Private Day Charter Classic Sailboat

St John is at its best from the water, and this private charter gives you a full half-day aboard a classic 40-foot sailboat rather than a crowded sightseeing boat. Captain Mike may even let you take the helm, then guide you to two snorkeling spots, including a quiet anchorage near Honeymoon Beach.

I like the private six-person limit, which gives your group room to spread out and lets the captain shape the day around sailing, swimming, or sunbathing. I also like the all-in setup: lunch, snorkeling gear, drinks, a restroom, and a shaded cockpit are included.

The main consideration is the meeting arrangement. You meet at the Saint John Ferry Terminal in Cruz Bay, then take an inflatable tender to the sailboat. Private transportation is not included, so you need to arrange your own way to Cruz Bay.

Key points to know

• A true private charter: The boat is reserved for your party of up to six people.
• Captain Mike may teach you to sail: One guest received a hands-on sailing lesson, making this more than a simple boat ride.
• Two water stops: Expect snorkeling, swimming, or sunbathing, with the second stop at an anchorage near Honeymoon Beach and Caneel Bay.
• Lunch and a very open bar: Gourmet deli sandwiches, salads, beer, spirits, sparkling wine, soft drinks, juice, and water are included.
• Comforts rarely found on a small boat: You have a shaded cockpit, a working restroom, and WiFi onboard.
• Plan around the weather: Poor conditions can cancel the trip, with a new date or full refund offered.

Sailing away from Cruz Bay on a 40-foot boat

The day begins at the Saint John Ferry Terminal in Cruz Bay. From there, you take an inflatable tender out to the larger sailboat. This transfer is part of the character of the trip, but it is worth understanding before you book: you are not simply walking from a dock onto the charter boat.

Once aboard, the pace is relaxed. The boat gives you a proper sailing experience, not just a motorized ride with a sail raised for decoration. Captain Mike has been praised for clear instructions, careful handling, and an easy manner, and he has offered at least one passenger a chance to learn the basics of sailing.

That hands-on option can make the day special for families and curious first-time sailors. You can enjoy the ride from the shaded cockpit, or ask questions and take part when conditions allow. The experience is private, so the captain is not trying to entertain a large crowd or rush everyone through a fixed script.

The boat is large enough for six people, but the group limit matters. Six is a comfortable maximum for a private outing, especially when you add snorkel gear, lunch, drinks, towels, and the general movement that comes with getting in and out of the water. Couples and small families will have plenty of room. Six adults should expect a friendly, shared setup rather than the space of a large yacht.

What the private format changes

A private charter lets you spend your time according to your group’s mood. You can focus on sailing, get in the water at both stops, or spend more time resting in the sun. The listed duration is about four to five hours, so the captain has enough time to combine several activities without making the day feel like a series of rushed stops.

The private format also helps if your group has mixed interests. One person can snorkel while another stays aboard. Someone eager to learn sailing can ask for instruction, while others relax with a drink in the cockpit. On a shared boat, the group schedule usually wins. Here, your party has more say.

There is one tradeoff. A flexible private charter still depends on safe sailing and water conditions. You should not expect to dictate every stop or guarantee a particular wildlife sighting. The captain decides what is practical on the day, and weather can lead to a rescheduled trip or full refund.

Snorkeling at the first stop

The itinerary includes a couple of snorkeling stops in the clear waters around the Virgin Islands. Snorkeling equipment is provided for everyone, which saves you from renting masks, fins, and other gear separately.

The first stop is designed for time in the water. You can snorkel, swim, or stay aboard if you prefer. The appeal is simple: the boat takes you away from the most accessible shore areas and gives your group a chance to enjoy the water without a beach full of people immediately around you.

I would treat the snorkeling as an important part of the day, but not as a guaranteed wildlife expedition. The information provided does not promise specific fish, coral, turtles, or visibility conditions. Water clarity and marine life change with weather and sea conditions.

One guest described an unusual dolphin encounter in Scotts Bay, along with a beautiful snorkeling spot. That is a memorable possibility, not a standard part of the route. Book this for the sailing and water time, and consider any wildlife encounter a fortunate extra.

The boat’s size also matters here. You are not packed onto a large platform with dozens of swimmers. Your group can use the supplied gear, return to the shaded cockpit, and set your own pace.

The Honeymoon Beach anchorage near Caneel Bay

The second stop is a secluded anchorage off Honeymoon Beach near Caneel Bay. This is the quieter part of the itinerary, with time for another snorkel, a swim, or sunbathing.

Honeymoon Beach gives the stop a scenic setting, but the main value is the chance to slow down. After sailing and the first water stop, you can choose a gentle swim or stay aboard with lunch and a drink. If your party includes people with different energy levels, this second stop should work well because it does not require everyone to snorkel.

Do keep expectations realistic about the word secluded. The stop is described as a secluded anchorage, not a private beach or an isolated island. Conditions, boat traffic, and the day’s route can affect how quiet it feels.

This is also where the shaded cockpit and restroom become useful. A small boat can be tiring if everyone must sit in direct sun or wait for a shore facility. Here, you can take a break without ending the outing.

Lunch from North Shore Deli

Lunch is included, and the menu is more substantial than a basic bag of chips and fruit. You choose from nine gourmet deli sandwiches and five gourmet salads from North Shore Deli’s menu.

That detail adds real value to a half-day charter. You do not need to leave the water to find food, and you can keep the day moving without packing a separate meal. The menu also gives your group more choice than a single preselected sandwich.

The supplied information does not list each sandwich or salad, so check the available menu and mention dietary needs when you book. Do not assume that every special diet or substitution is covered unless the operator confirms it.

Lunch is paired with a generous drink selection. The bar includes beer, soda, juice, water, vodka, rum, gin, tequila, sparkling wine, and more. This works well for a celebration, a relaxed afternoon with friends, or a family group where some people want alcohol and others do not.

Drink responsibly on the water. The open bar is a convenience, not a reason to overdo it before snorkeling or sailing. Water, juice, soda, and soft drinks are available too.

Comfort aboard the boat

The shaded cockpit is one of the most practical features. St John’s sun can make several hours on the water feel long, especially when you are moving between swimming, eating, and sailing. Having a covered place to sit lets you enjoy the views without staying in direct sun the whole time.

A functional restroom is another major advantage. Small boats do not always have one, and the tender transfer makes it inconvenient to count on returning to shore. The onboard facility gives you more freedom to settle in for the full outing.

WiFi is also available. I would treat it as a useful extra rather than the point of the trip. You can stay connected when needed, but the best use of the charter is likely to keep your phone nearby for photos and let the sailing take up most of your attention.

Snorkeling equipment is included for all passengers. That lowers the hassle and makes it easier for an undecided passenger to join the group in the water. You can still choose to remain on deck, sunbathe, or enjoy lunch.

Captain Mike and the feel of the day

Captain Mike is the key personality in this experience. The strongest praise centers on his attentiveness, safety, clear communication, and ability to make people feel comfortable on the boat. He has also been described as an excellent bartender, which fits the informal character of a private charter with an open bar.

His nephew Beau, also involved on one outing, helped create a friendly and welcoming crew. The exact crew arrangement may vary, so do not assume he will be onboard every time.

The sailing lesson is a particularly useful detail. If you have always wanted to understand how a sailboat works, ask Captain Mike about participating. He may be able to give you a turn or explain what is happening, depending on the conditions and the needs of the group.

This is not a formal sailing course. It is a vacation charter with the chance for informal instruction. Still, that small opportunity can make the outing more memorable than sitting passively on a boat.

Is $1,395 a good value?

The price is $1,395 per group of up to six people. At the full six-person capacity, that works out to $232.50 per person. For four people, it becomes $348.75 each, and for two people, the per-person cost is much higher.

The value depends on how many people you bring and what you would otherwise pay for separately. The price includes a private sailboat, a captain and crew, snorkeling equipment, lunch, alcoholic and nonalcoholic drinks, use of the restroom and shaded cockpit, and WiFi. It also includes the privacy that comes with not sharing the boat with strangers.

For a full group, the cost is easier to justify. You are buying several hours of sailing, two water stops, food, and drinks in one package. A group celebrating a birthday, anniversary, reunion, or family vacation may find the private setting worth more than choosing a cheaper shared cruise.

For two people, compare carefully. The experience may still be exactly what you want, but the cost per person is high. The strongest reason to book for a couple is the private sailing atmosphere, not a bargain price.

Private transportation is not included. You need to factor in the cost and effort of reaching the Cruz Bay ferry terminal yourself. Pickup is listed as offered, but because private transportation is also listed as not included, confirm the pickup arrangement before paying for a transfer.

Who should book this St John charter?

I would recommend it for a group that values time on the water over a packed sightseeing schedule. It suits families, couples traveling with friends, and small groups that want privacy and flexibility.

It is also a good match for people who want more than snorkeling. The chance to sail a real boat, learn a little from Captain Mike, stop at Honeymoon Beach, eat a proper lunch, and relax with drinks gives the day variety.

Most people can participate, and service animals are allowed. The activity is near public transportation, but the meeting point is still the Saint John Ferry Terminal, so plan your arrival carefully.

You should think twice if your main goal is a long snorkeling session, a guaranteed dolphin encounter, or a low-cost group cruise. The outing combines sailing, food, drinks, swimming, and snorkeling in four to five hours. It does not promise a particular animal sighting or a full-day exploration of every bay.

Book as early as you can if your dates are fixed. This experience is often reserved about 65 days ahead, which suggests that popular vacation weeks may fill well before arrival.

Practical booking details

Confirmation is sent within 48 hours of booking, subject to availability. The tour returns to the same meeting point at the Saint John Ferry Terminal in Cruz Bay.

The listed operating dates cover the main travel seasons, with hours changing by date range. From March 26, 2019 through December 14, 2025, hours are listed as 8:00 AM to 9:00 PM daily. From December 15, 2025 through January 11, 2026, the hours are 9:00 AM to 9:00 PM, and from January 12 through December 10, 2026, they are also 9:00 AM to 9:00 PM.

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

Should you book it?

Book this charter if you want a private, easygoing day that mixes real sailing with snorkeling, swimming, lunch, and an open bar. The strongest reasons are the small group size, Captain Mike’s attentive approach, the chance to learn a little sailing, and the useful onboard comforts.

Skip it if you are mainly seeking the cheapest way to snorkel or if you need a fixed promise of dolphins, specific marine life, or a particular number of hours in the water. For up to six people, the price can be good value because so much is included. For only one or two people, it becomes a special-occasion splurge.

FAQ

Where does the private sailboat charter begin?

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

Where does the tour 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 sailing experience lasts approximately four to five hours.

How many people can join the private charter?

The charter is private for your group and allows up to six people.

Is transportation included?

Private transportation is not included. Pickup is offered, but you should confirm the exact pickup arrangement before booking.

Is lunch included?

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

What drinks are included?

The included drinks include beer, soda, juice, water, vodka, rum, gin, tequila, sparkling wine, and more.

Is snorkeling equipment provided?

Yes. Snorkeling equipment is available for all passengers.

Does the boat have a restroom?

Yes. The boat has a fully functional restroom and a shaded cockpit.

What happens if bad weather cancels the trip?

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