Luxury Catamaran Private Day Sail from St. Maarten to Anguilla

Anguilla is the star here, but the real treat is reaching it aboard Freedom, a private 42-foot Lagoon 42 catamaran. You sail from St. Maarten with your own captain and crew, then spend much of the day around Anguilla’s beaches and clear water.

I like the thoughtful service, from the cool scented towel and handmade chocolate at boarding to the open bar, fresh meals, towels, sunscreen, and water gear. I also like the relaxed pace: roughly eight hours in Anguilla gives you time to sail, swim, snorkel, eat, and simply stretch out on the teak deck. The main drawback is the price, $698.75 per person, plus gratuity, so this makes the most sense for a special occasion or a group that will use the private-boat setting fully.

Key points to know before booking

• Private Lagoon 42 catamaran: Only your group takes part, with a captain and crew caring for the boat and onboard service.
• Long Anguilla day: The outing lasts about nine and a half hours, including the sail from Port de Plaisance and the return through Simpson Bay Bridge.
• All-day food and drinks: Breakfast, lunch, snacks, desserts, cocktails, beer, wine, prosecco, soft drinks, and juices are included.
• Water time built in: Two paddle boards, a floating lily pad, snorkeling equipment, and crystal-clear swimming areas are part of the day.
• Comfortable start: Boarding begins at 8:00 a.m. at Port de Plaisance Yacht Club in Cole Bay, on the Dutch side of St. Maarten.
• Weather matters: The route can change with sea conditions, and poor weather may lead to a new date or a full refund.

Setting sail from Port de Plaisance at 8:00 a.m.

Your day begins at Renegades, at Port de Plaisance Yacht Club, 155 Union Road in Cole Bay. This is on the Dutch side of St. Maarten. You make your own way there because hotel pickup and drop-off are not included.

The first 30 minutes are for boarding, a short tour of the boat, and the safety briefing. That matters on a private charter because the crew can explain the boat directly to your group instead of rushing through a generic welcome for a large crowd.

Freedom is a 2022 Lagoon 42 sailing catamaran with a broad teak deck and several lounge areas. The boat is designed for comfort as much as movement, so you are not limited to one seat for the entire day. You can settle into a lounge, walk around the deck, or move closer to the water when it is time to swim.

The welcome sets a polished tone. You receive a cool scented towel and a handmade chocolate, then can begin the morning with a mimosa and a light breakfast. The food includes fresh fruit, artisanal cheese, and French pastries. That is a useful touch on a morning sail, since you are not expected to wait until lunch before eating.

Captain Andre and Diane are specifically associated with the high level of care on this trip. The crew handles the sailing, safety, food, drinks, and gear, leaving you free to enjoy the crossing. The service is personal, but you should still remember that gratuity is not included.

The crossing to Anguilla with breakfast and mimosas

The sail to Anguilla is not just transportation between two islands. It is one of the main parts of the day. You can watch the St. Maarten coastline recede, sip a mimosa, and take in the open sea while the crew manages the route.

The suggested plan allows for about eight hours in the Anguilla area. That is a generous amount of time compared with a short beach transfer or a quick island stop. You should have room in the schedule for several kinds of activity: swimming, snorkeling, paddle boarding, beach time, eating, and quiet time on deck.

The exact route is not fixed. The itinerary can change with weather and sea conditions, so do not book this expecting every stop or maneuver to happen in a precise order. That flexibility is sensible on a sailing boat, but it also means the experience depends on the day’s conditions.

The open bar operates throughout the day. It includes craft cocktails and mocktails prepared fresh, standard mixed drinks, beer, wine, prosecco, soft drinks, juices, and infused water. You must be at least 18 to drink alcohol. If you prefer not to drink, the mocktails, juices, soft drinks, and infused water keep the package useful.

Anguilla: beach time, clear water, and room to slow down

Anguilla is known for calm, beautiful beaches, and the sailing plan gives you time to enjoy the island from the water rather than treating it as a rushed photo stop. The exact beach or anchorage can vary, but the stated plan includes swimming, a look at the coastline, and time around award-winning beaches.

The strongest part of the Anguilla stop is choice. You can use the floating lily pad as a simple platform for lounging, take one of the two paddle boards out, or use the snorkeling equipment to inspect the water close to the boat. You can also stay dry and enjoy the views from the catamaran.

That range is important for a private group. One person can swim while another sits with a drink, and someone else can paddle or snorkel. You are not forced into the same activity at the same time. The boat’s restroom also means you do not need to plan the day around finding shore facilities.

The supplied equipment includes reef-safe sunscreen and towels. I would still pack the personal items you prefer, but having the main water gear and sun protection already onboard makes the day easier. You do not need to arrange a separate snorkeling rental or carry bulky equipment from St. Maarten.

The water can be the day’s main attraction, but the boat itself is part of the appeal. The teak deck, lounge areas, steady catamaran platform, and open bar create a relaxed setting for a long stop. If you want a busy sightseeing schedule with many shore visits, this may feel slow. If you want a day with few transitions, it is a strong fit.

A full lunch, snacks, and happy hour onboard

Food is more substantial than the usual packet of snacks on a boat trip. Breakfast comes early, followed by lunch with barbecued skewers, fresh salads, and other selections. Dessert includes 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. That gives you something savory between meals and works well with the drinks service.

The all-inclusive setup has real value because food and beverages can add up quickly during a full-day private charter. You do not need to bring lunch, stop to buy drinks, or search for a beach restaurant during the main part of the outing. You also avoid losing time to a shore meal if the goal is to stay on or near the water.

Still, keep the price in view. At $698.75 per person, the food and drinks alone do not justify the booking. The cost is tied to the private boat, crew, long duration, fuel, equipment, and personal service. This is a premium day on the water, not a basic ferry ride with a beach stop.

The return through Simpson Bay Bridge

After the Anguilla portion, the boat heads back to Port de Plaisance. The return route passes through the Simpson Bay Bridge, where you can wave to people watching from shore before docking at the yacht club.

The final 30 minutes are listed for the return and docking. That gives the day a clear finish at the same place where you began. Since there is no hotel transportation, plan your onward ride from Port de Plaisance after the boat returns.

A full day at sea can feel long if you are not comfortable with extended time on a boat. The private setting helps because you can move around and set your own pace, but this is still about nine and a half hours away from shore. I would choose it for people who genuinely like being on the water, not only for those who want to reach Anguilla quickly.

What the $698.75 price buys you

The price is high, but the inclusions are unusually broad. You receive:

• A private catamaran for your group
• Captain and crew
• Fuel and all fees and taxes
• Breakfast, lunch, snacks, and dessert
• Alcoholic and nonalcoholic drinks
• Towels and reef-safe sunscreen
• Snorkeling equipment
• Two paddle boards
• A floating lily pad
• An onboard restroom

You also receive the convenience of not having to coordinate separate transport, boat rental, food orders, drink purchases, and water equipment. For a group marking a birthday, anniversary, honeymoon, or family milestone, that can make the rate easier to accept.

Group discounts are available, which may improve the value for a larger private party. The exact discount is not specified, so check the price for your group before assuming the per-person total will fall.

Gratuity is not included. If Captain Andre and Diane provide the attentive, personal service this outing is built around, plan for a tip in addition to the advertised cost.

Who will get the most from this private sail

I would recommend this trip to a group that values privacy, food, drinks, and a flexible day more than a low price. It suits couples, families, and friends who want to spend a major vacation day together without sharing a boat with strangers.

It is also a good fit for mixed groups. Strong swimmers can use the paddle boards and snorkeling equipment, while anyone who prefers a quieter day can remain on deck with a drink or a plate of food. The private format means you do not need to follow another group’s activity level.

The trip is less suitable if your main goal is to explore Anguilla by road, visit many inland sights, or spend the day shopping. Most of the scheduled time is focused on sailing and the coast. It is also not the best choice for a strict budget.

Most travelers can participate, and service animals are allowed. The boat is near public transportation, but hotel pickup is not included. Confirmation arrives at booking, and mobile tickets are available.

Weather, cancellation, and practical planning

Good weather is required. If conditions force cancellation, you can choose another date or receive a full refund. You can also cancel for a full refund if you do so at least 24 hours before the local start time.

Cancellations or changes made less than 24 hours before departure are not accepted for a refund. That deadline matters because this is a private charter with a crew, boat, food, fuel, and a planned route.

Start at 8:00 a.m. and allow enough time to reach 155 Union Road in Cole Bay. Bring the usual personal items you want for a long day on the water, but the main towels, sunscreen, snorkeling gear, food, and drinks are supplied.

The route may change with sea conditions. Treat the published plan as a guide rather than a promise of an exact beach, order of activities, or sailing path. That is normal for a day built around wind and water, and it is worth accepting before you book.

Should you book Freedom to Anguilla?

Book it if you want a polished, private day where the boat, crew, food, and water activities are all part of one package. The strongest reasons are the long Anguilla stop, the all-day catering, the personal service from Captain Andre and Diane, and the freedom to choose between swimming, snorkeling, paddle boarding, and relaxing on deck.

Skip it if $698.75 per person feels uncomfortable, if you want a quick and inexpensive crossing, or if you would rather spend most of your time touring Anguilla on land. For the right group, this is less a simple excursion than a special occasion built around a private catamaran. The current rating is 5 out of 5 from 10 ratings, with every one recommending it, but the price and long time on the water still deserve an honest look before you commit.

FAQ

Where does the catamaran sail from?

The tour starts at Renegades, Port de Plaisance Yacht Club, 155 Union Road, 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 day last?

The experience lasts about nine hours and 30 minutes, including the departure and return portions.

Is the boat private?

Yes. This is a private activity, and only your group participates.

Is food included?

Yes. 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. Snacks include a beet and garlic hummus platter with vegetables, pita chips, and rice crackers.

Are drinks included?

Yes. The 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 are included.

What happens if the weather is poor?

The itinerary may change because of weather and sea conditions. If the experience is canceled due to poor weather, you can receive a full refund or choose a different date.