Luxury Catamaran Private Day Sail from St. Maarten to Anguilla

The main draw here is simple: you get a full day aboard Freedom, a private 42-foot Lagoon 42 sailing catamaran, with Anguilla as your swimming and beach stop. Captain Andre and Diane handle the sailing and service while you move from breakfast to mimosas, clear water, barbecue lunch, and an open bar without juggling transport or restaurant bookings.

I like the private setting, since only your group takes part. I also like the food and drink program, which goes well beyond a bag of chips: French pastries and fruit in the morning, fresh salads and barbecue skewers at lunch, homemade cookies, local ice cream, and cocktails made throughout the day.

The main caution is the price, $698.75 per person. That is a serious spend, even with the food, drinks, crew, equipment, fuel, and private boat included. The day also depends on good weather, and the suggested route can change with wind and sea conditions.

Key points to know before you book

• Freedom is a 2022 Lagoon 42 catamaran: You get a modern boat with broad teak deck space, lounge areas, a restroom, and room to spread out.
• The private format matters: Only your own group participates, with a captain and crew focused on your party.
• Anguilla gets most of the day: The crossing and return take about an hour total, leaving roughly eight hours for sailing, swimming, beaches, and onboard meals.
• Food is a real part of the package: Breakfast, barbecue lunch, snacks, hors d’oeuvres, cookies, and local ice cream are included.
• The bar stays open: Prosecco, beer, wine, standard mixed drinks, craft cocktails, mocktails, soft drinks, juices, and infused water are available.
• Weather can change the plan: Poor conditions may lead to a different date or a full refund, while the route may shift during the day.

Starting at Port de Plaisance at 8:00 a.m.

Your morning begins at Renegades, 155 Union Road in Cole Bay, at the Port de Plaisance Yacht Club on the Dutch side of St. Maarten. You need to arrange your own way to the meeting point because hotel pickup and drop-off are not included.

The opening half hour is useful rather than rushed. You board, receive a short tour of the catamaran, and listen to the safety briefing before the boat gets underway. The crew welcomes you with a cool scented towel and a handmade chocolate, small touches that set the tone for a day built around comfort.

You can settle into one of the lounge areas or find space on the teak deck. The catamaran is fitted for relaxed cruising, not just transport, so the boat itself is a major part of what you are paying for.

Breakfast includes fresh fruit, artisanal cheese, and French pastries. A mimosa is available as you begin the sail, though the minimum drinking age for alcohol on this experience is 18.

Sailing from St. Maarten toward Anguilla

The trip to Anguilla is meant to feel unhurried. You can watch the coastline, sip a drink, and let the crew manage the sailing while you get comfortable on board.

That pace is one of the strongest reasons to choose this trip over a simple point-to-point transfer. You are not only getting to Anguilla. You are spending much of the day on a purpose-built sailing boat, with food, drinks, shade or sun, and room to move around.

The catamaran carries two paddleboards, snorkeling equipment, and a floating lily pad mat. Those items give you several ways to use the water once you reach calmer swimming areas. Reef-safe sunscreen and towels are included, which means fewer things to pack.

The schedule is not rigid. Weather and sea conditions can alter the suggested itinerary, so you should treat the route as a plan rather than a guarantee. That flexibility is sensible on a sailing day, but it also means you should not book this expecting every stop or timing to be fixed.

Eight hours around Anguilla

Anguilla is the main event, and the boat allows about eight hours in the area. The day can include a quiet sail along the coast, a swim in clear water, time near award-winning beaches, and use of the onboard water equipment.

The supplied details do not promise a specific beach, snorkeling site, or lunch anchorage. That is worth noting. The crew can adjust the day to suit conditions, but you should ask for the planned route when you arrive if a particular part of Anguilla matters most to you.

I like the amount of time set aside for the island. A shorter excursion could leave you feeling rushed between sailing, swimming, and eating. Here, the long middle portion gives the crew room to shape the day around the sea and your group’s preferred pace.

The private format also helps. You are not trying to match the timetable of a large boat filled with strangers. You can spend more time in the water, stay on deck with a drink, or simply enjoy the ride without needing to follow a crowded group from one activity to the next.

Breakfast, barbecue lunch, and an open bar

Food is one of the clearest strengths of this outing. The morning spread includes fruit, artisanal cheese, and French pastries. Later, you get barbecue skewers, fresh salads, and other lunch items, followed by homemade cookies and locally made ice cream.

There is also a beet and garlic hummus platter with crudités, pita chips, and rice crackers for happy hour. This is useful because a full day on the water can make you hungry between meals, especially if you are swimming and paddleboarding.

The premium bar remains open all day. It includes craft cocktails and mocktails prepared fresh, standard mixed drinks, beer, wine, prosecco, soft drinks, juices, and infused water.

This is where the cost starts to make more sense for some people. You are not paying only for a boat seat and a ride to Anguilla. You are also covering a private captain and crew, fuel, meals, drinks, towels, sunscreen, water gear, and onboard facilities.

Still, the value depends on how your group uses the package. If several people do not drink alcohol, eat lightly, or prefer a basic beach day, the price may feel high. If you want a polished private day with food and drinks already handled, the inclusions are substantial.

Captain Andre and Diane set the tone

Captain Andre and Diane are named as the key crew members, and their service is a major part of the experience. The strongest praise centers on how carefully they look after the people on board, from the welcome at the marina to the final return.

That kind of attention matters on a private charter. A good crew does more than steer the boat. They explain the setup, keep food and drinks moving, help you use the water equipment, and adjust the rhythm of the day.

The tone appears warm and personal rather than formal. The crew has been praised for treating people like longtime friends and for making the whole day feel carefully looked after. That is especially valuable if you are celebrating a birthday, anniversary, honeymoon, or simply want one special day during a St. Maarten stay.

You should also keep expectations grounded. This is a private sailing charter, not a guaranteed luxury resort service with a fixed resort-style schedule. Wind, waves, and conditions still shape the day, and the boat is an active marine setting rather than a land-based dining room.

Returning through Simpson Bay Bridge

After the Anguilla portion, the catamaran returns to St. Maarten and heads back through the Simpson Bay Bridge before docking at Port de Plaisance. The return portion takes about 30 minutes within the stated itinerary.

Passing through the bridge gives the trip a neat closing scene. You can wave to people watching from shore before the boat reaches the marina.

The full outing lasts about nine and a half hours, with an 8:00 a.m. start. That makes it a full-day commitment. You should avoid booking anything that requires you to be back at a hotel or airport soon after the stated end, since sailing times can shift with conditions.

What the $698.75 price really buys

At $698.75 per person, this is among the more expensive ways to visit Anguilla from St. Maarten. The right question is not simply if the price is high. It is whether your group will use the privacy, service, meals, drinks, and equipment enough to justify it.

The price includes:

• A private captain and crew
• Fuel and all listed fees and taxes
• Breakfast and snacks
• Barbecue lunch with salads
• Homemade cookies and locally made ice cream
• An open bar with alcoholic and nonalcoholic drinks
• Towels and reef-safe sunscreen
• Snorkeling equipment
• Two paddleboards
• A floating lily pad mat
• An onboard restroom

Group discounts are available, which may improve the cost for a larger private party. You should check the actual group rate before assuming the per-person price will drop, since the supplied details do not specify the discount amount.

The value is strongest for people who want one carefully organized splurge day. You can avoid paying separately for meals, beach gear, drinks, and a private boat. The value is weaker if your main goal is simply to reach Anguilla and spend the day ashore.

Who should book this private sail

I would look closely at this trip if you value comfort, personal service, and time on the water more than a low price. It suits couples, families, and groups of friends who want the boat to themselves and enjoy having the day’s details handled by a crew.

It is also a good match for people who want more than a sightseeing cruise. You can swim, snorkel, use a paddleboard, relax on the lily pad, eat several times, and spend long stretches simply sailing.

The experience may be less suitable for anyone who dislikes a long day at sea or wants a tightly fixed schedule. It is also not the best fit if you want hotel transportation included, since you must reach Port de Plaisance on your own.

Most people can participate, and service animals are allowed. The meeting point is near public transportation, but no specific transfer service is included.

Booking, weather, and cancellation details

You receive confirmation when you book, and a mobile ticket is available. The activity is commonly reserved about 80 days ahead, so booking early makes sense if your dates are limited.

You can cancel for a full refund up to 24 hours before the start time. Changes or cancellations made less than 24 hours before departure are not accepted for a refund.

Good weather is required. If poor conditions force the operator to cancel, you can choose another date or receive a full refund. During a running trip, the suggested itinerary may change because of wind and sea conditions.

That policy is fair for a sailing experience, but it is another reason to keep some flexibility in your St. Maarten plans.

Should you book the Freedom catamaran?

Book it if you want a polished, private day where the boat, meals, drinks, swimming gear, and crew service all come as one package. The strongest reasons are the spacious 2022 Lagoon 42, the long Anguilla stop, the generous food program, and the personal care from Captain Andre and Diane.

Skip it if $698.75 per person feels uncomfortable or if you mainly want beach time at the lowest possible cost. For the right group, this is a memorable all-day splurge. For everyone else, a simpler Anguilla visit may leave more money for the rest of your trip.

FAQ

Where does the catamaran depart from?

It departs from Renegades at Port de Plaisance Yacht Club, 155 Union Road in Cole Bay, on the Dutch side of St. Maarten.

What time does the experience start?

The scheduled start time is 8:00 a.m.

How long does the full experience last?

The experience lasts approximately nine hours and 30 minutes.

Is this a private activity?

Yes. Only your group participates in the activity.

Is hotel pickup included?

No. Hotel pickup and drop-off are not included, so you must make your own way to the meeting point.

What food is included?

Breakfast includes fresh fruit, artisanal cheese, and French pastries. Lunch includes barbecue skewers, fresh salads, and more, followed by homemade cookies and locally made ice cream. Snacks include a beet and garlic hummus platter with crudités, pita chips, and rice crackers.

What drinks are included?

The open bar includes craft cocktails, fresh mocktails, standard mixed drinks, beer, wine, prosecco, soft drinks, juices, and infused water.

Is snorkeling equipment provided?

Yes. Snorkeling equipment is included, along with two paddleboards and a floating lily pad mat.

Can children participate?

Most people can participate, but the supplied details do not state a specific minimum age for the activity. The minimum age for drinking alcohol is 18.

What happens if the weather is poor?

The experience requires good weather. If it is canceled because of poor conditions, you will be offered another date or a full refund. The route may also change during the day because of weather and sea conditions.