Simply Sailing Private Sail from Sapphire Marina

Trade roads for open water. This private three-hour charter from Sapphire Beach gives you a quiet way to see St. Thomas and St. John aboard a 40-foot pilothouse mariner. I like the private setting for up to six people and the fact that snacks, bottled water, soda, and alcoholic drinks are included. I also like the choice of a morning or afternoon sail. The main consideration is that the standard trip is sailing only, with no planned stop, so anyone hoping for a full beach-and-snorkel outing should request that add-on ahead of time.

Captain Rob and Captain Deb host the charter aboard Cosmos, and their warm, welcoming style is part of the appeal. I would choose this trip for easy boarding, unhurried views, and time on the water without a crowded boat. At $799 per group, it makes the most sense when six people share the cost, and you should also budget for the customary 20 percent crew gratuity.

Key points to know before you book

• Private boat for up to six: Your group has the entire charter, which makes the outing more relaxed than a large shared cruise.
• Sailing around St. Thomas and St. John: The focus is the ride itself, with views of the islands from the water rather than a busy schedule of stops.
• Three-hour morning or afternoon trip: You can fit the charter around other plans, including a beach day or dinner reservation.
• Snacks and drinks are included: Soda, bottled water, alcoholic beverages, and snacks are provided aboard.
• Snorkeling is available by request: The regular plan is pure sailing, but a snorkel stop can be added if arranged.
• Easy dock boarding at Sapphire Beach: The tour begins and ends at Sapphire Beach in Smith Bay, St. Thomas.

Setting out from Sapphire Beach

The charter begins at Sapphire Beach in Smith Bay, on the eastern side of St. Thomas. You board directly at the dock, which keeps the start simple. There is no need to wade through the surf or transfer from a smaller boat, a useful detail if you are carrying bags, managing children, or simply prefer a straightforward start.

The tour returns to the same meeting point. Public transportation is nearby, though the provided details do not specify exact routes or schedules, so you will want to check those before relying on them. Your confirmation arrives at booking, giving you the meeting details for the day.

The boat is a 40-foot pilothouse mariner. That size gives you room to settle in without the feel of a large commercial vessel. The pilothouse also offers some shelter, though this is still an outdoor sailing outing, so bring sun protection and clothing suited to changing conditions.

The sailing area includes the waters around St. Thomas and St. John. From the boat, you get a different angle on the islands, with the shoreline and hills forming the backdrop while the vessel does the work. One of the strongest impressions from the available comments is the pleasure of seeing the islands from the water after years away. That is the heart of this experience: not a packed checklist, but a change of pace.

What the three-hour sail is really like

The name says a lot. This is simply sailing, not a rapid tour that races between several attractions. The standard outing lasts about three hours and is built around being aboard the boat for the full time.

That can be a real advantage. You are not spending part of the trip waiting for people to reboard, changing boats, or hurrying through a short stop. You can sit with your group, watch the islands pass, and enjoy the rhythm of the water. If you have already spent several days moving from one activity to the next, this kind of open schedule can feel like a welcome reset.

It also means you should set your expectations correctly. There is no listed beach stop, lunch stop, or sightseeing walk. If you want an active excursion with several planned attractions, this charter may feel too spare. If you want the sailing itself, the format is refreshingly clear.

The morning and afternoon departure choices add practical flexibility. A morning sail may suit you if you want the rest of the day free. An afternoon departure can work well after a slow start or a morning at Sapphire Beach. The trip lasts only about three hours, so it can fit into a broader St. Thomas schedule, though you should allow extra time around the start and end rather than planning another activity too tightly.

Seeing St. Thomas and St. John from the water

The best part of a sailing trip is often the view that cannot be found from a road. St. Thomas and St. John look different when you are offshore. You see the islands as a connected group rather than as separate stops reached by car or ferry.

The charter is especially appealing if you have already explored St. Thomas on land. A boat changes the scale of the place. Hills, beaches, and bays make more sense when viewed from the water, and the ride itself becomes the main attraction.

I also like that the private format lets your group decide how social or quiet the trip feels. You can enjoy conversation, watch the scenery, or settle into the afternoon without sharing the boat with a large crowd. Captain Rob and Captain Deb are praised for their warm hosting, which suggests the atmosphere is friendly rather than formal. That matters on a short charter. Three hours goes quickly, and a welcoming crew can make the outing feel personal from the first boarding.

The available comments also highlight the breathtaking views and the pleasure of making family memories aboard Cosmos. Those details point to the experience’s strongest audience: families, couples traveling with friends, and small groups who want time together more than a packed activity list.

Snacks, drinks, and the small comforts

The charter includes snacks, soda, bottled water, and alcoholic beverages. That saves you from having to organize refreshments for a short outing, and it makes the $799 group price easier to assess.

The provisions are not a substitute for a meal. The information only promises snacks, so I would not book this as a lunch cruise. If anyone in your group has dietary needs, confirm what snacks are available before departure. The same practical advice applies to drinks if you have a particular preference.

Alcohol is included, but you still need to pace yourself. Three hours on the water and strong sun can catch up with you quickly. Bottled water and soda are part of the package, so use them as well.

These inclusions are most valuable when your group would otherwise buy separate drinks and snacks at the beach or bring supplies aboard. They also help keep the trip uncomplicated. You arrive, board, and settle into the sail without turning the morning into a provisioning exercise.

Snorkeling is possible, but it is not the main plan

The regular outing is described as no stops and pure sailing. A snorkel stop can be included if you request one, but it should not be treated as automatic.

This distinction matters. If snorkeling is a priority, ask for it when booking or well before departure. You should also clarify how adding the stop affects the sailing time, since the charter is approximately three hours. The provided details do not name a snorkeling site or promise equipment, so do not assume either one without confirmation.

For a group with mixed interests, the request option can be useful. One person may want to snorkel while others mainly want to sail and enjoy the scenery. Still, the experience is best chosen by people who see sailing as the main event. If you want a dedicated snorkeling tour with long water time, multiple sites, or a beach stop, you may need a different type of charter.

How the private price works for a group of six

The price is $799 per group of up to six people, not per person. Split six ways, that comes to about $133.17 per person before gratuity. With the customary 20 percent crew gratuity, the group total would be about $958.80, or roughly $159.80 per person when six people share it.

For four people, the base price works out to $199.75 each. For two people, it becomes $399.50 each before gratuity. That is why the charter offers much better value for a full group than for a couple.

The price includes a private boat, crew, approximately three hours of sailing, snacks, and several types of drinks. You are paying for space, privacy, and a relaxed schedule as much as for transportation. If the alternative is a large shared boat with a fixed route and many passengers, the private setting may justify the premium.

I would compare the cost with your group’s priorities. If you value quiet time, easy boarding, and seeing St. Thomas and St. John without a crowd, the price can be fair when divided among six. If you mainly want the cheapest way to get on the water, a shared cruise will likely cost less. The separate 20 percent gratuity is not included, so include it in your real budget.

Captain Rob, Captain Deb, and the feel aboard Cosmos

Captain Rob and Captain Deb are named as the hosts of the charter aboard Cosmos. Their role is more than steering the boat. On a private sail, the crew shapes the mood, answers questions, and helps determine whether the trip feels easy and personal.

The strongest praise centers on their warmth and enthusiasm. One family described the experience as creating special memories, while another highlighted the hosts and the pleasure of a beautiful afternoon sail. That makes this a good choice if you want a friendly human touch rather than a scripted, anonymous cruise.

At the same time, you should remember that a private charter remains a weather-dependent outdoor activity. The captains can make the trip comfortable and enjoyable, but wind and sea conditions still shape the day. The tour requires good weather. If poor weather causes cancellation, you are offered another date or a full refund.

Morning or afternoon: which departure suits you?

The best time depends on how you plan to use the rest of your day.

Choose the morning if you want an early-water experience and a free afternoon afterward. This can be useful if you plan to visit another part of St. Thomas later, though the available information does not provide a complete schedule for combining activities.

Choose the afternoon if you prefer a slower morning or want the sail to be the main event after time at the beach. An afternoon trip also fits the feel of the experience described by one commenter, a pleasant sail on a beautiful day with island views and time on the water.

Either choice gives you about three hours aboard. Since the trip starts and ends at Sapphire Beach, you do not need to arrange a separate return point. Still, leave a cushion around the charter in case you are using public transportation or have dinner reservations afterward.

Who will enjoy this charter most

I would recommend Simply Sailing for:

• A family or friend group of up to six people
• Couples who want a private boat and do not mind paying more per person
• Anyone who prefers a calm outing over a packed excursion
• People who want to see St. Thomas and St. John from the water
• Groups that appreciate included snacks, drinks, and easy dock boarding
• Sailors or first-time boat riders who want sailing to be the central activity

It may be less suitable for you if you need a guaranteed snorkel stop, a beach landing, a full meal, or a long list of scheduled sights. The charter gives you time and space, but it does not promise a busy itinerary.

Most people can participate, and the activity is private, with only your group aboard. The supplied details do not give further information about mobility accommodations beyond easy boarding at the dock, so contact the operator if someone in your party has specific access needs.

Booking timing and cancellation

This charter is typically booked about 26 days ahead, so I would reserve early if you have fixed vacation dates or need a particular morning or afternoon departure. Confirmation is provided at the time of booking.

You can cancel for a full refund up to 24 hours before the experience starts. Changes or cancellations made less than 24 hours before the start time are not accepted for a refund. Cutoff times follow local time in St. Thomas.

Because the trip depends on good weather, a cancellation caused by poor conditions gives you the choice of another date or a full refund. That policy offers useful protection, but you should still avoid placing an important connecting activity immediately afterward.

Should you book Simply Sailing?

Book it if you want the boat ride itself: a private group, open views of St. Thomas and St. John, friendly hosts, included drinks, and three hours without a crowded schedule. The $799 price is easiest to justify when six people share it, and the 20 percent gratuity should be part of your calculation.

Think twice if your ideal day requires snorkeling, a beach stop, or a meal. Those are not part of the standard plan, though snorkeling can be requested. For the right group, this is a pleasant and unhurried way to spend part of a St. Thomas vacation, with Cosmos, Captain Rob, and Captain Deb providing the personal touch that turns a basic sail into a memorable outing.

FAQ

Where does Simply Sailing depart from?

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

Where does the experience end?

The activity ends back at the Sapphire Beach meeting point.

How long is the sailing charter?

The charter lasts approximately three hours.

Is the boat private?

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

How many people can join?

The $799 group price covers up to six people.

What drinks are included?

Soda, bottled water, and alcoholic beverages are included.

Are snacks provided?

Yes. Snacks are included aboard the charter.

Is snorkeling included?

Snorkeling is not part of the standard no-stop sailing plan, but a snorkel stop can be added if requested.

Can I choose a morning or afternoon departure?

Yes. The charter offers morning or afternoon departure options.

Is crew gratuity included in the price?

No. A customary 20 percent crew gratuity is not included.

Can I cancel for a full refund?

Yes. You can cancel at least 24 hours before the start time for a full refund.

What happens if bad weather cancels the trip?

If poor weather causes cancellation, you are offered a different date or a full refund.