Luxury Catamaran Private Day Sail from St. Maarten to Anguilla

Anguilla is the main event here: a full day of clear water, beautiful beaches, and easygoing sailing aboard Freedom, a 2022 Lagoon 42 catamaran. Captain Andre and Diane handle the boat and service while you settle into the wide teak deck with a mimosa, fresh breakfast, and no strangers joining your group.

I like the generous food and drink program, especially the French pastries in the morning, barbecue skewers at lunch, homemade cookies, and locally made ice cream. I also like the practical water gear: two paddle boards, a floating lily pad, snorkeling equipment, towels, and reef-safe sunscreen. The main consideration is cost: at $698.75 per person, this is a polished private splurge, not a budget day at sea.

Key points to know before you book

• Private sailing from St. Maarten: Only your group participates, with a captain and crew focused on your day.
• A full Anguilla day: The schedule allows about eight hours around the island, not a quick photo stop.
• Food is part of the experience: Breakfast, barbecue lunch, snacks, desserts, and an open premium bar are included.
• Freedom is a 2022 Lagoon 42: The 42-foot catamaran offers a broad teak deck, lounge areas, a restroom, and stable twin-hull comfort.
• Water activities are ready to go: You can use snorkeling gear, two paddle boards, and a floating lily pad without arranging rentals.
• Weather controls the plan: Sea conditions may change the suggested route, and poor weather can lead to a new date or a refund.

Why this private sail feels different from a standard boat trip

The strongest feature is the private format. You are not buying a seat on a large excursion boat with a fixed crowd. Your group has the catamaran, captain, and crew for the day, which gives the outing a more personal feel and makes the long duration easier to enjoy.

That matters on a nine-and-a-half-hour cruise. A short sightseeing ride can survive a crowded deck and limited food service. A full day needs room to stretch out, a place to cool off, a restroom, and a crew that keeps the pace comfortable. Freedom is designed around those needs, with lounge areas, a broad teak deck, and service from Captain Andre and Diane.

The welcome sets the tone. At Port de Plaisance Yacht Club in Cole Bay, you receive a brief tour and safety briefing before setting off. You are greeted with a cool scented towel and a handmade chocolate, then invited to settle in with a sparkling mimosa and a light breakfast.

That polished opening will appeal to people marking a birthday, anniversary, honeymoon, or simply a rare day when they want the boat to do the work. It may feel more formal than necessary if you prefer a simple, bring-your-own-lunch sailing trip. This is meant to be an all-day treat.

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

The meeting point is Renegades at 155 Union Road in Cole Bay, on the Dutch side of St. Maarten. The activity begins at 8:00 a.m. and ends back at the same meeting point, so you should plan your own way there and back. Hotel pickup and drop-off are not included.

Starting early is useful. You have time for a calm morning sail, breakfast on board, and a long stretch around Anguilla before the return journey. Since the day runs until roughly 5:30 p.m., this is best treated as your main activity for the day rather than something you squeeze between other plans.

The crew begins with a safety briefing and a short orientation to the catamaran. That is simple but important. You will know where the facilities are, how the boat works, and what to expect before the sails fill.

The route may change with weather and sea conditions. That is normal for a sailing trip, and you should see it as a practical safety measure rather than a flaw. The exact order of swimming, beach time, snorkeling, and meals can shift.

The morning sail to Anguilla

Once Freedom leaves St. Maarten, the morning is built for slow enjoyment. You can sit in one of the lounge areas, watch the coastline, and work through the breakfast spread rather than rushing toward the first stop.

Breakfast includes fresh fruit, artisanal cheese, and French pastries. The bar opens early with mimosas, and it remains available throughout the day with prosecco, wine, beer, mixed drinks, craft cocktails, mocktails, soft drinks, juices, and infused water.

The drink selection is unusually broad for a day cruise. You can keep things light with juice or infused water, or make the morning feel more celebratory with prosecco or a fresh cocktail. Since the boat day is long, the nonalcoholic choices are just as useful as the bar service.

The catamaran itself is central to the experience. Freedom is a 42-foot Lagoon 42 launched in 2022, with a custom setup aimed at comfort and sustainable cruising. A catamaran gives you more open deck space than many smaller monohull sailboats, and that extra room helps when your group wants different things at once.

One person can read in a lounge area while another watches the coast from the deck. Others can prepare for snorkeling or sit near the bar. You will still be on a boat, so movement and sun exposure are part of the day, but the layout gives you options.

Eight hours around Anguilla

The Anguilla portion takes up about eight hours, which is the reason to choose this trip over a brief island transfer or short coastal cruise. You have time to enjoy the water at a comfortable pace and to visit award-winning beaches without treating every stop like a timed assignment.

Anguilla is known for its calm, clear water and broad beaches. The exact route can change, but the plan includes cruising along the coastline, swimming, snorkeling, and exploring the island’s beaches. This combination gives the day variety: sailing between spots, relaxing on board, and getting into the water.

The included snorkeling equipment removes one small nuisance. You do not need to arrange a separate rental before boarding, and the crew can make the gear available when conditions suit. The same applies to the two paddle boards and floating lily pad. You can choose active water time or simply float and enjoy the view.

The lily pad is particularly useful for a private group with mixed energy levels. One person may want to paddle, another may want to snorkel, and someone else may prefer to lie in the sun. The boat carries enough water equipment to keep the day from becoming only a seated cruise.

Still, do not book this expecting a rigid list of guaranteed beach stops. The suggested route may change because of wind, waves, or other sea conditions. The appeal is the day on the water, with Anguilla as its setting, rather than a promise that every planned point will happen in a fixed order.

Lunch, snacks, and the premium bar

Lunch is a proper part of the day, not an afterthought. The crew serves barbecued skewers with fresh salads and other accompaniments, followed by homemade cookies and locally made ice cream.

That menu works well after swimming and paddleboarding. You get something filling without a formal restaurant stop, and the meal keeps the boat day moving. The fresh salads also give you a lighter option beside the grilled food.

A snack service adds another layer. The morning includes fruit, cheese, and pastries. Later, happy-hour hors d’oeuvres include homemade beet and garlic hummus with crudités, pita chips, and rice crackers.

I like this setup because it spaces food across the day. You are not forced to wait for one large meal, and you can eat according to your activity level. If you spend a while in the water, the later hummus platter and drinks will be welcome.

The bar is included in the price, with craft cocktails and mocktails shaken fresh, standard mixed drinks, beer, wine, prosecco, soft drinks, and juices. Alcohol consumption requires a minimum age of 18. If some people in your group do not drink, the mocktails, juices, soft drinks, and infused water keep the package useful for them too.

The only practical warning is to pace yourself. A nine-hour boat day with sun, swimming, and alcohol can catch up with you quickly. Use the water, eat regularly, and remember that the crew is there to make the day comfortable, not to push you into constant activity.

What the return through Simpson Bay adds

After the Anguilla portion, Freedom sails back toward St. Maarten. The final approach takes you through the Simpson Bay Bridge before docking again at Port de Plaisance Yacht Club.

The bridge crossing gives the return a clear ending. You can wave to people watching as the catamaran passes through, then step off at the same place where the morning began. It is a small detail, but it makes the day feel like a complete loop rather than simply a boat ride that stops without ceremony.

The return also gives you time to wind down. After the beach and water activities, you can use the lounge areas, enjoy one more drink, and watch St. Maarten come back into view. The exact timing depends on conditions, so do not plan a tight evening reservation immediately afterward.

Is $698.75 per person a fair price?

The price is high. At $698.75 per person, this belongs in the luxury category, and you should judge it as a private charter package rather than compare it with a basic group boat ticket.

The value comes from what is bundled into the day. You receive the catamaran, captain and crew, fuel, all listed fees and taxes, breakfast, lunch, snacks, dessert, a premium bar, snorkeling equipment, two paddle boards, a floating lily pad, towels, reef-safe sunscreen, and use of the onboard restroom.

Food and drinks alone do not make the price a bargain. The real question is how much you value privacy and service. If your group wants a special day with no strangers, a dedicated crew, a long stay around Anguilla, and no need to organize meals or water rentals, the package can make sense.

If you mainly want transportation to Anguilla, this is too much. A private luxury catamaran is the wrong tool for a low-cost beach visit. You are paying for the boat, time, staff attention, comfort, and the ease of having the whole day arranged around your group.

Group discounts are available, so larger parties should check the final rate before deciding. Since this is a private activity, the economics may improve when the cost is shared across your own group, though the listed rate is still given per person.

Who will enjoy Freedom most?

I would recommend this for couples, families, and groups of friends who want a special occasion day and care about comfort. It also suits people who like being on the water but do not want to plan every detail themselves.

The private setup is especially useful for a group with different preferences. You can combine swimming, snorkeling, paddleboarding, beach time, food, and quiet stretches on deck without having to follow a large group’s mood.

It is also a good match for people who value service. Captain Andre and Diane are part of the experience, and the emphasis is on being looked after from the first towel and chocolate through the final return to the marina. The warm, personal approach is one of the strongest reasons to choose this trip.

I would hesitate if you dislike full-day activities, get uncomfortable in the sun, or want a tightly guaranteed schedule. Weather can change the route, and nine and a half hours is a long commitment. You should also be comfortable paying for a luxury experience even if you do not use every included drink or water activity.

Service animals are allowed, and the activity is near public transportation. Most people can participate, but specific personal needs should be checked before booking. Alcohol is limited to people age 18 and older.

Booking, weather, and cancellation details

Confirmation is provided when you book, and mobile tickets make arrival straightforward. The meeting point is in Cole Bay, with no hotel transportation included, so allow time to reach Port de Plaisance for the 8:00 a.m. start.

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

Good weather is required. If poor conditions cause the operator to cancel, you can choose another date or receive a full refund. Since sea conditions may also change the route during the day, keep your plans flexible.

Should you book this Anguilla catamaran?

Book it if you want Anguilla wrapped inside a polished private day at sea, with Captain Andre and Diane, strong food service, a full bar, and water equipment ready when you are. The long Anguilla stop, broad Lagoon 42, and genuinely personal format make this much more than a simple transfer.

Skip it if your priority is low cost, a short outing, or a fixed schedule. At $698.75 per person, you need to use and value the privacy, food, service, and time on the water.

For a celebration or a group that wants one easy, memorable day, I think the price can be justified. Just arrive ready for an early start, protect yourself from the sun, and let the weather guide the pace.

FAQ

Where does the catamaran sail from?

The tour starts and ends at Renegades, Private Catamaran Charter, at 155 Union Road in Cole Bay, Sint Maarten. The marina is at Port de Plaisance Yacht Club on the Dutch side of St. Maarten.

What time does the experience start?

The start time is 8:00 a.m. The full activity lasts about nine hours and 30 minutes.

Is this a private tour?

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

What food is included?

Breakfast includes fresh fruit, artisanal cheese, and French pastries. Lunch includes barbecued skewers, fresh salads, and other items, followed by homemade cookies and locally made ice cream. The day also includes beet and garlic hummus with crudités, pita chips, and rice crackers.

Are drinks included?

Yes. The premium bar includes craft cocktails, mocktails, standard mixed drinks, beer, wine, prosecco, soft drinks, juices, and infused water. The minimum age for alcohol consumption is 18.

Is snorkeling equipment provided?

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

What happens if the weather is poor?

The experience requires good weather. If it is canceled because of poor weather, you can choose a different date or receive a full refund. The suggested route may also change because of weather and sea conditions.