Private Day Charter Classic Sailboat

A small sailboat can make a big day. This private St John charter gives you a 40-foot boat, a flexible pace, and the rare luxury of sharing the water only with your own group. I especially like the private setting and the chance to learn basic sailing from Captain Mike, who has even let passengers take the helm.

I also like the practical extras: lunch from North Shore Deli, snorkeling gear, a shaded cockpit, and a fully functional restroom. The main consideration is price. At $1,395 for up to six people, this works best with a full group. A smaller party pays much more per person, and private transportation to Cruz Bay is not included.

Key details that shape the day

• Your own 40-foot sailboat: The charter is private for your group of up to six, with no unrelated passengers sharing the boat.
• Two water stops: The outing includes snorkeling, swimming, or sunbathing, with a second stop at a quiet anchorage near Honeymoon Beach and Caneel Bay.
• Captain Mike may let you sail: Guests have described clear instruction, careful handling, and the chance to take part rather than simply sit aboard.
• Lunch and a broad open bar: You can choose from nine gourmet deli sandwiches and five salads, with beer, wine, spirits, soft drinks, juice, and water included.
• Useful boat comforts: A shaded cockpit, restroom, WiFi, and snorkeling equipment make four to five hours on the water easier.
• A strong choice for a small group: The price is easier to justify when six people share it, especially if you value privacy over a larger shared cruise.

Meeting your sailboat at Cruz Bay

The day begins at the Saint John Ferry Terminal in Cruz Bay. This is a central, sensible meeting point if you are already on St John, but you need to arrange your own ride there. Private transportation is not part of the charter.

From Cruz Bay, you take an inflatable tender out to the 40-foot sailboat. That short transfer is part of the character of the trip. You are not stepping straight from a dock onto a large tour boat. Instead, you move from shore to tender to sailboat, which feels more like joining a small water expedition than boarding a standard harbor cruise.

The tender also means you should plan your belongings sensibly. Keep cameras, phones, and other items secure during the transfer. The boat has WiFi, but this is still a day built around open water, salt spray, and time away from land.

The advertised duration is about four to five hours. That is enough time for sailing, two stops, lunch, and drinks without turning the outing into an exhausting full-day commitment. Exact timing can depend on weather and conditions, so I would avoid scheduling a tight appointment immediately afterward.

Sailing a classic 40-foot boat

Once aboard, the main pleasure is the space and pace of a smaller sailing charter. A 40-foot boat gives your group room to settle into the shaded cockpit, watch the water, and move around without the crowds found on a large excursion vessel.

You are not buying a packed schedule. You are paying for private use of the boat and for the captain to shape the outing around sailing, snorkeling, swimming, and rest. That distinction matters. If you want constant narration, a long list of scheduled stops, or a party boat atmosphere, this may feel too quiet. If you want time on the water with family or friends, the private format is a major advantage.

Captain Mike receives especially strong praise for his approach. He is described as attentive, safety-minded, and clear about what passengers need to do aboard. That matters on a sailing boat, where a calm captain makes the trip feel relaxed rather than uncertain.

He has also given passengers sailing instruction. One guest received a lesson, while another had the chance to sail the boat. You should not assume that everyone will take the helm, since it depends on conditions and the captain’s judgment, but the possibility adds real value. You are not simply watching someone else handle the boat.

Captain Mike’s nephew Beau has also helped with the outing. The two are described as friendly and easy to be around, which suits the small-group format. With only your party aboard, the tone can feel more personal and less scripted.

The first snorkel and the rhythm of the outing

The boat heads out toward the clear waters around St John, with a couple of stops planned for snorkeling. The exact first location is not specified, so you should think of the day as weather-dependent rather than a fixed sightseeing route.

That flexibility is useful. The captain can choose a spot that fits the day’s conditions instead of forcing the group into one location. It also means the precise scenery and water conditions may vary from one departure to the next.

Snorkeling equipment is supplied for all passengers. That saves you from bringing fins, masks, and related gear, and it makes the charter easier to join on short notice. You can also choose to swim or sunbathe instead. Not everyone in a group needs to spend every stop in the water.

The clear Virgin Islands water is a major reason to book this trip. Snorkeling is often best when you are not rushed, and a private charter gives you more control over how long you spend enjoying a stop. Still, four to five hours is a limited window. With sailing time, the tender transfer, lunch, and two stops included, this is a compact introduction to the area rather than an all-day snorkeling mission.

One account describes an unusual encounter with dolphins in Scotts Bay. That is an exciting possibility, but wildlife is never guaranteed. Treat it as a lucky extra, not as something promised by the charter.

Honeymoon Beach near Caneel Bay

The second stop is at a secluded anchorage off the shoreline of Honeymoon Beach near Caneel Bay. This is the clearest picture of the day’s slower side: drop anchor, swim, snorkel, or stretch out in the sun.

Honeymoon Beach is a good setting for a mixed group because the stop does not demand one activity. Strong swimmers can snorkel, casual swimmers can enjoy the water, and anyone who wants a break can remain aboard or sunbathe. That choice is one of the private charter’s best features.

The anchorage also provides a change from the sailing portion. After moving across the water, you get time to settle into one place and enjoy the coastline at a calmer pace. I would bring reef-safe sun protection, a hat, and a cover-up, though the supplied information does not specify a particular sunscreen policy.

The word secluded should not be read as a promise of complete solitude. St John’s popular beaches and anchorages can vary with conditions and boat traffic. The private part of the trip means your own party is on your charter, not that the surrounding bay will be empty.

Lunch from North Shore Deli

Lunch is included, and the menu is more substantial than the usual basic boat snack. You can choose from nine gourmet deli sandwiches and five gourmet salads, supplied through North Shore Deli.

That range is valuable for a group of six with different tastes. A sandwich is easy to eat during a casual boat stop, while a salad gives you a lighter option after swimming. The menu also helps explain part of the cost. You are not only paying for the boat and crew, but also for a proper meal and drinks during the charter.

Because the full menu is offered, check the available selections when you book or confirm your choices with the operator. The provided information does not list individual sandwich ingredients or dietary substitutions, so you should ask directly if someone in your group has an allergy or strict dietary need.

The very open bar and boat comforts

The included drinks selection is unusually broad for a half-day private charter. It includes beer, soda, juice, water, vodka, rum, gin, tequila, sparkling wine, and more.

The open bar can make this feel like a celebration, but use it sensibly. You are on a moving boat, and swimming after drinking calls for good judgment. The captain remains responsible for operating the vessel, while you remain responsible for pacing yourself and keeping your group safe.

The shaded cockpit is one of those details you appreciate more as the hours pass. Shade gives you a place to get out of direct sun between stops and makes lunch more comfortable. The onboard restroom is another practical benefit, particularly for a group spending several hours away from shore.

WiFi is included as well. It is useful if you need to stay reachable, but I would treat it as a convenience rather than the reason to book. The main value is being on the water with your group, not keeping up with a screen.

What the $1,395 price really buys

The charter costs $1,395 per group of up to six. Split six ways, that comes to $232.50 per person. With four people, the cost is $348.75 each. For two people, it becomes $697.50 each.

That math tells you exactly who should book. A full group of six gets a fairer value, especially with lunch, drinks, equipment, a private captain, and a four to five hour outing included. A couple or small family may still love the experience, but the price is harder to defend unless privacy and personal service are top priorities.

Compared with a shared boat trip, you are paying for control and comfort. Your group does not have to adapt to strangers, and the captain can spend more attention on your interests. You also get the chance to ask questions, learn a little sailing, and choose how much time to spend snorkeling or resting.

The price is less compelling if your main goal is simply to reach the water for a quick swim. St John offers many ways to enjoy the coast, and this charter makes sense when you want the boat itself to be the main event.

The 100 percent recommendation rate and 5 out of 5 rating from 69 ratings point to a very consistent experience. The praise centers on Captain Mike’s care, sailing instruction, friendliness, and ability to make the day feel special. Those are the qualities worth paying for here.

Who should book this private sailing trip?

I would recommend it most strongly for a family or friend group of four to six people. It suits people who want a private day, enjoy a drink and a good lunch, and like the idea of mixing sailing with snorkeling instead of spending the entire outing in one activity.

It also fits first-time sailors who want a gentle introduction. Captain Mike’s clear instructions and willingness to teach can turn the boat ride into an active experience. You may get to learn how the boat works rather than simply watch the crew handle everything.

The charter is also a good match for a celebration. The private boat, sparkling wine, full lunch, shaded seating, and scenic anchorage give a birthday or anniversary more shape than a standard beach visit.

I would think twice if you dislike boats, have a very tight schedule, or want a guaranteed wildlife sighting. The dolphin encounter in Scotts Bay was memorable for one group, but no wildlife appearance can be promised. I would also hesitate if your party has only one or two people and the cost per person feels uncomfortable.

Most people can participate, and service animals are allowed. The meeting point is near public transportation, which helps if you do not have a private car. The supplied details do not give specific information about mobility access on the tender or sailboat, so ask Morningstar Sailing and Power Charters before booking if anyone in your group needs special assistance.

Booking, weather, and cancellation details

Confirmation is sent within 48 hours of booking, subject to availability. The charter is often booked about 65 days ahead, so reserve early if you need a particular date, especially for a full group.

The experience requires good weather. If poor conditions cause cancellation, you will be offered another date or a full refund. You can cancel for a full refund up to 24 hours before the start time. Cancellations or changes made less than 24 hours ahead are not refunded or accepted.

The operating hours vary by season. From March 26, 2019 through December 14, 2025, the listed hours are 8:00 AM to 9:00 PM daily. From December 15, 2025 through January 11, 2026, and again from January 12 through December 10, 2026, the listed hours are 9:00 AM to 9:00 PM daily. Confirm the exact departure time when you receive your booking confirmation.

Should you book Morningstar Sailing and Power Charters?

Book this private sailing charter if you can fill most of the six spaces and want a relaxed, personal day on St John. The strongest reasons are Captain Mike’s attentive style, the chance to try sailing, two water stops, a real lunch, and an open bar that is already included.

Skip it if you only want the cheapest way to snorkel or if you need a guaranteed route and guaranteed wildlife. For the right group, though, the combination of privacy, instruction, comfort, and time at Honeymoon Beach makes the $1,395 price reasonable. Bring a flexible attitude, let the captain work with the day’s conditions, and enjoy the rare pleasure of having the boat largely to yourselves.

FAQ

Where does the charter begin?

The charter begins at the Saint John Ferry Terminal in Cruz Bay, St John, USVI.

Where does the activity end?

The activity ends back at the meeting point in Cruz Bay.

How long does the sailing charter last?

The 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.

Is lunch included?

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

Are drinks included?

Yes. Alcoholic beverages, soft drinks, juice, water, beer, spirits, and sparkling wine are included.

Is snorkeling equipment provided?

Yes. Snorkeling equipment is available for all passengers.

What happens if the weather is poor?

If poor weather causes the charter to be canceled, you will be offered a different date or a full refund.