Private Day Charter Classic Sailboat

St John’s best hours may be spent away from the roads, on a private 40-foot sailboat with only your own group aboard. Captain Mike handles the boat, mixes drinks, and may even let you take a turn at the wheel. The day includes two snorkel stops, lunch, and a very open bar.

I like the small private setting, since your group can enjoy the day at its own pace rather than sharing a crowded excursion boat. I also like the practical comforts: shade, a restroom, lunch, snorkeling gear, and drinks are all included. The main drawback is the price. At $1,395 for up to six people, this makes the most sense for a full group, not one or two passengers.

Key points to know before booking

• Private 40-foot sailboat: Only your party takes part, with room for up to six people.
• Captain Mike at the helm: He may offer basic sailing instruction and keeps the day personal and hands-on.
• Two water stops: Expect snorkeling, swimming, or sunbathing, including an anchorage near Honeymoon Beach.
• Lunch and a broad drink selection: Sandwiches, salads, beer, spirits, sparkling wine, soft drinks, juice, and water are included.
• Useful onboard comforts: You get a shaded cockpit, working restroom, WiFi, and snorkeling equipment.
• Cruz Bay meeting point: You meet at the Saint John Ferry Terminal and return there when the charter ends.

Setting out from Cruz Bay on a private sailboat

Your day begins at the Saint John Ferry Terminal in Cruz Bay. From there, you take an inflatable tender out to the 40-foot sailboat. That short transfer is part of the character of the trip, but it also means you should be ready to step between boats and manage a small amount of movement on the water.

This is not a large sightseeing cruise with a fixed crowd. The charter is private for your group, with a maximum of six people. That changes the feel of the day. You can spend more time swimming if that is what your group wants, settle into the shade when you have had enough sun, or ask questions as you sail.

The advertised duration is about four to five hours. That is long enough to include sailing, two stops, lunch, and time to relax, but short enough to fit into a wider St John holiday. The schedule can feel full, especially if your group wants long swims at both locations, so it is best to think of this as a focused half-day on the water rather than a leisurely all-day cruise.

Sailing with Captain Mike and Beau

Captain Mike is a major part of the experience. He is described as attentive, clear about what passengers need to do, and comfortable balancing safety with a relaxed mood. If you have always wanted to try sailing, he may give you a basic lesson and let you take a turn. That hands-on touch gives the trip more personality than simply sitting on a motorboat while someone else handles everything.

Beau, Captain Mike’s nephew, may also join the crew. The two-person setup can be useful when your group is swimming, eating, and moving around the boat. It also gives you more opportunity to ask questions about the area or the mechanics of sailing.

Do not book this expecting a formal sailing course. The focus remains a private outing with food, drinks, swimming, and snorkeling. Still, the chance to learn a little about handling the boat is a fine bonus for curious passengers.

The crew’s style also suits groups that appreciate attentive service without a stiff tone. Captain Mike is known for clear communication and careful handling of the boat. That matters on a small vessel, where simple instructions help everyone move around safely and enjoy the day.

The first stretch of open water

Once you are aboard, the boat heads out from Cruz Bay toward the snorkeling areas. The sailing itself is part of the attraction, not just transportation between stops. You can sit in the shaded cockpit, watch the coastline, and enjoy the change from land-based sightseeing to a slower day on the water.

The boat has WiFi, though the value of that feature depends on how much you want to stay connected. I see it as a useful backup rather than the reason to book. You can share a message or check something if needed, but the better use of the trip is to put the phone away for a while.

A working restroom is another small but important advantage. On a four to five-hour charter, you will appreciate not having to wait for the boat to return to shore. The shaded cockpit also gives you somewhere to get out of direct sun, which is especially useful between swims.

Because this is a private charter, you can make the day as social or quiet as your group prefers. Families can spread out between activities, couples can keep the pace calm, and friends can use the boat as a floating base for swimming and lunch.

Snorkeling in the Virgin Islands waters

The charter includes snorkeling equipment for everyone, so you do not need to bring your own mask, snorkel, or related gear. That makes packing easier, especially if you are fitting this trip into a larger vacation with limited luggage.

The water around St John is clear, and the day includes two snorkeling stops. The exact conditions can change with weather and sea conditions, so you should keep your expectations flexible. One location may offer better visibility, while another may be calmer or more comfortable for a relaxed swim.

The first stop comes before the second anchorage, giving you two chances to get in the water rather than one quick swim at the end of the trip. You can snorkel, swim, or simply stay aboard and enjoy the boat. The private format makes that choice less awkward because nobody in your own group has to follow a stranger’s schedule.

The second stop is at a secluded anchorage off Honeymoon Beach near Caneel Bay. This location is described as a place for another snorkel, swim, or stretch of sunbathing. It sounds particularly useful for groups with mixed interests. Strong swimmers can explore, casual swimmers can stay close to the boat, and anyone who has had enough water can relax in the cockpit.

Keep in mind that snorkeling is weather-dependent. Wind, waves, and visibility can affect what you see and how comfortable the water feels. The operator requires good weather for the trip itself and offers a new date or full refund if poor weather causes cancellation.

Honeymoon Beach and the second stop

The anchorage near Honeymoon Beach gives the outing a change of pace. The first water stop is part of the outward sailing route, while this second stop lets you settle in for a longer period of swimming, snorkeling, or sunbathing.

You should not expect a busy beach visit here. The description centers on an anchorage off the shoreline, so the experience is about being on the boat and in the water rather than walking ashore. That is a plus if you want a quiet swim and a simple day without adding another land transfer.

This stop can also be the most flexible part of the charter. If your group is tired after snorkeling, you can stay aboard in the shade. If everyone is eager to swim, you have another chance to use the included equipment. If sunbathing is the priority, the boat becomes a comfortable floating platform.

Lunch, drinks, and the open-bar setup

Lunch is included, with a choice of nine gourmet deli sandwiches and five salads from North Shore Deli. That is a better arrangement than a single fixed meal because different members of your group can choose according to appetite and preference.

The food matters here because a four to five-hour boat trip is long enough for people to get hungry, especially after swimming. Having lunch included also means you do not need to arrange a separate meal during the middle of the outing.

The drink selection is unusually broad. It includes beer, soda, juice, water, vodka, rum, gin, tequila, sparkling wine, and other beverages. The operator calls it a very open bar. You can keep things simple with water or soft drinks, or order an alcoholic drink while relaxing after a swim.

That said, I would treat the bar as an optional extra, not the main reason to choose the charter. Alcohol and sun can be a poor mix, particularly on a small boat. Eat lunch, drink water, and pace yourself. The boat’s restroom and shaded cockpit make the day easier, but they do not remove the need for good judgment on the water.

What $1,395 really buys you

The price is $1,395 per group of up to six people. Divided evenly, that is about $232.50 per person for six passengers. For four people, it works out to about $348.75 each, and for two people it becomes a costly private outing.

The value comes from the combination of exclusivity and included extras. You are paying for the boat, crew, private format, snorkeling gear, lunch, alcoholic and nonalcoholic drinks, a restroom, shade, WiFi, and the flexibility of having only your own group aboard. A large part of the price is the private charter itself.

For a family of six, two families traveling together, or a group of friends, the cost can be reasonable compared with booking several separate activities. It is especially appealing if everyone wants the same kind of day and will use the included food, drinks, and water stops.

For a couple, the calculation is harder. You are paying for privacy and personal service rather than a lower-cost seat on a shared boat. If your priority is simply snorkeling, you may find a group excursion more economical. If your priority is control over the pace, space, and company, the private price may feel justified.

The booking pattern also suggests that planning ahead matters. This experience is often booked about 65 days in advance. I would not leave it until the last minute if your St John dates are fixed, particularly if you need a specific day.

Who should book this charter

This outing suits families, couples traveling with friends, and groups that want one special water day without strangers aboard. It is also a good match for anyone who wants more than a standard boat ride, since Captain Mike may include a bit of sailing instruction.

You will get the most from it if your group enjoys a mix of activities. One person can snorkel while another swims, someone else can eat lunch in the shade, and the whole group can regroup for drinks or a second water stop.

The trip may be less suitable if you dislike boat transfers, prefer a full-day schedule, or want a highly structured tour with extensive narration. It is also not the best value for a very small party unless privacy is your top priority.

Most people can participate, and service animals are allowed. The meeting point is near public transportation, but private transportation is not included. Plan to reach the Saint John Ferry Terminal in Cruz Bay on your own.

Practical booking details for a smooth day

Confirmation is sent within 48 hours of booking, subject to availability. The tour ends back at the same meeting point, which makes it easier to plan the rest of your day in Cruz Bay.

The listed operating hours vary by season. From March 26, 2019 through December 14, 2025, the stated hours are 8:00 AM to 9:00 PM daily. From December 15, 2025 through January 11, 2026, they are 9:00 AM to 9:00 PM daily. From January 12 through December 10, 2026, the stated hours are also 9:00 AM to 9:00 PM daily.

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 experience depends on good weather, a weather cancellation brings the choice of another date or a full refund.

Pack lightly but use common sense: swimwear, sun protection, and anything you personally need for the boat. The operator supplies snorkeling equipment, lunch, and drinks, so you do not need to carry a full beach kit.

Should you book the Morningstar private sail?

I would book this charter if you have four to six people, want a private day on the water, and value personal attention over the lowest possible price. Captain Mike’s sailing instruction, the two water stops, and the included meal and bar make it feel like a complete half-day rather than a bare boat rental.

I would hesitate if you are traveling as only one or two people, do not care about privacy, or mainly want a short snorkeling trip. In that case, a shared excursion may stretch your budget further.

For the right group, this is a well-rounded St John outing: sailing instead of simply motoring, snorkeling at two locations, a comfortable boat, and a crew that keeps the day personal. The strongest reason to book is not any single feature. It is the freedom to enjoy all of them with your own people and at a pace that suits you.

FAQ

Where does the private sailboat charter begin?

The charter begins at the Saint John Ferry Terminal in Cruz Bay, St John, US Virgin Islands.

Where does the activity end?

The activity ends back at the Saint John Ferry Terminal, the same meeting point where it begins.

How long does the charter last?

The experience lasts approximately four to five hours.

How many people can join the private charter?

The charter is private for your group and can accommodate 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 included?

Yes. The included selection features beer, soda, juice, water, vodka, rum, gin, tequila, sparkling wine, and other beverages.

Is snorkeling equipment provided?

Yes. Snorkeling equipment is available for all passengers.

What happens if the weather is poor?

If poor weather causes the experience to be canceled, you will be offered another date or a full refund. You can also cancel up to 24 hours before the start time for a full refund.