Are you looking to book the best Caribbean sailing vacation, but feeling overwhelmed by the myriad of confusing choices for charter yachts? We can help you choose the right boat and crew to make sure that you have the best Caribbean sailing vacation under the sun. Just follow these 10 easy steps then visit our featured yacht page to start looking at yachts!

1. Decide Which Type of  Charter Yacht You Prefer for the Best Caribbean Sailing Vacation

Is it a monohull sailboat, a catamaran or a motoryacht that comes to mind when you think about the Caribbean sailing vacation that is best for you?

Avoid the pitfalls and book the best Caribbean sailing vacation. IyachtClub shows you 10 steps | iYachtClubKnow the difference between these yachts and which one is best suited for the type of Caribbean sailing vacation you are seeking. Learn about monohull sailboats and why people choose that style of charter yacht for the classic feel of sailing and the history and tradition they represent.

Find out why a catamaran might be the best boat for your Caribbean sailing vacation | iYachtClubExplore different catamarans, such as Karizma , R-S-Cape, or Elixir and find out why so many guests consider them the best platform for a Caribbean sailing vacation.  

Or maybe a Motoryacht is your preference? Take a look at the different types of boats and what sets them apart before booking your vacation.

2. Identify Your Group Type

10 Great Reason to Book a Caribbean Yacht Charter for ChristmasAre you a family with young kids, a group of couple friends or honeymooners? Some yacht charters are ideally suited for kids while others have a more adult vibe.

Other boats specialize in couples and offer honeymoon discounts or packages. If you know the KIND of Caribbean sailing vacation you are looking for, you can make sure it is the best by narrowing down your choices.

If you are looking for Scuba Diving or Fishing, make sure that you screen for those activities, as well. Not all boats are dive boats (with a dive master on board)  and some boats are not really set up for fishing.



3. Decide WHEN is the Best Time to Take Your Sailing Vacation in the Caribbean

Discover the magic of a crewed yacht charter aboard Hypnautic. Experience the #1 charter catamaran in the Caribbean.Spring break, New Year’s week, Summer? When is the best time for your Caribbean sailing vacation? It all depends on when is right for you! 

Christmas and New Year’s weeks are the busiest here in the Caribbean, and that is considered “prime season.”  Spring break is also a busy time here with really beautiful, clear and dry weather, AND if you book after May 1st, you will be out of “winter season” rates which are often higher than summer rates.

Summertime is a great time to be in the Caribbean, especially if you are interested in SCUBA diving and want to take advantage of the calm seas. Summer is also quieter and the popular destinations are not crowded.

If you have a week narrowed down, you can check availability by looking at each yacht’s calendar on the featured yacht page.

4. Calculate Your Best Caribbean Sailing Vacation Budget

Yacht rates are based on one week (7 nights and 8 days). If you are chartering for less than that time or more, the rate will have to be pro-rated. So it could be more or less than what is posted on the website. You will want to factor in your flight costs, and remember that a crew gratuity of 15 to 20% is expected.

Many yachts offer special deals at certain time so so make sure and ask if there are any discounts offered on any of the boats you are considering. There are many ways to find the best Caribbean sailing vacation that doesn’t break the bank. Just ask us!

Decide what type of Caribbean sailing vacation is best for you? All-inclusive , Half Board, Captain –Only or Bareboat? 

5. Look at Lots of Photo Galleries

Each yacht has a photo gallery that displays all of the different areas of the boat.

The interior living spaces such as the saloon (livingroom), galley (kitchen) and cabins (bedrooms) are always shown.

The outdoor spaces are important, as well, because this is where you will be spending most of your time. Take a look at the cockpit seating area – is it big enough for your group to sit around the table?

Is there a forward seating area or a flybridge (upper helm with benches)? Does the boat have plenty of shaded places as well as areas for sunning?

Often photos of the water toys are displayed in the gallery, too, as well as pictures of people having fun.

6. Read the Crew Bios on the Featured Yacht’s Webpage

Book Zephyr for unforgettable crewed yacht charters in the BVI with Matt and Kendra! | iYachtClubSee if the crew are people you want to spend a sailing vacation week with! Usually the bios say something about where the crews are from and what they did in their prior lives. Look for some sort of connection with the crews.

Do you prefer young, fun and fit crews, older and more experienced crews or crews with top chefs? The crew bios will give you all of that info to make a good match. Guests tell us again and again that the crew were the most important factor that made their charter trip the best Caribbean sailing vacation of their lives.

7. Read What Guests Say About What Made Their Caribbean Sailing Vacation the Best

Guests really tell the story of their Caribbean sailing vacations on board in the guest comment sections of the yacht’s featured page. Read through a few of these to get a good sense of what your time aboard will be like. You can get ideas for itinerary destinations you will want to visit, too!

8. Check out the Water Toys!


Get ready for fun aboard crewed yacht charter Hypnautic | iYachtClubThe best Caribbean sailing vacations involve a lot of time moored at beaches and quiet coves for exploration. What sort of activities do you enjoy? Stand up paddle boarding, kayaking, scuba diving? Make sure your charter yacht has the right water toys for you.

If you have kids on board, you will want to make sure there are plenty of games and toys to keep them happy in the water and on board!

If you plan on active water towing activities for the kids such as tubing or kite boarding make sure your charter yacht has a dinghy with at least a 25 hp outboard.


9. Read the Sample Menus

Book Aliwe - Luxury Caribbean yacht charters | iYachtClub


If you are planning an all-inclusive Caribbean sailing vacation or a half-board, you will want to know what sort of meals the chef prepares. Are you plain eaters, or gourmet foodies? The sample menus give you a good idea of the chef’s proficiencies and the style of cuisine prepared.

Keep in mind, that these are “sample menus,” and most chefs will tailor their menus to meet guests’ preferences and any special diets to make sure that each guest enjoys the best Caribbean sailing vacation possible.

Often it is the high quality of the food served aboard that most impresses the guests. Even when they go ashore and dine at some of the excellent resorts found along their itinerary, guests tell us that the food served aboard was far better.

An all-inclusive Caribbean sailing vacation is the best way to feel as if you staying aboard a floating 5 star resort with a chef catering to your culinary desires every day.


10. For the BEST Caribbean Sailing Vacation – Don’t Be Afraid To Ask Questions!

Reserve-a-Yacht-in-the-Caribbean-with-iYachtClub-GreenIf you want the best Caribbean sailing vacation, contact us and let us answer any of your questions! We love to talk about our yachts! We live here in St. Thomas, USVI (where most of the yacht charter trips begin and end), and our office is located in the marina where we see the boats and crews on a daily basis.

We can answer any question you have, so contact us! We want to get you out exploring our paradise and enjoying the very best Caribbean sailing vacation that we know will exceed your every expectation.


Contact Us!

Now you have the tools to book the best Caribbean sailing vacation for you and your group, go ahead and start exploring our featured yacht page. Over and over again we are told by our guests that this trip was the very best experience they have ever had. We know how great this vacation is, and we can’t wait to share it with you!