Adonis Gay Holiday
Windjammer Caribbean Gay Cruise

Windjammer Caribbean
Tall Ship All-Gay Cruise

St.Maarten, St.Barts, St.Kitts, Nevis, Anguilla & Tintamarre

8 Days from/to Philipsburg, St.Maarten

February 12 – 19, 2022
February 19 – 26, 2022


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Gay Caribbean sailing cruiseAdonis Holiday YouTube Channel8 glorious days in the playground of socialites and celebrities, with a start and end on the Dutch side of Sint Maarten, and a week on our own private 156-foot all-gay sailboat cruising the Caribbean! We'll spend this unforgettable trip island-hopping along the most stunning and exclusive islands in the Caribbean from Sint Maarten to St. Barts to St Kitts to Anguilla and more.

Quote or Reservation


All your breakfasts, lunches, afternoon snacks, dinners, drinks, snorkelling and more - it's ALL INCLUDED too!


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On board, you'll be joined by 2 Detours trip leaders, plus a crew of 10 including your chefs and captains, as well as 24 other all-gay cruise shipmates. We'll explore stunning secluded beaches and unique towns together, snorkel beautiful reefs, hike to impressive viewpoints, then return to our ship for plentiful meals and fun under the sun - and stars.

An unforgettable 8 days in paradise!


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What's Included?

• All breakfasts on board, plus Sint Maarten

• All lunches on board

• All dinners on board, plus welcome dinner in Sint Maarten

• Unlimited beer, wine, rum punch

• 7 days / 6 nights private sailing charter accommodation

• 1 night accommodation Sint Maarten

• Group port transfers

• 2 Detours trip leaders

• 10 onboard ship crew including captains and chefs

• Snorkeling gear including fins

• Port taxes & government fees & all other taxes


What isn't included?

• International flights

• Optional crew/leader tips at traveler's discretion

• Optional shore excursions.


St Maarten gay cruise Simpson Bay


Windjammer Caribbean Tall Ship Gay Cruise Itinerary

Day 1 - Sint Maarten
Our adventure starts on the Dutch side of Sint Maarten, full of unique shops and restaurants lined by beautiful white-sand beaches.

Our hotel is situated right on the beach where our adventure will start at 4:00pm on this day. We'll gather our everyone together for a big land-based welcome evening to kick-off our 8 days in paradise together.

If you've got some extra time, we suggest adding an additional night or two at this beachfront hotel to fully chill out before the group adventure begins.

Hotel: Simpson Bay Resort, Marina & Spa, Sint Maarten


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Day 2 - Embark and Set Sail
We'll take the morning to explore the Simpson Bay beach area, check out the iconic spot where airplanes land barely above the heads of beachgoers, sip some local rum, then we'll jump on board our home for the coming week - the impressive 156-foot sailing vessel that'll take us to some of the most gorgeous corners of the Caribbean.

We'll set sail with capitan, crew, and our fun-loving band of pirates, ready for our own Pirates of the Caribbean adventure.


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Days 3 to 7 - St.Barts, St.Kitts & Nevis, Anguilla, Tintamarre
For 7 days we'll cruise into some of the most beautiful coves, ports, and beaches that the Caribbean has to offer. The exact itinerary will depend on current sea conditions, the captain's advice, and of course our own desires as the ship is ours for the full week.

We'll share jokes and stories on the expansive deck under the stars, jump overboard into the impossibly-blue waters, check out beach bars and unique ports, and soak up the heat and sunshine of these beautiful February days.


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Expect to spend the week barefoot in the sunshine, packing just your swimsuits, some comfortable shoes for exploring, and maybe a nice outfit if you're feeling like having a land-based dinner at some point.

Onboard our ship, we've got a large social deck and indoor dining saloon on the upper deck, then a lower deck full of cabins - each above the water with a porthole and private bathroom.


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Day 8 - Disembark and Depart
On our 8th and final day we'll sail back into Sint Maarten as we wind down the fun and say our goodbyes to our crew and fellow Detours gay sailors.

Feel free to add on additional nights in Sint Maarten, or book your flight out of SXM airport with a departure time any time after 1:00pm this day.

You'll be returning home full of stories after 8 days of fun in the sun of the Caribbean.


Simpson Bay Resort, Sint Maarten



Sint Maarten
Simpson Bay Resort, Marina & Spa
Located directly on a beautiful white-sand beach, with the waves at our doorstep, our adventure begins in paradise in Simpson Bay, just minutes from the SXM airport.

Tropical gardens, extensive pool areas, and of course the white sand awaits us at the Simpson Bay resort for one night before we set sail on board our ship for the coming week.

The Simpson Bay Resort, Marina & Spa is set in the shores of Simpson Bay Beach. It offers 6 outdoor swimming pools, sun terrace, spa, casino and the on-site water sport facility Aqua Mania Adventures.


Island Windjammers Vela


Island Windjammers Tall Ship Vela

Her name means "sail". Once aboard our 156-foot home at sea, we’ll be taken back to a time when tall ships ruled the waves. Everything about her will light your imagination and inspire a sense of wanderlust.


Island Windjammers Vela dining


Newly refitted, the ship's snug cabins all feature portholes and private bathrooms. Her teak decks are spacious and inviting with plenty of room to spread out.

It's the kind of adventure that fulfills your pirate soul in 21st-century comfort!


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Trip Notes

Arrival & Departure
All travelers should arrive and depart using St Maarten airport, code SXM. Official trip start time is 4:00pm on day 1. Departure flights should be booked on the 8th day of the trip with a departure time of 1:00pm or later. Additional nights pre/post trip can be arranged - just ask!


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The Food and Drinks
Meals are delicious and plentiful! Breakfast, lunch, and dinner are served on board, as well as afternoon snacks and are all included in your trip cost. Every effort is made to buy provisions locally which helps the local economy and brings you the freshest fruits, meats, fish and vegetables available. Dining is usually alfresco, out on the deck, but an indoor dining saloon is also available.

Special diets such as vegetarian and gluten-free will be accommodated, however, more restrictive diets such as vegan and kosher cannot be accommodated.

Unlimited beer, wine, soft drinks and rum punch is available through the sailing week. You're welcome to bring any other drinks you'd like onto the boat. Included soft drinks include cola, diet cola, lemon-lime soft drink, ginger ale and tonic water.


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The Weather
We've chosen the absolute BEST time of year to sail in the Eastern Caribbean. Expected daily temperatures between 75 and 83F (24-28C), and water temperature around 77F / 25C. The dry season brings very little rain, and hurricane season is long gone as well as the seasonal Christmas winds.

While February is known for calm seas in the area, it's important to note that there will always be some movement on a sailboat. If you've experienced motion sickness in the past, or aren't sure how you'll adjust, please bring your preferred remedy with you. Most motion sickness medications aren't effective if taken after you start feeling sick.


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While you won't need any money on board, we'll be making some port stops along the way where you'll want to have some cash on hand. The US dollar is accepted in most ports, while the Euro is preferred in French ports, while Visa and MasterCard are accepted at almost all merchants.


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Staying Connected.... Or Not
Most cell phone carriers provide international roaming service on Caribbean networks. Call your provider to ensure you have coverage, and ask about cost-saving international service plans. We will be in data/call range often. Our ship does not have WiFi, but WiFi can be found during port stops if necessary.


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Dress on board is very casual at all times. There's a chance you may want to dine on shore, in which case you may want to pack a nice outfit. Given that you'll likely spend the vast majority of the trip in flip flops and shorts we strongly recommend packing light. Cabin space is limited so keep that in mind when packing the kitchen sink ;-)


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Solo Sailors
Two cabins on the ship are intended for solo sailors in private rooms, while 4 additional cabins contain 2 beds each and are perfect for solo travelers sharing, with a lower and an upper bunk. The remaining cabins are outfitted with one double, queen, or king bed each. Solo travelers wishing to book any double-occupancy cabins as private can do so at the rate of 2 sailors.


Vela tall ship


Yes, this is a true sailing vessel! If conditions are right, the captains will take advantage of it to turn the engine off and proceed under sail alone. Most of the time, however, the sails and engines will be used together during morning or nighttime travel. Take a turn at the helm, or simply relax and watch the action.


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Motion In the Ocean
Sensitivity to motion is not always based on weather conditions. If you have experienced motion sickness in the past, or you’re not sure how you will adjust, we recommend that you pack your preferred remedy. If you are prone to seasickness, you should take your medication prior to sailing.


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Fun, On Board or Off
This is our home for the week and we intend to have as much fun as we possibly can. From bow to stern we'll make ourselves comfortable and soak in the adventure of the high seas. Take a jump from the ship then laze around on a floatie mat. Take a turn at the helm, or simply relax and watch the action. Hike to viewpoints, or stroll around unique ports. Soak up the sun on an impossibly-white sand beach, or snorkel through the crystal-clear water. Tell jokes and have a dance party after sunset - the possibilities are endless. Board games and playing cards are available.

Let us know what you came to enjoy, and we’ll do our best to ensure that you’re a happy sailor.


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Quote or Reservation


Windjammer Caribbean Tall Ship All-Gay Cruise Prices

Cabin Category Description
February 12, 2022
Per person
$ (USD)
February 19, 2022
Per person
$ (USD)

Vela Owners Suite

Cabin Nr.7. King Bed, double occupancy, private large bathroom

$ 4,770

$ 4,770

Vela Topsail Cabin

Cabin Nr.9. The only one of it's kind on the ship, the cabin boasts a queen size bed and luxury bathroom.

$ 4,340

$ 4,340

Vela Compass Cabin

Cabins Nr.16 & 17. Compass Cabins are located in the aft section of the ship. These spacious cabins feature a queen size bed (no upper bunk) and an ensuite bathroom with shower.

$ 4,230

$ 4,230

Vela Staysail Cabin

Cabins Nr.11 - 15. Staysail Cabin features a roomy double berth, and a private bathroom with shower.

$ 3,760

$ 3,760

Vela Deluxe Cabin

Cabins Nr.5 & 6. Deluxe Cabin: Double lower and single upper berth and a private bathroom with shower. Top bunk in shared cabin - $3,780

$ 3,980

$ 3,980

Vela Standard Cabin

Cabins Nr.3 & 4. Full Lower Bed, Single Upper Bed, double occupancy, private all-in-one bathroom. Top bunk in shared cabin - $3,480.

$ 3,680

$ 3,680

Vela Solo Cabin

Cabins Nr.1 & 2. Cadet Solo Cabin: Single occupancy cabin with a twin berth and a compact, all-in-one bathroom.

$ 3,960

$ 3,960

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Taxes of $140 pp, and optional travel insurance are additional.

Min. Deposit: $750. Balance Due not later than 90 days before departure

Price does not include 3% payment card charges. No additional charges on bank transfer payments.

Solo travelers wishing to book any double-occupancy cabins as private can do so at the rate of 2 sailors.


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