A day like this is built for easy fun. You get a private charter on a 40-foot sailboat in St John with snorkeling stops in clear water, plus a crew that keeps things organized. I especially like that the trip includes lunch and a true bar setup, so you’re not budgeting for every little extra.

What I’d also call out is the small-group feel: it’s just you and your party (up to 6 people), with snorkeling equipment provided and a working restroom on board. One thing to plan for: the sail experience depends on weather, and you may need to reschedule if conditions are poor.

Key Points to Know Before You Go

• Private group up to 6 means more time actually on the water, less time waiting around.
• Lunch + Very Open Bar keeps the day simple: food and drinks are handled for you.
• Snorkeling gear included so you can show up with swimwear and a good attitude.
• Honeymoon Beach near Caneel Bay is your second anchorage stop for snorkel, swim, and sun time.
• Restroom and shaded cockpit make longer deck time much more comfortable.
• Captain Mike and Beau bring both safety-first sailing and a hands-on vibe if you want it.

Why a 40-Foot Private Charter Works Best in St John

St John is at its best when you get off the busy shore and into the water. This private day charter is built for that exact mood: you’re on a classic sailboat, with a couple of snorkeling stops, and you’re not competing with a crowd.

I like the balance here. It’s not a rigid “checklist only” trip. You’ve got structure—sailing, snorkeling, and time to swim and relax—plus enough flexibility for the day to feel like yours.

And because it’s private, the crew can match the pace to your group. If you want to snorkel more, they’ll generally give you the time to do it. If you’d rather hang in the cockpit with a cold drink, you can do that too.

Meeting in Cruz Bay and Boarding the Sailboat (Tender Included)

Your day starts at the Saint John Ferry Terminal in Cruz Bay. After meeting up, you’ll head out to your sailboat using an inflatable tender, which is pretty common in island setups where the boat can’t pull right up to shore.

This matters because it affects how you pack and what you wear. Wear water shoes if you have them. Bring something simple for your phone or camera, since you’ll be moving between boat and water.

Once you’re on board, the shaded cockpit and working restroom are a big deal. On a 4 to 5 hour day, those comforts help you stay out longer without feeling like you have to rush everything.

Snorkeling Stops Designed for Clear Water and Real Swim Time

The day is centered on snorkeling, with multiple stops where you can get in the water and enjoy the visibility around the Virgin Islands. That’s the main reason to book a sail charter versus staying on shore: you trade crowds and limited access for better access to calmer spots.

Here’s what I think is smart about the way this is run. You’re not just “dropping anchor and hoping.” You’re doing sailing between stops, then spending actual time at each one. That gives you enough water time to remember it, not just enough for a quick look.

Also, since snorkeling equipment is included, you don’t have to start your trip with a rental hunt. You’ll still want to double-check how the mask fits before you put your head underwater, but the gear is there for you.

One more note from the type of day this crew has put together: some charters have included an incredible dolphin experience in Scotts Bay. It’s not something you can assume will happen every day, but it’s a sign the crew watches the conditions and looks for chances to make the day special.

Honeymoon Beach Near Caneel Bay: Your Second Stop for Snorkel, Swim, and Sun

The second stop is the one many people picture when they think of St John water time. You’ll anchor off the shoreline near Honeymoon Beach, close to Caneel Bay, and you’ll have time for a second snorkel, swimming, or sunbathing.

What makes this stop valuable is that it’s not just about seeing fish for five minutes. You get a pause in the day where the priority shifts from sailing to relaxing. You can rinse off, reset your gear, and then jump back in if you want.

Practical tip: bring reef-safe sunscreen and apply before you’re out there for a while. With snorkeling and sun time, you’ll get more exposure than you’d expect, even if you keep moving.

And if you’re traveling with mixed-energy folks—one person wants to snorkel hard, another wants to float—this stop is a good compromise. The water time and the deck time both work.

Lunch and the Open Bar Setup You’ll Actually Enjoy

This is one of the easiest parts of the whole day: lunch is included, and the food program is specific. The menu is built around North Shore Deli, with 9 gourmet deli sandwiches and 5 gourmet salads to choose from.

Why I like that: it’s not vague. You’re not relying on snacks and a vague description of what’s in a cooler. You can pick something that fits what you’re in the mood for—especially helpful if some people in your group prefer lighter options.

Then there’s the drinks. The charter includes soft drinks and alcoholic beverages, and it’s described as a Very Open Bar. That list includes beer, soda, juice, water, and spirits like vodka, rum, gin, tequila, plus sparkling wine and more.

This matters for your planning. You don’t have to decide ahead of time how much you’ll spend on drinks or whether you’ll ration them. You can focus on enjoying the day—and if you’re the designated planner in your group, that’s a win.

Also, because there’s a restroom and shade, you’re not just dealing with the sun and heat. You can take breaks without leaving the boat.

Captain Mike’s Sailing Touch: Safety, Clarity, and a Little Teaching

The crew experience is a big reason this charter earns top marks. Captain Mike is known for being attentive and thoughtful about how the day runs, and he’s the kind of skipper who communicates clearly so you always know what’s next.

One standout detail: Captain Mike has been described as giving sailing lessons. If you’ve ever watched sailboats from shore and wondered what the basics feel like, this is the sort of extra that can turn a nice day into a memory.

Another name that comes up is Beau, sometimes written as Bo. He’s part of the crew and helps keep the day friendly and smooth.

Even if you’re not into sailing lessons, the safety-and-clarity vibe is what you’ll feel most. On a boat, it’s not just about having fun—it’s about knowing where to stand, when to move, and how to enjoy the stops without stress.

Price and Value: What $1,395 Buys for Up to 6

The price is $1,395 per group for up to 6 people, for a total day around 4 to 5 hours. It’s private, which is where the value starts to make sense.

Here’s the quick math:

• If you fill all 6 spots, you’re at about $232 per person.
• If you book for 4, that becomes about $349 per person.

Whether that feels “worth it” depends on your group and what you’d otherwise pay for. The charter includes snorkeling gear, lunch, drinks (including alcohol), and a private boat with restroom and shade. Many day trips start cheaper but then add up fast once you include rentals, food, and the cost of getting everyone out to good water.

For me, the value argument is simple: you’re paying for a day that covers the core costs while you get a private experience. If your group would hate waiting in lines, splitting up, or hauling snorkel gear from store to beach, this charter avoids a lot of friction.

Also, note that it’s often booked about 65 days in advance on average. If you’re traveling during peak dates, don’t wait for last-minute vibes.

Weather and Timing: Plan for a Day That Can Move

This trip requires good weather, which is standard for sailing days. If the charter can’t run because of conditions, you’ll be offered a different date or a full refund.

That means you should treat this as a highlight day, not the only plan you can’t lose. If you’re staying multiple days in St John, you’re in better shape to swap dates if needed.

Timing-wise, the experience runs during the provider’s open hours window, so you’ll generally have flexibility across the day. But because sailing is weather-dependent, expect that the actual outing to happen on the right day matters more than what your calendar says.

Who Should Book This Sailboat Charter (and Who Might Feel It’s Not For Them)

This charter fits best if you want St John water time without the hassle.

It’s a great choice for:

• Couples or friend groups who want privacy and don’t want to manage logistics.
• Families with a mix of snorkelers and sunbathers, since the day includes both.
• Anyone who wants lunch and drinks handled, not improvised.

You might think twice if:

• You’re strongly price-sensitive and would rather do a shared tour.
• You get stressed about weather changes. If conditions aren’t right, the day can shift.

Good news: the experience says most travelers can participate, and service animals are allowed. Still, you’ll want to be comfortable with getting on and off a tender and spending time on a boat deck.

Should You Book This Private Day Charter?

I’d book it if you want a classic St John day that feels like a treat from the first hour to the last. The combo of a private 40-foot sailboat, included snorkeling gear, lunch, and a Very Open Bar makes the day easy to enjoy without constant decisions.

You should skip it (or at least be cautious) if you can’t be flexible about weather. Sailing days live and die by conditions, and that’s the trade.

If your group can fill most of the spots and you want that mix of snorkeling plus true relaxation, this charter is a strong value way to spend a few hours in St John.

FAQ

How long is the private sailboat charter in St John?

The charter lasts about 4 to 5 hours.

What does it cost and how many people can go?

It’s $1,395 per group for up to 6 people.

Where do we meet, and where does the tour end?

You start at the Saint John Ferry Terminal in Cruz Bay, St John 00830, USVI, and the activity ends back at the same meeting point.

Is pickup available?

Pickup is offered, but private transportation is not listed as included. It’s best to confirm what pickup means for your exact location.

Is snorkeling equipment provided?

Yes. Snorkeling equipment is included for all passengers.

What’s included for food and drinks?

Lunch is included, and soft drinks plus alcoholic beverages are served as part of a Very Open Bar.

Is there a restroom on board?

Yes. There is a fully functional restroom and you’ll have restroom access on the boat, plus a shaded cockpit.

Is WiFi available during the trip?

Yes. WiFi is available on board.

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