Private Day Charter Classic Sailboat

A private 40-foot sailboat carries your group away from Cruz Bay for a half-day of sailing, snorkeling, lunch, and swimming. You first take an inflatable tender from the Saint John Ferry Terminal to the boat, then head out toward clear Virgin Islands waters and quiet coves.

I like the freedom of a private charter, and I like that Captain Mike may let you take the wheel and learn a little sailing. The included lunch, full bar, shade, restroom, and snorkel gear also make this feel like a real day on the water, not just a short boat ride.

The main drawback is the price: $1,395 is a serious outlay for a four to five hour trip. It makes far more sense for a group of four to six than for a couple, and you’ll need to arrange your own transportation to Cruz Bay.

Key Points Before You Book

• Private boat for up to six: You get the sailboat and crew for your own party, without sharing the day with strangers.
• Captain Mike leads the sailing: He is known for clear safety instructions, a calm manner, and offering sailing lessons when conditions allow.
• Two water stops: The second anchorage is near Honeymoon Beach by Caneel Bay, a good spot for snorkeling, swimming, or sunbathing.
• Lunch and a very open bar are included: Choose from nine deli sandwiches and five salads, with beer, wine, spirits, juice, soda, and water.
• Comforts matter here: The boat has a shaded cockpit, a working restroom, WiFi, and snorkeling equipment for all passengers.
• The cost favors groups: At $1,395 per charter, six people pay about $233 each before any extra transportation costs.

Setting Out From Cruz Bay on a Private Charter

Your day begins at the Saint John Ferry Terminal in Cruz Bay. Pickup is offered, but private transportation is not included, so confirm exactly what pickup means for your party before booking. The listed meeting point is the ferry terminal, and the trip returns there at the end.

You do not simply step from the dock onto the sailboat. You take an inflatable tender out to the 40-foot vessel. That short transfer is part of the adventure, but it also means you should be ready to move carefully between boats. If you have limited mobility, ask about the transfer before paying.

Once aboard, you have the boat to yourself. That changes the whole feel of the trip. Captain Mike can shape the pace around your group, spending more time in the water, letting you relax in the cockpit, or giving interested passengers a chance to handle the boat.

The charter lasts about four to five hours. That is long enough for sailing and two water stops, but it is not a full-day cruise. You will want to arrive ready to make the most of the time, since the tender transfer and meal are part of the same compact outing.

Captain Mike, Beau, and the Human Side of the Trip

The crew is a major part of this charter. Captain Mike receives especially strong praise for being attentive, safety-minded, and clear about what he needs from passengers. That matters on a sailboat, where a friendly captain is good, but a captain who communicates well is better.

Mike also seems comfortable sharing the basics of sailing. One passenger received a personal sailing lesson, and that kind of hands-on moment can turn a scenic boat ride into something you remember. You should not assume you will take over the boat, but if sailing interests you, ask Mike what is possible.

Beau, Mike’s nephew and crew member, has also been part of the day. The two work as a friendly team, helping with the boat, the snorkeling stops, food, and drinks. The arrangement sounds relaxed without losing the safety focus you want on open water.

The bartending gets its own share of praise. Mike may be running a sailboat, explaining local waters, and mixing drinks in the same afternoon. That is useful if you want a festive outing, but you can also keep the day quiet with water, juice, soda, or a swim.

Sailing Out Toward the Virgin Islands Water

The sailing portion is not just transportation between snorkeling sites. It is the core of the outing. From the boat, you get a different view of St John than you do from a beach or road. The shoreline opens up, the water sets the pace, and your group can enjoy the ride without a larger crowd around you.

The exact sailing route can depend on weather and water conditions. The experience description identifies two snorkeling stops, with the second at a secluded anchorage off Honeymoon Beach near Caneel Bay. That flexibility is useful because a good captain can choose safer, more pleasant water instead of forcing a fixed route.

You might spend part of the sailing under way and part sitting at anchor. Bring a willingness to let the day unfold rather than expecting a tightly timed checklist. The boat has a shaded cockpit, so you can get out of direct sun while watching the water or eating lunch.

For passengers who are new to boats, the shade and restroom are more than small comforts. Four or five hours in the sun can wear you down, especially with swimming and drinks mixed in. Having a place to sit out of the sun, use the restroom, and settle in makes this much easier than a bare-bones boat trip.

First Water Stop: Snorkeling With Your Own Group

The charter includes snorkeling equipment for everyone. You do not need to bring a full set of gear, though you may prefer to bring your own mask if fit is important to you. The boat’s crew can help get the equipment ready and direct you toward the water.

The two stops give you a choice of how active you want the day to be. You can snorkel, swim, or simply remain aboard. That makes the charter workable for a mixed group, such as strong swimmers, casual swimmers, and someone who mainly wants to sunbathe.

The water conditions will affect what you see. Clear Virgin Islands water can make snorkeling the main attraction, but visibility and comfort are never fully guaranteed on a boat day. If snorkeling is your top priority, ask the captain about current conditions and the planned stops before leaving Cruz Bay.

A private group also changes the snorkeling rhythm. You do not have to keep up with a large tour or return on someone else’s schedule. At the same time, you should not expect a guided reef lesson or a guaranteed wildlife encounter. The supplied information promises snorkeling stops, not a specific animal sighting.

One unusual possibility has been swimming with dolphins in Scotts Bay. Treat that as a lucky event, not part of the contract. The reliable plan is sailing, snorkeling, swimming, and time in the sun.

Honeymoon Beach Near Caneel Bay

The second stop is a secluded anchorage off Honeymoon Beach near Caneel Bay. This is the most clearly defined stop on the route, and it offers three good ways to spend your time: snorkel, swim, or sunbathe.

Honeymoon Beach gives the stop a scenic setting, but the real benefit is the anchorage. Instead of rushing in and out of the water, your group can settle into the cove and choose its own pace. If you are tired after the first swim, stretch out in the sun. If the water looks inviting, go back in with your mask and fins.

The word secluded should not be read as a promise of total isolation. Popular beaches and anchorages can change with the day, weather, and other boats. Still, a private charter gives you more privacy aboard your own boat than a shared excursion.

This stop is also a good reason to book a private trip for a family or close group. People can split up without arguing over the schedule. Some can snorkel, some can eat, and some can relax in the shaded cockpit.

Lunch From North Shore Deli

Lunch is included, and the menu is more useful than a generic snack tray. You can choose from nine gourmet deli sandwiches and five gourmet salads through North Shore Deli. That gives your group enough variety for different tastes without asking you to pack a separate meal.

The meal is served during a day when you may be moving between sailing and water activities. A sandwich or salad is practical boat food, and it is easier to eat than anything that needs a knife, plate, or formal table. Ask about the selection and timing if anyone in your group has dietary needs, since the provided details do not list specific allergy or vegetarian arrangements.

The included lunch adds real value to the charter. Buying food separately for six people, then carrying it to the meeting point, would add work and expense. Here, the crew handles the meal as part of the day.

You also get a broad drink selection: beer, soda, juice, water, vodka, rum, gin, tequila, sparkling wine, and more. The phrase very open bar means the drink package is generous, but drink responsibly. Alcohol and sun can catch up with you quickly on a boat, especially after snorkeling.

What the $1,395 Charter Really Buys

The price is $1,395 per group of up to six. For a full group, that works out to about $233 per person. For four people, it is roughly $349 each. For two people, the same charter becomes much harder to justify.

You are paying for privacy, a dedicated captain and crew, a 40-foot sailboat, two water stops, lunch, drinks, equipment, a restroom, and a shaded place to sit. That package compares differently from a low-cost shared boat tour, where you might pay less but give up control over the route and company.

I would consider the charter good value for a group that wants a special boat day and plans to use the full package. It is especially reasonable for six people celebrating a birthday, family occasion, or final day on St John. You can spread the fixed cost across the group and make use of the food, drinks, and private schedule.

For a couple, the math is less friendly. You are still getting the same boat and crew, but you pay the full charter fee. If your main goal is simply to snorkel for an hour, a shared excursion may be a better fit. If the private setting and personal sailing attention are the point, the higher cost may feel worthwhile.

WiFi is available on board, but I would treat it as a convenience rather than a reason to book. The value is being on the water, not staying connected. The restroom, on the other hand, is genuinely helpful on a four to five hour trip.

Who Will Enjoy This Sailing Day Most

This charter suits a group that wants control, comfort, and time on the water. Families can appreciate the flexible pace, while friends may make the most of the lunch and open bar. Couples can enjoy it too, but the cost is easier to accept when shared among several people.

It is a good choice for people with mixed interests. One person can snorkel, another can sunbathe, and another can sit under the shade with a drink. You do not all have to be equally athletic or equally social.

The trip also suits anyone curious about sailing itself. Captain Mike may provide a lesson or allow you to take part, depending on conditions and his judgment. That personal instruction is more memorable than simply riding from one beach to another.

I would think twice if you dislike boat transfers, need a highly structured schedule, or want guaranteed wildlife sightings. The itinerary depends on weather and sea conditions, and the tender ride to the sailboat requires some care.

Service animals are allowed, and most people can participate. Still, the boat-to-tender transfer is worth discussing in advance if anyone has mobility concerns. The experience is near public transportation, but you are responsible for getting to Cruz Bay unless a separate pickup arrangement has been confirmed.

Booking Timing, Weather, and Cancellation

This charter is often booked about 65 days ahead. That is a useful clue for planning, especially if you are visiting during a busy period or have only one day available for sailing. Confirmation arrives within 48 hours of booking and remains subject to availability.

Weather matters. If poor conditions cancel the trip, 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 start time. Cancellations or changes made inside 24 hours are not refunded or accepted.

The listed operating dates include daily service through December 10, 2026, with seasonal hours changing from 8 a.m. to 9 p.m. in one period to 9 a.m. to 9 p.m. in later periods. Confirm your exact departure time when booking, since the broad opening hours do not tell you when your particular charter leaves.

Should You Book This St John Sailboat Charter?

I would book this for a group of four to six that wants a private day with a real sailing feel, not a basic transfer between beaches. Captain Mike’s attentive approach, possible sailing lesson, two water stops, included lunch, full drink selection, shade, and restroom give the outing substance.

I would skip it if you are traveling alone or as a couple on a tight budget. The cost is fixed per boat, so the value improves sharply as your group grows.

For the right group, this is a polished and personal way to see St John from the water. Set aside enough time to enjoy the sailing itself, ask about participating at the helm, and keep your expectations flexible around weather and sea conditions.

FAQ

Where does the private sailing charter begin and end?

The meeting point is the Saint John Ferry Terminal in Cruz Bay, St John. The activity ends back at the same meeting point.

How long does the charter last?

The sailing experience lasts approximately four to five hours.

How many people can join the private charter?

The price covers one private group of up to six people. Only your group participates in the activity.

Is lunch included?

Yes. Lunch includes a choice from nine gourmet deli sandwiches and five gourmet salads through North Shore Deli.

What drinks are included?

The included drink selection features beer, soda, juice, water, vodka, rum, gin, tequila, sparkling wine, and more.

Is snorkeling equipment provided?

Yes. Snorkeling equipment is available for all passengers.

What happens if the weather cancels the trip?

If poor weather causes cancellation, you can choose a different date or receive a full refund. You can also cancel at least 24 hours before the start time for a full refund.