Private sailing off St. Thomas feels effortless. This charter takes you out on a 40-foot pilothouse mariner with easy dock boarding at Sapphire Marina, and it’s built for pure time on the water with snacks and drinks included. I like the laid-back feel of a simple sailing route around St. Thomas and St. John, plus the welcome from Captain Rob and Captain Deb, which makes the whole trip feel smooth. One thing to consider: it’s weather-dependent, and a snorkel stop is only added if you request it.

You also get real scheduling flexibility with a morning or afternoon departure, and the group limit of up to six people keeps it truly private. It’s about three hours on the water, then you return back to Sapphire Beach, Smith Bay. For me, that combo is the value: fewer logistics fights, more sailing time.

Key Points at a Glance

• Private charter for up to six on a 40-foot pilothouse mariner
• Morning or afternoon departure to match your day
• Snacks plus soda, bottled water, and alcoholic beverages onboard
• Pure sailing time around St. Thomas and St. John
• Snorkel stop available on request
• Easy dock boarding at Sapphire Beach, Smith Bay (Sapphire Marina area)

From Sapphire Beach to Open Water in Minutes

The best part of this sail is how quickly you can switch into vacation mode. You start at Sapphire Beach in Smith Bay on St Thomas, right where the marina experience is set up for boarding, so you’re not fighting with remote docks or long walkways. You also come right back to the same meeting point at the end, which makes planning the rest of your day easier.

Because it’s a private group charter (not a shared cruise with strangers), the whole vibe stays calmer. You can talk, take photos, and actually relax without waiting for a bunch of people to gather. The mobile ticket format also helps—no paper hunt, no extra steps at the dock beyond what you’d expect for boarding.

The Boat and the Crew: Captain Rob and Captain Deb

This is operated by Sailing The Cosmos Charters, and the experience is clearly shaped by the crew’s tone. In the reviews, Captain Rob and Captain Deb come through as warm hosts, the kind of people who make you feel welcome as soon as you step aboard. That matters more than many people think. On a three-hour trip, there’s little time to “settle in” later—your first five minutes set the mood.

The ship is a 40-foot pilothouse mariner. A pilothouse style boat usually means you’ve got a more protected area for steering and viewing, which can be helpful when the sun is high or the breeze gets a bit spicy. I also like the practical footprint: it’s big enough for comfort, but still small enough that you don’t feel lost in a crowd.

Most travelers can participate, and since this is your group only, it’s a good fit if you want a trip that feels tailored to your pace.

What “Simply Sailing” Means Around St. Thomas and St. John

This is not a hop-on, hop-off sightseeing tour with a lineup of stops. It’s built around one idea: get out on the water and stay there. You’ll sail the waters around St Thomas and St John, with the goal of soaking in sea views from a moving vantage point.

Here’s why that matters for your trip. From the water, coastlines read differently. Coves, bays, and shorelines don’t look like they do from the road or from a single viewpoint. Even if you’ve seen plenty of photos already, the angle you get during an actual sail tends to feel more “real” and less like a postcard.

A possible drawback: if you’re hoping for multiple timed land-based photo stops or a long list of named landmarks, this style may feel too simple. The experience stays focused on sailing, not structured stops.

About the optional snorkel stop

You can request a snorkel stop. That’s great if you want one active moment without turning the whole trip into a schedule. The flip side is that you shouldn’t assume it’s automatic—request it up front when you book (or as soon as you can after booking). Also, since the charter needs good weather, snorkeling timing and feasibility can depend on conditions.

If you like snorkeling, it’s smart to plan like you might do it: bring a simple swim-ready setup if you have one, and wear what you’d be comfortable getting wet in. Since gear isn’t listed as included, I’d come prepared with your own essentials if that’s part of your plan.

Food, Drinks, and the Real Value of “Included”

The charter includes snacks, soda/pop, bottled water, and alcoholic beverages. That’s not just a nice extra. On a short three-hour outing, “included” food and drink can be the difference between paying for little add-ons all day or actually treating it like a complete experience.

For $799 per group (up to six people), you’re paying for the boat time plus the crew service, not for a ticket per person. So the real value depends on how you’ll use that group size. If you can fill closer to six seats, the cost spreads out in a way that feels much more reasonable. If it’s only two people, it’s still a private charter, but you’ll feel the per-person price more.

Also, because drinks are included, you can keep the mood easy. This is the kind of outing where you can skip the “where are we eating next” scramble. Just remember that alcohol is part of the package, so if anyone in your group isn’t drinking, still plan to enjoy the ride comfortably—bottled water is included, and you’ll want it in the heat.

Pricing for Up to Six: When $799 Feels Fair

Let’s talk straight. $799 is a lot of money if you think in per-person terms. But for a private sailing charter, it’s normal that you pay for the whole group experience.

What makes this one feel like better value is the combination:

• Private time on a 40-foot boat
• Snacks and multiple drink options included
• A set duration of about three hours, so you get a clear chunk of time on the water
• A “simple sailing” format that keeps things easy, with the option of one snorkel stop if requested

Timing also matters for value. The average booking lead time is about 26 days. That’s a clue that popular dates can go fast, especially if you’re traveling in busier seasons. Booking earlier gives you a better shot at the departure window you want (morning or afternoon).

If you’re trying to decide between a shared cruise and a private charter, ask yourself this: do you want the freedom to set your own pace and keep your day simpler? If yes, private sailing often wins even when the headline price looks high.

Scheduling Your Morning or Afternoon Like a Pro

You can choose a morning or afternoon departure. That choice is more useful than it sounds. Morning often means you can get sailing done before the rest of the day’s plans, which is great if you’re hopping between sights on St Thomas. Afternoon can be a nice way to break up your day and still get plenty of time back on land afterward.

Since you only have about three hours, treat it as a true anchor activity. Plan around it, not on top of it. You’ll want a little buffer for getting to Sapphire Beach, taking care of anything you need before boarding, and then letting the sailing clock run without rushing.

One practical plus: the meeting area is near public transportation. If you don’t want to rely on renting a car for the whole trip, that can help you keep the day simpler.

Weather and Expectations: Plan for Good Conditions

This experience requires good weather. That’s not a small footnote; it’s the whole game with sailing. If conditions aren’t right, the trip can be rescheduled or refunded, depending on what the provider offers when weather turns.

So here’s my advice: book it with flexibility in mind. If you’re only in town for one day, you’ll have less cushion if weather changes. If you can build in time for a backup date, you’ll sleep better.

Who This Sail Works Best For

This charter is a strong match if you want:

• A private outing with a small group (up to six)
• More time on open water, less time on busy logistics
• A calm, straightforward plan around St Thomas and St John
• Included snacks and drinks so you can focus on the sailing

It’s also a good choice for families or small groups who want a special activity without stacking a lot of separate tours. In one review, the trip was described as a way to be out on the water again after many years, which says a lot about the accessibility of the experience and how it can feel welcoming.

If you want a heavily structured, stop-by-stop sightseeing day, this might feel too simple. If you want a relaxed “out there on the sea” feel, you’ll likely love it.

Should You Book This Private Sail from Sapphire Marina?

I’d book it if you’re looking for a short, high-comfort, private sailing experience with snacks and drinks included and a focus on sailing around St Thomas and St John. The biggest reason to choose it is also the simplest: it keeps the day focused. You’re not wrestling with multiple stops, crowds, or complicated pacing.

Skip it if your top priority is a tour packed with land stops, lots of scheduled photo stops, or snorkeling that you’re counting on without needing to request it.

If you want an easy win for your time on St Thomas, this one is a solid bet—especially when you can fill more seats in your group.

FAQ

Where does the Simply Sailing Private Sail start?

It starts at Sapphire Beach, Smith Bay, St Thomas 00801, USVI.

How long is the private sail?

The experience lasts about 3 hours.

How many people can be in a group?

It’s priced for a group of up to six people.

Is this a private tour?

Yes. It’s private, so only your group participates.

Is a snorkel stop included?

A snorkel stop isn’t automatically included. It can be added if you request it.

What’s included onboard?

The charter includes snacks, soda/pop, bottled water, and alcoholic beverages.

What should I budget for if I want to tip?

Crew gratuity is not included. It’s customary to tip about 20% of the trip.

Do I need paper tickets?

No. It uses a mobile ticket.

What happens if weather is poor?

The experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Is there a cancellation window?

You can cancel up to 24 hours before the experience’s start time for a full refund.