Simply Sailing Private Sail from Sapphire Marina

The best part of this charter is its simplicity. You board at Sapphire Beach, settle onto a 40-foot pilothouse mariner, and spend about three hours under sail around St. Thomas and St. John. There is no forced beach stop or busy group schedule. You can simply enjoy the water, or request time to snorkel.

I like the private six-person limit, which makes the $799 price easier to justify for a family or small group. I also like that snacks, bottled water, soda, and alcoholic drinks are included, so you do not need to pack a floating picnic. The main consideration is that the standard plan has no stops, and the 20 percent crew gratuity is extra.

Key points to know before booking

• Private sailing for up to six: The $799 rate covers your whole group, not each person separately.
• A true sailing-focused outing: The standard trip keeps moving around St. Thomas and St. John instead of building in several scheduled stops.
• Optional snorkeling: Ask for a snorkel stop when arranging the charter if that matters to your group.
• Captains Rob and Deb host the Cosmos: Their warm welcome and easygoing style are a major part of the experience.
• Morning or afternoon departures: You can fit the three-hour cruise around the rest of your St. Thomas plans.
• Simple dock access at Sapphire Beach: The trip starts and ends at Sapphire Beach in Smith Bay.

Sailing the Cosmos from Sapphire Beach

This is a small, private charter for people who want time on the water without a packed boat. The meeting point is Sapphire Beach in Smith Bay, on the east side of St. Thomas. You receive confirmation when you book, and the area is near public transportation.

Boarding is described as easy, with access right at the dock. That matters in St. Thomas, where a day on the water can become tiring before the boat even leaves if you must manage a long transfer or awkward entry. Here, the setup is more direct: arrive at Sapphire Beach, board the boat, and get underway.

The activity lasts about three hours. You can choose a morning or afternoon departure, which gives you useful control over the rest of the day. A morning trip can leave your afternoon open for the beach or another island activity. An afternoon sail gives you a relaxed way to break up a busy sightseeing day.

Your group has the entire boat to itself. The private format is especially useful when people in your party want different things. One person can focus on the views, another can enjoy a drink, and someone else can ask about snorkeling without affecting a large group schedule.

What the three-hour route feels like

The standard plan is pure sailing around the waters of St. Thomas and St. John. You are not promised a string of stops, a formal sightseeing lecture, or a packed list of attractions. The value comes from the time itself: open water, island views, wind, and a boat shared only with your own party.

That makes this a good match for anyone who finds organized excursions too busy. You do not have to keep checking the clock for the next activity. You can sit back, watch the shoreline change, and enjoy seeing the islands from the water instead of from a road or hotel terrace.

The boat is a pilothouse mariner, which gives the outing a more substantial feel than a tiny open skiff. The available details do not promise a particular seating layout or cabin arrangement, so I would not book this expecting a specific luxury setup. The important point is that you have a 40-foot private sailing platform and a crew focused on your group.

The route includes the waters around both St. Thomas and St. John. Exact sailing paths can vary, and no particular bay or landmark is guaranteed. That flexibility is part of the appeal, but it also means you should not treat this as a fixed sightseeing itinerary with named stops.

Why a no-stop sail can be the right choice

Many boat outings try to fit in snorkeling, beach time, lunch, and sightseeing in a single half-day. That can be fun, but it can also leave you feeling as if you spent the day moving from one task to another.

This charter takes the opposite approach. The regular plan is simply to sail. I like that clarity. If your group already has beach plans and only wants a calm stretch on the water, there is no need to spend part of the trip climbing in and out of the boat.

A no-stop plan also suits people who prefer a quieter outing. You can use the time to talk, take photos, watch the islands, and enjoy the motion of the boat. A family that praised the experience after sailing aboard Cosmos described making special memories with Captains Rob and Deb. Another party enjoyed seeing the islands from a different perspective after many years away from the water.

There is one obvious drawback. If your main goal is snorkeling, this is not automatically a snorkel tour. A stop can be added if requested, but you should make that request before the trip rather than assume it will be part of the standard route. The available information does not specify the snorkeling location, equipment, or length of the stop.

Captains Rob and Deb and the feel onboard

The charter is operated by Sailing The Cosmos Charters, with Captains Rob and Deb hosting the trip. Their names are worth noting because the human side of a private boat charter can matter as much as the route.

The feedback attached to this experience repeatedly praises the captains as warm hosts. One family specifically highlighted how warmly Rob and Deb welcomed them aboard. Another described them as great hosts during a beautiful afternoon sail. That points to an outing that feels personal rather than transactional.

I would choose this charter if you want a crew that helps set a friendly tone while leaving room for your group to enjoy itself. At the same time, the available information does not promise a formal narration or a detailed history talk. If you want a highly structured island tour with constant commentary, ask about the style of the trip before booking.

The boat is called Cosmos in the available comments. That detail gives the experience a personal identity and helps distinguish it from an anonymous boat transfer. You are not just buying transportation between two points. You are hiring Rob and Deb for a private period on the water.

Drinks, snacks, and what is included

The charter includes snacks, soda, bottled water, and alcoholic beverages. That is a useful inclusion on a three-hour sail, especially if you are booking for a small group and do not want to organize supplies before arriving at the marina.

The drinks also make the morning or afternoon format more flexible. You can keep the outing light with water and soda, or enjoy an alcoholic drink while sailing. The supplied information does not list specific brands, snack choices, or cocktail service, so contact the operator if someone in your group has dietary needs or wants a particular beverage.

The inclusion of alcohol is not a reason to treat the boat like a floating bar. You are still on a moving vessel, and a comfortable pace is best. Bottled water is provided, which is important in the Caribbean sun even on a breezy day.

Because food and drinks are included, I would compare the total cost with the cost of booking several seats on a larger sailing trip and then buying refreshments separately. The private setting is the bigger value here, but the onboard supplies make the price easier to understand.

Is $799 a good value for six people?

The listed price is $799 per group of up to six people. At full capacity, that works out to about $133 per person before gratuity. A customary 20 percent crew gratuity would add about $159.80 to the group bill, bringing the approximate total to $958.80, or about $159.80 per person for six people.

That is a different calculation from a per-person excursion. If only two people book, the effective cost rises to about $399.50 each before gratuity. For a couple, this is a premium private outing. For a family or group of six, the price becomes much more reasonable.

I see the strongest value in the privacy. You are paying for a boat reserved for your group, a three-hour sailing experience, easy dock boarding, and drinks and snacks. You are not paying for a long list of scheduled attractions. If you want snorkeling, confirm that the requested stop fits within the same charter and ask if any extra charges apply, since no added fee is stated.

The gratuity deserves attention when budgeting. It is not included in the advertised price, and 20 percent is customary according to the trip details. I would plan for it from the start rather than treat it as an unexpected add-on at the dock.

Who will enjoy this private sail most?

I would recommend this outing to a group that values time and privacy more than a packed itinerary. It suits families, close friends, and couples willing to pay for a boat that is not shared with strangers.

It is also a good choice for people who have already done the main St. Thomas sights and want a different view of the islands. One of the strongest details from the available feedback is the pleasure of seeing St. Thomas and St. John from the water after many years. That perspective can make familiar places feel fresh again.

The charter may work well for a mixed-age group because most travelers can participate, and the boat has easy boarding access at the dock. Still, the activity is on the water, and the operator requires good weather. Anyone with specific mobility needs should confirm details before booking, since the information only states that boarding is easy and does not give full accessibility specifications.

I would not make this my first choice if your group wants a guaranteed snorkeling session, a beach picnic, or a long list of stops. The normal plan is sailing without stops. Requesting a snorkel stop may solve that concern, but it changes the simple rhythm of the outing.

Timing, weather, and cancellation

The charter runs in the morning or afternoon and returns to Sapphire Beach. The return to the original meeting point is convenient because you do not need to arrange a separate ride from another harbor.

Good weather is required. If poor weather causes the operator to cancel, you are offered a different date or a full refund. That policy is sensible for a sailing trip, but you should leave some flexibility in your vacation schedule if the boat is an important part of your plans.

You can cancel for a full refund up to 24 hours before the experience begins. Cancellations or changes made less than 24 hours before the start time are not accepted for a refund. The cut-off follows local time in St. Thomas, so check the clock carefully if you are arranging the trip from another time zone.

Booking tips for a smoother sail

Reserve ahead if your dates are fixed. The experience is booked an average of 26 days in advance, which suggests that popular vacation weeks may fill before you arrive.

When booking, be clear about three things:

• Tell Rob and Deb if you want a snorkel stop rather than the standard no-stop sail.
• Count everyone in your group carefully, since the $799 price covers up to six people.
• Add the customary 20 percent gratuity to your budget.

You should also decide if morning or afternoon better suits your plans. The choice is not just about convenience. A morning sail leaves time later for other activities, while an afternoon departure lets you keep the morning free and still get several hours on the water.

Use the mobile ticket and keep your booking confirmation available. The meeting point is Sapphire Beach, Smith Bay, St. Thomas, and the trip ends there as well.

Should you book the Simply Sailing charter?

Book it if you want a private, easygoing sail with no crowd and no forced schedule. The best reasons are the six-person format, the time spent sailing around both St. Thomas and St. John, the included snacks and drinks, and the personal hosting of Captains Rob and Deb.

Think twice if your priority is a guaranteed snorkel stop or a packed sightseeing route. You will need to request snorkeling, and the standard experience is intentionally simple.

For six people, the cost is fair for a private three-hour charter, especially when you include the refreshments and avoid paying for separate seats on a larger boat. For two people, it is a splurge. The 5 out of 5 rating from 19 ratings and a 100 percent recommendation record support the idea that this works best when you value warm hosts, beautiful views, and unhurried time on the water.

FAQ

Where does the sailing charter start?

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

Where does the activity end?

The charter ends back at the Sapphire Beach meeting point.

How long does the sailing experience last?

The experience lasts approximately three hours.

How many people can join the private charter?

The $799 group price covers up to six people.

Are food and drinks included?

Yes. Snacks, soda, bottled water, and alcoholic beverages are included.

Is snorkeling part of the regular plan?

No. The standard plan is sailing without stops, but you can request a snorkel stop.

Can I choose a morning or afternoon departure?

Yes. The charter offers a morning or afternoon departure.

What happens if bad weather cancels the trip?

If poor weather causes cancellation, you can choose a different date or receive a full refund.