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Starlight Sailing Charters
Gay Owned Tour Operator in St. John, USVI
Gay Owned Tour Operator
PRIVATE LUXURY SAILING CHARTERS

Starlight Sailing Charters provides friendly and fun private sailing vacations aboard the large, modern, and luxurious sailing yacht, Starlight. Starlight sails November through May in the wonderful Virgin Islands and Eastern Caribbean. During Summer Months, Starlight sails from Sag Harbor, New York on exquisite Hamptons day charters and sailing vacations. A Starlight vacation is wonderful for a special occasion, or a fantastic way to relax and escape in paradise. Starlight accommodates up to six guests, but is also appropriate for smaller groups and solo travelers.

Captain Toby Stull is your host for charters exploring paradise in the Virgin Islands, St Maarten and St Barths, Antigua and Lower Caribbean. With a lifetime of sailing experience and a decade chartering in the Caribbean, Capt. Toby knows exactly where to bring guests and how to tailor your experience depending on your desired activities aboard. Our vacations can be booked as "captain-only," on which guests eat half their lunches and dinners at local Caribbean restaurants, or "all inclusive" where a chef joins to prepare all meals. Either way, Delicious onboard meals can be suited to all types of dietary restrictions. Also, the Captain's adorable yet unobtrusive boat dog, "Bamboo," joins on all charters.


Our Upcoming Tours

Private Charter from St. Lucia to the Eastern Caribbean Private Charter from St. Lucia to the Eastern Caribbean - Saint Lucia, Rodney Bay
When: Weekly Thru May 31 Website: Click Here
The Windward Islands provide a wonderful escape for a private yacht charter. Starlight picks up guests all winter from St. Lucia to bring through Martinique and Les Saints. This one or two week trip is perfect for 1-6 guests. All Starlight Charters are Private.


A Hamptons Summer Day A Hamptons Summer Day - USA, NY, Sag Harbor: 37 Wharf St.
When: Memorial Day - Sept 30 Website: Click Here
Starlight Sailing Summer Day Charters and Cocktail Cruises depart from Sag Harbor, New York. Suitable for groups up to 12, all our charters are private. We sail to see the beautiful sites of the Hamptons and Shelter Island by water often taking a swim spot along the way. Catering is available and guests are invited to bring whatever they'd like along with a picnic.


A Tropical Getaway - Virgin Islands A Tropical Getaway - Virgin Islands - USA, US Virgin Islands, St Thomas: Red Hook
When: Custom Website: Click Here
Starlight is pleased to offer a wonderful unique week long private sailing adventure through the US and British Virgin Islands from December through May. Perfect for one or two couples (or 1-4 guests), this trip on our 58' yacht can be booked 'bed and breakfast style' on a Captain Only cruise or 'All Inclusive' by employing one of Starlight's Fantastic Freelance Chefs. It is a dog lover's treat with our Boat Dog "Bamboo" aboard. With stops including beautiful Virgin Gorda, the Natural Wonder of Anegada and the National Parks and fantastic restaurants of St. John, the highly experienced Starlight crew ensures a wonderful Caribbean adventure filled with the best water activity spots and food. Prices on this tour range from $9500 to $17000/week based on chef options and whether booked during the Holiday and New Years season.


A September Hamptons Sailing Getaway A September Hamptons Sailing Getaway - United States, New York, Sag Harbor: 37 Wharf Street
When: Custom Website: Click Here
Enjoy a wonderful four-night to one-week private tour of the Hamptons, Vineyard and Islands of Eastern Long Island by boat this September aboard Starlight (Day charters also available). Perfect for a couple or group of 1-4 people, September in the Hamptons is stunning. Since 2009, Captain Toby Stull has been captaining tours out of Sag Harbor, New York and knows the prettiest places with the best sights and food around. Paddle Boards and water toys are on board for guests to use. Classic East End destinations include Shelter Island, the North Fork wine vineyards, chic Montauk and Sag Harbor itself. This trip on our 58' yacht can be booked 'bed and breakfast style' on a Captain Only cruise or 'All Inclusive' by employing one of Starlight's Fantastic Freelance Chefs. It is a dog lover's treat with our Boat Dog "Bamboo" aboard. Prices range from $8800 - $20,000 depending on duration, number of guests and chef options selected.


Fall in New England: A Couple's Sailing Getaway Fall in New England: A Couple's Sailing Getaway - United States, Rhode Island, Newport
When: Custom Website: Click Here
Starlight is excited to offer week long sailing getaways in the New England Islands starting the first week of September. Starting in Newport, we venture to scenic Block Islands with cute restaurants and bike rides, the tiny rustic old fishing and Whaling port of Cuttyhunk where raw bar is served by boat before ice cream on the dock and a majestic sunset. A visit to Vineyard Haven and Edgartown in Martha's Vineyard brings more classic New England before ending in Provincetown, MA. Nantucket is an option for those wanting an adventurous sail.


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