Private Day Charter Classic Sailboat

St John’s best moments often happen away from the roads, and this private charter gets you onto the water in a classic 40-foot sailboat with your own small group. From Cruz Bay, you ride an inflatable tender to the boat, then spend four to five hours sailing, snorkeling, swimming, and sunbathing.

I like the private format, which lets your group set the tone instead of sharing a schedule with strangers. I also like the practical extras: lunch, snorkeling gear, an open bar, a shaded cockpit, and a working restroom. The main consideration is the price. At $1,395 per group, it makes the most sense for up to six people who will use the full package.

Key points to know before booking

• A private 40-foot sailboat: Your group of up to six has the boat to itself.
• Two water stops: The second stop is at a secluded anchorage near Honeymoon Beach and Caneel Bay.
• Captain Mike may let you sail: A sailing lesson can turn a scenic cruise into a hands-on experience.
• Lunch and drinks are included: Choose from nine deli sandwiches and five salads, with beer, wine, spirits, soft drinks, juice, and water.
• Comfort is better than on a basic day boat: You have shade, a restroom, and WiFi onboard.
• Meet in Cruz Bay: Private transportation is not included, so you must get to the Saint John Ferry Terminal yourself.

Starting at Cruz Bay and reaching the sailboat

Your meeting point is the Saint John Ferry Terminal in Cruz Bay. This is the practical starting point for the excursion, but it is not the sailboat itself. You will take an inflatable tender from the waterfront out to the 40-foot charter boat.

That transfer is worth noting when you plan your morning. You are not simply walking from a dock onto the vessel, so wear something comfortable for a short boat transfer and keep track of small items such as phones, hats, and cameras.

The charter ends back at the same meeting point. Since private transportation is not included, you need to arrange your own way to Cruz Bay. If you are already staying on St John, that may be simple. If you are coming from another island, allow enough time to reach the terminal without cutting things close.

The exact sailing route can change with conditions and the captain’s judgment. That is normal for a small sailing charter. The important point is that the outing is built around time on the water rather than a fixed list of shore attractions.

What four to five hours feels like on a private boat

This is a half-day charter, not an all-day cruise. Four to five hours gives you enough time for sailing and two water stops without making the outing feel endless, especially if your group includes children or people who are new to boating.

The private setup changes the mood. You can talk with the captain, settle into the shaded cockpit, enjoy lunch when it suits you, and spend more or less time in the water according to your group’s interests. A shared boat often asks everyone to follow the same rhythm. Here, your party has much more control.

Captain Mike is the named captain associated with this charter, and the experience can include more than a simple ride. One notable feature is the chance to receive a basic sailing lesson. If you have always wanted to understand how the boat moves under sail, ask about taking part. You may find that the hands-on element becomes one of the day’s best memories.

Captain Mike has also worked with his nephew Beau on some outings. That gives you the possibility of a two-person crew, though the exact crew arrangement may vary. The important advantage is clear communication about what you need to do as a passenger and careful attention to safety.

First sailing time and the Virgin Islands water

Once everyone is aboard, the boat heads out from Cruz Bay. The sailing itself is part of the attraction, not just transportation between snorkeling spots. You get time to watch St John from the water, feel the boat move, and enjoy a slower pace than you would on a powerboat.

The charter includes snorkeling equipment for every passenger. That removes one common hassle: you do not need to rent masks, snorkels, or related gear separately for the outing. If you have your own equipment that fits better, you can still ask the crew about using it, but the included gear makes the trip easier to plan.

The water stops are intended for snorkeling, swimming, or simply relaxing. You may see clear water and underwater life, but conditions vary by weather, visibility, and the day’s route. I would treat the snorkeling as an important part of the trip, not as a guaranteed wildlife show.

This is also where the captain’s local judgment matters. Water conditions can affect which cove is comfortable and worthwhile. A private charter can adjust its stop choices more easily than a large scheduled cruise, although the final plan remains subject to safety and weather.

The Honeymoon Beach anchorage

The second stop is a secluded anchorage off Honeymoon Beach near Caneel Bay. This is the clearest picture of the day’s relaxed side: the boat pauses, you can swim or snorkel, and anyone who prefers to stay dry can sunbathe in the boat’s shaded or open areas.

Honeymoon Beach offers a different feel from the sailing portions of the trip. Instead of moving from one view to the next, you have time to settle in. That matters because short water excursions can sometimes rush through a snorkel stop. Here, the private format gives your group a better chance to enjoy the stop at a comfortable pace.

The word secluded should not be read as a guarantee that you will have the whole bay to yourself. It describes the anchorage used for the stop, not exclusive ownership of the surrounding water. Still, the setting near Caneel Bay is a strong reason to choose this trip if your idea of a good day includes quiet water time rather than a packed activity schedule.

You can snorkel, swim, or stay aboard. That flexibility is useful for mixed groups. Strong swimmers may want more time in the water, while someone who prefers shade, conversation, or a drink can enjoy the same stop without feeling left out.

Lunch, drinks, and the comfort factor

Lunch is included, and the menu is more substantial than the usual bag of snacks. You can choose from nine gourmet deli sandwiches and five gourmet salads from North Shore Deli. That is useful for a private group because people can select different meals rather than accepting one fixed lunch.

The charter also includes an open bar. Available drinks include beer, soda, juice, water, sparkling wine, vodka, rum, gin, tequila, and other beverages. The selection makes the boat feel more like a relaxed private outing than a basic snorkeling transfer.

Use good judgment with alcohol, especially before swimming or while the boat is moving. The drinks are an added convenience, not a reason to overdo it. Water and nonalcoholic options are included, which is important in the sun.

The boat has a shaded cockpit and a fully functional restroom. Those features may sound minor when you first compare tours, but they matter during four or five hours on the water. Shade gives you a break from direct sun, and an onboard restroom means you are not dependent on reaching shore between stops.

WiFi is also available onboard. I would regard it as a convenience rather than the main reason to book. The point of the charter is to be on the water, but having a connection can help with messages, weather updates, or sharing a photo without waiting until you return.

What the $1,395 price really buys

The listed price is $1,395 per group of up to six. With six people, that works out to $232.50 per person before any separate transportation costs. For four people, the effective price is $348.75 each, so group size has a major effect on value.

You are paying for more than a seat on a boat. The package includes a private 40-foot sailboat, captain and crew service, snorkeling equipment, lunch, alcoholic and nonalcoholic drinks, a restroom, shade, WiFi, and the freedom to spend the day only with your own party.

That can be a fair price for a full group that wants privacy and convenience. It is less compelling for one or two people who simply want a short swim or snorkel. In that case, a shared cruise may cost less, though it would not offer the same control over the group experience.

The best value comes when each person enjoys several parts of the package. If your group wants to sail, swim, snorkel, eat onboard, and use the private setting, the cost is easier to justify. If half the group dislikes boats or plans to stay dry, you may not get as much from the price.

Who will enjoy this charter most

This outing suits families, couples traveling together, and small groups of friends who want a flexible day on the water. The private arrangement is especially useful when people have different interests. One person can snorkel, another can swim, and someone else can relax in the cockpit while still sharing the day.

It is also a good fit for anyone curious about sailing. Captain Mike’s willingness to offer a sailing lesson adds a personal touch that a standard sightseeing ride may not provide. If you want to learn how the boat works, ask directly rather than assuming every moment will include instruction.

The charter is less suitable if you want a packed sightseeing program with many shore stops. The focus is sailing, snorkeling, swimming, sunbathing, food, and drinks. You should also think carefully about the weather. This experience requires good conditions, and a poor-weather cancellation may lead to a different date or a full refund.

Most people can participate, and service animals are allowed. The boat is near public transportation, but your own transport to the ferry terminal is not included. Confirmation is sent within 48 hours of booking, subject to availability, so do not treat a booking request as final until it is confirmed.

Booking timing, weather, and cancellation rules

This charter is often reserved well ahead of time, with bookings averaging about 65 days in advance. That is a useful signal for planning. If your dates are fixed, especially during a busy holiday period, booking early gives you a better chance of getting the day you want.

The experience operates daily within the stated seasonal schedule. Hours change during the year, so check the available start time when selecting your date.

You can cancel for a full refund up to 24 hours before the start time. Cancellations or changes made within 24 hours are not refunded or accepted. Since the trip depends on good weather, a cancellation by the operator for poor conditions comes with the choice of another date or a full refund.

Is this private St John sailing charter worth booking?

I would book this charter if your group has close to six people and wants a comfortable, private day with real time for sailing and water activities. The strongest reasons are the flexible format, the Honeymoon Beach anchorage, the included lunch and drinks, and the chance to learn a little about sailing from Captain Mike.

I would think twice if you have only one or two people, want the lowest-cost way to snorkel, or prefer a packed itinerary. The price is easier to defend when you use the private boat, food, open bar, gear, shade, and restroom as a complete package.

For the right group, this is a relaxed and personal way to experience St John from the water. Bring a willingness to follow the weather, decide how active you want to be, and leave room for the captain to shape the day. That is where this charter offers its real value.

FAQ

How long does the private sailing charter last?

The experience lasts approximately four to five hours.

Where does the charter begin and end?

It begins at the Saint John Ferry Terminal in Cruz Bay and ends back at the same meeting point.

How many people can join the private charter?

The charter is private for your group, with space for up to six people.

Is lunch included?

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

Are drinks and snorkeling equipment included?

Yes. Snorkeling equipment is provided, and the drink selection includes beer, soda, juice, water, sparkling wine, vodka, rum, gin, tequila, and other beverages.

What happens if the weather is poor?

The experience requires good weather. If it is canceled because of poor conditions, you can choose another date or receive a full refund. You can also cancel up to 24 hours before the start time for a full refund.