Caribbean Sailing Adventure

Anse Marcel, St. Martin
Amazing Iguanas Roam the Island
Fresh Lobster, Grand Case, St. Martin
Sunset on the Catamaran
Sandy Island, Anguilla
Rum Punch, Sunshine, Caribbean Breezes
Motor Scooter Tour, Gustavia, St. Barts
Surfing Lessons at Gallion Beach, St. Martin
French Pastries at a Local Boulangerie
Carambola, better known as Starfruit
Pewa Growing from a Palm Tree
Trip questions? Call 865-310-8562

Enjoy days filled with bright sunshine, starry nights, and warm tropical breezes on a 7-night cruise aboard your own private luxury catamaran with stops on the French and Dutch side of Saint-Martin, British Anguilla, and sophisticated St. Barts (short for Saint-Barthélemy). Visit deserted islands rimmed with powder white sand and snorkel with sea turtles and colorful fish. Take a hike up one of the hills to gaze down at the sparkling turquoise water. Marvel as dolphins or other sea creatures swim around our yacht and huge iguanas greet us at ports. Enjoy island nightlife at colorful local beach bars or take in the most amazing multitude of stars at some of our remote anchorages. Enjoy shopping and French cuisine in ultra-swanky Gustavia and Bohemian artsy Grand Case. See the Caribbean like never before with a professional crewed sailboat charter!

Adventure Activities Available (at an additional cost): Surf ski at Kim Sha Beach, horseback riding on Gallion Beach and through a nature reserve, motor scooter tour of St. Barts, Hobie Cat sailing on Orient Bay, stand up paddle boarding, surfing, or windsurfing lessons, and parasailing or jet ski rentals at Orient Beach.

What's Included

  • Professional Captain
  • Experienced Stew/Chef
  • Double occupancy onboard accommodations
  • Daily breakfast, four lunches, and three gourmet dinners aboard
  • Snacks and beverages
  • Daily open-bar (beer, wine, and rum punch)
  • Airport transfers
  • Environmental Fees and Permits
  • Mooring fees
  • Snorkeling Gear
  • Snorkeling and hikes guided by crew
  • Organization and accompaniment on adventures and meals ashore as necessary
  • Qualified onboard emergency medical care and maritime emergency management

Note: Air travel to Sint Maarten, and meals and activities onshore other than noted are not included in the price

The following is a proposed itinerary. All planned activities are dependent on the weather and a host of other variables. Sometimes we begin our trip from the other side of St. Martin, resulting in the same or similar daily activities and overnight stops, just in a different order. The safety of the guests and the well-being of the vessel are paramount as we customize our itinerary to the conditions of the day. We have a bank of activities to keep us active and comfortable in almost any condition.

Day One: Welcome Aboard 

One of the four cabins on the boat

Our driver will meet your party at the airport to bring you directly to our awaiting yacht in Oyster Pond. As soon as you board, we will make the short sail over to the deserted isle of Tintamarre where we will moor in time for sunset. You will have time to settle in to your cabin before we enjoy cocktails and dinner aboard.

Day Two: Tintamarre and Anguilla

Sea TurtleAfter breakfast, we will have time for exploring the island and snorkeling among the sea turtles before we set sail for Anguilla. We’ll have lunch underway as we round the western end of the island. By mid-afternoon, we will be safely anchored in the quaint harbor at Road Town. We will take the dinghy in for island nightlife and dinner ashore.

Day Three: Sail to St. Barts

Bob HirscheAfter breakfast, we will head south for the exhilarating open water sail to St. Barts with lunch underway. We will anchor in the harbor at Gustavia in time to clear customs and enjoy a nice dinner in town.

Day Four: St. Barts

Scooters on St. BartsThe adventurous among us will head into town to rent scooters for a busy day on the island. We will see the best of St. Barts stopping at fine restaurants, scenic mountaintops, and the world’s most famous beaches. We will return our scooters to Gustavia where everyone can enjoy the ultra-swanky Euro-Caribbean city on their own for the remainder of the afternoon. When we return to the boat, we will make the short sail to one of St. Bart’s remote anchorages for dinner aboard. After dinner, we will turn off all the lights and  watch the dazzling display of thousands of twinkling stars.

Day Five: The Dutch Side of Sint Maarten

Surf Skiis on Simpson Bay Beach, Sint MaartenAfter breakfast and a morning snorkel excursion, we will make the downwind passage back to Sint Maarten where we will have lunch aboard. We will dinghy ashore for a surf ski lesson at Kim Sha Beach followed by happy hour on the boat before heading into town for dinner at one of the islands famous waterfront establishments.

Day Six: The French Side of St. Martin

Grand Case Restaurant Specials, French Side of St. Martin (1)We will weigh anchor in the morning to sail around the west side of Sint Maarten with a snorkel stop at Baie Rouge or Creole Rock. We will enjoy lunch aboard as we continue north to Grand Case for Bohemian arts and French cuisine. We’ll make recommendations for dinner, but feel free to wander on your own.

Day Seven: Orient Bay

Beach Bar at Orient Bay, St. MartinWe will make the short hop to Orient Bay and take the dinghy ashore. We will walk over to Bayside Equestrian Club to ride horses on and around the beach. We will return to Orient bay for lunch and a walk on the very active and always entertaining beach before returning to the yacht. If the sea is calm, we will spend the night in Orient Bay. Otherwise, we may sail back to Tintamarre for dinner on board and a good night’s rest.

Day Eight: Back to Oyster Pond

Captain Oliver's Marina at Oyster Pond, Saint MartinAfter an early breakfast, we will make the quick trip back to Oyster Pond where we will return our yacht. Our driver will pick us up to bring us back to the airport in time for our return flight.


2016 Rates for Caribbean Adventure from Oyster Pond, St. Martin

Peak Season:  January 1 – April 30        Off Season:  May 1 – November 30

  • Off season double occupancy: $3195 per person
  • Peak season double occupancy: $3995 per person

Call 865-310-8562 to schedule your trip

Guest Reviews

Amazing adventure

5 5 1
A week sailing in the Caribbean with Captain Trey was a unique and exciting vacation. His sailing expertise, familiarity with the ports, and his focus on safety made this a vacation to remember. I traveled with two teenagers and they allowed my son to help sail and encouraged his curiosity. Not only was I able to build memories with my kids, but by the end of the week it felt like I had a boatload of new friends!

Loved It!

5 5 1
Expert Sailor, Captain Trey and Pirate Chef extraordinaire, Jean are a great team! We (new friends and old) learned the basics of sailing ~ participating as much or as little as we liked. Enjoyed fabulous breakfasts, lunches, and dinners on board that catered to our personal preferences ~ see her menu! "Dinghied" in for occasional dinners at some colorful local establishments and danced into the night at a beach bar. Scootered around the beautiful island of St. Bart's. Learned how to surf ski and not topple overboard. Snorkeled to our hearts content. Or just hung out on the hammocks listening to the sounds of the waves and taking it all in. So much fun!

Epic Adventure!

5 5 1
“It was amazing! Best week of my life!”

Tons of Fun!

5 5 1
The trip with captain Trey was a ton of fun. His knowledge of both the sea and the ports of call is extensive and he keeps safety always in mind. I look forward to going again.

1st Mate

5 5 1
I was lucky enough to be 1st mate for Captain Trey on the first Blue Moon Adventure. Captain Trey can tweak a sail. A wonderful learning experience, not to mention just an extravagantly beautiful sail. Will never forget my trek up to the top of “whatever the name of that lil island was...”

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