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Caribbean Sailing Charter

Detours 10th Birthday Special


8 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 sailboat cruising the Caribbean!  As the first of three unique celebratory "10th birthday" itineraries in 2022, 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. 

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

Day 1 - Saint 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.

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.

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.

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.  Check out the accommodation page for more info about our ship.

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 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.

Cabins aboard our ship come in 7 options ranging from single-occupancy compact rooms, to the large "owners suite" with a king size bed.  All rooms are air-conditioned and have a porthole, private bathroom, and power outlets.  Due to bedding availability, cabins #1 through #6 are reserved for solo travelers, while cabins #7 and above are available for coupled travelers.


  Hommage Hotel

 Hommage Hotel, with its 5 striking white buildings, overlooks the beautiful Simpson Bay Lagoon on the French side of the Saint-Martin island, just minutes from the SXM airport.
This hip & calm modern hotel offers spacious rooms, local and flavored cuisine, an outdoor museum and lush tropical gardens. Enjoy panoramic sunsets, immerse yourself in nature and live the French Caribbean style.
The most beautiful beaches of the island, Baie Rouge, Baie Longue and Baie aux prunes are  minutes away.


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. 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!

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!

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.

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. 


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.

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.


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 ;-)

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.


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.

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.

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.

  • 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

Not Included:  International flights, optional crew/leader tips at traveler's discretion, optional shore excursions.

(Cabin #1) $3,960 USD per person - One Single Bed, single occupancy, private all-in-one bathroom"
(Cabin #2) $3,960 USD per person - One Single Bed, single occupancy, private all-in-one bathroom
(Cabin #3) From $3,480 USD per person - Full Lower Bed, Single Upper Bed, double occupancy, private all-in-one bathroom
(Cabin #4) From $3,480 USD per person - Full Lower Bed, Single Upper Bed, double occupancy, private all-in-one bathroom
(Cabin #5) From $3,780 USD per person - Queen Lower Bed, Single Upper Bed, double occupancy, private bathroom with shower
(Cabin #6) From $3,780 USD per person - Queen Lower Bed, Single Upper Bed, double occupancy, private bathroom with shower
(Cabin #7) $4,670 USD per person - King Bed, double occupancy, private large bathroom
(Cabin #9) $4,340 USD per person - Queen Bed, double occupancy, private large bathroom
(Cabin #11) $3,960 USD per person - Double Bed, double occupancy, private bathroom with shower
(Cabin #12) $3,960 USD per person - Double Bed, double occupancy, private bathroom with shower
(Cabin #14) $3,960 USD per person - Double Bed, double occupancy, private bathroom with shower
(Cabin #15) $3,960 USD per person - Double Bed, double occupancy, private bathroom with shower
(Cabin #16) $4,130 USD per person - Queen Bed, double occupancy, ensuite bathroom with shower
(Cabin #17) $4,130 USD per person - Queen Bed, double occupancy, ensuite bathroom with shower

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Trip Reviews

Our travelers love us, and you will too.

Kevin B. - USA

February 12, 2020

I've done 2 trips with Detours and they have both been wonderful. The tour leaders - Shane & Dan - were excellent, the accommodations were good and conveniently situated. The a la carte format of most activities allows you the freedom to do as much or as little as you please making for a stress free, enjoyable vacation. Great job guys and I look forward to my next trip with you!

Larry J. - USA

May 20, 2020

We recently traveled with Detours to Greece. From the moment we began our initial inquiry to the time we returned home from our trip, Detours guided us each step of the way. We especially love that Detours planned everything, but developed the itinerary so that we didn’t feel pressured for time and allowed us to break away and do our own thing if we wanted to. And the trip is an incredible value! We also love the small groups size. Our trip guide, Miles, truly went out of his way to make sure that any needs were met, and was always available to answer questions and provide advice. When storms in the U.S. prevented us from returning from Greece for two days, Miles was right there to make sure we had accommodations during our delay. We loved our trip so much that we booked another trip to Egypt this summer. The recent pandemic derailed our trip, but they allowed us to rebook another trip, so we’ll be traveling with Detours to Portugal and Morocco soon! I recommend Detours Travel without reservation.

Joe F. - USA

May 21, 2020

I took my first trip with Detours in November 2018 to Israel and Jordan. It was one of the best trips of my life, aside from a great destination, the guys I met were great and in a few instances I have maintained ongoing friendships. So it was a no brainer when I learned one of my friends from that trip booked Greece for this June. Unfortunately the universe had other plans and the worldwide Covid pandemic forced Detours to cancel our trip. During this time of total uncertainty on every level, general communication to the public has not been great. Miles and Detours are the exception, even as I know they are dealing with business related issues far beyond the impact to their customers, Miles somehow manages to find time to put out weekly detailed updates. His updates are factual and sympathetic to his clients when we are only losing a vacation (for now). This is amazing considering he is fighting to maintain his livelihood. He also finds time to answer individual emails in very detailed responses when I’m sure at times he wants to toss his laptop against the wall and walk away! It’s a true measure of who Miles and the entire Detours group are and why anyone should feel confident working with them. While the current pandemic has forced that trip to be cancelled, I did not hesitate to rebook a new trip next April to Egypt with Detours. They can't control the pandemic or the consequences of it but they can control how they react to it and they have reacted in the best way possible. I can't wait to join them in April for Egypt and eventually I will get to Greece, with Detours of course!

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