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. As the European capital of the Caribbean, with both Dutch and French heritage, 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 an exhilarating open water experience. Enjoy a relaxing vacation aboard our crewed yacht and discover dozens of sparkling, secluded beaches - all while toasting the sunset in one memorable anchorage after another. Aboard our charter, you'll visit the beautiful island of St. Barts, known for 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


We sailed at the end of January on the Smitten Kitten, out of St. Martin.  The weather was absolutely perfect and the sea was calm.  Captain Xavier took us to exceptionally beautiful bays for snorkeling, and calm anchorages for peaceful night's rest.  He was professional, knowledgeable and enjoyable. Gail is an excellent first mate, an even better chef and a delightful person to be around.  She fed us delicious gourmet foods presented beautifully. We visited several islands, my personal favorite being the Prickly Pear Cayes.  The sand there was like none I had ever seen.  It was like powder, but when you looked closely you could see millions of tiny bits of pink coral mixed into the white.  BEAUTIFUL.  St. Barths is a beautiful island as well.  We swam with turtles, stingrays and many other fish.  That was my favorite island for snorkeling. Our cabin was comfortable, the boat clean and well equipped.  We traveled as a group of 6 friends.  The boat was large enough to be comfortable when we wanted to gather as a group but also have space when we wanted quite time.  This trip exceeded my expectations.  It was one of my favorite vacations.  I highly recommend it.

–Jodi C., California, February 2020,

We've done two other sailing trips with Tradewinds and Festiva was so much better in every way! They don't have a Timeshare presentation to ruin your vacations and you can relax!!! Guy and Caz were super attentive and knowledgable of the Islands. Guy took us to the best places in the BVI and we didn't miss a thing! He manages to always reserve the best tables and he took us on time everywhere we went, The Soggy Dollar, Foxi and the Pirates show that it was fabulous! He took us to Anegada Island which is not something they always want to do in bad weather, but he made it look easy and pleasant. We ate at the fun Lobster restaurant with the most incredible lobsters and we danced all night. Caz was so sweet and generous with the meals, we were always full and surprised with every meal, always delicious and plentiful. We had the best vacation ever! The Bubbly pool and the Bath, which are places in the BVI you must see, were so much more memorable with Guy taking pictures for us, he made it very special. They are both unbelievable people, we couldn't say enough nice things about them, they are the best!

–Cristina W., Colorado, January 2020,

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 has 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 be sure to keep you busy.

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 - 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.

Will I be on the catamaran with people I don't know?

When you book a stateroom on one of our vessels, we ask that you complete a preference form which outlines the types of activities that you like to participate in and the type of experience you would most like your trip to be. We use this information to combine like guests when at all possible. Our crew are all very in tune with ensuring that individual personalities mesh while on the boat and will do their very best to make certain each guest needs are met.

Will I get sea sick?

Each of our sailing destinations varies in terms of the types of waters in which you will be sailing. The longest sail that we would do during any one day would be 3-4 hours and this is only in certain sailing destinations. The majority of our sails will be short distances (30-45 minutes) from point to point, in very well protected waters. We never sail at night and plan our itineraries to be at ideal anchorages well before dark. Because the catamaran has two hulls, the experience is very comfortable with very little motion in the evenings other than a gentle rocking. If you do have tendencies for getting sea sick, our crew can help you with some fool proof remedies they've learned through the years. There are also over the counter medications available that you can bring to help with any motion sickness.

How much physical activity is involved in a crewed sailing vacation?

Our trips can be best described as light adventure and suited best for those in good physical condition. Because we anchor at night and rarely pull up to docks other than at our base locations, boarding and disembarking the boat is primarily done via dinghy. There is some physical activity and dexterity required in doing this. For a substantial portion of the time, our guests are swimming and climbing in and out of the water from the catamarans swim ladder. The dinghy is used to take guests into shore at the various stops.

How should I plan my flight arrangements?

Based on your charter destination, plan your flight arrangements according to your charters departure date. For specific details, visit the corresponding destination section on our website and click on arrival information. You will board the yacht at 5 pm the first night of your charter and depending on guest arrival times, often we will not sail until the morning following your arrival. You disembark the yacht at 9 am on the last day of your charter.

How should we pack for my sailing vacation?

When packing, keep in mind that storage space is limited. Soft-sided luggage is strongly recommended, as all luggage will need to be stored in your cabin along with your personal items. Casual and breezy beach attire is certainly the order of the day on deck. Please avoid packing small appliances such as hairdryers and irons as these items will not be necessary. For evening attire slacks or a sundress is appropriate for the nights ashore. Shorts and t-shirts are also fine for dining ashore. While aboard the yacht, no shoes are worn. You will want to have a pair of shoes/flip flops for the night ashore. You may also find aquatic shoes convenient for beachcombing. Be certain to bring along plenty of protection from the sun. Suntan lotion is highly recommended as well as wide-brimmed hats or sailing caps and loose-fitting cotton cover-ups. A windbreaker jacket is nice to have for cool evenings during certain times of the year and something that is water resistant is also recommended. All bath and beach towels are provided. For more details on how to pack for your sailing vacation, visit our recommended packing list.

Will I be able to order special diet menus or request favorite beverages?

Once your charter is confirmed, the preference form will ask for specific details relating to your meals and beverages during your charter. Each charter comes with a standard stocked bar featuring liquors, soft drinks, wine and beers that can be provisioned in that specific location.

The menu featured is set in advance with a wide variety of meals. We do ask that you notify us of any allergies or special dietary requirements which can be accommodated by our crew.

Which meals are not included?

The meal plan on our Caribbean charters includes 5 dinners, 6 lunches and 7 breakfasts. The night of arrival you will also enjoy a welcome reception with heavy hors d'oeuvres. There are two dinners throughout the week when dining is ashore, on your own or as a group. Be certain to plan for these meals.

What activities are included in the sailing vacation and which have an additional fee?

All the equipment for the aboard activities is provided on the yacht. You can expect items such as a sea kayak, snorkeling fins/masks and swim floats. Your preference form will ask for details specific to your needs.

If you are interested in diving while aboard, we can arrange for a local dive company to meet the boat while on charter. The fee would be paid directly to the diving company at the rate of approximately $90-$120 per dive for certified divers (rate and conditions to be confirmed at the time of diving). You will need to have your valid certification card with you to present to the dive operator.


What is included onboard the yacht?

Just as you would expect in a fine resort hotel, our yachts have all the basic necessities. This includes: bath towels, linens and basic toiletries. It is recommended that you bring your own personal toiletries such as toothpaste, creams and shampoo. Please note that we request that you do not bring spray sunscreen as it creates a slippery deck surface as well as stains. Please bring lotion sunscreen only. We strongly suggest if you bring a hair dryer, bring a low wattage dryer (ie. travel size).

Will I be able to make and receive telephone calls or have internet access?

Each of our crew is equipped with limited cellular phone service. You can give your family the base telephone number to leave at home in case of emergencies. The base manager will pass on any information to you. In some locations throughout each of our destinations, there will be internet access however it is not a consistent amenity.

How much should we tip our crew?

Although standard in the charter industry, we sometimes find that guests, especially those sailing for the first time, approach to tipping is occasionally misunderstood. It is customary to tip the captain and crew at the end of the charter. The amount of tip runs in line with the way you would tip at a restaurant with the percentage based on the total amount paid for your charter, or in the case of Cruise Club members or RCI exchangers, the tip should be based on the normal retail charter rate. On average you can expect to tip $600/cabin (good service) - $1,000/cabin (superior service) which would be split between the captain and chef. Crews can accept gratuities in cash or via credit card.

What travel documents do I need?

All U.S. citizens must have a valid passport. Other citizens should check entry requirements with their home country's consulate.

What if the weather forecast prohibits me from my charter?

A myriad of weather factors is carefully considered before we ask yachts to return to the base and this could happen at any time, should the base decide it to be necessary. We do take precautionary measures so we can insure the safety of all our guests. During severe weather, guests are not allowed to remain on board, however, when on charter, the crew carefully monitors the weather and stays in contact with the base always. In the unlikely event that extreme weather conditions occur, Festiva Sailing Vacations will make the decision to recall yachts to the base or delay charter starts. Guests who have purchased a Trip Insurance Protection plan through CSA Travel Protection are eligible for trip delay reimbursement based on the pla

7 Night, All-Inclusive Packages

Rates for our 6 Passenger, Lagoon 440

Winter/Spring:  $4,895/couple
Season: January - May 2019/2020  &  November - December 2019/2020

Summer: $4,595/couple

Season: June - July 2019/2020

Value: $4,295/couple

Season: August - Mid November 2019/2020

*Dates indicate check-in date for 7-night package

Rates are all-inclusive, and include:

Other Important Information

Our Guaranteed Departure Policy:

When you purchase any of our stateroom packages for two, your catamaran will depart on the confirmed charter date for the confirmed stateroom price even if no other staterooms are reserved on that vessel.

Book By the Stateroom Yacht Assignment:

Every yacht within the Festiva Sailing Vacations' fleet is identical in terms of cabin layout and design. To create the best make-up when purchasing stateroom packages, we do not assign guests to a specific yacht until we receive each guest's preference form. This allows us to mix those couples with similar interests when possible.

Book By the Stateroom Provisioning Details:

Menu offered is a delicious variety of cuisine planned in advanced to accommodate our guests throughout the course of the week. Some snacks and fruit will be provided in addition to the set meals. Chefs cater to any food allergies or special dietary requirements and guests are asked to indicate this information on their preference forms.

Book By the Stateroom Occupancy Details:

Occupancy aboard our catamarans in St. Maarten is limited to 6 guests. When chartering with children under the age of 16, you must reserve all guest cabins on the yacht. When party exceeds eight guests, two or more yachts will sail in tandem. Special flotilla discounts may be available for reservations of more than one yacht.

Payment Details:

A 50% deposit is required for Caribbean bookings. Balance of charter amount is due 60 days prior to departure. A 100% deposit is required for reservations made inside 90 days.

What's Not Included in Package Price:

Two dinners ashore on Caribbean charters. Local cruising permits and park fees (if any), gratuities for crew, special requested liquors.


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'll have a leisurely morning sail and depart through the Dutch Bridge on our way to Road Bay, on the British island of Anguilla. We have 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 and 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 then we are off to Prickly Pear Cays, a remote uninhabited rocky atoll with amazing bird life and an 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. Here you can also see the pelicans diving! This area 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, enjoy the beach, beach bars, gift shop, hiking, snorkeling, and kayaking. In short, Pinel Island offers something to everyone. We'll 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'll spend several hours in this magnificent moonscape surrounding. For those who would like to climb to the summit, take in some breaktaking views. For those that want to enjoy the water, snorkel and float around. After lunch we sail to bay of Colombier on Saint Bart’s. Here we spend the rest of the day exploring the bay by kayak, walking on the beach or taking the cliff-path to treat ourselves to stunning views. 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 (maybe even doing an island tour!) enjoy a cocktail at Jimmy Buffett’s “Cheeseburger In Paradise” Café. After lunch, we take a leisurely sail back to Porto Cupecoy Marina. Enjoy 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.