Simply Sailing Private Sail from Sapphire Marina

The best thing about this charter is its simple promise: you spend your three hours on the water, sailing around St. Thomas and St. John rather than rushing from one planned stop to another. Captains Rob and Deb host the private outing aboard a 40-foot pilothouse mariner, with easy boarding at Sapphire Beach.

I like the private group setup, which keeps the outing personal and lets you request a snorkel stop if you want one. I also like that snacks, soda, bottled water, and alcoholic drinks are included, so you can settle in without packing a cooler. The main consideration is that this is primarily a sailing trip, not a packed sightseeing cruise. If you want several stops or a long snorkeling session, you should ask for that before setting sail.

Key Points for Your Day on the Water

• Pure sailing for about three hours: The standard plan keeps you moving around the waters of St. Thomas and St. John with no scheduled stops.
• Private charter for up to six: The $799 price covers your whole group, not just one seat.
• Captains Rob and Deb host the outing: Their warm, welcoming approach is a key part of the experience.
• Sapphire Beach boarding: You meet at Sapphire Beach in Smith Bay, with easy access from the dock.
• Snacks and drinks included: Expect soda, bottled water, alcoholic beverages, and light snacks onboard.
• Optional snorkeling: A snorkel stop can be added if requested, but it is not part of the standard no-stop plan.

A Three-Hour Sail Between St. Thomas and St. John

This is the kind of boat outing that works best when you want less scheduling and more time with the sea. You board at Sapphire Beach, step onto the 40-foot pilothouse mariner, and settle in for a private sail through the waters around St. Thomas and St. John.

The standard plan is deliberately spare. There are no planned beach visits, restaurant stops, or long blocks of free time at a snorkeling site. You sail. That makes the experience a good fit for anyone who would rather watch the islands pass by than keep checking the clock.

I find that approach refreshing. Many island boat trips try to pack in too much, and you spend part of the day moving from one activity to another. Here, the pace is the point. You have time to look out across the water, enjoy the changing views of the islands, and talk with your group without a crowded schedule.

The exact sailing route can vary, and no detailed stop-by-stop itinerary is provided. You should think of the trip as a moving view of the Virgin Islands rather than a tour built around specific attractions. If you need a particular route, ask about it when arranging your charter.

What the 40-Foot Pilothouse Mariner Means for You

A 40-foot boat gives this private outing a real boat-trip feel without the scale of a large party vessel. The pilothouse design also offers a sheltered area, which can be useful when you want a break from direct sun or wind.

The supplied information does not specify the exact seating arrangement, shade available, or onboard facilities, so ask the crew if those details matter to your group. Still, the boat’s size and private format should suit a small family or group of friends who want to share the outing rather than sit among a large crowd.

Boarding is described as easy, with access directly at the dock. That removes one common annoyance of island boat trips: climbing into a small dinghy or wading through the water to reach the boat. Most people can participate, though anyone with specific mobility needs should confirm the setup before booking.

Because the boat is private, you can spend the trip in your own circle. That matters more than it might sound. You are not trying to make conversation with strangers, competing for a seat, or adjusting your plans around another group’s preferences.

The Captains Set the Tone

Captains Rob and Deb host the charter, and their friendly welcome is one of its strongest features. You can expect a warm, personal introduction when you step aboard rather than a large commercial operation with a long line of passengers.

The available feedback praises both captains as gracious hosts and highlights the pleasure of seeing the islands from the water. That matches the nature of this trip. The crew is not simply transporting you to a beach. They are part of a relaxed sailing experience built around good company, open views, and time on the water.

A thoughtful touch is the way the charter can adapt to your wishes. The normal plan is pure sailing, but Rob and Deb are happy to add a snorkel stop if you request one. Be clear about that before departure, since a snorkel break changes the rhythm of a three-hour trip.

You should also be realistic about what a private charter can and cannot do in that time. A three-hour outing gives you enough room for a pleasant sail and perhaps one short activity, but it is not designed to cover every corner of St. Thomas and St. John.

Sapphire Beach Is a Handy Starting Point

The meeting point is Sapphire Beach in Smith Bay, St. Thomas. The boat returns to the same place at the end, which keeps the plan straightforward.

The area is near public transportation, making the starting point easier to reach than a more isolated marina. You still need to allow enough time to find Sapphire Beach and reach the dock, since no detailed arrival instructions are provided here. Bring your mobile ticket and keep your booking confirmation available.

Easy dock boarding is a practical advantage. You can move from shore to boat without adding a separate tender ride to the beginning of the outing. That is especially helpful if you are carrying snacks, beach items, or anything else you need for the afternoon.

The trip is offered in a morning or afternoon departure. I like having both options because you can fit the sail around the rest of your St. Thomas plans. A morning departure may leave your afternoon open, while an afternoon sail can work well after a relaxed start to the day. The specific departure time is not included, so confirm it when booking.

Pure Sailing, With No Forced Stops

The standard experience is all about motion. You sail around St. Thomas and St. John, enjoy the view from the boat, and let the water set the pace.

This is worth emphasizing because the phrase simply sailing is not a marketing flourish here. The plan specifically says no stops unless you request a snorkeling break. If you are hoping to visit a beach, shop, or landmark, this is not the right format unless the crew confirms that such a change is possible.

For the right group, the lack of stops is a major benefit. You do not lose time anchoring, unloading, gathering everyone back aboard, and repeating the process. You can stay with the feeling of being at sea. The scenery becomes the activity.

The drawback is just as clear. Some people need a destination to make a boat trip feel worthwhile. If your ideal day includes swimming, beach time, or a full snorkeling session, you may find three hours of sailing too focused. Ask for the optional snorkel stop before the outing, not once the boat is already underway.

Snacks and Drinks Keep the Trip Easy

The charter includes snacks, soda, bottled water, and alcoholic beverages. That helps keep the day relaxed and makes the $799 group price easier to assess.

You do not have to organize a separate cooler or stop midway for refreshments. The drinks also suit the pace of a private sail, where you can sit back and enjoy a cold soda, bottled water, or an alcoholic beverage while the boat moves between the islands.

The information does not specify the brands, snack selection, or alcohol choices. If someone in your group has dietary restrictions or wants a particular drink, check with the provider in advance rather than assuming it will be available.

You should still treat the onboard offerings as part of the charter, not as a full meal. The trip lasts about three hours, and snacks are included, but no lunch or substantial meal is promised. A morning or afternoon outing may be perfectly comfortable with the provided refreshments, depending on when you normally eat.

Optional Snorkeling Changes the Focus

A snorkel stop can be included if requested. This gives you a useful choice: keep the outing focused on sailing, or trade some sailing time for a swim and a look below the surface.

No specific snorkeling site, equipment details, or water conditions are provided. Ask whether gear is supplied and how much time would be available before you confirm that option. Those details matter, especially if snorkeling is the main reason you want a boat trip.

I would choose the snorkel stop only if your group agrees that it is worth giving up some sailing time. One person may want to swim while others would rather remain aboard, and a private charter gives you a better chance to settle that preference together.

If everyone wants a calm sail, skip the stop. If your group needs a little action, request it early. The flexibility is useful, but the trip remains a short charter, so it cannot give equal time to every activity.

Is $799 a Good Value for Six People?

The 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 $159.80, bringing the group total to about $958.80, or roughly $159.80 per person when six people share the cost.

That is a much better value for six than for two. A couple would still pay the full group rate, making the per-person cost about $399.50 before gratuity. For a family or group of friends, the private format, included drinks and snacks, and direct dock boarding help justify the price.

The value also comes from what you avoid. You are not paying for a crowded boat, a long passenger list, or a rigid schedule. You get the boat for your own group and can request a snorkel stop. If privacy and a quiet pace matter to you, that is meaningful.

The price is harder to defend if you mainly want a quick ride or a guaranteed snorkeling excursion. In that case, compare the cost with other boat activities and ask exactly what is included. This charter makes the most sense when the sailing itself is the main event.

Who Will Enjoy This Charter Most?

I would recommend Simply Sailing for a small group that wants a private, easygoing outing and does not need constant activity. It suits couples traveling with friends, families who prefer their own space, and anyone who likes the idea of seeing St. Thomas and St. John from the water.

It is also a good choice if you want to fit a boat trip into a busy St. Thomas schedule. The three-hour length is long enough to feel like a proper outing but short enough to leave room for other plans. Morning and afternoon departures add useful flexibility.

The trip may not suit you if you want a full-day sailing adventure, a packed sightseeing route, or a guaranteed swim stop. You should also consider the weather. The charter requires good weather, and a poor-weather cancellation results in either a different date or a full refund.

This is a private activity, so only your group participates. Most people can take part, and dock boarding is easy, but confirm any personal accessibility needs ahead of time.

Booking, Cancellation, and Weather Details

Confirmation is provided at booking, and the experience uses a mobile ticket. You can cancel for a full refund up to 24 hours before the local start time.

Changes or cancellations made less than 24 hours before departure are not accepted for a refund. Weather is handled more generously: if poor conditions cancel the trip, you are offered another date or a full refund.

The charter is often booked about 26 days ahead. That is a useful planning clue if your dates are fixed, especially if you want a particular morning or afternoon departure. Since the boat is limited to one private group of six, it is sensible to reserve before arriving in St. Thomas.

Should You Book Simply Sailing?

Book this charter if you want a private three-hour sail, easy dock boarding, and a calm way to see the waters around St. Thomas and St. John. The included snacks and drinks are convenient, and the option to request snorkeling gives you some control without forcing a stop on everyone.

I would be more cautious if your priority is beach time, a long swim, or a detailed island-hopping itinerary. The trip earns its value from privacy and pure sailing, not from the number of attractions it checks off.

For six people splitting the cost, the price is reasonable for a private boat with refreshments and a personable crew. For only one or two people, it becomes a much bigger splurge. If that tradeoff works for your group, Sailing The Cosmos Charters offers a pleasant, focused outing with Captains Rob and Deb at the helm.

FAQ

Where does the Simply Sailing charter begin?

The charter begins at Sapphire Beach in Smith Bay, St. Thomas, USVI. It ends back at the same 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. Only your private group participates.

Are food and drinks included?

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

Is snorkeling part of the standard trip?

The standard plan is pure sailing with no stops. A snorkel stop can be added if requested.

What happens if bad weather cancels the charter?

If poor weather causes a cancellation, you will be offered a different date or a full refund. You can also cancel up to 24 hours before the start time for a full refund.