Amazing Half Day Private Boat Charter on Luxury Sailing Catamaran

The best St. Thomas days happen offshore. This private four-and-a-half-hour sail aboard the catamaran Second Chance combines reef snorkeling, quiet coves, island views, lunch, drinks, and plenty of space to relax. Since your group chooses the stops, the outing can feel easygoing rather than locked to a fixed route.

I especially like the private format, which gives families and friends control over the pace and swimming locations. I also like the thoughtful inclusions: snorkel equipment, paddle boards, hammock chairs, lunch, fruit, pastries, rum punch, beer, soda, and water are all provided.

The main consideration is the cost, $250 per person, which makes the most sense for a group that will use the boat fully. Four and a half hours passes quickly, and the exact number of snorkeling stops depends on your choices, weather, and conditions.

Key points at a glance

• Choose your own water stops: Possible locations include Maho on St. John, Lovango Cay, and Christmas Cove, with other options available.
• A true private charter: Only your group participates, so you are not sharing the boat with strangers.
• More than a swim stop: You can snorkel, paddle board, sit in hammock chairs, or stretch out on bean bags over the catamaran’s trampolines.
• Food and drinks are covered: Expect morning fruit and pastries, turkey, cheese and vegetable wraps, chips, soda, water, one gallon of rum punch or painkillers, and a 12-pack of light beer.
• A good choice for mixed ages: Families can split up by activity, with some people snorkeling while others relax aboard.
• Weather matters: Poor conditions can lead to a date change or full refund, and changes or cancellations must be made at least 24 hours ahead.

Leaving Red Hook aboard Second Chance

The charter begins at Beach Charters VI, at VIDock B, slip 19, located at 6501 St. Thomas, 201 Red Hook Road. The boat returns to this same meeting point at the end, which keeps the day simple if you are staying near Red Hook or using nearby public transportation.

The sailing catamaran itself is part of the appeal. A catamaran gives you broad areas to sit and move around, rather than one narrow deck where everyone is packed into the same spot. You can settle on the bean bags over the forward trampolines, take a seat in the hammock chairs hanging off the stern, or move around when you want a different view.

I like that this is not presented as a race from one stop to the next. The ride between locations gives you time to look across the water toward St. Thomas, St. John, and the smaller cays. You also get the pleasant motion of a sailing boat, although the crew may use the engine when needed to keep the schedule and route practical.

The private setup matters most here. A standard group cruise has to follow a preset plan, even when the sea conditions or the group’s energy suggest another choice. On Second Chance, you can discuss the route with the captain and shape the outing around your own party.

That flexibility is useful for families with young children, older relatives, or a group with mixed interests. One person can snorkel, another can paddle board, and someone else can stay dry with a cold drink and a view.

The first hour: fruit, pastries, and a choice of route

A morning fruit and pastry tray starts the food service. It is a small but useful touch, especially if you are arriving from a hotel, cruise ship, or early morning transfer and do not want to organize breakfast before reaching the dock.

After the boat gets underway, you can settle into the day and talk through possible stops. Common choices include Maho on St. John, Lovango Cay, and Christmas Cove. The route is not guaranteed, since the captain must work with weather, sea conditions, timing, and your group’s preferences.

Maho on St. John is a strong choice for a scenic swim and snorkel stop. Lovango Cay offers a different setting, with the appeal of a smaller island environment and open water around the boat. Christmas Cove is another popular possibility and has also been used for quiet, personal moments on private sunset outings.

You should not treat the suggested locations as a promise of specific animals or underwater sights. Conditions change from day to day. Still, the range of possible stops gives you a useful mix of island scenery, swimming water, and snorkeling opportunities.

Two or three snorkeling stops, at your own pace

A typical half-day includes two or three snorkeling stops. That is enough variety to keep the water time interesting, while still leaving room for sailing, lunch, and relaxing aboard.

All snorkeling equipment is supplied, so you do not need to pack fins, masks, or snorkels unless you prefer using your own. The boat also provides paddle boards, giving you another way to enjoy a calm anchorage without spending the entire day swimming.

The snorkeling itself may be the main reason to book this charter. Past outings have included sightings of turtles, rays, many fish, an octopus, and even a shipwreck. Those sightings are not guaranteed, but they show the range of marine life and underwater features that can appear at the chosen sites.

The private format helps if your group has different comfort levels in the water. Strong swimmers can spend more time snorkeling, while less confident swimmers can remain close to the boat or use the paddle boards. You can also skip a stop or shorten your time in the water if someone becomes tired.

One practical point: do not assume every stop will suit every person equally. A reef stop may be exciting for a confident swimmer but less appealing to someone who prefers sunbathing. That is exactly where a private charter earns its keep, since you can adjust the day instead of asking the whole boat to follow one person’s plan.

Time aboard the boat between stops

The spaces between anchorages are not wasted time. You can sit on the trampolines, use the bean bags, take in the views, or settle into one of the hammock chairs at the back.

Those hammock chairs are a particularly nice feature for anyone who wants the feeling of being over the water without getting wet. They also give older family members or less active members of the group a comfortable place to enjoy the outing.

The crew has received strong praise for being attentive and friendly. Names connected with the charter include Ivy, TL, and James, although the exact crew working your departure may vary. Good communication has also been part of the experience, including help arranging transportation from a cruise port on some occasions.

That kind of personal attention can make a big difference on a private boat. You are not simply being dropped at a beach and left to organize yourself. The crew can help with equipment, timing, drinks, and the practical details of moving between activities.

Lunch and drinks without extra planning

The included lunch is a turkey, cheese, and vegetable wrap with chips. Soda and water are available throughout the outing, so you do not need to bring a large supply of drinks.

The food is straightforward rather than elaborate, but that is appropriate for a boat day. Wraps are easy to eat, chips require no utensils, and the meal will not slow down the schedule. The morning fruit and pastry tray adds a second food moment before lunch.

The alcohol package includes one gallon of rum punch or painkillers, based on your group’s choice, plus a 12-pack of light beer. You can enjoy a drink while anchored or during the ride, but anyone drinking should still take care in the sun and around the water.

Alcohol is available only to people aged 18 and over. Gratuities are not included, so plan to tip separately if the crew provides the kind of service you value.

What the private price means for your group

At $250 per person, this is not a budget sightseeing cruise. The value depends heavily on the size of your group, how much time you spend on the water, and how much you would otherwise pay for separate snorkeling, paddle board rental, food, drinks, and transportation.

For a couple, the total price may feel substantial. You are paying for privacy, a luxury catamaran, flexible routing, a dedicated crew, equipment, meals, and drinks. If your main goal is simply a quick swim, a less expensive shared cruise may be enough.

For a family or group of friends, the calculation improves. You are dividing the private boat experience among your own party, and you do not have to compromise with an unrelated group about music, swim time, lunch timing, or the number of stops.

The charter can also be good value for a special occasion. One party used it for an 80th birthday and a 60th anniversary, giving older family members a way to see the US Virgin Islands from the water without committing to a full-day outing. Another private trip centered on spreading cremated remains at Christmas Cove, where the group could have a quiet and personal moment.

Those examples show the range of this charter. It can be an active snorkeling morning, a family celebration, or a calm private sail with swimming added when the mood strikes.

Who should book this half-day sail

I would recommend this experience to families, couples traveling with relatives, groups of friends, and cruise passengers who want a private outing rather than a crowded boat. It is especially useful when your group has different ideas about what makes a good day on the water.

Families with older children and teens can make good use of the range of activities. Strong swimmers can snorkel, active people can use the paddle boards, and anyone who wants a quiet hour can stay on the deck with a drink.

It also suits multigenerational groups. The boat offers ways to participate without requiring everyone to swim or climb in and out of the water repeatedly. That said, you should consider your group’s mobility and comfort before booking, since this remains a boat-based activity with swimming stops.

The charter is also a sensible choice for a special event. Sunset cruises are available in the wider charter offering, and the boat has been used for family celebrations and meaningful private ceremonies. The supplied information focuses on the half-day daytime charter, so confirm the exact timing and meal plan if you want a sunset departure.

Timing, meeting point, and planning details

The advertised duration is about four hours and 30 minutes. That is long enough for two or three water stops, but not so long that everyone becomes worn out from sun, swimming, and boat motion.

You should arrive at the Red Hook meeting point with enough time to find VIDock B and slip 19. The activity ends at the same location. The area is near public transportation, and transportation assistance from a cruise port has been arranged for some groups, but you should confirm your own transfer needs before departure.

A mobile ticket is accepted, and confirmation is provided at booking. Service animals are allowed, and most people can participate, although you should consider individual mobility and swimming ability when deciding if this is suitable for your party.

The charter requires good weather. If conditions force a cancellation, you can receive a different date or a full refund. If you need to cancel yourself, do it at least 24 hours before the start time for a full refund. Changes made inside that 24-hour window are not accepted, and the local time in St. Thomas controls the deadline.

Small drawbacks to keep in mind

The main weakness is the limited time. Four and a half hours sounds generous when you book, but once you allow for departure, movement between locations, snorkeling, lunch, and the return to Red Hook, you cannot cover every possible island stop.

The private nature also means that your group has to make decisions. Some people enjoy choosing the route, while others would rather have a fixed schedule and no discussion. Before boarding, it helps to agree on your priorities: snorkeling, swimming, paddle boards, sightseeing, or simply relaxing.

The $250 price excludes gratuity, and there is no promise of particular wildlife. You are buying access to excellent water time and a flexible boat, not a guaranteed turtle, octopus, ray, or shipwreck sighting.

Finally, the outing depends on weather. That is true of any boat charter in the Virgin Islands, but it matters more when you have planned the day around a private celebration or cruise schedule.

Should you book Second Chance?

Book this charter if you want your own boat, your own pace, and a mix of snorkeling and relaxation. It is a particularly good fit for a group that values privacy, needs flexibility, or is marking a birthday, anniversary, family reunion, or other important day.

Skip it if you are traveling alone, watching every dollar, or mainly want a short inexpensive swim. For the right group, the price buys much more than transportation between beaches: it buys control over the day, room to spread out, equipment, food, drinks, and a crew focused on your party.

My best advice is to agree on your priorities before you arrive. Tell the crew if your group wants more snorkeling, more time at anchor, or a gentler outing for older relatives. With that plan in place, Second Chance offers an easy and memorable way to see the waters around St. Thomas and St. John.

FAQ

Where does the private catamaran charter begin?

The charter starts at Beach Charters VI, VIDock B, slip 19, at 6501 St. Thomas, 201 Red Hook Road, St. Thomas 00802, USVI.

Where does the activity end?

The charter returns to the same meeting point at the end of the outing.

How long does the charter last?

The experience lasts approximately four hours and 30 minutes.

Is this a private activity?

Yes. Only your own group participates in the charter.

How many snorkeling stops are included?

A typical outing includes two or three snorkeling stops, depending on the selected route and conditions.

Which locations might the boat visit?

Possible stops include Maho on St. John, Lovango Cay, and Christmas Cove, along with other locations chosen for your private trip.

Is snorkeling equipment included?

Yes. Snorkeling equipment is provided for use during the charter.

Are paddle boards included?

Yes. Paddle boards are included, along with hammock swings and hammock chairs on the boat.

What food and drinks are included?

The package includes a morning fruit and pastry tray, a turkey, cheese, and vegetable wrap with chips, soda, water, one gallon of rum punch or painkillers, and a 12-pack of light beer.

Who can drink alcohol on the charter?

Alcohol is available only to people aged 18 and over. Gratuities are not included.

Can I cancel for a full refund?

You can cancel at least 24 hours before the experience start time for a full refund. Cancellations or changes made less than 24 hours before departure are not accepted for a refund.

What happens if the weather is poor?

If the charter is canceled because of poor weather, you will be offered another date or a full refund.