Salt air and sea glass.

This private 40-foot sailboat charter turns St John into a calmer kind of vacation: you meet in Cruz Bay, transfer by tender to the boat, then head out for snorkeling in clear Virgin Islands water. I love that it’s laid-back but still well-run, with a captain who thinks about comfort and flow, not just points on a map. You also get real time at a secluded anchorage near Caneel Bay, where you can snorkel, swim, or just soak up the sun.

Two things I especially like: you get snorkeling equipment included for everyone, and the crew serves lunch that actually sounds like someone planned it. Captain Mike (and his nephew Beau) keep the vibe friendly and safe, and they also mix in small touches like sailing time when conditions and your comfort level line up. One consideration: private transportation isn’t included, so you’ll want to sort out how you’re getting to the Saint John Ferry Terminal area in Cruz Bay (pickup is offered, but it’s not automatic for every situation).

Key Highlights You’ll Care About

• Private charter for up to 6 with just your group onboard
• Snorkeling gear included so you don’t have to shop or pack
• Very Open Bar with beer, soda, juice, water, plus spirits and sparkling wine
• Lunch included from North Shore Deli (9 deli sandwiches and 5 salads)
• Comfort perks onboard: restroom, shaded cockpit, and WiFi
• A secluded Honeymoon Beach area stop near Caneel Bay for a second snorkel and swim time

A Classic Sail Day Off Cruz Bay, Not a Crowded Boat

This is a day built around the classic St John rhythm: meet near the ferry area in Cruz Bay, transfer out to the charter boat, then settle into the water-and-sun pace. The boat is a 40-foot sailboat, and the private format matters. Instead of squeezing into a busy schedule, you get a charter tailored to your group’s energy—swim more, snorkel more, or just hang in the shade with a drink.

The crew’s approach comes through in the details. Captain Mike is the kind of operator who watches what you’re doing, explains what’s next clearly, and keeps the day moving without rushing anyone. His nephew Beau (you may hear it said as Bo) adds a friendly energy, and multiple people mention the way Captain Mike is thoughtful and attentive.

If you’re the kind of person who hates the chaos of cruise-ship tours, you’ll likely appreciate the simplicity here. And if you do want to participate, the captain may include hands-on sailing time—one review notes a sailing lesson.

Getting to the Boat: Tender Transfer From Cruz Bay

Your day starts at Saint John Ferry Terminal in Cruz Bay. From there, you’ll head out by inflatable tender to the sailboat. That tender transfer is short enough to feel like part of the adventure, but long enough that it wakes you up: you get that first look at the water conditions and the color changes as you move away from shore.

Plan to dress for both land and water. You’ll want to be ready to step between boats and the waterline. The good news: the day is set up for snorkeling, so the crew is expecting everyone to go through the same basic routine—gear, quick safety talk, then into the water when you’re good to go.

If you have mobility concerns, keep it in mind that this is a water-to-boat transfer day. The charter does include a fully functional restroom and a shaded cockpit, which helps make the whole experience feel less like a sacrifice.

The Snorkeling Plan: Two Water Stops With Gear Included

Snorkeling is a core part of the charter, and the best part is that the basics are handled for you. Snorkeling equipment is available to all passengers, so you’re not stuck bringing a mask and hoping it fits or works.

You’ll get a couple of snorkeling opportunities while cruising the clear waters around the Virgin Islands. The schedule is structured as “sail, then stop,” which tends to work better than a frantic series of quick splashes. The crew handles timing so you’re not waiting forever, but you’re also not forced to race.

Practical tip: bring swimwear you can move in and a towel you’re okay with getting salty. Even if the crew is running a smooth operation, a private sail day is still a sail day—stuff gets wet.

First snorkeling stop: clear water, easy start

The first stop is the “get your bearings” snorkel. This is where you settle into the rhythm: gear on, brief guidance, then you swim around at your pace. It’s a nice setup if you’re not an experienced snorkeler. If you are comfortable, it still gives you a solid window before the longer second anchorage later.

Second snorkeling stop: more time near Caneel Bay

The second stop is at a secluded anchorage off the shoreline of Honeymoon Beach near Caneel Bay. This isn’t just a quick stop. You’ll have time to snorkel again, plus time to swim or sunbathe in a calmer setting. For many people, that’s the moment that turns the day from good to memorable.

Honeymoon Beach Area Time: Swim, Snorkel, Sunbathe

This is where the day slows down. After the sailing and the first snorkeling, you’ll anchor off the Honeymoon Beach near Caneel Bay shoreline for a second go at the water.

What I like about this setup is choice. You’re not locked into one activity. You can:

• snorkel a second time
• swim
• or just float and soak in the views

If your group has mixed preferences—one person loves snorkeling, one person hates it, and one person wants a sun moment—this kind of stop usually makes everyone happy. And it’s “secluded anchorage” time, which generally means less boat traffic and more peace.

One small caution: anchorage time still means you’re in the water environment. Sunscreen, a hat, and a rash guard (if you use one) are your friends. You can take shade under the cockpit, but the water time is still sun time.

Lunch From North Shore Deli + Drinks That Keep the Day Moving

Food and drinks can make or break a sail day, and this one does it right. Lunch is included, with a menu built around North Shore Deli: 9 gourmet deli sandwiches and 5 gourmet salads. That matters because it means you’re not dealing with a sad snack plate. It’s enough choice that people in your group can likely find something they actually want.

On the drinks side, you get a Very Open Bar with beer, soda, juice, water, and a full list of spirits like vodka, rum, gin, tequila, and more, plus sparkling wine. There’s also mention of the crew serving alcohol throughout the day.

Two practical notes for enjoying this well:

• Pace your drinking with your sun and water time. A sail day sneaks up on you.
• If your group includes people who don’t drink, there are non-alcohol options like soda, juice, and water built in.

Also, since the charter is private, you don’t have to wait in line for a drink. It’s simply part of the flow.

Onboard Comfort: Restroom, Shade, and WiFi

A 4 to 5 hour charter can feel long if the boat isn’t set up well. Here, it is. You’ll have a fully functional restroom and a shaded cockpit. That sounds like a basic promise, but on a day like this it makes a big difference. You’re not thinking about “where’s the bathroom?” every hour.

WiFi is also onboard, so if you need to check something quickly, you can. And if you don’t care about WiFi, you’ll probably still enjoy having it available—because it’s one less thing to worry about.

Price and Value: What $1,395 Really Buys

The price is $1,395 per group (up to 6). So the value depends on whether you fill the group. If you book for two people, the per-person cost is high. If you book for six, it becomes far easier to justify, especially because lunch, snorkeling gear, and drinks are included.

Here’s what you’re effectively getting “wrapped in” the charter fee:

• private sail time on a 40-foot boat
• tender transfer from Cruz Bay to the boat
• snorkeling gear for everyone
• lunch from North Shore Deli
• a very open bar
• onboard restroom, shaded cockpit, and WiFi

In other words, you’re paying for the whole package, not just “time on a boat.” For a family group, close friends, or anyone celebrating something, it can be a strong buy. For solo travelers, it might feel expensive unless you’re willing to treat it as your one big splurge.

A timing note: the charter is commonly booked about 65 days in advance on average. If you’re traveling during a popular season, booking earlier gives you better chances at your preferred day.

Who This Private Charter Fits Best

This is a good match if you want a day that feels personal and flexible. I’d especially recommend it for:

• small groups who want privacy over crowds
• couples who want a romantic day with a real swim/snorkel plan
• families who need comfort (restroom and shade are huge)
• anyone who likes being taught a little but still wants downtime

The reviews also highlight something meaningful: Captain Mike is attentive and communicates clearly, and people mention he may even offer sailing time or a sailing lesson. If you’re curious about how sailboats work, this can feel like more than a sightseeing day.

If your group prefers non-stop land attractions or long walking tours, this may feel too relaxed. But if you want water time with good food and zero stress, it’s built for you.

Booking a Classic Sail Day: Should You Go?

If your ideal St John day includes snorkeling plus comfort plus a private setting, I’d say yes. This charter is designed to take care of the big pieces—gear, lunch, drinks, and restroom access—so you can focus on the water and the company.

I’d only hesitate if you know you need private transportation handled for you, since private transportation isn’t included (pickup is offered, but you’ll still want to plan how you get to the Saint John Ferry Terminal in Cruz Bay). Also, if your group has very low tolerance for sun or water time, you may find the snorkeling and swimming-focused schedule less appealing.

FAQ

How many people can fit on the charter?

It’s a private charter for your group, up to 6 people.

How long is the sailing experience?

The duration is about 4 to 5 hours.

Where do we meet in St John?

The meeting point is the Saint John Ferry Terminal in Cruz Bay, St John 00830, USVI.

Is snorkeling equipment provided?

Yes. Snorkeling equipment is available to all passengers.

What food and drinks are included?

Lunch is included, along with soft drinks and alcoholic beverages. The bar includes beer, soda, juice, water, and spirits such as vodka, rum, gin, tequila, plus sparkling wine.

Is there a restroom onboard?

Yes. There is a fully functional restroom and a restroom on board, plus a shaded cockpit.

Is pickup available?

Pickup is offered, but private transportation is not included.

What’s the cancellation and weather plan?

You can cancel for a full refund if you cancel at least 24 hours before the experience start time. The experience requires good weather, and if it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

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If you tell me your group size and when you’re traveling, I can help you figure out whether booking this now is worth it for your exact budget and vibe.

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