Simply Sailing Private Sail from Sapphire Marina

The best part of this charter is its simple promise: three hours of private sailing around St. Thomas and St. John, without a packed boat or a forced schedule. You board easily at Sapphire Marina, settle in with a drink and snack, and let Captains Rob and Deb set the course.

I like the small private group, capped at six, and the choice between a morning or afternoon departure. I also like that the crew can keep the outing focused on sailing, or add a snorkel stop if you request one. The main consideration is that this is a short trip with no planned shore stop, so it may feel too quiet for anyone seeking a full-day island-hopping adventure.

Key points to know before you book

• Cosmos is a 40-foot pilothouse mariner: You get a proper sailing platform with shelter from the sun when needed, rather than a crowded shared excursion boat.
• The trip is built around sailing: The standard plan includes no stops, though a snorkel stop can be added if requested.
• Only your group joins: The private charter carries up to six people, making the $799 group price easier to assess for families and small groups.
• Captains Rob and Deb host the outing: Their warm welcome and easygoing style are central to the experience.
• Drinks and snacks are included: Expect soda, bottled water, alcoholic beverages, and onboard snacks.
• You return to Sapphire Beach: The activity starts and ends at the same meeting point, with morning and afternoon departures available.

Sailing from Sapphire Beach on Cosmos

Your outing begins at Sapphire Beach in Smith Bay, on the east side of St. Thomas. The boat offers easy boarding right at the dock, a useful detail when you are carrying beach bags, cooler items, or anything else you would rather not haul over a long stretch of sand.

The boat is a 40-foot pilothouse mariner named Cosmos. That size suits a private group well. It is large enough to feel like a serious sailing vessel, but the group limit of six keeps the mood personal. You are not trying to find a seat among dozens of people or compete for a good view.

Captains Rob and Deb handle the charter. Their welcome has been singled out for warmth, and that matters on a small boat. With only a few people aboard, the crew shapes much of the mood. You can expect a more relaxed exchange than you would get on a large scheduled cruise.

The meeting point is also the end point. You do not need to arrange a second pickup location or figure out how to get back from a different island. The activity is near public transportation, though no separate transportation service is included.

What three hours of pure sailing feels like

The standard plan is intentionally spare: sail the waters around St. Thomas and St. John, enjoy the views from the water, and keep moving. There is no fixed list of beaches or shopping stops. No shore lunch is built in. No rushed timetable tells you that it is time to get back aboard.

That simplicity is the point. I like this kind of outing for people who want time on the water rather than another land-based tour with a boat ride attached. You can watch the islands change shape as Cosmos moves along, feel the wind, and enjoy the fact that the boat belongs only to your group for the charter.

The exact route is not specified, and sailing conditions can affect the course. That means you should think of the trip as a sailing experience, not a sightseeing circuit with guaranteed photo stops. You will see the St. Thomas and St. John area from the water, but the attraction is the overall setting and motion of the boat rather than a promised list of named sights.

Three hours is a sensible length for a morning or afternoon. It gives you a real stretch of time aboard without taking over your entire day. You can still plan dinner, beach time, or another activity afterward. On the other hand, the short duration means you should not book this expecting an all-day cruise or a long visit to several bays.

Choosing the morning or afternoon departure

The two departure choices make this charter easier to fit into a St. Thomas schedule. A morning sail works well if you want the water to be the main event before the day gets busy. An afternoon departure lets you use the first part of the day for sleeping in, sightseeing, or time at the beach.

I would choose based on your group’s habits rather than chasing a supposedly perfect time. The information provided does not promise a specific sunset, wildlife encounter, or weather pattern. Pick the slot that gives you the least rushed start.

A morning or afternoon charter also helps families and mixed-age groups. Some people want an early start, while others prefer a slower morning. Since the boat is private, you do not have to fit your whole group into another operator’s fixed timetable.

Keep an eye on the weather before your trip. Sailing depends on good conditions, and poor weather can lead to a different date or a full refund. That policy is reassuring, but it also means you should avoid building an important same-day connection around this activity.

Snacks, drinks, and the small comforts

The charter includes snacks, soda, bottled water, and alcoholic beverages. That keeps the outing pleasantly uncomplicated. You do not need to plan a separate drink run before boarding, and you can settle into the sail without wondering when refreshments will appear.

The included alcohol is a nice touch for adults who want a casual drink while cruising. It is still wise to pace yourself on a moving boat and in the sun. Bottled water and soda give everyone a nonalcoholic option, including children and anyone who prefers to stay clearheaded.

The food is described as snacks, not a meal. Plan accordingly. If your group needs lunch, has dietary restrictions, or expects a substantial spread, confirm what is available before setting out. The charter’s value comes from the private boat time and the included refreshments, not from replacing a full meal.

These small inclusions matter more on a three-hour outing than they might on a quick harbor cruise. You are not spending the whole trip arranging drinks or stopping for supplies. The crew can focus on sailing, while you enjoy the view and conversation.

Adding a snorkel stop by request

The regular format is no stops and pure sailing. If you would like time in the water, a snorkel stop can be included when requested. That flexibility is useful because it lets your group choose the style of outing you actually want.

Ask for the snorkel option before the trip or as early as possible when arranging the charter. The available information does not specify the location, equipment, water conditions, or length of the stop, so you should not assume that gear or a particular reef is included. Treat snorkeling as an optional adjustment, not a guaranteed part of the standard plan.

This choice can make the charter work for different groups. One couple may want uninterrupted sailing and quiet time aboard. A family or group of friends may prefer to break up the trip with a swim. Since the boat is private, you have a better chance of shaping the pace around your own priorities, though any added stop will reduce the time spent under sail.

If everyone in your group wants snorkeling, mention it clearly when booking. If only one or two people are interested, ask how the stop will work for those who prefer to remain aboard. The provided details do not spell out that arrangement, so it is worth clarifying rather than making assumptions.

Why the private price can make sense

The price is $799 per group for up to six people, not $799 per person. That changes the calculation. Split six ways, the base cost is about $133 per person. For four people, it comes to roughly $200 each, while two people would pay about $400 each before gratuity.

The charter becomes better value as your group gets closer to six. A family of six or two groups of friends can enjoy a private boat for a price that may compare favorably with several individual seats on premium shared cruises. A couple can still book it, but the private-boat convenience comes at a much higher per-person cost.

You should also budget for the customary 20 percent crew gratuity. On $799, that is about $160, bringing the expected total to roughly $959 before any other personal expenses. For six people, that works out to about $160 per person including the customary tip. For two, it is close to $480 each.

I like the clean group pricing because it makes the decision easy. You know the base cost before you arrive, and the group limit prevents the boat from becoming overcrowded. The tradeoff is that the charter may not be the most economical choice for a solo visitor or a small pair.

The views from St. Thomas and St. John

The main sightseeing reward comes from seeing the Virgin Islands from the water. The islands look different when you are moving past them under sail than when you are standing on a beach or driving along a road. You get a broader sense of the coastline and open water, with time to simply watch the scenery change.

The strongest praise connected with this experience centers on the island views, the pleasure of being out on the water, and the feeling of making a special family memory. That tells you where to set your expectations. This is not mainly about checking off attractions. It is about sharing a calm, scenic stretch of the day with people you know.

You will also get a different perspective on St. John without committing to a separate land excursion there. The boat sails around the waters of both St. Thomas and St. John, though the exact route is not guaranteed. If you need a particular beach visit or named landmark, ask before booking.

The private setting helps the views feel less hurried. Your group can talk, sit quietly, take photos, or simply watch the boat move. On a shared boat, the atmosphere is partly determined by strangers. Here, you control the social side of the experience.

Who will enjoy this charter most

I would recommend Simply Sailing to a group that values time on the water over a packed itinerary. It suits families, couples traveling with friends, and small groups celebrating a relaxed occasion. It is also a good match for people who already have their beach visits and island tours planned and want something quieter between them.

The charter is especially appealing if you want:

• A private boat for up to six people
• A short outing that leaves most of the day free
• A choice between morning and afternoon
• Sailing without mandatory stops
• Drinks and snacks included
• The option to request snorkeling

I would hesitate if your group needs a full meal, a long list of stops, a guaranteed snorkeling site, or a full-day cruise. The standard trip is deliberately uncomplicated. That can feel refreshing, but it can also feel limited if you want constant activity.

The 40-foot boat and easy dock boarding should help most people participate, and the activity states that most people can take part. Still, the provided details do not describe specific mobility accommodations, so anyone with access needs should confirm those details before booking.

Booking, weather, and the gratuity

Confirmation is sent at the time of booking, and mobile tickets are accepted. You can cancel for a full refund up to 24 hours before the start time. Changes made inside that 24-hour window are not accepted, and the amount paid is not refunded for a late cancellation.

Weather is an important part of the decision. If poor conditions force a cancellation, you will be offered another date or a full refund. Since the activity depends on sailing conditions, avoid scheduling it so tightly that a weather change would disrupt the rest of your holiday.

The customary crew gratuity is 20 percent and is not included in the listed price. Plan for it from the start, especially if you are dividing the cost among six people. A clear budget makes the charter feel much better value once you are aboard.

Should you book Simply Sailing?

Book it if you want a private, low-pressure sail and your group can appreciate the journey itself. The combination of Cosmos, Captains Rob and Deb, included refreshments, and views around St. Thomas and St. John creates a focused three-hour outing rather than a crowded checklist tour.

The choice is less convincing for a small group watching every dollar, or for anyone expecting a full day of snorkeling and beach stops. For a group of five or six, though, the price becomes much more reasonable, and the private setting gives you control over the pace.

My practical advice is to request snorkeling in advance if it matters to you, confirm any food or access needs, and set aside the 20 percent gratuity. If your ideal Caribbean experience is simply wind, water, island views, and good company, this charter gives you exactly that.

FAQ

Where does the 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 is the sailing experience?

The activity lasts approximately three hours.

How many people can join the private charter?

The $799 price covers a private group of up to six people. Only your group participates.

Are food and drinks included?

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

Is snorkeling part of the regular itinerary?

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

What happens if bad weather cancels the trip?

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