SPECIAL – (Up to 4 Passengers) All Inclusive Day Sail

The best part of this private St John sailing trip is its small scale. Your group of up to four has a 40-foot sailboat, a captain who may let you take the helm, and a flexible route through calm waters near the Virgin Islands National Park. Captain Mike also teaches basic sailing, so this is more than a boat ride with a view.

I like the included lunch and very open bar, which save you from nickel-and-dime costs once you leave Cruz Bay. I also like the two-stop plan: first, a protected bay for snorkeling and swimming, then another spot for more sea life, beach time, and sun. The main consideration is price. At $1,346.67 per group, this makes the most sense when four people share it, and the published material also mentions a $755 all-inclusive price, so confirm the exact rate before paying.

Key points to know before you book

• Private sailing for up to four: You get the boat and crew for your own party rather than joining a large excursion.
• Two water stops: Expect snorkeling, swimming, a quiet anchorage, and time on white sandy beaches.
• Sea turtles are a regular goal: The crew looks for turtles each day, but wildlife sightings can never be guaranteed.
• Captain Mike teaches as he sails: You may learn basic sailing and even take the helm of the 40-foot boat.
• Food and drinks are included: Lunch, snacks, water, soft drinks, mocktails, cocktails, and other bar choices are part of the package.
• Five hours leaves room for Cruz Bay: The boat returns to the ferry terminal with time for a later drink or more island exploring.

Setting out from Cruz Bay on a 40-foot sailboat

The meeting point is the Saint John Ferry Terminal in Cruz Bay, and the trip ends there too. That makes the outing simple to fit into a day on St John, especially if you are already in Cruz Bay or arriving by ferry.

From town, the boat heads toward the protected western shoreline of St John and nearby cays. The waters here are suited to a relaxed sailing day: you can stretch out, sunbathe, watch the shoreline, or sit with a drink while the boat moves between bays.

The private format matters. With only your party aboard, you can talk with Captain Mike about sailing, ask for help with snorkeling, or simply enjoy a quiet ride without a crowded deck. The crew can also adjust the feel of the day for your group, within weather and safety limits.

I would not book this expecting a fast sightseeing cruise with a long list of fixed attractions. The appeal is the time on the water and the chance to settle into a slower Caribbean rhythm. The stated duration is about five hours, so the route needs to remain fairly close to Cruz Bay.

Learning the basics from Captain Mike

Captain Mike is part of what gives this trip more character than a standard boat transfer. He has been described as a gifted captain who is willing to teach the fundamentals of sailing, not just steer while everyone else watches.

If you are curious, you may be invited to take the helm of the 40-foot sailboat. This is a nice touch for first-time sailors and children old enough to follow instructions. It gives you a better sense of how a sailboat responds and makes the trip feel active without turning it into a formal lesson.

I would ask about taking the helm early in the day. The opportunity depends on conditions, timing, and the captain’s judgment. It should be treated as an extra part of the outing, not a guaranteed feature for every person in your group.

Bridget is also part of the crew, and the service is intended to be personal rather than hurried. One family outing included Captain Mike, Bridget, and their young son, showing that the operation can have a warm, family-run feel. The setup may vary by departure, but you can expect a small crew rather than a large commercial staff.

The first anchorage, snorkeling, and turtle search

The first stop is planned at a protected bay or nearby cay. Once the boat anchors, the crew fits you with snorkeling equipment and explains what you need to know. Equipment is included, which is useful because you do not need to arrange a separate rental in Cruz Bay.

The snorkeling is presented as suitable for different skill levels. If you are comfortable in the water, you can spend more time looking around the reef area. If you are less confident, the crew can help you get started at a calmer stop. Still, you should be honest about your swimming ability before leaving the dock.

Sea turtles are a central part of the outing. The crew looks for them daily, and one sailing group spotted a turtle while snorkeling. That is an encouraging sign, but it is important to keep expectations sensible. Turtles are wild animals, not a scheduled show, and weather, water conditions, and luck all affect what you see.

Bring patience and a mask that fits well. The boat provides snorkeling equipment, but personal comfort can vary from one person to another. Towels are not included, so pack your own. That small omission matters after repeated swims, particularly if you plan to stay out for the afternoon.

A second stop for beach time and more sea life

After the first round of snorkeling and swimming, the boat continues to a second location. The plan is to find another place with sea life, a white sandy beach, or both.

This second stop gives the day a useful change of pace. The first anchorage is about getting into the water and trying the snorkeling gear. The later stop lets you swim again, walk along the beach, or simply relax in the sun. You are not locked into one long session at a single bay.

The exact destination is not fixed in the information provided. That is a benefit when conditions shift, since the captain can choose among protected areas near St John. It also means you should not book this expecting a named beach or guaranteed reef.

The National Park setting is a major draw. St John is known for clear water, pale beaches, and protected coastal areas, and a sailboat gives you a quieter way to see them than a road trip around the island. I like that the day is built around bays and cays rather than a crowded schedule of stops.

Lunch, cocktails, and the value of an all-inclusive day

A full gourmet deli lunch is included, with a menu available for you to select before sailing. Snacks are also provided. That pre-trip selection is worth taking seriously, since a good meal matters after swimming and time in the sun.

The drinks package is unusually broad. It includes an open bar with island cocktails, mocktails, soda, juices, bottled water, and other drinks. Fuel, captain fees, taxes, and other listed fees are included as well.

That package changes how you should compare the price. You are not paying only for five hours on a boat. You are also covering a private captain, fuel, lunch, snorkeling equipment, snacks, and drinks for up to four people.

The published price information needs clarification. The tour summary gives a price of $1,346.67 per group, while the description also states an all-inclusive price of $755. Those figures are far apart. I would confirm the current total, what currency is being charged, and whether the higher figure reflects a booking platform price or a different departure before committing.

At $1,346.67, four people would pay about $337 each. That is a substantial day, but the private boat and included food and drinks help explain the cost. For two people, the same price becomes much harder to justify unless privacy and a custom feel are your main priorities.

Staying in USVI waters

The stated plan remains in local US Virgin Islands waters, with no extra customs or immigration charges. That keeps the day straightforward and avoids the border formalities that can come with a trip to the British Virgin Islands.

There is an important point to clarify when booking. A past outing with Captain Mike included stops in the British Virgin Islands, including Foxy’s and Soggy Dollar, but the experience described here is specifically presented as a local USVI sail. Do not assume a BVI route is included. Ask the operator if crossing to another territory is something you want, and confirm the required documents and fees separately.

For most people, staying local is a plus. You spend less time on formalities and more time swimming, sailing, and enjoying St John’s coast. The five-hour schedule also works better when the boat does not need to make a long international crossing.

Who will enjoy this private sailing day

I would recommend this for a family, two couples, or a small group of friends who want the boat to themselves. It suits people who value quiet time, swimming, snorkeling, and good service more than a packed sightseeing program.

It is also a good fit for someone who wants to try sailing without signing up for a technical course. Captain Mike’s willingness to explain the basics and let you take the helm, when conditions allow, adds interest for curious beginners.

The trip may be less suitable if you need a firm list of named sites, guaranteed turtle sightings, or a low-cost excursion. It is also not ideal for anyone who dislikes being on the water for several hours. Even calm protected waters can feel tiring if you are sensitive to sun, motion, or heat.

Most people can participate, and service animals are allowed. The meeting point is near public transportation. Confirmation is sent within 48 hours of booking, subject to availability, so do not assume your place is final until confirmation arrives.

Timing, weather, and the firm cancellation rule

The five-hour schedule should leave you with part of the afternoon free in Cruz Bay. You might use that time for a drink, a meal, or more island exploring. The return to the same meeting point also makes the end of the day easy to manage.

Weather matters. The operator can cancel for poor conditions and offer another date or a full refund. If the minimum number of participants is not met, you can also receive a new date, another experience, or a full refund.

Your own cancellation is different. The experience is non-refundable and cannot be changed for any reason once booked. I would wait until your plans and weather outlook are reasonably stable before paying, especially because the price is high.

Should you book Morningstar Sailing and Power Charters?

Book this if you want a private, relaxed day with Captain Mike and Bridget, a good chance to snorkel, included lunch and drinks, and room to enjoy the water without a crowd. The small group size, sailing instruction, two water stops, and possible turtle sightings give the outing real appeal.

I would be more cautious if the current price is $1,346.67 and your group has only two people. First confirm the price difference, the final menu, the route, and whether the boat will stay in USVI waters. If those details suit you and four people can share the cost, this can be a memorable way to spend one of your St John days.

FAQ

Where does the sailing trip begin?

It begins at the Saint John Ferry Terminal in Cruz Bay, St John, USVI.

Where does the trip end?

The activity ends back at the same meeting point at the Saint John Ferry Terminal.

How long does the sailing trip last?

The tour lasts approximately five hours.

How many people can join the private sailing?

The boat is reserved for your group, with a maximum of four passengers.

Is lunch included?

Yes. A full gourmet deli lunch is included, and you can choose from the menu before sailing. Snacks are included as well.

Are drinks included?

Yes. The package includes bottled water, soda, juices, mocktails, cocktails, and an open bar with island drinks.

Is snorkeling equipment provided?

Yes. Snorkeling equipment is included. Towels are not included, so you should bring your own.

Does the trip visit the British Virgin Islands?

The experience described here stays in USVI waters and does not add customs or immigration fees. A separate past outing included British Virgin Islands stops, so confirm the route directly if visiting the BVI is important to you.