Simply Sailing Private Sail from Sapphire Marina

Quiet water, open sails, and no crowded tour boat. Simply Sailing gives you a private three-hour charter from Sapphire Beach, with room for up to six people aboard a 40-foot pilothouse mariner. You sail around St. Thomas and St. John, enjoy snacks and drinks, and return to the same dock.

I like the freedom to choose a morning or afternoon departure, and I like that the price covers your whole group rather than charging per person. Captain Rob and Captain Deb are warm hosts aboard Cosmos, which adds a personal touch. The main thing to consider is the pace: this is mostly pure sailing with no scheduled stops, so it may not suit you if snorkeling or beach time is your top goal.

Key points to know before booking

• Private boat for up to six: Your group gets the charter to itself, with no strangers joining the sail.
• Sapphire Beach departure: Boarding takes place directly at the dock at Sapphire Beach in Smith Bay, St. Thomas.
• Three hours on the water: Choose a morning or afternoon trip and spend the full outing sailing around St. Thomas and St. John.
• Snorkeling is optional: A snorkel stop can be added if you request one, but it is not part of the standard no-stop plan.
• Food and drinks are included: Snacks, soda, bottled water, and alcoholic beverages are provided onboard.
• Plan for a 20 percent tip: Crew gratuity is not included, and 20 percent is customary.

Setting out from Sapphire Beach

Your trip begins at Sapphire Beach in Smith Bay, on St. Thomas. The meeting point is also the return point, which keeps the day simple. You do not need to arrange a separate ride from another marina after the sail.

The boat offers easy boarding access at the dock. That matters more than it may sound, especially when you are carrying beach bags, cameras, or drinks of your own. The activity is near public transportation, though the supplied details do not specify routes, fares, or exact pickup arrangements. You should plan to reach Sapphire Beach on your own unless the operator confirms something different.

Once everyone is aboard, the trip moves into the waters around St. Thomas and St. John. The exact route is not fixed in the information provided, and that is part of the charm of a private charter. You are not being marched from one scheduled stop to the next. The crew can focus on the conditions, the time available, and what your group wants from the sail.

What three hours of sailing really means

The heart of this trip is simply being on the water. You spend about three hours under sail, watching the islands from offshore and enjoying a slower view of the Virgin Islands. It is a good match for you if you want time to talk, take photographs, listen to the water, and let the boat carry the afternoon.

This is not a sightseeing cruise built around a long list of named attractions. You should not expect a formal narration at every turn or a series of shore excursions. Instead, the value comes from having a boat, a crew, and a broad stretch of water reserved for your group.

The supplied description is clear: the normal plan is no stops, just sailing. That makes the experience pleasingly straightforward. You are not losing half the charter to docking, transfers, or waiting for other groups to finish an activity.

At the same time, a no-stop plan will not please everyone. If you have young children who need frequent activity, or if you came mainly to swim and explore underwater, three hours of sailing may feel long. Ask for a snorkel stop when you book or before departure if that is important to you.

St. Thomas and St. John from the water

Sailing gives you a different view of the islands than you get from a road, beach, or hotel balcony. You see the shoreline from offshore, with the boat creating distance between you and the busy parts of St. Thomas. St. John is also part of the sailing area, so you get a wider sense of the two islands rather than staying in one small bay.

The route is not described in enough detail to promise a particular beach, cove, or viewpoint. That is useful to understand before you pay. You are booking time aboard a private sailboat in the island waters, not a guaranteed checklist of landmarks.

I like this format for people who have already spent time on St. Thomas and want a quieter change of pace. It also works well for a special half-day with family or friends. You can enjoy the company of your own group without a large boat crowd or a fixed public-tour schedule.

The private setting also gives you more control over the mood. You can make the outing social and celebratory, or keep it calm and low-key. The crew can include a snorkel stop if requested, but the available details do not promise snorkeling equipment, a specific reef, or a set amount of time in the water. Ask those questions before you go if they affect your decision.

Life aboard the 40-foot pilothouse mariner

The charter uses a 40-foot pilothouse mariner, a size that gives your group a proper sailing platform while keeping the outing personal. Up to six people can book together. You are not sharing the boat with unrelated passengers, so the outing feels more like a private day on the water than a standard excursion.

The boat is identified as Cosmos in the available feedback. Captain Rob and Captain Deb are named as the hosts, and the comments about them focus on a warm welcome and an enjoyable day aboard. That human element matters on a small charter. Three hours is enough time to notice whether the crew makes you feel comfortable, included, and relaxed.

You should still keep expectations practical. This is a sailboat, not a floating resort. The supplied information does not list cabins, restrooms, shaded seating, or specific onboard facilities. If anyone in your group has needs related to seating, sun exposure, or mobility, contact Sailing The Cosmos Charters before booking.

The easy dock boarding is a useful feature, but the data does not provide full accessibility details. The activity says most people can participate. That is encouraging, but it is not the same as a guarantee for every mobility need.

Snacks, drinks, and the right kind of celebration

Your booking includes snacks, soda, bottled water, and alcoholic beverages. That means you can settle into the sail without treating the charter as a bare-bones boat rental. The drinks are especially useful on a warm three-hour outing, though you should still follow the crew’s guidance about safe behavior on the water.

The included food and beverages also improve the price calculation. At $799 for the whole group, a party of six pays about $133 per person before gratuity. A group of four pays about $200 per person, and a couple would pay nearly $400 each. The private boat becomes much better value as your group gets closer to six.

The 20 percent crew gratuity is customary and not included. On the $799 base price, that would be about $160, making the expected total roughly $959 before any other charges. For six people, that works out to about $160 per person with the customary tip. It is wise to include that amount when comparing this charter with other island activities.

For a couple, the cost is harder to justify unless privacy and the sailing itself are worth the premium. For a family or group of friends, the math is more attractive. You are paying for exclusive use of the boat, not simply seats on a shared cruise.

Morning or afternoon: choosing your sailing time

The choice of a morning or afternoon departure gives you useful flexibility. A morning charter can fit well before a later dinner plan or another activity. An afternoon departure may suit you if you want an unhurried start to the day and a quiet period on the water afterward.

The exact departure times are not provided, so confirm the available options before you commit to other plans. The same advice applies if you are visiting St. Thomas from a cruise ship. The information does not promise cruise-port pickup or a schedule built around ship arrival and departure, so you need to allow enough time to reach Sapphire Beach and return.

Because the outing lasts about three hours, leave room for boarding and the ride to and from the marina. The activity begins and ends at Sapphire Beach, not at a separate drop-off point.

What the strongest praise tells you

The most positive comments focus on the hosts, the views, and the feeling of seeing the islands from the water. One family described the experience as an incredible time aboard Cosmos, with Captain Rob and Captain Deb welcoming them warmly from the start. Another called it a grand afternoon and enjoyed seeing the islands from a different perspective after many years away from sailing.

Those details point to the charter’s real strength. You are not buying a packed schedule. You are buying time with a friendly crew in a beautiful setting, with the freedom that comes from having the boat to yourself.

The perfect rating and full recommendation rate are encouraging, but a small number of comments cannot answer every practical question. They do not tell you the exact route, the seating layout, or the snorkeling arrangements. Use the strong praise as a sign that the personal service matters, not as proof that the trip will suit every kind of outing.

Who will enjoy this charter most

I would put this near the top of your list if you want a private, low-pressure sail and have a group large enough to share the cost. It works especially well for:

• Families who want an activity everyone can share
• Couples celebrating with friends
• Small groups who prefer privacy over a public cruise
• People who enjoy sailing more than a busy activity schedule
• Repeat visitors who want a fresh view of St. Thomas and St. John

It is less suitable if you need a guaranteed beach stop, a long snorkeling session, or a detailed island tour. It may also be a poor fit if your group dislikes time in the sun or wants a large boat with extensive facilities.

You should also be honest about the meaning of simply sailing. That phrase is not a marketing trick hiding a packed itinerary. The standard experience is intentionally simple. The boat goes out, you sail, you enjoy the view, and you return.

Booking details and weather planning

The tour costs $799 per group of up to six, and bookings are made about 26 days ahead on average. That advance timing suggests you should reserve early if your dates are fixed, especially if you want a particular morning or afternoon departure.

You receive confirmation at booking, and the experience uses a mobile ticket. Free cancellation is available if you cancel at least 24 hours before the local start time. Changes or cancellations inside that 24-hour window are not accepted for a refund.

Good weather is required. If poor weather cancels the trip, you are offered another date or a full refund. That policy is important in the Virgin Islands, where a water outing depends on conditions that can change. Keep some flexibility in your schedule if possible, rather than placing the sail on the only open afternoon of your visit.

Should you book Simply Sailing?

Book it if your ideal St. Thomas outing is a private boat, a friendly crew, island views, included drinks, and three uncomplicated hours under sail. The value is strongest for five or six people, when the $799 group price spreads across your party.

Ask for the snorkel stop if swimming matters to you, since it is not part of the standard no-stop plan. If your priority is a structured tour with several landings, named sights, or a full day of water sports, choose another activity.

For the right group, Simply Sailing offers a pleasant change from the usual island rush. Captain Rob, Captain Deb, and Cosmos give you a personal way to see St. Thomas and St. John, with no need to share the boat or follow someone else’s timetable.

FAQ

Where does Simply Sailing depart from?

The charter departs from Sapphire Beach in Smith Bay, St. Thomas, US Virgin Islands.

Where does the activity end?

The sail ends back at the Sapphire Beach meeting point.

How long is the sailing charter?

The experience lasts approximately three hours.

How much does the private charter cost?

The price is $799 per group, for up to six people.

Is the boat private?

Yes. This is a private activity, so only your group participates.

What is included onboard?

The charter includes snacks, soda, bottled water, alcoholic beverages, and easy boarding access at the dock.

Can I choose a morning or afternoon departure?

Yes. You can choose from a morning or afternoon departure, subject to availability.

Can the charter include snorkeling?

Yes. A snorkel stop can be included if you request one. The standard plan is sailing without stops.

What happens if the weather is poor?

If the experience is canceled because of poor weather, you are offered a different date or a full refund.