Simply Sailing Private Sail from Sapphire Marina

If you like your island time simple, this private sail is a great match. It’s a private 3-hour charter on a 40-foot pilothouse mariner, cruising the waters of St. Thomas and St. John out of Sapphire Marina.

I especially like two things. First, the group stays small, up to six people, so you get an easy, unhurried feel. Second, the charter includes snacks and drinks, including soda, bottled water, and alcoholic beverages.

One consideration: this is a sailing-focused outing with no scheduled stops. You can request a snorkel stop, but it won’t turn into an island-hopping day with lots of shore time.

Key highlights you will actually care about

• Private charter with time on the water as the main event
• Captain Rob and Captain Deb run the experience with a warm, personal touch
• 40-foot pilothouse mariner for a more comfortable sail
• Snacks, soda, bottled water, and alcoholic beverages included
• Optional snorkel stop if you request it
• Meet at Sapphire Beach, Smith Bay, and return to the same dock

A private 40-foot sail that keeps the day simple

This charter is built around one idea: you spend your time sailing, not waiting. You head out from Sapphire Beach in Smith Bay and cruise the St. Thomas and St. John area with the goal of pure time on the water.

You are not signing up for a checklist of land stops. That can be a plus if you want calm, scenery, and a slower pace. It can also be the wrong fit if you are hoping for a multi-stop tour where you hop on and off all day.

The boat matters here. A 40-foot pilothouse design typically gives you more cover and comfort than smaller open boats, which is handy when the sun is strong or the wind picks up.

St Thomas to St. John waters: what you will experience during the 3 hours

Your core day is a 3-hour sailing window, with the charter ending back at the meeting point. During that time, you will be out in the waters around St. Thomas and St. John, enjoying views from a different angle than you get on land.

Because the experience is described as simply sailing, the rhythm is straightforward. You settle in, enjoy the ride, and let the coastline and shoreline scenery do the work. If you are the type who loves photos, you will get plenty of opportunities just by being on the water rather than stopping constantly.

The main “add-on” is snorkeling. The charter can include a snorkel stop if you request it, so you can shape the day slightly toward swimming and underwater exploring. The tradeoff is simple: a snorkel stop uses part of your 3 hours, so you are balancing swimming time against extra sailing time.

Sapphire Beach, Smith Bay: the easy start you want on vacation

The meeting point is Sapphire Beach, Smith Bay, St Thomas 00801, USVI, and the charter ends back at the same spot. This kind of out-and-back plan keeps logistics easy, especially if you are pairing it with dinner plans, beach time, or another activity later.

I also like that the location is near public transportation. That matters because you are less locked into one way of getting there. If you are staying somewhere convenient to Smith Bay, you can likely keep your day flexible without stressing about timing too much.

Because boarding is described as easy at the dock, you can expect a straightforward start. In a private charter, that is a big deal. When getting on the boat is painless, you spend less energy on transitions and more energy on the actual experience.

Choose morning or afternoon, then let the water set the pace

You can book a morning or afternoon departure. That matters more than it sounds. A morning sail often feels quieter and cooler, while an afternoon sail can give you a different light on the islands.

Either way, the trip is designed to last about 3 hours, so you still have a full chunk of your day left for beaches, lunch, or exploring. If your schedule is tight, a half-day charter that returns to the same dock can be easier to place than a full-day boat tour.

One more practical point: the experience requires good weather. If conditions are poor, the operator will adjust with another date or a full refund. That flexibility is comforting when you are planning around island weather.

Included onboard: snacks and drinks that make the charter feel complete

This charter takes care of the basics that usually cost extra on group tours. You get snacks, soda/pop, bottled water, and alcoholic beverages included as part of the trip.

For me, this is one of the strongest value points. On a private sail, the boat itself and the captain’s time are what you are paying for, so having food and drinks included removes the “nickel and dime” feeling that can happen with other charters.

You can also treat this as a more relaxed way to enjoy the islands. Instead of coordinating a stop for refreshments, you can stay in vacation mode. Eat something, sip something, and focus on the water and the coastline as it slides by.

If you are the kind of person who wants a simple, no-fuss outing for your group, included onboard items help a lot. It makes the private experience feel more like a full service day rather than just transportation.

Snorkel stop by request: how to decide if you want it

A snorkel stop can be added if requested. That means you do not have to commit in advance if you are not sure. If you are curious about underwater time, you can ask and see what fits the day.

Here is how I would think about the choice. If your group is mostly there for sailing views and relaxing, you might enjoy keeping the entire chunk as sailing time. If you have at least a few people who are excited to swim and snorkel, adding a stop can turn the day into a more varied outing.

Remember, the charter duration is about 3 hours. So snorkeling is not an all-day activity, and it will likely be a shorter window. Still, for many groups, a brief snorkel break is enough to make the trip feel special without turning it into a rushed, stop-and-go schedule.

Captain Rob and Captain Deb: the hospitality that people remember

The private sailing experience is run by Sailing The Cosmos Charters, and the captains named in guest feedback are Captain Rob and Captain Deb. The standout theme in their hosting style is warmth and enthusiasm from the moment you step aboard.

That kind of welcome matters more than people think. On a private charter, you are not just buying a boat ride. You are relying on the crew to help you feel comfortable, to keep the trip running smoothly, and to make sure the day fits your group.

One guest shared that the experience was incredible for their family, and that the views were breathtaking. Another highlighted how Deb and Rob were great hosts and how it had been years since they had been out on the water. Both are good signals: this is not only a scenery day, it is also an experience that feels welcoming even if you have not sailed in a long time.

Value math: when $799 per group actually feels fair

The price is $799.00 per group, up to six people. If you do the simple split math, that’s about $133 per person when you reach six passengers.

That comparison is useful, because your cost per person drops fast with group size. If you go as a couple, your per-person cost is higher, and you are paying more for privacy and convenience. If you go with a group of friends or family and hit closer to six, the included snacks and drinks make the charter feel much more like good value.

Also, this is a private charter on a 40-foot boat, not a shared sail with strangers. You are paying for the entire setup: captain-led time on the water, a small group, and onboard refreshments. For many groups, that combination is exactly what they want in St. Thomas: a half-day experience that feels personal and easy.

One more practical note: this charter is booked on average about 26 days in advance. That suggests it is popular enough that you should plan ahead rather than hoping a slot opens up last minute.

Who this private sail is best for, and who should pass

This is a great fit if you want time on the water as the main event. It works well for couples who want a quieter day, families who want a comfortable boat outing, and friend groups who want privacy without a huge time commitment.

It is also a good choice if your group likes an easy schedule. You get a half-day, you return to the same dock, and you do not have to line up food stops since snacks and drinks are included.

Where it might not fit: if your dream day includes multiple land stops, extensive shore touring, or a full itinerary packed with activities. This charter is about sailing, with snorkeling only if you request it.

If anyone in your group is sensitive to weather changes, keep in mind the experience requires good weather. The operator can offer another date or a full refund if poor weather cancels the trip, which helps you plan with less stress.

Should you book this simply sailing charter?

Yes, if your group wants a private sail focused on scenery and relaxed time. The included snacks and drinks, the small group size, and the captain-led hospitality from Captain Rob and Captain Deb are exactly the kind of details that turn a boat ride into a memorable afternoon or morning.

I would skip it only if you need lots of on-shore stops, or if you are looking for a snorkeling-centered day rather than a sailing-first experience. If your goal is simple, calm, and beautiful, this one is a strong bet.

FAQ

How long is the private sail from Sapphire Marina?

The charter lasts about 3 hours.

What boat is used for the experience?

It’s run on a 40-foot pilothouse mariner.

Where do we meet, and where does the trip end?

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

What is included onboard?

Snacks, soda/pop, bottled water, and alcoholic beverages are included.

Can we add a snorkel stop?

Yes. A snorkel stop can be added if requested.

Is this tour private, and how many people can join?

It is private, and only your group participates. The group size is up to six people.

Is crew gratuity included in the price?

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

What happens if the weather is poor?

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

When can we cancel for a full refund?

You can cancel up to 24 hours in advance for a full refund. If you cancel less than 24 hours before the start time, the amount paid is not refunded.