Simply Sailing Private Sail from Sapphire Marina

Leave the shore behind for three quiet hours. Simply Sailing gives you a private 40-foot pilothouse mariner for a relaxed outing between St. Thomas and St. John, with Captain Rob and Captain Deb hosting the trip aboard Cosmos. I like the easy dock boarding at Sapphire Beach and the fact that the boat is reserved for your group alone.

I also like the choice of a morning or afternoon departure, plus the snacks, soft drinks, bottled water, and alcoholic beverages included in the fare. The main consideration is that this is built around sailing, not a busy string of beach stops. The standard plan makes no stops, although you can request a snorkel stop.

Key points about this Sapphire Beach sailing trip

• A private 40-foot boat for up to six: Your party gets the whole charter, which makes the outing more personal and easier to shape around your group.
• Three hours on the water: The time is focused on sailing around St. Thomas and St. John rather than rushing through several activities.
• Morning or afternoon departures: You can fit the sail around other plans in St. Thomas.
• Snacks and drinks are included: Soda, bottled water, alcoholic beverages, and snacks are provided onboard.
• Snorkeling is available by request: The normal plan is pure sailing, but you can ask to add a snorkel stop.
• Sapphire Beach is the start and finish: Boarding is at the dock, and the activity returns to the same meeting point.

Setting out from Sapphire Beach

The meeting point is at Sapphire Beach in Smith Bay, St. Thomas. That simple arrangement matters. You do not need to hunt for a second pickup location or arrange a separate boat transfer. The activity begins and ends at the same place, with easy boarding access at the dock.

You receive confirmation when you book, and the location is near public transportation. Still, I would allow enough time to reach Sapphire Beach without cutting it close. A private boat cannot wait forever for a late arrival, and a calm start is part of the pleasure of a short sail.

The boat is a 40-foot pilothouse mariner named Cosmos. That gives you a more substantial platform than a small open runabout, while keeping the group size limited to six people. The pilothouse design also suggests a boat made for spending time on the water, not simply racing from one stop to another.

Captain Rob and Captain Deb are the hosts named in the available guest feedback. Their warm welcome and easy company received repeated praise, which is especially important on a private charter. You are not joining a large crowd and hoping the crew notices your group. The tone is personal from the start.

Three hours of pure sailing

The heart of the trip is wonderfully simple: you sail around the waters of St. Thomas and St. John. The standard outing has no scheduled stops. You spend the time moving under sail, watching the islands from the water, and enjoying a slower pace than you get on many motorboat excursions.

That focus is the biggest reason to book this charter. If you want a quiet morning or afternoon with the wind, open water, and island views, the plan gives you exactly that. One guest described seeing the islands from a different perspective, which is the real point of the outing. From the water, the familiar shore becomes part of a wider scene.

I appreciate that the trip does not try to cram too much into three hours. There is no promise of multiple beaches, a full lunch, or a long list of activities. You get time to settle into the boat and let the sail itself be the activity.

The tradeoff is clear. If your ideal boat day includes several swim stops, a beach picnic, and a packed schedule, this may feel too restrained. The trip is called Simply Sailing for a reason. You should book it for the sailing, not because you expect a full-day island tour in miniature.

Seeing St. Thomas and St. John from the water

The route takes you around St. Thomas and beautiful St. John, though the exact sailing path is not specified. That leaves room for the crew to shape the outing around conditions and the day’s plans, but you should not expect a fixed list of named bays or landmarks.

The appeal is the broad view. From the boat, you can enjoy the relationship between the two islands rather than seeing only one beach from shore. You might find yourself paying attention to the changing views, the motion of the boat, and the simple pleasure of being away from roads and resort activity.

This is also a good choice if your group has mixed interests. One person can enjoy the sailing, another can take in the views, and others can snack or have a drink. Since the charter is private, you do not have to match the pace or preferences of a boatload of strangers.

The available comments describe the day as a beautiful afternoon and praise the chance to be on the water after many years. That detail is useful. This is not only for serious sailors. The experience is also aimed at people who want a pleasant, accessible way to spend time at sea.

The optional snorkel stop

The regular plan is no stops and pure sailing. If you want to add snorkeling, you need to request it. That distinction is important when you book. Do not assume a snorkel stop is automatically part of the three-hour schedule.

Adding snorkeling can make the charter more flexible for a group with different priorities. One person may want the calm rhythm of sailing, while another may want time in the water. The crew is happy to include a snorkel stop if requested, but the provided details do not identify a specific snorkel site or promise a particular amount of time in the water.

I would make your preference clear before departure. Asking in advance gives the crew a chance to account for the added stop while planning the sail. If every minute under sail matters to you, keep the standard route. If your group would regret missing a chance to snorkel, request the stop when arranging the trip.

Snacks, drinks, and the easygoing pace

The charter includes snacks, soda, bottled water, and alcoholic beverages. That is a useful benefit on a three-hour outing. You can settle in without arranging separate drinks for the boat, and the onboard refreshments help keep the experience relaxed.

The inclusion also adds value to a private charter, where the headline price can look high at first. You are paying for the boat, crew, private use, and refreshments in one package. You do not need to treat the trip as a bare boat rental with a long list of add-on costs.

Drink responsibly, of course, especially on a moving boat. The information provided does not specify the exact selection of snacks or alcoholic beverages, so I would not book this expecting a particular brand, meal, or cocktail menu. Think of the food and drinks as pleasant provisions, not a full dining service.

There is also something nice about not having to interrupt a short sail for lunch. Three hours passes quickly. Having snacks onboard lets you keep your attention on the water instead of searching for a meal during the outing.

What the private price really means

The cost is $799 per group of up to six people. For a full group, that works out to about $133 per person before gratuity. That is a reasonable way to view the price because the booking is for the boat, not six separate seats.

For four people, the base price comes to about $200 per person. For two, it is about $400 each. The charter becomes much better value as your group approaches six, so I would first see who wants to join before deciding.

A customary 20 percent crew gratuity is not included. On the $799 fare, that gratuity would be $159.80, bringing the total to about $958.80 if you choose the customary amount. For six people, that is about $159.80 per person including the tip.

That final figure helps you compare the outing honestly with other St. Thomas activities. You are paying more than you would for a large shared boat, but you receive privacy, a small group, flexible conversation, and a quieter format. If privacy matters, the premium can make sense. If your main goal is the lowest possible cost on the water, a shared excursion may suit you better.

Morning or afternoon: choosing your best time

You can choose a morning or afternoon departure. The best option depends on the rest of your day and on the kind of outing you want.

A morning sail works well if you want to make the boat trip the main event before other plans. It can also leave your afternoon open. An afternoon sail gives you a slower second half of the day and may suit you if you want a relaxed activity after spending the morning elsewhere in St. Thomas.

Because the entire trip lasts about three hours, timing matters more than it would on a full-day charter. Look at your plans before and after the sail, and leave room for getting to and from Sapphire Beach. The trip returns to the starting point, so you can plan around that fixed finish.

The available comments praise a grand afternoon on a beautiful day, but that should not be read as a promise about every departure. This is a weather-dependent activity. A sunny island forecast does not guarantee perfect sailing conditions at the exact time of your booking.

Weather, cancellation, and practical planning

You can cancel for a full refund up to 24 hours before the start time. Changes made less than 24 hours before departure are not accepted, and cancellations inside that window are not refunded. The cut-off follows local time in St. Thomas.

The operator can cancel because of poor weather. If that happens, you are offered another date or a full refund. I would keep a little flexibility in your vacation schedule if the sail is important to you, especially during a short visit.

Most people can participate, and the experience is private to your group. The information provided does not list special mobility details beyond easy boarding access at the dock, so if anyone in your party has particular access needs, ask the operator before booking.

A mobile ticket is available, which makes it easy to keep the confirmation with you. Bring your booking details and arrive ready for a dockside boarding rather than expecting a hotel pickup.

Who will enjoy Cosmos most

This charter is a strong match for couples, families, and small groups who want a private boat without filling a whole day. It also suits friends who would rather talk, watch the islands, and enjoy a few drinks than follow a loud, tightly timed program.

It is especially appealing if someone in your group loves sailing itself. Many boat outings use sailing as a way to reach a swim site. Here, sailing is the destination. That difference should guide your decision.

Families can appreciate the private format because the group does not need to adjust to strangers. Couples may like the quieter setting. A group of six gets the strongest price value, while a party of two should think carefully about the per-person cost.

I would choose another activity if your priority is extensive snorkeling, several beach landings, or a full-day cruise. The optional snorkel stop adds choice, but it does not change the basic character of the experience.

Is the private sailing charter worth booking?

I would book Simply Sailing if you want three focused hours on the water, a private boat, and a low-pressure route around St. Thomas and St. John. The combination of Cosmos, Captain Rob and Captain Deb, included drinks and snacks, and easy boarding makes the plan practical as well as pleasant.

The value is best for a group of five or six, and the standard outing is best for people who genuinely want to sail. Request the snorkel stop before departure if that matters to your group. Skip it if you would rather keep every minute devoted to the boat and the views.

This is not the right choice for an action-packed island tour. It is a better choice for slowing down, sharing the water with your own small group, and seeing the Virgin Islands from a different angle.

FAQ

Where does Simply Sailing depart from?

The charter starts at Sapphire Beach in Smith Bay, St. Thomas, USVI. Boarding is at the dock, with easy access.

Where does the sailing trip end?

The activity ends back at the Sapphire Beach meeting point.

How many people can join the private charter?

The price covers a group of up to six people. Only your group participates in the activity.

How long does the sailing experience last?

The trip lasts approximately three hours.

Are food and drinks included?

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

Can I add a snorkel stop?

Yes. A snorkel stop can be included if requested. The standard plan has no stops and focuses on sailing around St. Thomas and St. John.