Learn to Sail – Sailing Lessons All Inclusive

The best part of this St. John outing is the choice it gives you. You can take the helm of a 40-foot sailboat and learn the basics, or let the captain handle the boat while you stretch out, watch for wildlife, and enjoy the water. The private format keeps the day personal, not crowded.

I like the hands-on sailing time and the fact that snorkeling gear, lunch, drinks, fuel, and fees are bundled into one price. I also like the flexible route, with protected western-shore waters, a snorkel stop, and a second swimming or beach stop. The main consideration is cost: $1,395 covers up to six people, so it offers better value for a full group than for a couple.

Key points to know before you book

• You can take the helm: Your captain provides as much sailing instruction as you want, then takes over when you prefer to relax.
• The boat is private: Only your group participates, with room for up to six people aboard the 40-foot sailboat.
• Snorkeling is built in: Equipment is supplied, and the captain recommends a suitable stop.
• The package covers nearly everything: Deli lunch, snacks, cocktails, beer, sparkling wine, soft drinks, juice, water, fuel, taxes, and fees are included.
• The route can change with your interests: You can focus on sailing, snorkeling, swimming, sunbathing, or some mix of all four.
• The weather matters: Poor conditions can lead to a new date or a full refund, but the booking is otherwise non-refundable.

Setting out from Cruz Bay at 10 a.m.

Your day begins at the Cruz Bay Ferry Dock on Prince Street in St. John at 10 a.m. The activity ends at the same meeting point, which makes the plan simple if you are already in Cruz Bay or arriving by ferry.

Pickup is offered, but you should confirm the exact arrangement when you book. The meeting point is still Cruz Bay Ferry Dock, so do not assume that transportation from your accommodation is automatic.

The five-hour schedule gives you enough time for more than a quick sail past the coast. You can settle into the boat, receive sailing instruction, stop to snorkel, eat lunch, and make a second water stop without turning the outing into a rushed checklist.

This is a private charter for up to six people. That number matters. A group of six can spread the $1,395 price across the whole party, bringing the cost to $232.50 per person before gratuity. For two people, the same charter costs much more per person, but you also get the boat and the captain’s attention to yourselves.

Learning the ropes aboard a 40-foot sailboat

The lesson is designed around your comfort and interest. Your captain can explain the basics, guide you toward a snorkeling destination, and let you take the helm for more practice. If you have never sailed, you can ask for as much help as you need. If you already know a little, you can spend more time handling the boat.

I like this arrangement because it does not force every person in the group into a formal lesson. One person may want to learn how to steer, another may prefer to watch, and someone else may be happiest with a drink in hand and a place in the sun.

The boat is a 40-foot sailboat, large enough to provide a comfortable base for the day while still giving the outing a personal feel. The description does not specify cabin, restroom, or seating details, so ask Morningstar Sailing and Power Charters if those features matter to you.

Captain Mike is specifically associated with one particularly personal outing, including time tailored around a daughter and a comfortable, sound boat. If Captain Mike is assigned to your charter, you can ask for the same kind of family-focused pacing. Captain assignment is not guaranteed in the information provided, so confirm it directly if that is important to you.

Sailing along St. John’s protected west coast

The western shoreline of St. John provides the main setting for the day. Protected water can make a good place to learn because your attention stays on the boat, the captain’s directions, and the scenery instead of on a demanding open-water route.

You may spend much of the outing simply moving under sail, with the captain choosing a course that suits the conditions and your group. Keep your eyes open for local wildlife as you go. No specific animals are promised, so treat wildlife sightings as a possibility rather than a scheduled part of the trip.

The route is not locked to one destination. The captain can suggest stops based on the water, your interests, and how much time you want to spend sailing. That flexibility is useful, but it also means you should not book this expecting a fixed list of named bays or beaches.

If your group has mixed priorities, agree on a rough plan at the start. Tell the captain if sailing instruction is the main goal, or if snorkeling and swimming matter more. A simple conversation early in the day helps prevent one person from taking the helm for hours while everyone else hoped for beach time.

Snorkeling with gear already on board

Snorkeling is optional, but the equipment is included. Your captain recommends a snorkeling destination and fits you with the necessary gear before you enter the water.

That convenience saves you from renting masks, snorkels, or other basic equipment separately. It also keeps the group from spending part of the morning shopping for supplies. You can move from sailing to the water without changing operators or arranging a second activity.

The first water stop is intended for snorkeling, swimming, and time in the sun. You may see sea life, but the exact conditions and sightings depend on the day. The activity does not promise a particular species or guarantee clear water, so keep your expectations flexible.

The equipment list covers snorkeling gear, not towels. Bring or arrange your own towel, since towels are not included. You should also ask about any personal items you need to pack, as the supplied information does not specify storage or changing facilities.

A second stop for swimming and beach time

After the first swim and snorkel session, the plan calls for a second stop. This may offer more swimming, additional sea life, or time on a white sandy beach along the coast.

The second stop is a useful feature because it breaks up the day. Five hours on a boat can feel long if you never leave the deck, especially for children or anyone who likes regular changes of pace. Moving to another place gives you a fresh view and another chance to get in the water.

The exact beach or swimming site is not named in advance. That is good for flexibility, but it limits your ability to plan around a particular landmark. If you have a favorite type of stop, tell the captain at the beginning.

You can also return to the helm after snorkeling. The captain may provide more instruction, or you can hand control back and relax. This give-and-take is the heart of the outing: it works as a sailing lesson, a private boat day, or a blend of the two.

Lunch, snacks, and an open bar

Food and drinks are a real part of the value here, not an afterthought. A full gourmet deli menu is included for lunch, along with chips, granola, and other light snacks.

The beverage package is unusually broad for a half-day charter. It includes hand-crafted cocktails, mocktails, a full bar, beer, sparkling wine, soda, juice, and bottled water. You can keep things festive, stick with soft drinks, or choose water while you focus on sailing.

Because the group is on the water for about five hours, included food saves both time and hassle. You do not need to interrupt the outing to find lunch, and you can eat between sailing and swimming.

The open bar also calls for common sense. If you plan to take the helm, follow the captain’s directions about when it is appropriate to drink. The safest approach is to enjoy the sailing lesson first and leave most alcohol for your time relaxing on deck.

Is the $1,395 price a good value?

The price is $1,395 per group of up to six people. Fuel, all fees, taxes, snorkeling equipment, lunch, snacks, and the listed drinks are included. Gratuity is not included.

For six people, the price works out to $232.50 per person. That is a strong comparison point for a private five-hour outing with a boat, captain, instruction, snorkeling, food, and drinks included. For three people, the cost is $465 each. For two, it is $697.50 each, before gratuity.

That makes group size the key value question. Families, two couples, or a group of friends can spread the expense and gain the privacy of a charter. A couple may still prefer it for the personal instruction and freedom to set the pace, but the per-person cost is high.

The package also reduces surprise expenses. You are not separately paying for fuel, snorkel gear, lunch, or a basic bar package. The one major extra listed is gratuity, so include that in your budget.

Who will enjoy this private sailing lesson?

This outing suits people who want more than a standard boat ride. You get the chance to learn sailing, not just sit aboard while someone else operates the boat.

It is a good fit for:

• A family that wants a private day with flexible pacing
• Friends who want a boat, snorkeling, lunch, and drinks in one package
• Beginners who want personal instruction
• Experienced sailors who want some helm time without arranging a bareboat rental
• People who prefer choosing between active time and quiet time

It may not suit you if you want a fixed sightseeing route, a long formal sailing course, or a low-cost shared excursion. It is also not the best match if you need certainty about specific beaches or wildlife sightings.

Most people can participate, and service animals are allowed. The activity is near public transportation. Still, ask the operator about any personal mobility needs before booking, since the supplied details do not explain boarding arrangements or onboard facilities.

Booking rules and weather concerns

This experience is non-refundable and cannot be changed for personal reasons after booking. That makes your date choice important. Check your plans carefully before paying.

The weather policy is more forgiving. The activity requires good weather, and if poor conditions force cancellation, you will be offered another date or a full refund.

Because the sailing route and water stops depend on conditions, a good forecast is important even when the trip is not canceled. Calm weather may favor a relaxed sail and easy swimming, while rougher conditions could affect the pace or the captain’s choice of stops.

Should you book Morningstar’s sailing lesson?

Book it if you have a group of up to six and want a private St. John day that combines sailing instruction with swimming, snorkeling, lunch, and drinks. The strongest reason to choose it is control: you decide how much time goes to the helm, the water, the beach, or the deck.

I would be especially interested in this charter for a family or group of friends willing to split the price. The personal touch associated with Captain Mike, including a boat described as sound and comfortable, also makes it appealing for a special day with children.

Think twice if you are traveling as only two people and mainly want a cheap way to see the coast. In that case, the price may be hard to justify. But if privacy, flexible pacing, and hands-on sailing matter to you, the all-inclusive format gives this five-hour outing a clear advantage.

FAQ

Where does the sailing lesson begin?

It begins at the Cruz Bay Ferry Dock on Prince Street in Cruz Bay, St. John, USVI.

What time does the activity start?

The start time is 10 a.m.

How long does the experience last?

The experience lasts approximately five hours.

Where does the activity end?

It ends back at the Cruz Bay Ferry Dock meeting point.

How many people can join the private charter?

The private activity accommodates a group of up to six people.

Is pickup available?

Pickup is offered. The listed meeting point is still Cruz Bay Ferry Dock, so confirm the pickup details when booking.

Can I learn to sail during the outing?

Yes. The captain can provide sailing instruction and let you take the helm. You can request as much instruction as you need or return control to the captain.

Is snorkeling equipment included?

Yes. Snorkeling equipment is included, and the captain can recommend a snorkeling destination.

What food and drinks are included?

The package includes a full gourmet deli lunch, snacks, bottled water, soda, juice, beer, sparkling wine, hand-crafted cocktails, mocktails, and a full bar.

Are towels and gratuity included?

No. Towels and gratuity are not included.

What happens if bad weather cancels the trip?

If poor weather causes cancellation, you will be offered a different date or a full refund. The booking is otherwise non-refundable and cannot be changed for personal reasons.