Private Day Charter Classic Sailboat

Set sail, snorkel, and let someone else handle the day. This private St John charter gives you a 40-foot sailboat, two water stops, lunch, drinks, and room for only your own group. I especially like the personal feel of having Captain Mike at the helm, with past guests praising his calm manner, clear instructions, and willingness to teach sailing. I also like the value for a group of six, since the $1,395 price works out to $232.50 per person before any private transportation costs.

The main consideration is the weather. This is an outdoor sailing trip, and rough conditions can change or cancel the plan. The charter lasts about four to five hours, so it offers a fine half-day on the water, but it is not a full-day cruise with hours to explore several islands. You also need to reach the Saint John Ferry Terminal in Cruz Bay on your own unless an arranged pickup applies to your booking.

Key points to know before booking

• A private 40-foot sailboat means your group of up to six gets the boat, crew, and schedule without strangers aboard.
• Captain Mike is a major part of the experience, with a reputation for attentive service, clear safety guidance, and hands-on sailing instruction.
• Two water stops give you time for snorkeling, swimming, or simply stretching out in the sun.
• Honeymoon Beach near Caneel Bay is the named second anchorage, a scenic place to settle in after sailing.
• Lunch and a broad open bar are included, with deli sandwiches, salads, beer, wine, spirits, soft drinks, juice, and water.
• A shaded cockpit, onboard restroom, WiFi, and snorkeling gear make this more comfortable than a bare-bones boat outing.

Starting at Cruz Bay and boarding by tender

Your meeting point is the Saint John Ferry Terminal in Cruz Bay. This is the practical center of St John, so you will need to plan your own way there unless your booking includes a pickup arrangement. Private transportation is not included in the charter price.

From Cruz Bay, you take an inflatable tender out to the 40-foot sailboat. That small transfer is part of the outing, not just a detail at the dock. If you have mobility concerns, keep in mind that boarding involves moving between the ferry terminal area, the tender, and the sailboat. Service animals are allowed, the meeting point is near public transportation, and the operator says most people can participate.

Once you are aboard, the private format begins to matter. You are not sharing the boat with a large crowd, and your party can settle into the shaded cockpit, watch the crew manage the boat, and enjoy the coast at a slower pace. Captain Mike is known for being attentive without making the day feel stiff or formal. One especially nice touch is his willingness to let interested passengers try some sailing under his guidance.

That sailing lesson is not guaranteed as a formal part of every departure, but it has been a memorable feature for some people. If you have ever wanted to understand how a sailboat responds to the wind, ask Captain Mike. He has also been praised for explaining what passengers need to do clearly, which helps first-time sailors feel useful instead of nervous.

Sailing out from St John

The sailing portion is the backbone of the trip. Rather than rushing from one swimming stop to another, you spend time moving across the Virgin Islands waters aboard a classic sailboat. The boat gives you a different view of St John than you get from a road or beach. You can watch the shoreline recede, feel the wind, and take in the open water without the noise of a packed excursion boat.

The pace depends on the conditions and the captain’s plan. A sailboat is not a speedboat, which is part of its charm and part of the tradeoff. I like this trip best for people who want the journey itself to count. If your only goal is to reach a snorkeling site as quickly as possible, a faster powerboat may suit you better.

The crew also brings a relaxed social rhythm to the boat. The open bar includes beer, soda, juice, water, sparkling wine, vodka, rum, gin, tequila, and more. That is generous for a four to five-hour charter, but drink sensibly. Sun, wind, salt water, and alcohol can catch up with you faster than expected.

The shaded cockpit gives you a place to get out of the sun. The onboard restroom is another practical advantage, especially for a private group that does not want to cut the outing short for a shore break. WiFi is also available on board, though the real point of the trip is to look up from your phone now and then.

The first snorkeling stop

The first stop is set aside for snorkeling in the clear Virgin Islands waters. The exact location is not specified, so you should think of this as a captain-selected stop rather than a fixed attraction with a guaranteed reef, beach, or wildlife sighting.

Snorkeling equipment is provided for everyone. That saves you from packing fins, masks, and other gear, and it also makes the experience easier for a mixed group. Strong swimmers can spend more time in the water, while others can choose to swim briefly or remain on board.

The boat format gives this stop a useful advantage: you reach water spots that may not be as simple to access from shore. That does not mean every stop will have perfect visibility or a large concentration of fish. Sea conditions change, and snorkeling depends on wind, water clarity, and the day’s local conditions. Still, having a captain who can choose the stop helps keep the outing flexible.

If snorkeling is important to you, tell the crew early. Captain Mike has been praised for finding enjoyable spots and for paying attention to what each group wants. You may prefer a longer swim, a quieter anchorage, or more time sailing. A private charter gives you a better chance of discussing those preferences than a large scheduled cruise.

Honeymoon Beach near Caneel Bay

The second stop is a secluded anchorage off the shoreline of Honeymoon Beach near Caneel Bay. Here, you can snorkel again, swim, or stay aboard and sunbathe. The stop is less about checking off another attraction and more about giving you a pleasant stretch of unhurried water time.

Honeymoon Beach is a strong choice for the second stop because it offers several ways to enjoy the hour. You do not need to be an enthusiastic snorkeler to have a good time. One person can swim, another can use the provided gear, and someone else can sit in the shaded cockpit with a drink and lunch.

A few people have had unusually memorable wildlife encounters in the area, including a reported swim with dolphins near Scotts Bay. Treat that as a lucky possibility, not a promised feature. The charter’s dependable offer is sailing, snorkeling, swimming, sunbathing, food, and drinks. Wildlife sightings are always a bonus.

The second anchorage also helps break up the day. After the boat ride and first swim, you can eat lunch, relax, and enjoy the view without feeling pushed back into the water. If you are traveling with children or a mixed-age family group, that flexibility is worth more than a tightly timed series of stops.

Lunch from North Shore Deli

Lunch is included, and the menu comes from North Shore Deli. You can choose from nine gourmet deli sandwiches and five gourmet salads, with the full menu available for the charter.

That is a better setup than a single fixed sandwich for everyone. A private group may include different appetites and dietary preferences, so having several sandwich and salad choices makes the meal easier to manage. You should still check the available selections when booking if anyone in your group has allergies or strict dietary needs, since no specific allergy policy is provided.

Lunch also fits the pace of the outing. You can eat in the shaded cockpit between swimming and sailing, rather than losing time going ashore. The meal is not a restaurant stop, so do not book this expecting a long table service lunch. It is a convenient boat meal that lets the water time continue.

Bring only what you need. The charter already covers snorkeling equipment, food, drinks, and the boat’s basic comforts. A swimsuit, sun protection, and a towel are sensible choices, but the supplied information does not list a formal packing list.

What Captain Mike adds to the day

The boat matters, but the captain often decides how a private charter feels. Captain Mike has earned strong praise for being thoughtful, safe, friendly, and clear about what passengers need to do. Those qualities are especially useful on a small boat, where good communication affects both comfort and safety.

His role is not limited to steering. He has taught passengers the basics of sailing, helped groups find good snorkeling water, and kept the atmosphere light. One memorable account even praised his skills as a bartender, thanks to the drinks service on board.

A family group can benefit from that personal approach. So can a couple celebrating a special occasion, a group of friends who want a private day, or anyone who finds large cruises too noisy and impersonal. The crew has also included a relative named Beau, sometimes referred to as Bo, who has been described as friendly and helpful.

The private setting gives you more room to speak up. Tell the captain if you want more sailing, more swimming, a quieter pace, or help with the snorkeling gear. You are paying for a private boat, so use that advantage.

Is $1,395 a fair price?

The $1,395 price covers the entire group, up to six people. With six aboard, the cost is $232.50 per person. For four people, it becomes $348.75 per person, and for two people, it is $697.50 each.

That makes the charter strongest for a full group of six. You receive a private boat, crew, snorkeling gear, lunch, a large selection of drinks, a restroom, shaded seating, and WiFi. A comparable shared cruise may cost less per person, but it will not offer the same privacy or control over the pace.

The price is harder to justify for only two people unless privacy is the main goal or you are marking a special occasion. You are not simply buying transportation to a snorkeling site. You are paying for the whole boat and a personal sailing experience. If that sounds like the heart of your St John plans, the cost can make sense.

Remember that private transportation is not included. You need to account for getting to the Saint John Ferry Terminal in Cruz Bay. Pickup is offered as a feature, but confirm the exact arrangement before you rely on it.

Timing, weather, and who should book

The trip runs about four to five hours. That length works well if you want a major water activity without surrendering the entire day. It also leaves room for a beach, dinner, or other plans, though you should allow flexibility around the return time.

The charter requires good weather. If poor conditions force a cancellation, you are offered another date or a full refund. You can cancel for a full refund up to 24 hours before the start time. Inside 24 hours, the amount paid is not refunded, and changes are not accepted.

I would recommend this outing to:

• A group of up to six who wants a private day on the water
• Families who need swimming, sunbathing, food, and shade in one plan
• Couples or friends celebrating a special occasion
• First-time sailors who would enjoy a hands-on lesson
• People who prefer a calm, personal boat experience to a large shared cruise

I would hesitate if you dislike boats, want guaranteed wildlife sightings, need a fully fixed itinerary, or prefer a fast ride with many stops. The open water is the point here, and the day works best when you are comfortable letting the captain adjust to conditions.

Should you book this St John sailing charter?

Book it if you can fill most of the six seats and want the boat to feel like your own floating base for the day. The strongest reasons are the private setting, Captain Mike’s attentive style, the chance to try sailing, and the rare combination of snorkeling, lunch, drinks, and shaded comfort.

Before paying, confirm the pickup details, the lunch choices, and any needs related to mobility or food allergies. Then check the forecast and keep your schedule loose. For a group that values personal service over the lowest possible price, this is a polished and highly enjoyable way to see St John from the water.

FAQ

Where does the private sailing 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 at the Saint John Ferry Terminal.

How long does the charter last?

The sailing experience lasts approximately four to five hours.

How many people can join the private charter?

The private charter accommodates up to six people per group.

Is lunch included?

Yes. Lunch includes choices from North Shore Deli, with nine gourmet deli sandwiches and five gourmet salads.

Are drinks included?

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

Is snorkeling equipment provided?

Yes. Snorkeling equipment is available for all passengers.

Is there a restroom on the boat?

Yes. The sailboat has a fully functional onboard restroom and a shaded cockpit.

What happens if the weather is poor?

If poor weather causes the charter to be canceled, 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.