Pure sailing, zero rushing. This private charter from Sapphire Marina takes you around St. Thomas and St. John at an easy pace, hosted by Capt Rob and Capt Deb who make boarding feel smooth and friendly. I loved the warm, personal welcome and the way the trip stays focused on being out on the water, though if you want frequent beach stops or lots of sightseeing checkpoints, this one is more about sailing than touring.

You pick a morning or afternoon departure, and you can request a snorkel stop if you want a little extra underwater time. With onboard snacks and alcoholic beverages plus soda and bottled water, you’re set up for comfort without having to plan every detail.

Key things to know before you go

• A true private boat for up to six: It’s only your group aboard the 40-foot pilothouse mariner.
• Three hours built for sailing time: The schedule focuses on time on the water, not constant stops.
• Capt Rob and Capt Deb are part of the experience: Their hosting style is part of why people leave happy.
• Optional snorkel stop on request: You can keep it simple sailing or add a water break.
• Snacks and drinks are included: Expect soda, bottled water, snacks, and alcoholic beverages onboard.
• Easy dock boarding at Sapphire Beach: You start right at the water, no long walk or complicated transfers.

A 40-Foot Pilothouse Sail From Sapphire Beach

This is the kind of charter that feels like a vacation plan instead of an activity checklist. You board at Sapphire Beach in Smith Bay, St. Thomas, and you’ll use the whole time sailing rather than waiting around for a sequence of stops.

The boat is a 40-foot pilothouse mariner, which matters because it gives you that more protected, practical feel on the water. Even when conditions are a little breezy, you’re not stuck out in the elements the whole time. And because the meeting point is right on the dock area, it’s also less stressful at the start. You show up, you step aboard, and you’re on the move.

From there, your route runs around St. Thomas and St. John. The real payoff is seeing the islands from the water level. From a boat, you get angles and depth you just don’t get from shore, and you can watch the coastline change as the boat turns. It’s the kind of perspective that makes the trip feel like more than just transportation from one place to another.

You also get a simple choice up front: a morning sail or an afternoon sail. If you like lighter morning vibes, mornings can feel fresh and calm. If you prefer the slower rhythm of later in the day, afternoons let you enjoy the water with a more relaxed pace.

Price and What You Get for $799 (Up to Six People)

The price is $799 per group, capped at up to six people. That’s how you should think about the value: you’re paying for a private experience with a whole boat’s attention on your group, not per ticket the way you’d do on a bigger tour.

If you fill the boat with six people, your effective per-person cost drops a lot compared with many private charters that price closer to a per-person model. And even if you don’t max out the six spots, you’re still buying the benefit that matters most here: your own time and space on the water.

What’s included is also part of the equation. You’ll have snacks, soda, bottled water, and alcoholic beverages onboard. That can save money and planning, because you don’t need to figure out what to bring for drinks and small bites. It’s a practical “vacation setup” bundle.

One cost detail to plan for: crew gratuity isn’t included. The customary rate is 20% of the trip, so I treat that as part of the real budget when deciding if this fits.

A small planning tip: this charter is often booked around 26 days in advance on average. If you have a specific day in mind, you’ll have an easier time locking it in if you book a few weeks ahead rather than hoping for a last-minute slot.

Simply Sailing Means No Fixed Stops, Just the Water

Here’s the core idea: this charter is built for simple sailing. It’s not set up like an island-hopping tour with constant anchoring, tendering, and rapid-fire sightseeing stops. The experience stays focused on being out there, moving through the water while you watch the islands slide by.

That approach is a strength, especially if you’re tired of tours that feel like you spend half your day lined up for the next photo spot. If what you want is a calmer, more personal time on the water, this fits that perfectly.

The one place where the trip can change is the snorkel option. There isn’t automatically a snorkel stop built into the plan, but you can ask to add one. That’s a good compromise for mixed groups: people who just want the sail get their wish, and anyone who wants a chance for underwater time can request it.

The possible drawback is also tied to that “no fixed stops” style. If your dream day includes lots of on-and-off sightseeing—beach time, quick walks, or multiple destination stops—this may feel too minimalist. Think of it as a water-focused experience first, and a snorkeling add-on only if you ask for it.

Snorkel Stop Options and How to Think About Them

If you’re considering snorkeling, the key is understanding the tradeoff. You’re buying a charter where the default is sailing time, and snorkeling is a request-based addition. That means you should be ready for the fact that snorkeling depends on conditions and what the crew can safely do during your charter window.

The good news is that the crew is flexible about adding a snorkel stop if requested. That gives you control over your balance of “pure sailing” versus “time underwater.”

If you’re traveling with a group that includes beginners or non-swimmers, the structure can actually help. You can ask for the snorkel stop for the people who want it, while others can relax onboard and enjoy the sail. Just keep expectations realistic: this is still a 3-hour charter, so it’s more about adding one short water moment than turning it into a full snorkeling excursion.

Snacks, Alcohol, and the Right Pace for a 3-Hour Charter

The onboard food-and-drink setup is one of the most practical parts of this experience. You’ll have snacks, bottled water, and soda, plus alcoholic beverages included. That combination is what turns a private boat ride into a true “show up and relax” day.

Because the drinks and snacks are already part of the charter, you don’t need to pack for that part of the day. You can focus on the essentials that actually change your comfort: sunscreen, sunglasses, and whatever you use to stay comfortable in sun and salt air.

The pacing also helps. In three hours, you don’t want a chaotic schedule, and you don’t need one. The sailing style here is built for a slow shift in scenery rather than a checklist of stops. It feels good for couples who want quality time and for families who want a calm break from walking-heavy vacation days.

There’s also something specific people seem to appreciate about the hosting. In particular, Capt Rob and Capt Deb set a welcoming tone right from boarding. One family experience described the start as warm and enthusiastic, and another noted how the captains were great hosts and good for people who hadn’t been on the water in years. That matters because on a small private charter, the crew’s vibe becomes part of the whole thing.

Timing, Weather, and Booking Smart at Sapphire Marina

You’ll choose either a morning or afternoon departure, and the total time on the water is about 3 hours. That’s a sweet spot. It’s long enough to feel like a real outing, but short enough that you’re not giving up your whole day.

Plan around weather. The experience requires good weather, and if it’s canceled due to poor conditions, you’ll be offered a different date or a full refund. That’s standard for sailing, but it’s worth keeping in mind when you pick your day and when you’re building the rest of your schedule.

If you’re trying to be strategic, think about what you want most from the sail: morning can feel bright and fresh, afternoon can feel more relaxed as your day winds down. Either way, you’re still in control of the feel because it stays focused on sailing rather than rushing through multiple stops.

Also, look at the booking timing. With an average booking window around 26 days in advance, you’ll likely get the best selection by booking early if your dates are firm.

On the logistics side, you’ll use a mobile ticket, and the meeting point is described as being near public transportation. That’s useful if you’re not driving or you’re coordinating rides.

Who This Private Sail Works Best For

This is a great fit for people who want a private boat day without turning it into an all-day production. Since it’s a private tour with only your group onboard, you’re not negotiating crowd noise or waiting for other schedules.

It also makes sense for mixed groups. If some people just want to relax and enjoy the water, they can do that. If others want a snorkel break, the crew can add one when requested. The charter’s structure makes it easier to keep everyone content.

Families can also like it, especially if you’re after a memory-making outing that doesn’t require nonstop hiking. One family-focused experience emphasized that the whole time felt special from the moment they stepped aboard, and the captain-host attention helped set that tone. If you’re coming with kids or adults who get tired quickly, the “stay on the water” format is often the right kind of easy.

Couples and friends also tend to benefit because the boat time feels personal. You can talk, take photos, and watch the islands move past without feeling like you’re sprinting to a new stop.

Who might not love it: anyone who wants a packed itinerary with multiple structured stops and land activities. This is pure sailing as the main event, with snorkeling as an optional add-on.

Should You Book This Simply Sailing Charter?

I’d book it if your ideal day in St. Thomas is about time on the water, not about ticking off a long list of sights. The value is strongest when you treat it as a private boat experience with snacks and drinks included, and when you’re okay with a schedule that stays simple.

You should also book if you want the vibe of being welcomed and guided by a captain team that clearly enjoys hosting. Capt Rob and Capt Deb show up again and again in guest feedback for being warm and easy to enjoy, and that kind of crew matters on a small charter.

Only skip it if you’re looking for a busy itinerary with frequent beach time. If you want a lot of on-land exploring, this may feel too focused on sailing.

If you’re flexible about weather and you plan your day around a three-hour window, this is exactly the kind of charter that can turn into a top memory from your trip.

FAQ

How long is the Simply Sailing Private Sail charter?

It’s about 3 hours.

What’s the group size limit for the private charter?

The price is for up to 6 people per group.

Where does the tour start and end?

It starts at Sapphire Beach, Smith Bay, St Thomas 00801, USVI and ends back at the same meeting point.

What’s included onboard?

Included items are soda/pop, bottled water, alcoholic beverages, and snacks. Easy boarding access at the dock is also included.

Can I request a snorkel stop?

Yes. A snorkel stop can be added if requested.

What happens if the weather is bad or I need to cancel?

The experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund. You can cancel for a full refund up to 24 hours in advance of the experience’s start time.