Private Day Charter Classic Sailboat

The best part of this St John charter is the freedom of a private 40-foot sailboat. You are not sharing the day with a boatload of strangers, and Captain Mike may even let you take the wheel and learn a little sailing. The plan includes open-water sailing, two snorkel opportunities, lunch, drinks, and time to simply stretch out in the sun.

I like two things right away: the small private group makes the outing feel personal, and the included food and drink remove much of the usual boat-day fuss. The boat also has a shaded cockpit, working restroom, and WiFi, useful comforts on a half-day at sea.

The main consideration is cost. At $1,395 for up to six people, this makes the most sense for a full group. A couple pays a steep per-person rate, and you must make your own way to the Cruz Bay ferry terminal unless pickup arrangements are confirmed in advance.

Key points to know before you book

• Captain Mike may offer hands-on sailing: A sailing lesson has been a memorable part of the day for some passengers.
• Honeymoon Beach is the second water stop: The boat anchors near Caneel Bay for snorkeling, swimming, or sunbathing.
• Lunch is more than a basic boat snack: You choose from nine deli sandwiches and five salads from North Shore Deli.
• The open bar is unusually well supplied: Beer, sparkling wine, soft drinks, juice, water, and several spirits are included.
• Your group gets the boat to itself: The charter accepts up to six people, with no unrelated party joining you.
• Practical comforts come onboard: You have snorkeling equipment, a restroom, shaded seating, and WiFi.

Setting out from Cruz Bay on a classic 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 experience, but it also means you should arrive ready to move between boats rather than expecting to step directly from the dock onto the main vessel.

Cruz Bay is the natural starting point for a St John water outing. Once you are aboard, the pace changes quickly. This is not a rushed sightseeing circuit with a guide calling out landmarks every few minutes. You have a private boat, open water, and a captain who can shape the day around your group.

The charter lasts about four to five hours. That is enough time for sailing and two water stops, but it is not a full-day expedition. I would think of it as a comfortable half-day on the sea, with enough room for swimming and lunch without leaving you worn out by late afternoon.

Captain Mike is a major part of the experience. He is described as attentive, clear about what passengers need to do, and careful on the water. His nephew Beau has also helped with the charter, giving the crew a friendly family feel. If you enjoy learning how a boat works, ask about taking a turn at the wheel. A hands-on sailing lesson has been one of the strongest personal touches connected with this outing.

Sailing, snorkeling, and the value of a private boat

The private format changes the whole mood. Your group can spend more time at a snorkel spot if everyone is happy in the water, or return aboard if someone would rather sit in the shade. You are not working around the preferences of a large mixed group.

That matters for families and friends with different energy levels. One person can sunbathe while another snorkels. Someone who wants a drink and a quiet view can remain in the shaded cockpit. Since the boat has a restroom, you are not limited to staying in the water or waiting until you return to shore.

The exact first snorkeling location is not specified, so you should not book this expecting a named reef or a guaranteed wildlife sighting. The captain chooses the stops as part of the day’s route. Water conditions, visibility, and weather can affect what you see.

The second stop is more clearly defined: a secluded anchorage off Honeymoon Beach near Caneel Bay. This is the place for a second snorkel, a swim, or simple sun time on the boat. The word secluded should be taken as a description of the anchorage, not a promise that you will have an entire bay to yourself.

Snorkeling equipment is supplied for all passengers. That saves you from packing fins and masks, though anyone with a favorite personal mask may still prefer to bring it. The important point is that the activity does not require you to rent gear separately before boarding.

The water time is flexible, but this is still a sailing trip rather than a dedicated snorkeling cruise. If your main goal is to spend every minute looking underwater, a specialized snorkel tour may suit you better. If you want a mix of sailing, swimming, food, and relaxed time aboard, the balance is more appealing.

Honeymoon Beach near Caneel Bay

The second stop gives the outing its clearest sense of place. The boat anchors off Honeymoon Beach near Caneel Bay, where you can choose between three simple pleasures: snorkel, swim, or stay aboard and sunbathe.

I like this arrangement because it does not force every passenger into the same activity. A private charter works best when a group can split up without anyone feeling they are holding the boat back. The shaded cockpit gives non-swimmers a comfortable place to watch the water and enjoy a drink.

The stop also gives you a chance to slow down after the sailing portion. There is no listed rush from one attraction to the next. You have time to enjoy the setting, eat lunch, and let the captain manage the boat.

Still, the experience is weather dependent. Wind, rain, and sea conditions can affect the route and whether the trip operates at all. If the charter is canceled because of poor weather, you are offered another date or a full refund. That policy is useful, but it is wise to keep some flexibility in your St John schedule rather than placing this outing on your final available day.

Lunch from North Shore Deli, plus a serious drink selection

Lunch is included, and the choices are better than the usual pile of packaged snacks. The menu includes nine gourmet deli sandwiches and five gourmet salads from North Shore Deli. That gives each person a real choice, which is especially helpful when six people have different tastes.

A private lunch also keeps the day moving. You do not need to leave the boat for a restaurant or sacrifice part of your water time. Eat in the shaded cockpit, then return to the water or settle in for more sailing.

The drink service is another strong part of the price. The open bar includes beer, soda, juice, water, vodka, rum, gin, tequila, sparkling wine, and more. This is a broad selection for a half-day charter, although you should pace yourself. Alcohol and sun can catch up with you quickly on the water.

I would treat the included water and soft drinks as just as important as the spirits. Staying hydrated makes the outing more comfortable, especially if you plan to snorkel and spend time in direct sun. The list includes juice and water, so you are not required to drink alcohol to make use of the bar.

The boat also has WiFi. That may sound minor, but it can matter if you need to check in with family, share a quick photo, or stay reachable. You are still going out to sea, so do not make constant connectivity the reason you book this experience.

What the $1,395 charter really costs

The price is $1,395 per group, with up to six passengers. At full capacity, that works out to $232.50 per person. For six people who value privacy, the price can compare well with booking several separate activities, especially since lunch, drinks, snorkeling equipment, and onboard facilities are included.

For two people, the calculation is different. The total price remains the same, making the per-person cost $697.50. That is a premium price for a four to five hour outing, even with food and an open bar included.

I see the value in the charter itself rather than in any single feature. You are paying for the boat, captain, private use of the vessel, flexible water time, food, drinks, and the chance to learn a little sailing. A shared tour may cost less, but it will not give your group the same control over the mood and pace.

The best value comes when your party has four to six people. A family, two couples, or a group of friends can divide the cost and use the private setting well. If your group is smaller, consider how much you value privacy before committing.

Meeting point, timing, and small practical details

The listed meeting point is the Saint John Ferry Terminal in Cruz Bay, and the outing ends back there. Private transportation is not included, so plan how you will reach the terminal. Pickup is indicated as an available feature, but because the detailed meeting instructions name the ferry terminal and exclude private transportation, confirm the exact pickup arrangement before booking.

Confirmation is sent within 48 hours, subject to availability. The activity is offered daily during the listed operating periods, with hours that vary by season. Since the charter normally lasts four to five hours, check the start time carefully if you are coordinating it with a ferry, hotel transfer, or another reservation.

The boat is near public transportation, and service animals are allowed. Most people can participate, though the trip involves getting into a tender, moving around a boat, and entering the water for snorkeling or swimming. The supplied information does not give specific accessibility details, so contact the operator if anyone in your party needs assistance.

You can cancel for a full refund up to 24 hours before the start time. Changes or cancellations within 24 hours are not refunded. Because weather can cancel the outing, I would avoid pairing it with a nonrefundable activity immediately afterward.

Who will enjoy this St John sailing charter most

This outing fits a group that wants a private day on the water without planning every detail itself. You get a captain, a boat, snorkeling gear, food, drinks, and a route with two water stops. That combination works well for families, couples traveling together, and friends marking a special occasion.

It is also a good match for passengers who want more than passive sightseeing. Captain Mike has provided a sailing lesson, and the captain’s clear instructions make it possible to participate without needing prior sailing experience. Ask about this early in the day if learning to steer is important to you.

The charter suits mixed groups particularly well. Strong swimmers can snorkel, less active passengers can stay in the cockpit, and everyone can share lunch aboard. The restroom and shade make the boat more comfortable than a basic open skiff.

I would be more cautious if your group wants a guaranteed encounter with a certain animal or a specific reef. One memorable account included swimming with dolphins in Scott’s Bay, but wildlife is never promised by this itinerary. Treat that as a lucky possibility, not the product being sold.

Likewise, this is not the best choice if you dislike boats, want a land-based beach day, or need a full eight hours of activity. Four to five hours passes quickly once you include the tender ride, sailing, two stops, lunch, and the return to Cruz Bay.

Should you book Morningstar Sailing and Power Charters?

I would book this private sailboat charter if you can fill most of the six seats and want a relaxed, personal day rather than a low-cost group cruise. The combination of Captain Mike’s attentive style, optional sailing instruction, Honeymoon Beach snorkeling, lunch, drinks, and a shaded boat makes the outing feel thoughtfully planned.

I would skip it if you are traveling as only one or two people and the price feels hard to justify. In that case, look for a shared sailing or snorkeling trip. But for a full group that values privacy and wants several activities combined in one outing, this is a strong St John choice.

FAQ

Where does the private sailing charter begin?

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

How long does the experience last?

The charter 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.

Is lunch included?

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

What drinks are included?

The open bar includes beer, soda, juice, water, vodka, rum, gin, tequila, sparkling wine, and more.

Can I cancel for a refund?

Yes. You can cancel at least 24 hours before the start time for a full refund. Cancellations or changes made within 24 hours are not refunded. If poor weather cancels the experience, you are offered another date or a full refund.