Private Day Charter Classic Sailboat

Sailboat days are hard to beat. This private St John charter gives you a 40-foot classic sailboat, two chances to snorkel, lunch, and an open bar without sharing the boat with strangers. I especially like the relaxed pace and the chance to let Captain Mike teach you some sailing, rather than simply ferrying you from one swim stop to another.

I also like the practical comforts: a shaded cockpit, onboard restroom, WiFi, and snorkeling gear for everyone. The main drawback is the price, especially for a small party. At $1,395 for up to six people, it becomes much better value when you fill the boat, but a couple traveling alone will pay a premium for privacy.

Key points at a glance

• Private boat for up to six: Your group gets the sailboat, crew, itinerary, and conversation to yourselves.
• Two water stops: The outing includes snorkeling, swimming, or sunbathing, with a second stop near Honeymoon Beach by Caneel Bay.
• Captain Mike may let you sail: Personal sailing instruction has been one of the most memorable parts of the trip for some passengers.
• Lunch and a generous drink selection: Nine deli sandwiches, five salads, beer, wine, spirits, juice, soda, and water are included.
• Comforts that matter: The boat has a shaded cockpit, working restroom, snorkeling equipment, and WiFi.
• Plan around the pickup point: The listed meeting place is the Saint John Ferry Terminal in Cruz Bay. Private transportation is not included.

Setting out from Cruz Bay on a private sailboat

The day begins at the Saint John Ferry Terminal in Cruz Bay. From there, you head out to the water and use an inflatable tender to reach the 40-foot sailboat. That transfer is part of the character of the outing, but it also means you should pay attention to where and when you are expected to meet.

Pickup is offered in the tour details, yet private transportation is not included. Since the stated start and end point is the ferry terminal, confirm the exact meeting arrangement before the morning of your trip. This is a small point, but it can prevent a rushed start.

Once aboard, the private format changes the whole feel of the day. You are not trying to keep up with a large group or squeeze into the one remaining seat. Captain Mike and his crew can shape the pace around your party, within the limits of weather, daylight, and the boat’s route.

The trip lasts about four to five hours. That is long enough for sailing, two water stops, lunch, and time to relax, but short enough to fit into a busy St John vacation. You should still think of this as a half-day outing, not an all-day cruise.

Captain Mike brings more than boat-handling skills

Captain Mike receives especially strong praise for being attentive, clear, and safety-minded. Those qualities matter on a private boat because you spend much of the day close to the captain and crew. Good communication helps you know what is expected when boarding the tender, moving around the deck, or preparing to snorkel.

He also appears willing to make the outing personal. One passenger was given a sailing lesson, turning a pretty boat ride into a hands-on introduction to how the sailboat works. If learning a little about sailing appeals to you, ask about it early in the day. It may depend on conditions, timing, and the captain’s judgment.

Captain Mike’s nephew Beau has also worked aboard the boat. The crew is described as friendly and easy to spend time with, which is useful on a private charter where personality matters almost as much as the scenery.

The crew also handles the bar and lunch service. One passenger singled out Captain Mike’s bartending skills, so the drinks are not merely an afterthought. Still, the bar should support the day rather than dominate it. St John’s water is the main attraction, and drinking heavily before snorkeling is never a smart plan.

The first sail gives you room to settle in

The first portion of the trip is your chance to get comfortable with the boat. You can sit in the shaded cockpit, watch the coast, and enjoy the sailing before the first water stop. The cockpit is an important feature in the strong Caribbean sun, especially for anyone who needs a break from direct light.

The boat also has a fully functional restroom. That is a major convenience on a four to five-hour outing. You do not have to wait until returning to Cruz Bay, and you can relax more fully knowing the facility is available.

WiFi is included as well. I would treat it as a useful extra, not the reason to book the charter. Connection quality can vary on the water, and the best part of the day is likely to be looking up from your phone. Still, WiFi can help with basic communication or a quick message home.

The boat is private, but private does not mean silent or completely unstructured. The captain still needs to manage the route, weather, sail handling, tender, and water stops. You get a more personal day, not a completely custom voyage without limits.

Snorkeling in the Virgin Islands water

Snorkeling is one of the main reasons to choose this trip. Equipment is available for every passenger, so you do not need to pack a full set of fins, mask, and snorkel. That makes the outing easier for families and mixed groups, especially when some people are regular snorkelers and others are trying it for the first time.

The exact quality of your snorkeling depends on conditions. Clear water is part of the appeal, but visibility, wind, current, and sea conditions can change. The captain chooses the stops, and that local judgment is valuable because the best place on one day may not be the best place on another.

The first stop gives you time to enter the water and get used to the gear. You may snorkel, swim, or simply remain aboard if you are not comfortable in the water. That flexibility is important for a family group with different energy levels.

Do not expect a formal lesson or a large organized snorkeling operation based on the information provided. The focus is a private sailing day with snorkeling built in. If someone in your party is a nervous swimmer, mention it to the crew before entering the water.

One unusual possibility has occurred in Scotts Bay: a passenger had a rare chance to swim with dolphins. That is a lucky wildlife encounter, not a promised part of the itinerary. You should book for the sailing and snorkeling, then regard any dolphin sighting as a bonus.

The second stop near Honeymoon Beach

The second stop is at a secluded anchorage off Honeymoon Beach near Caneel Bay. This is the part of the day designed for slowing down. You can snorkel again, swim, or stay aboard and sunbathe.

Having a second stop matters because the day does not depend on one short swim. If the first location is not perfect for your group, you get another chance to enjoy the water. It also lets stronger swimmers spend more time snorkeling while others rest in the shade.

Honeymoon Beach gives the stop a scenic setting, but the word secluded should not be taken as a guarantee of complete solitude. Conditions, other boats, and the day’s route can affect the feeling of privacy. The charter itself remains private, even if the surrounding bay is not empty.

Sunbathing is a real part of the plan, so bring sun protection and use the cockpit shade when you need a break. The trip includes drinks and lunch, but it does not list personal towels or special sun gear. Pack the beach basics you normally want for a half-day on the water.

Lunch is better than a token boat snack

Lunch is included, and the choices are more substantial than a bag of chips or a basic fruit plate. The menu includes nine gourmet deli sandwiches and five gourmet salads from North Shore Deli.

That range is helpful for a private group. You can choose different meals rather than accepting one fixed dish for everyone. A sandwich works well after snorkeling, while a salad may suit someone looking for a lighter meal.

Because the full menu is offered, it is sensible to check the available choices when you book or before departure. The supplied details do not specify how far ahead food selections must be made, so do not assume the crew can handle every last-minute dietary request without notice.

Lunch also adds real value to the price. Buying separate meals and drinks after a boat trip can add up quickly, especially for six people. The included meal keeps the day simple and means you are not watching the clock for a return to shore.

What the open bar includes

The included bar is unusually broad for a half-day charter. Drinks include beer, soda, juice, water, sparkling wine, vodka, rum, gin, tequila, and more.

For a group, that can make the price easier to justify. You are not paying for the boat and then adding every drink separately. Water and juice are included, which matters just as much as the alcoholic choices during a sunny day with swimming.

The practical advice is simple: pace yourself. Snorkeling, sun, wind, and alcohol do not mix well in large quantities. The crew can serve drinks, but you should decide ahead of time how much you want to drink before getting in the water.

The open bar also makes the charter appealing for a birthday, anniversary, or small family celebration. It is less useful if your group does not drink, since part of the advertised value then goes unused.

Does $1,395 offer good value?

The price is $1,395 per group of up to six. At full capacity, that works out to $232.50 per person. For six people, the cost includes a private 40-foot sailboat, crew, snorkeling equipment, lunch, alcoholic and nonalcoholic drinks, restroom, shaded seating, and WiFi.

That is a fairer calculation than comparing the total price with a basic group boat tour. You are buying privacy and a more flexible day, not just transportation over water. The sailing lesson option and personal attention from Captain Mike add value if your group wants interaction rather than a simple ride.

For two people, the same price works out to $697.50 each. That is a steep spend for a four to five-hour activity, even with food and drinks included. Couples may still choose it for a special occasion, but the financial case becomes much stronger when three to six people share the cost.

Families and groups of friends are likely to get the best value. You can split the cost, choose your own companions, and avoid paying separately for lunch, snorkel rentals, and a bar tab. I would compare the total against other private charters on St John, but the inclusions here make the price easier to understand.

Who should book this charter?

This outing suits people who want a private day on the water without managing a boat themselves. It works particularly well for families, couples traveling with friends, and small groups celebrating something special.

You will probably enjoy it most if you like a mix of activity and rest. The schedule includes sailing, two water stops, lunch, drinks, and time in the shaded cockpit. You are not locked into snorkeling every minute.

It is also a good fit if you want a more personal connection with the captain. Captain Mike may explain the sailing, offer a lesson, and adjust the feel of the day to your group. If you only want a fast route from one snorkeling site to the next, a simpler boat trip may be enough.

This is less ideal for anyone seeking a full-day cruise or a guaranteed wildlife encounter. The outing lasts four to five hours, and dolphins are a lucky possibility rather than a scheduled stop. The weather also matters, so keep some flexibility in your St John plans.

Service animals are allowed, and the activity is near public transportation. Most people can participate, but the details do not specify exact accessibility arrangements for the tender or sailboat. If anyone in your group has mobility needs, ask the operator for a clear boarding description before booking.

Booking timing and weather rules

This charter is often booked about 65 days ahead. That does not mean you must reserve exactly that early, but it is a useful sign that popular dates can fill well in advance. I would book early for a vacation with fixed dates, particularly if you need a specific day for a celebration.

Confirmation is sent within 48 hours, subject to availability. The cancellation policy allows a full refund if you cancel at least 24 hours before the start time. Cancellations or changes inside that window are not refunded or accepted.

Weather can also cancel the trip. If poor conditions force a cancellation, you are offered another date or a full refund. That policy is fair, but you should avoid placing this charter on the final day of a short trip if missing it would leave you with no replacement date.

Should you book the Morningstar charter?

Book it if you can fill most of the six seats and want a relaxed, private day with real comforts. The strongest reasons are the personal service from Captain Mike, the chance to learn a little sailing, two water stops, and the fact that lunch and drinks are already covered.

Think twice if you are traveling as only two people and price matters. The charter becomes expensive per person, and a shared boat may give you more value. Also confirm the pickup details, tell the crew about food needs, and keep an eye on the weather forecast.

For a small group that values privacy, good food, a shaded cockpit, and time in the water, this is a polished way to spend half a day around St John. Just book it for the sailing, snorkeling, and easy company, not for a guaranteed dolphin encounter or a full-day adventure.

FAQ

Where does the private sailboat charter begin?

The listed meeting point is the Saint John Ferry Terminal in Cruz Bay, St John, USVI.

Where does the activity end?

The charter ends back at the meeting point in Cruz Bay.

How long does the charter last?

The experience lasts approximately four to five hours.

How many people can join the private charter?

The price covers one private group of up to six people.

Is lunch included?

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

Are drinks included?

Yes. The included drinks include beer, soda, juice, water, sparkling wine, vodka, rum, gin, tequila, and more.

Is snorkeling equipment provided?

Yes. Snorkeling equipment is available for all passengers.

What happens if the weather cancels the trip?

You can choose another date or receive a full refund if poor weather causes the cancellation.