Sailing to Anguilla feels like hitting pause. This private day trip on the 42ft Freedom, a 2022 Lagoon 42 catamaran, turns the usual hop-on-the-water day into a full-on luxury cruise with your own captain and crew, plus an all-inclusive food and drink setup.

I love how quickly you settle in once you board, with a scented towel and a cool welcome, then mimosas and breakfast to start the day without rushing. I also like the way the crew handles the details, so you can focus on the water, the beaches, and the easy fun like paddle boards and snorkeling gear.

One consideration: it’s a full day on the water, about 9.5 hours, and the itinerary can shift with weather and sea conditions, so you’ll want to plan your day back in St. Maarten with a little breathing room.

Key Things That Make This Sail Worth Your Time

A brand-new 2022 Lagoon 42 catamaran (42ft) with a spacious teak deck

All-day bar service plus breakfast, happy-hour bites, and a full lunch

Snorkeling gear included, plus a floating lily pad mat and two paddle boards

Reef-safe sunscreen and towels provided, so you travel lighter

Your captain and crew include Andre and Diane, and they run a tight, friendly ship

You get a real Anguilla day, then a scenic return through Simpson Bay Bridge

Freedom on the Water: What You’re Really Booking

This is a private catamaran day sail from St. Maarten to Anguilla, run by Renegades with your own captain and crew. The boat is a 42ft Lagoon 42 catamaran called Freedom (brand-new in 2022), which matters because catamarans typically feel steady and roomy—exactly what you want for a long, relaxing day on the water.

You’re not crammed into a crowded tour boat. It’s your group only, so the vibe is calmer, and the crew can tailor the pace—slower morning, fun in the water when you want it, then an unhurried return.

Also, this trip is built around “included” from the start. You’re not spending the day adding up small extras like snacks, drinks, or basic water toys. That can be the difference between a fun day sail and one that feels like you got your money’s worth.

Leaving St. Maarten at 8:00am: The Easiest Start Possible

The sail starts at 8:00am from Renegades – Private Catamaran Charter – St. Maarten & Anguilla, 155 Union Rd, Cole Bay. The meeting point is close enough to public transportation, but you’ll still want to plan to get there early enough to park, walk, and settle before boarding.

Once you’re on board, the day flows like a guided experience, but without feeling scripted. The welcome includes a cool, scented towel and a small handmade chocolate moment—these tiny touches set a higher bar than the typical water taxi vibe.

What I like about an early start is you get more daylight for the Anguilla portion and you’re not rushing your meal plan. You’ll have time to enjoy breakfast and still have hours left to stretch out and actually do the fun stuff.

Teak Deck Comfort and a Crew That Sets the Tone

Stepping aboard Freedom is meant to feel like a switch flips: from travel mode to vacation mode. You’ll head to the lounge areas right away, settle into the rhythm, and get refreshments as the crew takes over the sailing details.

From the experience details, the crew is a big part of what people remember. Names that come up are Andre and Diane, and the tone is consistent: you’re treated like long-time friends rather than another number on a schedule. That matters most when conditions change or when you want to know what’s worth your attention at the beaches.

Also included:

• Reef-safe sunscreen and towels
• Restroom on board (huge for comfort on a long day)
• A full bar setup, plus water and juices throughout the day

If you’ve ever been stuck on a boat where you’re constantly waiting for something, this kind of service approach is the point.

Princess Port de Plaisance: Boarding, Safety, and a Quick Welcome Loop

The first stop is Princess Port de Plaisance on St. Maarten’s Dutch side, with time set aside for docking and getting you settled. There’s a brief tour and a safety briefing when you arrive.

Why this stop is worth noticing: it’s where your day gets organized. You’re not just tossed onto a boat and left to figure it out. You get a quick orientation, you know where things are, and you’re reminded how to enjoy the water time safely.

Timing-wise, it’s about 30 minutes in this port portion. That’s long enough for smooth boarding and setup, but short enough that you don’t feel like you’re waiting around before the fun begins.

The Anguilla Crossing: Mimosas, Breakfast, and Real Time on the Water

Once you’re headed toward Anguilla, the tone turns into “slow cruise.” This is when you settle in with mimosas and enjoy a laid-back breakfast. Expect the breakfast spread to include fresh fruit, artisanal cheese, and French pastries.

Then you get the kind of sightseeing you can’t get from shore: a long look at the coastline while the boat moves at a relaxed pace. If you like taking photos, the angle from a stable catamaran is usually easier on your arms and your patience.

This sailing segment is part of what you’re paying for. Yes, Anguilla is the star—but the crossing time is what makes the day feel like a true escape rather than a quick “arrive and leave” outing.

Once You’re in Anguilla: Beaches, Swimming, and Easy Exploration

The Anguilla portion is about 8 hours, which is generous for a day trip. You’ll have time to explore and take breaks between water activities.

Here’s the practical way to think about it: with a full day, you can do a mix of calm and active. You can pick one or two beach areas you’re curious about, spend time swimming, then return to the boat to cool down and refuel.

Keep in mind the trip is guided by sea conditions, so the exact feel of the water and timing of your beach hours can shift. But the basic promise is consistent—a long day on Anguilla, not a rushed stop.

Snorkeling Gear, Paddle Boards, and the Lilly Pad Mat

This is where the included items start to add up.

Freedom provides:

• Snorkeling equipment
• Floating lily pad mat
• Two paddle boards

You don’t have to hunt down rentals or bring your own gear. That saves both money and friction. It also makes it easier to try the activities even if you’re not an ultra-confident swimmer—because you can do the gentle version first, like floating on the mat or paddling around for short bursts.

One smart tip for these kinds of days: use your time in the water in chunks. Do a snorkel or paddle session, take a break to dry off and eat, then go again. With an all-day schedule, that rhythm is what keeps it fun instead of exhausting.

Food and Drinks: The All-Inclusive Part That Actually Feels Worth It

This is a standout category. The day is built around multiple eating moments, and the drink setup is more than just a token bar.

Breakfast and snacks

Breakfast includes fresh fruit, artisanal cheese, and French pastries. Then you’ll also have happy hour hors d’oeuvres, including a homemade beet and garlic hummus platter served with crudités, pita chips, and rice crackers.

Lunch

Lunch is a barbecue format: barbecued skewers, plus fresh salads. Dessert follows with homemade cookies and locally made ice cream.

Bar all day

The premium bar is open all day and includes:

• craft cocktails and mocktails made fresh
• mixed drinks
• beer, wine, prosecco
• soft drinks and juices
• infused water

Also note the minimum age for alcohol consumption is 18. If you’re traveling as a mixed-age group, this is worth flagging up front so everyone can relax.

I like trips where food doesn’t feel like an afterthought. Here, it’s part of the experience. You’re fed well enough that you don’t need to budget for extra meals, and you can actually enjoy beach time without running hungry.

Heading Back Through Simpson Bay Bridge: A Nice Little Bonus

On the return, you’ll head back through Simpson Bay Bridge, where you can wave at onlookers. It’s a small moment, but it adds character to the day—like a real local crossing, not just a straight shot back to dock.

Then you return to Princess Port de Plaisance and head back to the meeting point. The port time for this final leg is about 30 minutes.

That final portion matters more than people think. A smooth docking means you can end the day without chaos, grab your belongings, and head to dinner without feeling wrung out.

Price and Value: Is $698.75 Per Person Fair?

At $698.75 per person, this isn’t a bargain trip. It’s a premium day sail.

So here’s how I’d judge value based on what’s included:

• You’re paying for a private experience on a 42ft 2022 Lagoon 42 catamaran, not just shared sightseeing.
• Drinks aren’t limited to one hour. The bar is open all day, with craft cocktails and mocktails.
• Food coverage isn’t “snacks and a sandwich.” You get breakfast, happy-hour bites, and a barbecue lunch with dessert.
• You also get water toys and gear: paddle boards, snorkeling equipment, and a floating mat.
• Comfort items are included like reef-safe sunscreen, towels, and a restroom.

If you were to price these components separately—boat time, captain/crew, alcohol, meals, and rentals—it’s the all-inclusiveness that makes the total feel logical. If you’re the type who likes a simple plan and doesn’t want to track expenses all day, this price starts to look more like a package deal than a splurge.

One more thing: it’s often booked about 80 days in advance on average. That’s a hint that dates can fill, especially in good weather windows.

Who This Trip Fits Best (and Who Might Want Something Else)

This day sail is ideal if you want:

• Luxury comfort on a catamaran
• a private group setup
• all-day drinks and a real meal plan
• included water time like snorkeling and paddle boarding

It’s also a great option if you’re planning a special occasion or just want one day where everything feels handled.

You might choose differently if you prefer:

• a lighter, do-it-yourself beach day with no alcohol or no included meals
• a shorter outing with minimal time at sea

Because this is a full-day cruise, your enjoyment will track with how much you like being on the water.

Quick Practical Tips Before You Go

A few small things can make the day smoother:

• Bring swimwear and a cover-up you’re comfortable wearing in and out of the sun.
• Reef-safe sunscreen is provided, but you can still bring your own if you have a favorite brand.
• Plan your beach time as sessions: snorkel/paddle, then relax and eat, then go again.
• If alcohol isn’t for you, the mocktails and juices are part of the bar setup, so you’re not stuck with only water.

Also, since the itinerary may change based on weather and sea conditions, I’d treat it like a day plan guided by the ocean—not a rigid checklist.

Should You Book Freedom to Anguilla?

If you want a day that feels like a floating resort—private, calm, and thoughtfully stocked—then I’d book this. The combination of a spacious 42ft catamaran, the full-day food and bar program, and the included water activities is exactly what makes it easy to relax and actually enjoy Anguilla without logistics headaches.

I’d think twice only if you’re looking for a cheaper outing or you don’t want to be on the water for around 9.5 hours. Otherwise, Freedom is the kind of trip where you pay for comfort and ease, and you feel it from the first welcome towel to the last return through the bridge views.

FAQ

What time does the Luxury Catamaran private day sail depart?

The start time is 8:00am.

Where is the meeting point in St. Maarten?

You meet at Renegades – Private Catamaran Charter – St. Maarten & Anguilla, 155 Union Rd, Cole Bay, Sint Maarten.

Is this a private tour?

Yes. It’s private, and only your group participates.

What’s included for food and drinks?

Breakfast is included, along with happy hour hors d’oeuvres and a lunch with barbecue skewers and salads. Alcoholic beverages are included all day, plus craft cocktails and mocktails, beer, wine, prosecco, soft drinks, juices, and infused water.

Is snorkeling equipment included?

Yes. Snorkeling equipment is included, along with a floating lily pad mat and paddle boards (two).

Is hotel pickup or gratuity included in the price?

No. Hotel pick up and drop off are not included, and gratuity is also not included.

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