Sail Starlight - Caribbean best crewed sailing charters | iYachtClub

Starlight is an elegant 58-foot Beneteau center cockpit sailing yacht offering sailing charters for up to 6 guests. Starlight features an exceptionally rich and spacious solid teak interior.

Yacht Starlight - BVI sailing charters like no other! | iYachtClub

The master stateroom aft has a private head with separate walk-in shower.

Her three private staterooms allow guests and crew to sleep in privacy and enjoy separate spaces. The master stateroom aft features a walk around queen bed, with luxury linens. The private head has a separate walk-in shower. Forward of the salon 2 double cabins have private heads and share a walk-in shower. Crew quarters are separate with their own head.

Her well-equipped galley (kitchen) and roomy salon allow for easy entertaining aboard, while her canvas biminis above the spacious cockpit keep the sun at bay for outdoor dining and lounging.

Sailing charters aboard yacht Starlight. BVI and New England | iYachtClub

The drop down swim platform makes for easy entry into the water.

The big aft deck opens into a drop down transom staircase to a swim platform. – ideal for easy entry into the crystal clear waters

Starlight has been recently updated and is fully equipped with water toys, generator, water-maker, A/C and more. Guests looking for a crewed sailing charter in the BVI or in New England will find Starlight to be as fast and beautiful as she is comfortable.


Sail away aboard Starlight. All inclusive yacht charters in the BVI and New England | iYachtClub

Bamboo holds court in the shaded cockpit.

Sail aboard yacht Starlight. All inclusive BVI yacht charters. | iYachtClub

The interior dining table in the air conditioned salon.













Water Toys and Sailing Charter Amenities

Book Starlight for affordable luxury. Crewed sailing charters BVI and New England | iYachtClub

Easy steps lead down to water fun.

12′ Dinghy with 18hp engine

10×6 Giant Floating Mat

2 Stand Up Paddleboards

Beanbag chairs on deck

Sun Lounger

Sailing Instruction





Yacht Layout


Sailing yacht charters aboard Starlight. All inclusive, affordable luxury | iYachtClub

Starlight features 3 cabins for guests: 1 master Queen stateroom aft with private head and walk-in shower. 2 guest double cabins forward with private heads and shared walk-in shower. Crew sleeps in bunk bed cabin midships with separate head and sink shower.



















Yacht Photo Gallery



Meet Starlight’s Crew: Captain Toby, Chef Will and First Mate, Bamboo!

Book yacht Starlight for amazing crewed sailing charters. | iYachtClub

Captain Toby, Will and First Mate, Bamboo are ready to welcome you aboard Starlight.

Captains Toby Stull and Will Bishop, along with the Boat Dog Bamboo, work in unison to create a fun, safe and unique sailing experience. Partners, the two have sailed together for many years between New England and the Caribbean, are passionate about sailing, and have over 20-years combined charter experience. They pride themselves on tailoring every charter to suit each guest’s desires. Whether onboard for a day in Sag Harbor or for two weeks in the Caribbean, Will and Toby truly believe their first mission is to make your sailing dreams come true.

Book yacht Starlight for outstanding crewed sailing charters. New England and BVI | iYachtClub

Bamboo a small “Coconut Retriever” is the chief morale officer aboard Starlight.

Captain Toby Stull has sailed his entire life. He holds a USCG Master Captain License and several American Sailing Association Instructor certifications. He was on boats before he could walk. Toby has an intricate knowledge of waters surrounding Sag Harbor, as well as the Virgin Islands, allowing him to know exactly where the action is, where the activities are, and exactly where to bring guests who want to stay “off the track.” Captain Toby has also served on the board of directors for “Sailing Heals,” a 501(c)(3) non-profit that provides cancer patients with a day of respite under sail and loves to share sailing with all.

Captain Will Bishop is also a life-long sailor. Since the age of 19, he has captained several luxury monohull charter yachts of many sizes in the Caribbean and New England. He has worked as a yacht manager, captain, and engineer aboard some of the world’s finest vessels. Beyond his sailing acumen, Will is an excellent cook who’s onboard prepared meals (Caribbean) and catering (Hamptons) are focused on balanced and healthy appealing combinations. He enjoys a varied cooking style incorporating every type of foods from latin to Asian, and everything in between. He has an acute understanding and love of locally grown fare.

Bamboo is a small St. John ‘Coconut Retriever’ who was originally a Puerto Rican street dog (Sato). She is 6-years old and has been aboard for nearly two years. She is friendly, yet unobtrusive, and is the favorite part of the vacation to many guests.

Bamboo is easy to get along with and is both friendly and keeps to herself. She likes to sit behind the helm and give orders under sail and watch the activity from her perch atop the cabin while at anchor.


Sample Menu



Why We Recommend Starlight Sailing Charters

Starlight is a very elegant 58-foot Beneteau sailing yacht – as beautiful as she is fast. Captain Toby is an ASA instructor and loves to teach sailing. Toby and Will offer a full-service charter with delicious food, wonderful cocktails, and great company! Starlight is also LBGT friendly. She is perfect for up to six guests to enjoy unforgettable sailing vacations in the winter in the BVI or summertime in New England. We also love first mate Bamboo – their adorable Coconut Retriever!

Guest Testimonials

Life Changing

Sailing charters aboard Starlight are like no other! | iYachtClubSailing the USVI and BVI has been the dream vacation that we saved for my 40th birthday. We were beyond nervous about picking the right captain and the right boat as we could not imagine a week aboard with the wrong choice . The captain, Toby and crew, Will, were HIGHLY knowledgeable and professional but at the same time so naturally flexible, easygoing and fun to be around. Their immense knowledge of the islands and other boats in the area was absolutely impressive and in hind sight, imperative. They knew the ins and out of of every island, the timing to visit each island , every restaurant to go to for dinner and every MUST DO experience that we didn’t even know that we wanted to do. The boat, Starlight, is stunning, clean , spacious and well appointed. The main cabin provided the deepest sleep that I desperately needed (mom of two). The breakfasts/ lunches and cocktails aboard were plentiful and delicious. They covered more than you can imagine in a week, had the gear that we needed and came on adventures to keep us safe while at the same time ensuring your privacy and romantic alone time. Daily operations of the boat were done seamlessly and safely and every anticipated need, including a serious food allergy was handled almost magically.

This double Birthday/ Valentines Day trip was an adventurous, relaxing and romantic week long cruise for two, executed with class, professionalism and easygoing fun. We will be returning without a doubt as we are forever ruined and can no longer imagine just sitting at a resort for a week. Thank you so much Toby, Will and Bamboo for a life changing first days of 40!! ~ Lori and Jay, Montauk NY

Outstanding in Every Way

Book yacht Starlight for amazing sailing charters in the BVI! | iYachtClubMy wife and I just spent 2 weeks sailing on Starlight in the Virgin Islands with Toby; it was outstanding in every way. The boat was comfortable, sailed well, was a joy to live aboard, a true classic yacht.

Captain Toby knows his boat and the American and British Virgin Islands very well, is professional, personable, and completely dependable, a rare combination especially on a boat. ~Jan and Kitty, Santa Fe, NM

Loved Our Time Aboard!

So, my friend and I planned a rather last-minute trip to the Virgin Islands for peak winter season, figuring it would be no problem to get hotels. Well, we quickly realized just how stupid we were, until I unearthed Captain Toby and the beautiful Starlight, after which we could not have counted ourselves any more fortunate. We booked a 4-day sail through the BVI, and it was by far the highlight of the trip. The ship was gorgeous, comfortable and well-maintained.

Captain Toby could not have been a better companion – experienced, easy-going, flexible, and fun. I had looked into bareboat chartering in this area, and this was by far the best deal I found. Not only did prices include breakfast, lunch, gas, and insurance, but we paid for 3 nights on board and Toby gave us basically four full days, even dropping us off on another island so we wouldn’t have to take any ferries, despite that fact that he really did not have to do that. We both LOVED our time aboard Starlight, and I honestly cannot wait to book and come aboard again. Thanks so much, Toby. Say hey to Bamboo! ~ Katie and Ivana, Bklyn NY

Starlight Sailing Charters – Calendar

Currently booked or requested dates:

Date Start Date End Status

Starlight – Sailing Charter Rates

Caribbean: Winter 2017 – December through June 1 (5 day Min)

Fully crewed, full board: all meals chef prepared aboard, snacks and drinks, yacht’s bar, BVI customs, cruising permits port fees and mooring fees, fuel and water along with all onboard expenses included. On shore activities, meals, tours and transfers are guest’s responsibility.

Best Rate
Passengers 2 3 4 5 6
Winter 2017
Per Person $$4,500 $3,333 $2,750 $2,400 $2,167
Totals $9,00 $10,000 $11,000 $12,000 $13,000
Rates are All Inclusive

Hamptons and New England Summer 2017 – June 14th through September (4 day Min)

Fully crewed, full board New England sailing vacations originate from several ports throughout New England and can include stops in Block Island, Fisher’s Island, Gardiner’s Bay, Martha’s Vineyard, Nantucket, Cuttyhunk and more. One way charters  with return flights available. Inquire for half-board charter discounts

Best Rate
Passengers 2 3 4 5 6
Summer 2016
Per Person $4,500 $3,333 $2,750 $2,400 $2,167
Totals $9,000 $10,000 $11,000 $12,000 $13,000
Rates are All Inclusive

Sag Harbor, Southhampton and Shelter Island Day Rates

Hamptons abnd Shelter Island day sail rates range from $1100 -$2500 based on the length of the charter and the number of guests aboard.