Floating in clear water feels like cheating. A private luxury sailing catamaran charter out of St. Thomas lets you pick your own reef stops (usually 2–3), then kick back on bean bags and hammock chairs while the boat glides. I especially love the choose-your-snorkel-stops freedom and the calm, smooth ride on Second Chance, with hosts like Ivy and TL and Captain James keeping everything organized. The one drawback to plan for is weather: the experience depends on good seas, and your day can shift if conditions aren’t right.

At about 4 hours 30 minutes, it’s long enough to snorkel, snack, and actually relax, but short enough to keep your whole trip moving. You’ll get a morning fruit and pastry tray, a turkey wrap-style lunch with chips, and water and soda around the day, plus snorkel gear and paddle boards included.

This works well for mixed-age groups, from adults to kids, and even includes service animals if you need them. One more consideration: alcohol is part of the package, but you have to be 18+ to drink.

Key highlights at a glance

• Private catamaran, not a crowded boat with Second Chance and your own group tempo
• Pick the snorkeling stops with options like Maho on St. John, Lovango Cay, and Christmas Cove
• Snorkel gear, paddle boards, and hammock swings included so you don’t waste vacation time shopping
• Food and drinks are built in: fruit + pastries, turkey/cheese/veggie wrap lunch, water, soda, rum punch, and light beer
• Hosts Ivy and TL plus Captain James help make communication easy and keep the day running smoothly
• You can plan for special moments at the right spot (they’ve supported a private water memorial at Christmas Cove on a charter)

St. Thomas by sail: what makes this half-day feel special

St. Thomas from the water is a totally different vacation mode. From the catamaran, you’re not stuck watching scenery through a bus window. You’re moving between islands, getting sun on deck, and choosing where to stop for the day.

The big reason this charter feels like a treat is the vibe: it’s a sailing catamaran, not a jostling powerboat. That smooth ride matters when you’re traveling with kids, aging parents, or anyone who doesn’t love bumpy rides. The boat layout also gives you real “do nothing” space, not just seats.

Second Chance is set up for hanging out. You can claim space on the bean bags up on the trampolines, swing off the hammock chairs at the back, or grab a paddle board when you want to work your core a little. If you want an all-water day without strict timing, this style of charter fits.

And you get to make it yours. The captain can help steer decisions, but the charter is private, so you’re not locked into someone else’s schedule. That freedom is a big part of the value at $250 per person.

Meeting in Red Hook: where you’ll start and end

You’ll meet at Beach Charters VI at VIDock B slip 19, 6501, St. Thomas, right by 201 Red Hook Rd (USVI 00802). The trip ends back at the meeting point, so you’re not stuck figuring out a second transportation step.

Bring what you’d normally bring for a water day: swimwear under clothes, sunscreen, and a small bag for your phone and wallet. You’ll also want to arrive with enough time to get squared away before you’re pushed out to the first stop.

This is handled with a mobile ticket, and the team provides confirmation at booking. Service animals are allowed too, which is helpful if your travel style includes them.

4.5 hours of food, drinks, and floating fun

This is a half-day charter, and the pacing is built for maximum comfort. You’re typically out long enough to snorkel multiple times, but short enough that you’re back in time to enjoy the rest of St. Thomas.

Here’s what’s included for eating and drinking:

• Morning fruit and pastry tray
• Turkey, cheese, and veggie wrap with chips for lunch
• Water and soda available through the day
• Alcohol included: one gallon rum punch (guest choice of rum punch or painkiller) and a 12-pack of light beer
• Ice is included

That mix is practical. Fruit and pastries before you get in the water help you feel human early. The wrap-style lunch keeps you from getting stuck on a sit-down meal while your day is slipping away. And having water and soda ready means you’re not hunting for a store between snorkel stops.

One clear rule: alcohol is only for 18+. If your group includes teens, kids, or anyone who doesn’t drink, the rest of the package still makes the day feel complete.

Also note: gratuities are not included. If you’re trying to budget, plan for that extra cost.

How your crew chooses 2–3 snorkeling stops

Most private charters make snorkeling feel like a compromise. This one avoids that by letting you choose locations. The typical plan is 2–3 snorkeling stops, and there are common options like:

• Maho on St. John
• Lovango Cay
• Christmas Cove
• and other possible sites depending on timing and conditions

The real advantage is flexibility. If your group wants more reef time, you can lean that way. If someone isn’t up for multiple stops, you can adjust the plan. In practice, that means your day feels tailored instead of rushed.

What you might see in the water depends on the reef and the day, but the common theme is variety. On charters like this, people often spot sea turtles, plus rays and lots of fish. There’s also been mention of seeing an octopus and even shipwreck-related details during snorkeling, which is exactly the kind of payoff you hope for on a “get in the water” day.

A smart tip: snorkel gear is included, but you should still do a quick check once onboard. Confirm the fit of your mask and the length of your snorkel time so you don’t waste time adjusting mid-stop. When the captain is ready to anchor or drift into position, you’ll want to be ready to go.

What to do between reefs: trampolines, bean bags, boards, and hammocks

Snorkeling is the headline, but you’ll have plenty of time to relax between stops. That’s where this catamaran shines.

On top of the trampolines, you’ll find bean bags and room to spread out. It’s sunbathing that doesn’t feel like punishment. You’re up high, looking at the water while the boat moves gently, and you can switch between shade and sun without fighting for a spot.

At the back, the charter includes hammock chairs that hang off the stern. If you’re traveling with people who don’t snorkel, this is often the best “activity” of the day. They get the ocean experience without the gear.

You can also use the paddle boards. That’s great fun for folks who want movement, but it’s also a way to explore the surface without committing to a full swim.

And yes, if you want to just watch the sea go by, you can do that too. The boat setup supports a low-stress pace.

One small detail that matters: because it’s private, you’re less likely to feel like you’re in a rotating schedule. Your group can stay at a stop as long as everyone’s comfortable before moving again.

Lunch timing and water comfort: why this setup works

A half-day trip fails when meals and drinks are an afterthought. This one doesn’t treat food like an optional extra.

That fruit and pastry tray helps you start without feeling empty or cranky. It’s especially useful if your group includes kids or older adults who don’t do well waiting for a later lunch.

The lunch itself is a freshly sliced turkey, cheese and veggie wrap with chips, plus soda and water. Wrap-style meals are easy on the stomach, and chips are easy on hands—perfect for eating without slowing the day down.

What I like about the inclusion list is that it removes small friction. Snorkel gear, paddle boards, ice, water, soda, and the drinks plan are already covered. You’re not stuck paying for each thing while you’re out on the water.

Alcohol on the water: fun with rules

Rum punch and light beer being included is a major reason this charter feels like a celebration cruise. The key is it’s structured: one gallon of rum punch (or painkiller) plus a 12-pack of light beer, all included.

The rule you can’t ignore is the 18+ requirement to consume alcohol. If your group has mixed ages, it’s smart to talk it through before you depart so everyone knows how you’ll handle it.

Also, remember gratuities aren’t included. If alcohol is part of your plan, budgeting a little extra for tipping makes the whole day feel more balanced.

Communication and crew care: Ivy, TL, and Captain James

The standout operational piece is how smooth the day feels when the planning is clear. Ivy and TL are the names you’ll hear connected to the booking and communication, and Captain James is part of the guiding team that keeps things running well onboard.

People also highlight help with transportation from a cruise port to their dock and back. If you’re in St. Thomas on a cruise ship, it’s worth asking about timing so you can get to Red Hook without stress.

On water days, tiny details matter: clear instructions, fast check-ins, and a captain who can read conditions and keep the group comfortable. When those pieces click, the charter feels easy.

There’s also been mention of dogs onboard—another reminder that this isn’t a stiff, formal setup. It’s more like a friendly private experience on a serious piece of sailing equipment.

Price and value: is $250 per person worth it?

At $250 per person, this isn’t a casual impulse buy. It’s a “we’re doing the fun thing for real” cost.

Where the value shows up is in what you don’t pay for separately:

• Snorkeling gear included
• Paddle boards included
• Hammock swings included
• Lunch included
• Water and soda included
• Rum punch and light beer included

Many boat outings charge extra for gear, drinks, and snacks, and they still leave you with a crowd. Here, you’re paying for privacy plus the parts that usually become add-ons.

This price tends to make the most sense when:

• your group wants a private day, not a shared schedule
• you care about snorkeling but don’t want to manage rentals
• you want real downtime onboard, not just transportation between stops
• you’re traveling with a family mix and want one plan that works for everyone

If you’re traveling solo and want quiet solitude, you can still make it work. The value is best when you can share the boat experience with a small group and get the most out of the half-day time window.

One more practical note: the average booking lead time is about 39 days. If you’re traveling during a peak window or on a holiday, booking earlier helps lock in your preferred timing.

Who should book this private charter?

This is a great fit if you want a St. Thomas day that feels flexible. You’ll likely enjoy it most if you:

• want to choose your snorkeling locations
• like the idea of a sail-powered, smooth ride
• want time for both snorkeling and relaxing
• appreciate a private format for families or anniversary-style trips

It also works well for multi-age groups. There’s been a charter described with kids to adults, plus older parents, where the day stayed fun because the boat offers options: snorkel for the people who want it, hammock time for the people who don’t, paddle boards for the adventurous.

If you’re someone who only tolerates water activities for 20 minutes, this might feel like too much. But if you like the idea of a water day with breathing room, it’s a strong match.

Should you book this half-day Second Chance charter?

Book it if your vacation goal is simple: clear water, good snorkeling odds, and a private sailing setup where food and drinks don’t become a second job. The mix of 2–3 reef stops, included gear, and onboard hangout spaces makes it feel like a complete half-day plan.

Pass or reconsider if:

• the group is very weather-sensitive and you don’t handle plan changes well
• you’re trying to do a tight schedule with no buffer (rough seas can affect timing)
• you’re strictly cost-minimizing and don’t value privacy

If you’re on the fence, here’s the deciding question: do you want control of where you snorkel, plus a comfortable boat day with real included extras? If yes, this is the kind of charter that turns a half-day into a highlight.

FAQ

How long is the private boat charter?

The experience lasts about 4 hours 30 minutes.

What snorkeling stops are available?

Your captain can arrange 2–3 snorkeling stops, and common options include Maho on St. John, Lovango Cay, and Christmas Cove, along with other possibilities. You get to choose your locations.

What’s included for food, drinks, and activities?

It includes a morning fruit and pastry tray, a turkey wrap with chips lunch, water and soda, snorkel gear, paddle boards, and hammock swings. Alcohol is also included: one gallon of rum punch (guest choice of rum punch or painkiller) and a 12-pack of light beer.

Is there alcohol included, and is there an age requirement?

Yes. Alcohol is included, but only travelers aged 18+ can consume alcohol.

Where do we meet for the charter?

You’ll start at Beach Charters VI, VIDock B slip 19, 6501 (201 Red Hook Rd), St. Thomas, USVI 00802, and the activity ends back at the meeting point.

What if weather is bad or I need to cancel?

There’s free cancellation up to 24 hours before the experience start time for a full refund. This experience requires good weather, so if it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

You Might Also Enjoy

Historical attractions of Alexander Hamillton Mother’s GravesiteDays End Sunset Sail Open Bar & Hors D’oeuvres STT Ritz-CarltonSmall Group Sea Turtle Tour (Guaranteed to see turtles)Cas Cay – Kayak Hike and Snorkel Adventure