St. Maarten

In the north of the Caribbean's Lesser Antilles chain lies St. Maarten / Sint Martin, a small territory shared by two cultures, two countries, and thousands of tourists each year. The European capital of the Caribbean, delightfully Dutch and fantastically French, this tiny island of just 36 sq. miles is the smallest country shared by two nations.

Excellent winds and blue water seas make for superb sailing and exhilarating open water sailing. Enjoy a relaxing vacation aboard our crewed yacht and discover dozens of sparkling, secluded beaches, while toasting the sunset in one memorable anchorage after another. Aboard our charter you'll visit the beautiful island of St. Barts, an island of high fashion and haute cuisine. For a complete change of pace, we'll sail to Anguilla and give you a chance to experience the Caribbean at its unspoiled best.

This pristine island, with its charming villages and stretches of powdery white beach, has a great selection of excellent restaurants. You'll also explore the deserted islands of Prickly Pear Cays, with their dazzling beaches and incomparable snorkeling. St. Maarten is the perfect place for your next sailing vacation.

Package Includes
7 Nights sailing on a beautiful Lagoon 440 catamaran
Air-conditioned staterooms with en-suite private bathroom
Experienced Captain and Chef
5 dinners, 6 lunches and 7 breakfasts
Appetizers and desserts
Standard open bar (beer, wine and liquor)
Onboard sporting equipment
Mooring fees/taxes


"Outstanding crew ,one of the best we have had in 5 years...They were very flexible and took us where we wanted to go!"


"Our sailing trips with Festiva are truly the best vacations my wife and I have each year." 


"The meals exceeded our expectations!!! Delicious and healthy and always a beautiful presentation!! One of our guests had dietary restrictions which were cheerfully met at every meal."


Prickly Pear Cays

This small island is located approximately six miles from the Anguillan mainland. It is well known and popular among swimmers and snorkelers looking for a less crowded experience.

Little Bay

This beautiful and very secluded cove is perfect for a quiet afternoon on the beach.


Marigot, the capital of French St. Martin, is an appealing residential area with brightly colored houses, a scattering of restaurants and lively produce and crafts markets. It’s a great base for exploring St. Martin’s secluded beaches suitable for persons of all ages. Marigot is within easy reach of the famed restaurants at nearby Grand Case, said to have the Caribbean's best dining.

Pinel Island

Snorkeling on Pinel is known to be the best snorkeling in St. Martin.  The snorkel trail is protected by the marine reserve and therefore, have guidelines to follow in order to protect its natural state.

St. Barths

Known for its eclectic mix of iguanas, night-blooming cactus, and fabulous beaches, St. Barth's has an array of natural wildlife and Caribbean activities that will help you busy as you scout out for celebrities or shop at the local boutiques.

By Plane:

Fly into Princess Juliana International Airport on the Dutch side of the island. Our yacht is located at Porto Cupecoy Marina, just a few moments away from the airport. Taxi service is available from the airport to our home base. You will check-in at the boat which is indicated by the Festiva Sailing Vacations flags and markings.

Our Base Location:

Porto Cupecoy Marina is where our base is located on the Dutch side of St. Maarten which is approximately fifteen minutes from the airport. The meeting time to board the yacht is at 5pm on Saturday. You will have dinner aboard the yacht at the base that evening and the yacht will depart on Sunday morning. Because of crew time needed for provisioning and yacht preparation, no one will be able to board prior to 5pm on Saturday.

Please Note:

U.S. citizens must have a valid passport. Other citizens should check entry requirements with their home country's consulate. A $20 tax is imposed upon departure from the Princess Juliana Airport.

All guests must bring proof of "onward accommodations" (flight or hotel confirmation for their plans directly after cruise is over). This information will be required if the yacht gets stopped by immigration.

New Site Sale!

Save up to 25% on a Package for Two*

Choose any sailing week in 2019

Package for Two Includes:
7 Nights sailing on a beautiful Lagoon 440 catamaran
Air-conditioned stateroom with en-suite private bathroom
Experienced Captain and Chef
5 dinners, 6 lunches and 7 breakfasts
Appetizers and desserts
Standard open bar (beer, wine and liquor)
Onboard sporting equipment
Mooring fees/taxes

Book Now and Use Promo Code: SITE

*Based on double occupancy. Offer is not valid on previously made reservations, or in conjunction with other discounts, promotions, packages, member usage or referral pricing. Valid for any available sailing date  in St. Maarten in 2019.  A cruising permit fee may apply at the time of reservation. A 50% deposit is required under this promotional offer. Call for details.


There is a reason why it is recognized as the European Capital of the Caribbean, delightfully Dutch and fantastically French, this tiny island of just 36 square miles is the smallest country shared by two nations. Fly into Princess Juliana international Airport on the Dutch side. After a short taxi ride to the Porto Cupecoy Marina, meet your crew and store your bags, we encourage you to stroll around the duty-free shopping and sidewalk cafes. You will board your catamaran at five o’clock in the afternoon and enjoy cocktails and dinner on board.

Cruising Day 1:

After breakfast we depart through the Dutch Bridge on our way to Road Bay on the British island of Anguilla. We have a leisurely morning sail and lunch at Road Bay after which you will have the opportunity to go ashore and mingle with the locals at Johnos' bar and enjoy the live jazz music, see the locally made sailboats on the beach ready for the next regatta, which is the national sport of Anguilla.

Cruising Day 2:

Breakfast and we are off to Prickly Pear Cays, a remote uninhabited rocky atoll with amazing bird life and unspoiled lagoon surrounded by a living coral reef. Snorkel to the white powdery beach and over the magnificent coral. You can also explore the water of little bay where schools of small fish totally surround you and you can see the pelicans diving. This area and has been designated as a marine park providing excellent snorkeling and swimming in the azure waters. After lunch we will sail Marigot on the French side of Saint Martin.

Cruising Day 3:

In the morning you will have an opportunity to go ashore to explore the picturesque town of Marigot, visit fort Luise, enjoy the beautiful mall, and do some shopping in the street market. After lunch we sail to Roche Creol to do some snorkeling, after that we will enter Anse Marsel marina, while the crew is filling the water tanks you will have an opportunity to walk the grounds of the Radisson Hotel. Upon completion of topping up the water tanks we will motor to Grand Case where you will dine ashore in the gourmet Capital of the Caribbean.

Cruising Day 4:

After breakfast we head off around the north end of the island into Pinel island (Il. Pinel), here you can go ashore, enjoyed the beach, Beach chairs/umbrellas, beach bars, gift shop, hiking, snorkeling, kayaking. In short Pinel island offers something to everyone. We shall stay at Pinel Island until the next morning.

Cruising Day 5:

Today we shall sail to Saint Bart’s, On the way after two hours of open ocean sailing we shall stop at Il. Fourche (fork island), this island is the rocky remains of an extinct volcano with nothing but lizards and cactus, we shall spend several hours in this magnificent moonscape surrounding, for those who would like to climb the to the summit there are the most spectacular views, the rest can enjoy the water and snorkeling around. After lunch we sail to bay of Colombier on Saint Bart’s, where we can spend the rest of the day exploring the bay in the kayak, walking on the beach or taking the cliff-path into the next day where the views are stunning. The bay is inaccessible by car and is totally unspoiled. There is also plenty of time for our last snorkeling to see all the varieties of Caribbean fish you could wish for.

Cruising Day 6:

A short sail in the morning takes us to the beautiful harbour of Gustavia, the capital of Saint Bart’s. This island boasts the gateway homes of many celebrities and magnificent mega-yachts. After exploring the wonderful array of old Caribbean houses and varying French shops, and maybe doing an island tour, enjoy a cocktail at Jimmy Buffett’s “cheeseburger in paradise” café. After lunch we take a leisurely sail back to Simpson Bay, Saint Maarten to be in time for the Dutch bridge at 5:30 PM and then back to Simpson Bay Marina. Enjoy an exquisite cuisine of your choice ashore tonight.

Departure Day:

A continental breakfast will be served and then we say our farewells to you until your next cruise with us.