Private Day Charter Classic Sailboat

Make St John your playground. This private half-day charter gives you a 40-foot sailboat, clear-water snorkeling, lunch, and plenty of room for your own group. I especially like the small private setting and the chance to learn a little sailing from Captain Mike, who has even handed the lines to willing passengers. The open bar and onboard restroom also make a long afternoon on the water much easier.

The main consideration is cost. At $1,395 for up to six people, the price works best for a full group, not a couple traveling alone. You will also need to arrange your own transportation, and the trip depends on good weather.

• A private 40-foot sailboat keeps the day personal and avoids sharing the boat with strangers.
• Two snorkeling opportunities include a secluded anchorage near Honeymoon Beach and Caneel Bay.
• Captain Mike may offer sailing instruction if you want more than a scenic ride.
• Lunch and a generous open bar are included, with sandwiches, salads, beer, spirits, wine, juice, soda, and water.
• A shaded cockpit, restroom, and WiFi add comfort during the hours between swims.
• The charter begins at the Saint John Ferry Terminal in Cruz Bay and returns there at the end.

Setting Sail from Cruz Bay

Your day begins at the Saint John Ferry Terminal in Cruz Bay. From there, you take an inflatable tender out to the 40-foot sailboat. That short transfer is part of the adventure, but it also means you should arrive ready to step into a smaller boat and manage the move between vessels.

The charter lasts about four to five hours. That is enough time for sailing, two water stops, lunch, and some relaxed time aboard, but it is not a full-day expedition. The pace should feel pleasantly unhurried, with the captain adjusting the outing to the weather and the group’s interests.

Because this is a private charter, your party controls the mood more than on a shared excursion. You can spend longer snorkeling, settle into the shaded cockpit, or ask questions about sailing without worrying about a boatload of strangers. For a family or group of friends, that privacy is a large part of the value.

Pickup is listed as available, but private transportation is not included. The clearest plan is to make your way to the ferry terminal in Cruz Bay and confirm any pickup details before booking. The meeting point is also near public transportation.

Sailing Lessons, Sea Views, and Captain Mike

Captain Mike receives especially strong praise for being attentive, clear, and safety-minded. Those qualities matter on a private boat, where a good captain does more than steer. He needs to explain what is happening, give you simple instructions, and read the conditions while keeping the group comfortable.

If you want to take an active role, ask about sailing the boat yourself. Captain Mike has given passengers a chance to learn the basics, turning a pleasant cruise into a hands-on experience. You should not expect a formal sailing course, but even a brief lesson can make the trip more memorable.

Captain Mike has also been joined by his nephew Beau, sometimes written as Bo. Their friendly manner adds to the easy family feel of the charter. One especially happy group praised Mike not only for his sailing skills but also for his ability to mix a good cocktail. That is a useful clue about the tone of the day: practical seamanship, relaxed conversation, and a little vacation indulgence.

The exact route can change. Wind, sea conditions, and the captain’s judgment will shape the outing. That flexibility is useful in the Virgin Islands, where the best snorkeling spot can change with the weather. It also means you should see the published stops as a guide rather than a rigid promise.

First Water Stop and Snorkeling Time

The trip includes snorkeling equipment for everyone. That removes one common hassle, especially if you are arriving without fins, masks, or snorkels of your own. You can move from the boat into the water without paying a separate rental fee or carrying extra gear around Cruz Bay.

The first stop is described as one of the snorkeling locations along the sailing route. Since the exact site is not fixed in the supplied details, your captain will choose the place based on conditions and the day’s plan. You might find the water calm and clear, or you may get a stronger sailing experience if wind makes snorkeling less suitable.

The private format gives you more say in how you use the stop. Confident swimmers may want more time in the water. Others may prefer a quick look with a mask, then return to the boat for lunch or a drink. Families can also discuss their comfort level directly with the captain rather than follow a fixed group schedule.

Snorkeling is a major part of the appeal, but you should keep expectations sensible. Marine life and visibility change from day to day. The charter provides the setting and equipment, not a guarantee of a particular animal or underwater sight.

One exceptional outing included a dolphin encounter near Scotts Bay. That is a wonderful possibility, but it should be treated as luck rather than part of the promised itinerary. The reliable features are the sailing, the water stops, and the time to swim or sunbathe.

The Honeymoon Beach Anchorage Near Caneel Bay

The second stop is a secluded anchorage off Honeymoon Beach near Caneel Bay. This is the most clearly defined stop and likely the calmest part of the afternoon. You can snorkel again, swim, or stay aboard and sunbathe.

Honeymoon Beach gives the trip a strong St John flavor. Instead of spending the whole charter moving from point to point, you get a quiet pause near shore. The boat becomes your base, with the shaded cockpit available when you need a break from the sun.

This stop also shows why the private setup matters. If one person wants another swim while someone else wants to eat, read, or sip a drink, the group can set its own rhythm. On a shared trip, you may be pulled away just as you get comfortable. Here, the captain can work with your party within the available time.

The word secluded should not lead you to expect total isolation or a guaranteed empty shoreline. The anchorage is chosen as a quieter stop, but conditions and other boats can vary. Still, a sheltered pause near Honeymoon Beach is a fine way to spend the middle of a sailing charter.

Lunch from North Shore Deli

Lunch is included, and the menu is more substantial than the usual boat trip snack. You can choose from nine gourmet deli sandwiches and five gourmet salads through North Shore Deli. That range helps the charter work for mixed groups, including people who want a proper meal after snorkeling.

A sandwich-and-salad menu is also practical at sea. It is easy to eat in the cockpit, does not require a formal setup, and should suit different appetites. If your group has special dietary needs, check the available choices before the day of departure rather than assuming every request can be handled.

The food matters because a four to five hour outing can feel long if you are left with only chips and drinks. Here, lunch breaks up the sailing and swimming. It also lets you stay on the boat rather than look for a separate meal before or after the charter.

What the Open Bar Really Adds

The charter includes what is described as a very open bar. Drinks include beer, soda, juice, water, vodka, rum, gin, tequila, sparkling wine, and more. The selection is broad enough for people who want a cocktail, a celebratory glass of sparkling wine, or a simple soft drink.

This is a nice extra, but it comes with an obvious reminder: alcohol and swimming require care. You should decide how much you want to drink before getting in the water, and follow the captain’s instructions throughout the trip. The boat’s shaded cockpit gives you a place to sit out of the sun while you enjoy a drink.

For a group celebrating a birthday, anniversary, or reunion, the bar can make the charter feel like a private party on the water. For a family with children or non-drinkers, the soda, juice, and water mean the package is not built only around alcohol.

The value of the bar depends on your habits. If you rarely drink, it should not be the reason you book. The real value comes from combining drinks with private use of the boat, lunch, snorkeling gear, and captain service.

Comfort on a 40-Foot Sailboat

A sailboat offers a different experience from a large motorboat. You may feel more connected to the wind and the water, with the boat’s movement shaping the ride. That can be wonderfully peaceful, though anyone prone to motion sickness should plan carefully.

The boat has a shaded cockpit, which is essential in the strong Caribbean sun. You can enjoy the views without spending every minute exposed to heat. A fully functional restroom is another useful feature, especially since the charter lasts several hours and includes time away from shore.

WiFi is available onboard. That can help if you need to stay reachable, though the best use of the trip is probably to put the phone away for a while. The service animals are allowed, and most people can participate, but you should discuss any mobility or boarding concerns with the operator before arrival because the experience includes a tender transfer.

The boat is private for your group, up to six people. That limit keeps the setting intimate and makes the $1,395 price easier to assess. Split six ways, the cost comes to about $232.50 per person before transportation. For six people who would otherwise pay separately for a boat trip, snorkeling gear, lunch, drinks, and a private guide, that can be reasonable.

For two people, the calculation changes. You would be paying nearly $700 each, so the charter makes more financial sense for a full family or friend group. If privacy and flexibility matter more to you than the lowest possible price, the premium may still be worthwhile.

Planning the Day and Cancellation Rules

The experience is often booked about 65 days ahead, so advance planning is sensible, especially if you are visiting during a busy period or need a particular date. Confirmation is sent within 48 hours of booking, subject to availability.

You can cancel for a full refund up to 24 hours before the start time. Cancellations or changes made within 24 hours are not refunded or accepted. Since the trip requires good weather, the operator will offer another date or a full refund if poor conditions force a cancellation.

The listed operating dates include daily service periods from 8:00 AM to 9:00 PM during part of the schedule, with later 9:00 AM starts during other seasonal periods. Those hours describe availability rather than the exact departure time of your charter, so confirm the start time when you book.

Bring the practical basics: swimwear, sun protection, and anything you need for comfort between swims. Lunch, drinks, and snorkeling equipment are included, so you do not need to pack a full picnic or rent gear separately.

Who Will Enjoy This Private St John Charter

I would choose this outing for a family that wants an easy day together, a group celebrating a special occasion, or friends who prefer a private boat to a crowded shared excursion. The shaded cockpit, restroom, lunch, and drink selection make it easier for different personalities to enjoy the same outing.

It also suits anyone curious about sailing. The chance to take a short lesson from Captain Mike gives the day more character than a simple boat transfer. You can sit back and watch the captain work, or ask for a more active role if conditions allow.

This may not be the best choice if you want a long, intensive snorkeling session. The charter has two water stops, but the total duration is only four to five hours and includes sailing, lunch, and relaxing aboard. It is also a poor fit for anyone seeking the cheapest way to get on the water.

The boat’s good facilities make it friendly for many participants, and service animals are allowed. Still, the inflatable tender and movement between boats are worth considering for anyone with mobility limitations. Ask the operator directly about boarding support before you commit.

Should You Book Morningstar Sailing and Power Charters?

I would book this private St John sailing charter if you can fill most of the six seats. The strongest reasons are the personal service from Captain Mike, the chance to learn a little sailing, the two snorkeling stops, and the fact that lunch and drinks are already covered.

The $1,395 group price is not modest, but it includes a private 40-foot boat, captain, food, open bar, snorkeling equipment, restroom, shaded seating, and WiFi. Split among six people, it becomes a fairer deal. Split among two, it becomes a luxury purchase.

Book with realistic expectations. Dolphins, perfect visibility, and a completely empty anchorage are possible but not guaranteed. What you can count on is a private outing from Cruz Bay, time on the water near St John, and a captain who aims to make the day safe, relaxed, and personal.

FAQ

Where does the private sailing charter begin?

The charter begins at the Saint John Ferry Terminal in Cruz Bay, St John, US Virgin Islands.

Where does the experience end?

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

How long does the charter last?

The charter lasts approximately four to five hours.

How many people can join the private charter?

The charter is private for your group and can include up to six people.

Is lunch included?

Yes. Lunch includes a choice of nine gourmet deli sandwiches and five gourmet salads from North Shore Deli.

Are drinks and snorkeling equipment included?

Yes. Snorkeling equipment is provided, and the included drinks cover beer, soda, juice, water, spirits, sparkling wine, and more.

What happens if bad weather cancels the trip?

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