Three hours of pure sailing sounds perfect. This private charter on a 40-foot pilothouse mariner sails the waters between St. Thomas and St. John, with snacks and beverages included so you can stay relaxed and focused on the views.

You get real, friendly hosting, with Captain Rob and Captain Deb setting the tone from the dock. One possible drawback to plan around: this trip is built as a no-stop sail, so if you want a snorkel break, you’ll need to request it.

Key Highlights You’ll Actually Care About

• Private group of up to six means less waiting and more time on the water with your people
• Sailing-forward schedule with no pre-set stops keeps the vibe simple
• 40-foot pilothouse mariner is a solid size for a day on the sea, not a tiny boat experience
• Snorkel stop available on request if you want one taste of the water
• Snacks and beverages included (soda, bottled water, alcoholic beverages, snacks) so you do not need to bring much
• Sapphire Marina dock boarding makes it easy to get on and off without a long process

Simply Sailing from Sapphire Marina, the Easy Way

If you like your day on the water to feel calm and direct, this charter fits. You start at Sapphire Beach in Smith Bay, St Thomas, and you head out with one goal: sailing the Virgin Islands waters. The boat is a 40-foot pilothouse mariner, so it is set up for a proper charter experience rather than a quick skim around the harbor.

What I like most is how the experience is designed for low effort. Boarding is described as easy at the dock, you choose a morning or afternoon departure, and the charter includes the basics that usually slow people down. You do not have to stage a snack run. You also do not have to think about where your drinks come from once you are underway.

There is another practical win here. Because this is private, you are not working around a crowd. A group up to six keeps things comfortable and flexible in the moment. Even better, the captains, including Rob and Deb, have a reputation for warm, welcoming hosting. On the water, that small human factor matters, because it sets your pace from minute one.

The 3-Hour Sailing Time Budget, and Why It Works

This is about three hours on the water. That timing is short enough to feel effortless, but long enough to actually see the islands from multiple angles as you sail between St. Thomas and St. John waters.

A 3-hour charter can go two ways: either it feels rushed, or it feels like you got the point. This one leans toward the second option because the plan is simple. The format is pure sailing, with no planned stops. Translation: your day does not get eaten by transitions, brief sightseeing segments, and regrouping.

For you, that means the time mostly stays on the water, where the magic is. You get the visual payoff of moving sea views, coastline angles, and that slow-change feeling that only happens when you are actually sailing.

The one timing consideration is that you are choosing either a morning or an afternoon departure. If you are trying to line this up with other island activities, pick your slot based on how your day usually goes. Want the water early, before plans start stacking up? Choose the morning. Want a slower start and maybe cooler conditions later? Choose the afternoon.

Also, the charter requires good weather. When weather is cooperative, the schedule makes sense. If conditions are poor, plans may shift to a different date or you can receive a full refund, depending on what happens.

No Stops by Default, So the Sea Gets Most of the Attention

Here is the deal: this charter is built around not stopping. You go out and you sail. That might sound boring on paper, but on a good sailing day, it is often the best part.

Why? Because frequent stops can break the rhythm. If your goal is to enjoy the movement, the wind, and the horizon line as it keeps changing, then a no-stop sail is exactly what you want. You spend your time doing the thing, not waiting for the next segment.

That said, this is also where one possible mismatch can happen. If you are the type who wants set photo moments, beach time, or a rigid sightseeing checklist, the lack of stops can feel limiting. The good news is that you can add one snorkel stop if you request it. If snorkeling is a priority for you, make sure you plan for that request before you head out.

In other words, you get a very clean sailing experience, and you can add one optional water-focused break if it fits your interests.

Optional Snorkel Stop on Request, How to Think About It

Snorkeling is not automatically part of the standard flow. The charter can include a snorkel stop if you request it.

That matters for how you should think about the booking. If you want a snorkel moment, do not assume it is guaranteed. Decide what you want your time to accomplish:

• If you want maximum sailing time, keep it as pure sailing.
• If you want a quick snorkel break, request it and be ready for that to shape how the three hours are used.

Because your charter is three hours total, any added stop affects the pacing. You might still end up with plenty of sailing time, but your best payoff will come from setting expectations early. If you go in wanting one simple snorkel window, you will likely be happy. If you go in expecting long snorkeling sessions, you might feel shorted.

The practical tip: if snorkeling is important, communicate clearly when you book. Ask for the snorkel stop so the captains can decide what is possible based on conditions.

What’s Included on Board, and What That Actually Means for Your Day

The charter includes:

• Soda/pop
• Bottled water
• Alcoholic beverages
• Snacks

In real-world terms, that is a big value win. A private sailing outing can become expensive once you add drinks and snacks on the fly. Here, the essentials are handled. That keeps your budget more predictable, and it keeps the “day flow” smooth.

It also means you do not need to pack a complicated food plan. You can show up, hang out, and spend your energy on the views and the sailing itself.

One more detail that helps: the charter is a mobile ticket experience, so you likely will not be dealing with paperwork on site. That is a small thing, but small things reduce stress.

And since you are capped at six people, the included snacks and drinks also make it easier for everyone to enjoy the trip without the awkward “who brought what” moment.

Captain Rob and Captain Deb, and Why Hosting Quality Matters on Water

A private sail lives or dies on the crew vibe. When the captains are warm and upbeat, you feel the difference right away. Captain Rob and Captain Deb are specifically mentioned as welcoming and enthusiastic, which is exactly what you want on a sailing day.

Why does that matter? Because sailing is not just sitting on a boat. The crew sets expectations, helps you feel comfortable moving around, and keeps the experience running smoothly as conditions change.

Good hosting also makes a private charter feel more like a special outing and less like a transaction. If you have not been on the water in a while, that kind of guidance can turn an unfamiliar experience into something easy and fun.

This charter also has a stellar track record: 5 out of 5 rating with 19 reviews and a 100% recommendation rate. That tells me most people are leaving satisfied, which is a good sign that the service level stays consistent.

Price and Value: Is $799 for Up to Six a Good Deal?

The price is $799 per group, up to six people. The trip length is about three hours.

So the value question becomes: how many people are actually in your group, and what do you compare it to. If you are traveling as a couple or a small group, the per-person cost is higher than if you spread it across a full six. But the trade-off is privacy and a sailing-first schedule that avoids the big-tour churn.

Here’s the simple way I look at it. You are not paying only for time on the water. You are paying for:

• A private boat
• Included snacks and beverages
• A crew that guides the experience
• The ease of boarding at the dock

If you would otherwise pay for a standard tour plus add drinks and snacks, the included items start to matter. Even more, you get to choose your timing with morning or afternoon departures, and you get a simple, focused itinerary that keeps your day from turning into a schedule puzzle.

One more value factor: this is booked about 26 days in advance on average. That does not guarantee availability, but it hints that demand builds. If your trip dates are set, I would not wait too long.

Morning vs. Afternoon: Picking the Slot That Fits Your Mood

You can choose a morning or afternoon departure. That flexibility helps a lot, because it lets you match the charter to your other plans on St. Thomas and St. John.

I would choose the morning if you like a fresh start and you want your sail early in the day. That often pairs well with beach time later, or it can work as your “main event” that sets the tone for the rest of your day.

I would choose the afternoon if your mornings are busy or you want to let the day unfold first. An afternoon sail can feel like a slower reset, and it often works nicely when you want to stay flexible with the weather window.

Either way, keep in mind that the trip is weather-dependent. So if the forecast looks sketchy, the best play is to pick the time you feel most comfortable rescheduling.

Who This Private Sail Is Best For

This charter is a strong fit if you want:

• A private group experience for up to six
• A straightforward, sailing-first day with St. Thomas and St. John waters
• Included snacks and beverages to keep things easy
• The option of a snorkel stop, if you request it

It is also a good match for families and mixed-age groups who do not want a complicated schedule. The three-hour duration is manageable for many people, and the boat boarding is described as easy at the dock.

If you are the type who loves switching activities every hour, this might feel too simple. But if you want a calm, sea-focused outing with minimal interruptions, you will likely love the pacing.

And if you are celebrating something, a private sail with drinks and snacks already handled can be a clean, low-stress way to mark the moment.

Should You Book Simply Sailing from Sapphire Marina?

I would book it if you want a private charter that focuses on sailing, not checklists. The combination of a small group (up to six), included snacks and beverages, and the no-stop sailing format makes this feel like a true “time on the water” experience.

I would hesitate only if snorkeling is your main goal and you need it guaranteed, on a specific schedule. Because the snorkel stop is only added if requested, you need to be clear when you book.

Also, consider value. At $799 per group, it is best when you can fill out your party. If you have four, five, or six people, it starts to look more like a smart buy for a premium day on the sea.

If your dates work, and you want a simple, warm-hosted sail between St. Thomas and St. John, this is an easy yes.

FAQ

Where is the meeting point for the private sail?

You meet at Sapphire Beach, Smith Bay, St Thomas 00801, USVI. The activity ends back at the same meeting point.

How long is the Simply Sailing private charter?

The sail lasts about 3 hours.

How many people can be in the group?

This is a private tour for up to 6 people.

What’s included on board?

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

Is snorkeling included?

There are no stops by default. A snorkel stop can be added if you request it.

What is the trip like if there are no stops?

It is a sailing-focused outing with pure sailing time, sailing around St. Thomas and the waters of St. John.

Is crew gratuity included in the price?

No. Crew gratuity is customary at 20% of the trip.

What happens if the weather is poor?

This experience requires good weather. If it is canceled due to poor weather, you will be offered a different date or a full refund.

Can I cancel and get a full refund?

Yes, you can cancel for a full refund up to 24 hours before the experience’s start time. If you cancel less than 24 hours before, the amount paid is not refunded.