Luxury Catamaran Private Day Sail from St. Maarten to Anguilla

Anguilla is best reached by water. This private sail from St. Maarten pairs a 42-foot Lagoon 42 catamaran with a full day of swimming, beach time, food, and open-bar service. I like the quiet privacy of having only your own group aboard, and I like that breakfast, lunch, snacks, snorkeling gear, paddle boards, and towels are already covered.

The main drawback is the price: $698.75 per person is a serious spend, even with the long nine-and-a-half-hour day. You also need to reach the marina yourself, and the route can change with weather and sea conditions. Captain Andre and Diane receive especially warm praise for their personal service, which helps explain why the experience has earned a 5.0 rating and a 100 percent recommendation rate from 10 published ratings.

Key points to know before booking

• A private 42-foot Lagoon 42: Only your group participates, with your own captain and crew aboard the 2022 sailing catamaran Freedom.
• A full Anguilla day: The schedule allows about eight hours around Anguilla for sailing, swimming, beach time, and water activities.
• Food from morning to afternoon: Fresh fruit, French pastries, artisanal cheese, barbecue skewers, salads, cookies, ice cream, and hummus with pita are included.
• A full drinks service: Mimosas, prosecco, beer, wine, cocktails, mocktails, soft drinks, juices, and infused water are available.
• Water equipment included: You get snorkeling equipment, two paddle boards, and a floating lily pad mat.
• A marina start in Cole Bay: Meet at 8:00 a.m. at Renegades, 155 Union Road, at Port de Plaisance Yacht Club.

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

Your day begins at Port de Plaisance Yacht Club in Cole Bay, on the Dutch side of St. Maarten. The listed meeting point is Renegades, 155 Union Road, and the tour does not include hotel pickup or drop-off, so you need to arrange your own way to the marina.

The first half hour is used for boarding, a short boat orientation, and a safety briefing. That is a sensible start for a day that includes open water, snorkeling, paddle boards, and a crossing to another island. You will also have time to settle in before the catamaran leaves the dock.

The boat is Freedom, a 2022 Lagoon 42 with a teak deck and several lounge areas. The welcome is more polished than a basic boat transfer. You receive a cool scented towel and a handmade chocolate, then can begin the morning with a mimosa and breakfast.

That small opening ritual sets the tone. This is not a crowded ferry ride where the crossing is simply a necessary chore. The sailing itself is part of the experience, and the private setup gives the crew room to adjust the pace to your group.

Why the private catamaran matters

The biggest difference here is privacy. You are not sharing the boat with a large public group, and only your own party takes part. That matters if you want a quiet day, need flexible space for children, or simply prefer not to spend a premium beach day surrounded by strangers.

A private charter also lets the captain and crew focus on your group. The supplied feedback gives special credit to Captain Andre and Diane, with one couple saying they were treated like long-time friends. Another review described the day as perfect and singled out Andre and Diane for the best service possible.

You should still keep expectations realistic. A private boat does not mean you control every detail of the route. The suggested plan can change because of weather and sea conditions, and the crew must make the final call on safe sailing and anchoring points.

The 42-foot size is a useful middle ground. You get more room than on a small day boat, but Freedom is still a sailing catamaran rather than a giant yacht. The teak deck, lounge areas, onboard restroom, and open arrangement make a nine-and-a-half-hour day easier on the body.

The morning sail to Anguilla

Once the boat leaves St. Maarten, the crossing becomes one of the main pleasures of the day. You can sit with a mimosa, eat the fresh fruit, cheese, and French pastries, and watch the coast recede while the captain handles the sailing.

The package includes fuel, so there is no extra fuel charge to worry about. It also includes reef-safe sunscreen and towels, practical touches that save you from packing quite so much. You will still want to bring a swimsuit, sun protection, and whatever personal items you need for a full day outdoors.

The bar is open all day. It includes craft cocktails and mocktails prepared fresh, along with standard mixed drinks, beer, wine, prosecco, soft drinks, juices, and infused water. That range is useful because not everyone wants alcohol during a long day in the sun. The minimum age for alcohol consumption is 18.

The crossing is not presented as a nonstop rush to Anguilla. The mood is slow and comfortable, with breakfast served while you sail. If you enjoy the movement of a boat and want the journey to feel like part of the holiday, this works well. If your main goal is simply to reach the beach as fast as possible, a direct transfer would be a cheaper and quicker choice.

Eight hours around Anguilla

The Anguilla portion takes about eight hours, which gives this outing more substance than a quick island stop. The day is built around the coast, the water, and the beaches rather than a long list of inland attractions.

You can expect time to swim in clear water, explore award-winning beaches, and use the equipment carried aboard Freedom. Two paddle boards, snorkeling gear, and a floating lily pad mat are included. The exact order of activities can change with sea conditions, so think of the schedule as a flexible day on the water rather than a fixed sequence of stops.

The floating mat is a particularly easy option if you want to enjoy the water without constantly swimming. Paddle boards suit anyone who wants a little more activity, while snorkeling equipment gives you the chance to look below the surface. No specific reef site or snorkeling location is guaranteed in the supplied details, so the crew will determine the safest and most suitable place to stop.

Anguilla’s appeal here is its calm pace. The island is known for beautiful beaches and clear water, and this trip gives you time to appreciate both without squeezing everything into a short shore visit. You can swim, sit on the boat, move between activities, or simply enjoy lunch with a view.

The trade-off is that the day is strongly water-focused. You should not book this expecting a detailed history tour, a shopping program, or a guided walk through Anguilla. Its strength is the combination of sailing, beach time, food, and personal service.

Meals that make the price easier to judge

Food is one of the strongest parts of the package. Breakfast begins with fresh fruit, artisanal cheese, and French pastries, a better start than the usual packaged snack on a boat trip.

Later, lunch includes barbecued skewers and a selection of fresh salads. Homemade cookies and locally made ice cream follow. There is also a happy-hour spread of homemade beet and garlic hummus with crudités, pita chips, and rice crackers.

That is a lot of food for a day on the water, and it changes how you should judge the cost. You are not paying only for transport from St. Maarten to Anguilla. You are paying for a private boat, captain and crew, fuel, meals, drinks, water equipment, towels, sunscreen, and a long day of service.

Still, the price will not suit every budget. At $698.75 per person, this is best considered a special occasion charter or a splurge shared by a group. Group discounts are available, but the exact discount is not provided, so check the current rate before committing.

I would compare it with the cost of booking several separate services: a crossing, a beach transfer, meals, drinks, snorkeling equipment, paddle boards, and a private boat. The combined convenience is meaningful, but you should choose this because you value comfort and privacy, not because it is the cheapest way to see Anguilla.

The return through Simpson Bay Bridge

After the Anguilla portion, Freedom sails back toward St. Maarten and returns to Port de Plaisance Yacht Club. The final half hour includes the passage through Simpson Bay Bridge, where you can wave to people watching from shore before docking.

That return gives the day a pleasant finish. You are not dropped at a different beach or left to arrange your way back. The activity ends at the same marina where it began, which makes the transport plan simple once you have arrived at the start point.

The full duration is about nine hours and 30 minutes, with an 8:00 a.m. start. Plan your day around a full morning-to-afternoon commitment. It is not a casual half-day outing, and the long duration is important when deciding if children or anyone prone to seasickness will be comfortable.

Service, comfort, and the small practical details

The strongest praise is directed at the crew. Captain Andre and Diane are named specifically in the feedback, and the comments describe a warm, attentive style rather than a distant charter operation. One published comment says the day was so good the writer nearly cried when it ended. Another says there were not enough stars to give the experience.

That enthusiasm should be balanced against the small sample size of 10 ratings. The 5.0 score and 100 percent recommendation are excellent signs, but they cannot promise that every group will have the same weather, sea conditions, or personal chemistry with the crew.

The boat has an onboard restroom, which is important on a long sailing day. Service animals are allowed, the meeting area is near public transportation, and most people can participate. The supplied information does not give detailed accessibility specifications, so you should contact the operator directly if you need particular boarding or mobility arrangements.

Your booking confirmation is provided at the time of reservation. Free cancellation is available if you cancel at least 24 hours before the local start time. Changes or cancellations made inside that window are not accepted for a refund, unless the operator cancels because of poor weather. In that case, you are offered another date or a full refund.

Who should book Freedom to Anguilla?

I would choose this for a couple celebrating something special, a family or friend group that values private space, or anyone who wants Anguilla as a full-day sailing destination rather than a quick stop.

It suits you best if you enjoy:

• A relaxed day with food and drinks already arranged
• Swimming, snorkeling, paddle boarding, and beach time
• Personal attention from a small crew
• A private boat instead of a shared excursion
• A long day where the crossing is part of the pleasure

I would look elsewhere if you want the lowest-cost way to reach Anguilla, dislike spending many hours on a boat, or prefer a structured sightseeing tour on land. The weather policy also matters. Since the route can change with sea conditions, flexibility is part of the deal.

Should you book this St. Maarten to Anguilla sail?

Book it if you want a polished, private day where you can stop thinking about logistics. The captain and crew handle the sailing, the kitchen provides several rounds of food, the bar stays open, and the water gear is ready when you want it.

The cost is high, but the package covers far more than a simple boat ride. The clearest reasons to pay the premium are the private setting, the nearly full-day schedule, and the level of service associated with Captain Andre and Diane.

For a special day on the water, Freedom offers a strong blend of comfort, activity, and unhurried time around Anguilla. Just arrive knowing that you must arrange your own transport to Port de Plaisance, accept possible weather changes, and decide whether the private charter is worth the substantial per-person price.

FAQ

Where does the catamaran tour start?

The tour starts at Renegades, 155 Union Road, at Port de Plaisance Yacht Club in Cole Bay, St. Maarten.

What time does the experience begin?

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

How long does the experience last?

The total duration is approximately nine hours and 30 minutes.

Is the tour private?

Yes. Only your group participates, with a private captain and crew.

Is hotel pickup included?

No. Hotel pickup and drop-off are not included, so you need to arrange your own transportation to and from the marina.

What food is included?

Breakfast includes fresh fruit, artisanal cheese, and French pastries. Lunch includes barbecued skewers and fresh salads, followed by homemade cookies and locally made ice cream. Happy-hour snacks include beet and garlic hummus, crudités, pita chips, and rice crackers.

What drinks are included?

The bar includes craft cocktails, mocktails, standard mixed drinks, beer, wine, prosecco, soft drinks, juices, and infused water. Alcohol is available to people aged 18 and older.

Is snorkeling equipment provided?

Yes. Snorkeling equipment, two paddle boards, and a floating lily pad mat are included.

What happens if poor weather cancels the trip?

You will be offered a different date or a full refund if the experience is canceled because of poor weather.