with their combination of great food, great beach, great people, and occational entertainment.
  4. Le Karibuni on Pinel Island in French St. Martin.  For people who live and vacation on St. Maartin, Pinel Island is their version of White Bay Jost Van Dkye.  Everyday is awesome, but the fun really cranks up on the weekends.  Le Karibuni comes in at number two because of their high-end cruisine, amazing drinks and staff, music and atmosphere and positively amazing beach.
  5. Nikki Beach Bar, St. Barts.  This year’s winner is Nikki Beach.  Labelled “the sexiest place on earth”, Nikki Beach is simply awesome.  The beach is truly just “ok”, but the food, drinks, party atmosphere (musicians playing on the tables while you eat/drink), this place is a step above the rest.  Try Nikki beach on a Sunday, which are themed days, but make a reservation…. You can thank me later.


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Covid-19 Safe Vacations To Take Right Now

Is It Safe For Vacation During The COVID-19 Pandemic Or What Are The Options?

Aerial Pic Covid-19 Safe Vacations

As airline travel starts to open up again around the world, vacationers are starting to ask “what is a safe vacation to take while the Corona Virus (Covid-19) is still around.   The answer is…. Caribbean sailing charters on small private sailing catamarans.   Yacht Vacations are the perfect choice for small groups of family and friends to vacation.

iYachtclub’s Caribbean sailing vacations feature yacht’s that are specifically setup to delivery vacations that are safe for as long as the Corona Virus lingers.

We take standards for hygiene and cleanliness very seriously and are taking additional steps to ensure the safety of our guests and associates. On a daily basis, our yachts  are working to ensure that they meet the latest guidance on hygiene and cleaning. Our charter yacht’s health and safety measures are designed to address a broad spectrum of viruses, including COVID-19, and include everything from handwashing hygiene and cleaning product specifications to common area cleaning procedures. Specific steps iYachtclubis taking include:

Associate Health, Safety and Knowledge: Crews – and their own health, safety and knowledge – are essential to an effective cleaning program. Here are some ways we’re supporting them:

  • Hand Hygiene:Proper and frequent handwashing is vital to help combat the spread of viruses. In our daily meetings, our teams are reminded that cleanliness starts with this simple act. It’s important for their health and that of our guests.
  • Ongoing Training:In addition to training on housekeeping and hygiene protocols, hotel associates are also completing enhanced COVID-19 awareness training.
  • Masks:iYachtclub crew teams are equipped with masks and have the option to wear them and will wear them if clients request this during the yacht charter vacation.

Cleaning Products and Protocols: Our yachts use cleaning products and protocols which are effective against viruses, including:

  • Guest Rooms:iYachtclub’s charter fleet use cleaning and disinfecting protocols to clean rooms after guests depart and before the next guest arrives, with particular attention paid to high-touch items.
  • Public Spaces:Our charter yachts  have increased the frequency of cleaning and disinfecting in common spaces, with a focus on the counter tops, and common outdoor sitting areas.

Compared to alternative vacation travel, small private yacht vacations are simply ideal.  You are isolated from others to the extent that you wish to be isolated.  You are in the fresh air.  You are in the sunshine.  And you are cruising in an area that has limited exposure to the virus in general.

As vacation travelers return to the process of planning their next trip, Caribbean sailing vacations on private yachts should be at the top of the list.  The trips are affordable.  And, they are a safe vacation alternative during the time of this Covid-19 event.  Caribbean sailing holidays are, in short, simply the safest place in the world to be!

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Where Is The Best Place To Charter A Yacht Vacation After The BVI

Where is the best place to charter a yacht vacation …. after the BVI

Almost 90% of all yacht vacations take place in the Virgin Islands.  There is a reason for this…. They are the easiest to get to, easiest to sail, and beautiful, making it ideal for yacht charter vacations of all kinds.  But, after you have been on a couple of  yacht charters in the BVI, where should you go next?  I’d say, all things considered, the Cyclades in Greece, Croatia’s coast, the Grenadines and St. Maarten would  make up the next best locations, with St. Maarten being the best of those choices for a sailing tour.

Below is a sample itinerary for the greater St. Maarten area for your next Caribbean Sailing Vacation.  The island of St. Maarten ( which is ½ French and ½ Dutch) is pretty much a round island, so, depending on the weather, you might start your vacation from any point on the island.  So, don’t focus on the numbered “days” on this itinerary, as they might come to you in any order.  Also, you can do any kind of yacht vacation in St. Maartin – bareboat, crewed all-inclusive, captain only, or crewed ½ board.  For me, while all options are great, the crewed ½ board option is superior, because a large part of these island’s fun is in exploring the culinary treats the islands have to offer.

Roxy’s Beach BarAfternoon 1.  After landing at Princess Julianna Airport, get your Caribbean sailing adventure started with a 10 minute taxi drive through busy Simpson Bay, past literally 100s of restaurants and bars, to the Simpson Bay Yacht Club where you will meet your charter yacht.  After a welcome drink, take a walk down Simpson Bay, explore the beach and/or the bars.  My favorite, and a great way to start your trip, is Roxy’s Beach Bar.

Day 2.  Exit the draw bridge and sail west, a very short ways to Mullet Bay beach, and beach bar.  This is a great snorkel spot, a wonderful beach and a funky little beach bar.  After lunch, continue on to Grand Case, on the French side of the island.  Grand Case is the Caribbean capital of fine French cuisine… and, home to another one of my favorite island bars, Rainbows.

Day 3.  Anguilla is a short 5 mile sail to the north.  If you have been to the BVI, and to Anegada, the beaches on Anguillaare even better!Anguilla is a great island to rent a car or scooter and explore.  You can easily go all the way around the island, stopping at beautiful beaches and cool bars in one day, but make sure you do not miss Blanchard’s Bar and BankieBanx Dune Retreat Bar.  Bankie is to this part of the Caribbean, what Foxy is to the BVI.

Day 4.  Just north of Anguilla are two amazing islands that will remind of you of Sandy Key, and Sandy Spit in the BVI.. but much, much better.  Take your pick for the morning, lunch and early afternoon at either Prickly Pear Island or Sandy Island.

Prickly Pear Island

Take a late afternoon sail from here to Tintamarre Island, a national park, for more snorkeling and a quiet dinner.

Tintamarre Island

Day 5.  Continue your sailboat trip, with a very short sail, less than 3 miles, takes you to PinelIsland, where you can spend your day snorkeling, kayaking and exploring.  On weekends, this is St. Maarten’s version of the Soggy Dollar Bar, but with a European cool vibe.  You might also elect to do a day trip from here, to Lottery Farm in the St. Maarten rain forest, where you can rent a cabana, zip line, play a little golf or just relax.

St. Maarten rain forest2

Day 6.  The biggest sail so far, you have about 20 miles to sail to amazing St. Bart’s.  St. Bart’s is an island where you could literally spend days, but if you only have one day to spare, you can’t miss Nikki Beach.  Dubbed the sexiest place on earth, this amazing beach and bar scene will blow you away. 

Nikki Beach

Day 7.  Another longer sail back to St. Maarten, but you have choices today.  You can sail to Philipisburg, a quaint Dutch town full of shopping and history, or sail back to Simpson Bay and to yet another amazing beach and beach bar scene, Karakters Beach bar.  This amazing place is built out of a restored touring bus and makes an amazing final afternoon on this amazing island.  Either way, you are a very short distance for your final morning ride back to the St. Maarten airport.

Karakters Beach bar

What Is The Best Island In The British Virgin Islands?

What is the best island in the British Virgin Islands?

British Virgin IslandsThe British Virgin Islands are made up four main islands, Jost Van Dyke, Tortola, Virgin Gorda and Anegada over (depending of your definition of an “island”), over 50 smaller islands/keys/rocks/land masses.  Only 12 of them are inhabited.  So, which one is the best one?

We have been providing Caribbean sailing charters for over 12 years, bringing hundreds of visitors to all of the islands each year.  We have asked them that question, which one is best?  And, we have watched their faces as they have explored each island while on their sailboat trip. 

We took the opinion of those yacht charter vacation guests and sprinkled in our own opinion from our personal trips to come up with the answer. 

We considered:

  1. Quality of beaches
  2. Number of nice beaches
  3. Crowds/isolation on those beaches
  4. Beach Bars
  5. Variety of activities
  6. Uniqueness
  7. Overall beauty
  8. Friendliness/character of the residents

British Virgin Islands BlogThe winner of iYachtClub’s vote for the best island in the British Virgin Islands is (drumroll)  Anegada.  The majority of BVI based Caribbean sailing vacations do not make it to Anegada.  And, if you are land based, it requires an extra and difficult manner of transportation to get there, as ferries do not run often.  But, Anegada is worth the effort.  The Anegada beach would rival beaches anywhere in the world.  Anegada’s beach bars are amoung the best, with 2 of my top 5 beach bars in the BVI being located there.  (Cow wreck beach bar is my favorite beach bar in the world).  The last time I counted, there were 216 people that called Anegada home, each of them warm, wonderful and charming.  And finally, you can stay busy there for a week, with activities like bone fishing, deep sea fishing, chasing pink flamingo, snorkeling, exploring conch shell island, and so much more.  For your next Caribbean sailing adventure, please insist that your captain take you to Anegada.  It is one of the world’s “out of the way” places, that truly is worth the effort.