Private Day Charter Classic Sailboat

A private day on a 40-foot sailboat in St John is interesting because your time is built around water, not just beaches. You start in Cruz Bay and then shift over by tender to your boat, which immediately changes the pace of the day. Captain Mike, plus his crew (including Beau), runs a tight, friendly trip that feels personal even with a small group.

I like two things a lot. First, snorkeling equipment is included for everyone, so you can show up and focus on the water. Second, I love that lunch is not an afterthought, it is deli-style with options from the North Shore Deli menu.

The one drawback to keep in mind is that this is a weather-dependent sailing day, so the plan can only happen when the sea cooperates. Also, private transportation is not included, even though pickup is offered.

Key things that make this charter worth your time

• Private group up to 6 means fewer logistics, more control of your day, and a calmer boat vibe.
• Snorkeling gear included for every passenger, so you are not hunting for rentals at the last minute.
• Very open bar on board with beer, soda, juice, water, vodka, rum, gin, tequila, sparkling wine, and more.
• Lunch from North Shore Deli with 9 deli sandwiches and 5 gourmet salads to choose from.
• On-water comfort with a fully functional restroom, shaded cockpit, and WiFi on board.
• Captain-led sailing moments are part of the fun, including the possibility of a sailing lesson.

A 40-foot sailboat day in St John, minus the crowds and chaos

If you have ever tried to do St John the usual way, you know how fast the day can get chopped up by schedules and packed boats. This charter flips that. You get a private outing for your group of up to six, on a classic sailing vessel that is meant for moving across the water.

What I find especially appealing is the tender-to-sailboat flow. You start in Cruz Bay, then take an inflatable tender out to the boat. That means you are not stuck waiting for a big vessel to do everything. You are active early, and the rest of the trip follows that same theme: sail, stop, snorkel, relax, repeat.

This is also a great length for a “vacation day” without turning it into a half-day sprint. You are out for about 4 to 5 hours, long enough to settle in, eat, swim, and get real water time.

Getting to the boat: Saint John Ferry Terminal and the Cruz Bay tender transfer

The trip begins back at the Saint John Ferry Terminal in Cruz Bay. The activity ends at the same meeting point, so you are not trying to solve a complicated return plan.

Two things matter here for how your day feels:

First, pickup is offered, so you might be able to reduce stress on arrival and return. But private transportation is not included, so do not assume your lodging pickup is automatic unless you confirm it.

Second, you should be ready for that tender transfer from shore to the sailboat. For most people, it is quick and fun. If you are sensitive to motion, plan for it. Wear grippy footwear, stay aware of where you put your balance, and keep your focus outside the boat. The captain and crew will handle the safe transitions.

You will also use a mobile ticket, which is a small thing that saves time on departure.

Snorkeling in the Virgin Islands: what you actually get on board

The charter is built around snorkeling. You get multiple stops out in clear Virgin Islands water, with gear included for all passengers. That is a big practical win. Snorkeling days often fall apart when half the group is still trying to rent equipment or figure out fit and sizing.

With equipment included, you can spend your energy on the part that matters: getting in the water and enjoying what you came for. You do not need to arrive early just to manage gear.

Here is how to think about the snorkeling rhythm on this kind of private sail day. It is not just a quick “in and out” photo moment. The day includes time at anchorage to swim and sunbathe, so you have more control over how long you stay in the water. If you want a slower pace, you can take it. If you love to snorkel hard, you can move quickly from one swim session to the next.

One more practical note: the captain will communicate what you need to do on the water, and the crew makes sure everyone is clear. In real-world terms, that is what turns snorkeling from stressful to easy, especially when you are boarding and returning from open water.

The Honeymoon Beach area anchorage near Caneel Bay: why stop number two hits

Your second stop happens at a secluded anchorage off the shoreline of Honeymoon Beach near Caneel Bay. This is the kind of spot that makes sense on a private charter: you are not stuck with a crowded schedule or a line of boats.

At this stop, the plan includes another snorkel session, plus time to swim and sunbathe. The word secluded is doing work here. When you are anchored away from heavy foot traffic, it is easier to settle in, float, and enjoy the water without feeling like you are competing for space.

Why this anchorage pairing matters is simple: Caneel Bay and the Honeymoon Beach area are known for clear water and great shoreline scenery, and the boat stop format lets you experience that directly. You are not just passing by from a distance.

Drawback to consider: because you are anchored and the trip is weather-dependent, the captain may adjust timing and conditions to keep it safe and comfortable. That is normal sailing. It is also why having an attentive captain matters. Captain Mike is praised for being thoughtful and keeping passengers informed, so you usually know what to expect as you go.

Lunch that feels like a treat: North Shore Deli sandwiches and salads on the water

On a charter like this, lunch is not just fuel. It is a morale boost in the middle of a salty, sun-heavy day.

Lunch is included, with a menu built around 9 gourmet deli sandwiches and 5 gourmet salads. The important part for value is that it is sourced from North Shore Deli, with their full menu used for your charter selections. That means you are not stuck with a generic sandwich situation.

Practically, you will eat on board, so you will not be searching for a restaurant or dealing with a late, rushed meal. It also pairs well with the overall pacing: you can snorkel, then come back, eat, and reset without leaving the water experience.

If you are traveling with people who prefer food comfort over “snack-only on boats,” this is a strong point.

A Very Open Bar, plus real comfort onboard

The charter includes drinks as part of the experience. You will have access to a Very Open Bar, with choices like beer, soda, juice, water, vodka, rum, gin, tequila, and sparkling wine, plus more.

This matters because alcohol on a boat is one of those things that can range from skimpy to truly fun. Here, the inclusion is broad, so you can actually enjoy a cocktail or a casual beer without paying extra.

Now for comfort, because it is not all about the drinks and snorkeling. The boat offers:

• A fully functional restroom and restroom on board
• A shaded cockpit for breaks from sun
• WiFi on board, which is handy if you want to keep in touch or check simple plans between stops

Also, the crew makes the day feel organized. That shows up in how smoothly passengers are guided through tender boarding, snorkeling transitions, and returning to the boat. When that flow is good, the whole day feels effortless.

One extra detail worth noting from experiences shared with me by others: Captain Mike has been known to bring people to Scotts Bay for a chance to swim with dolphins. It is not something I would assume on every sailing day, but it is a reason many people end up calling this the highlight of their trip.

Captain Mike and Beau: attentive sailing that makes the day feel small-group

Private charters live or die by the captain. On this one, you will see why the reviews are so consistent.

Captain Mike is repeatedly described as thoughtful, attentive, safe, and communicative. That last part is a big deal. When the captain explains what you need to do, and the crew backs it up, you are not guessing at the next step. You feel taken care of.

There is also a sailing angle that makes this more than a motorboat day. Captain Mike has been praised for giving a sailing lesson. If you have ever watched sailboats and wondered what it would feel like to do more than sit there, this is how you get a taste of it.

Crew support matters too. Beau, sometimes written as Bo?, is mentioned as friendly and knowledgeable. The vibe on this charter is welcoming, not stiff. That is important if you are traveling with kids, or with adults who just do not want a lecture, they want a good day on the water.

Price and value: $1,395 for up to 6, and when it feels like a smart splurge

The price is $1,395 per group, up to 6 people. On the surface, that can sound steep, until you break it down.

If you fill the boat with six people, you are roughly in the $230 per person range. If you go with four, it becomes closer to $350 per person. Either way, you are paying for privacy, gear included, lunch included, and an on-board bar setup. You are also paying for a captain and crew handling navigation, anchorage stops, and the tender transitions.

So when does it make sense?

• If you have a group of friends or a family that can realistically fill most of the spots
• If you want snorkeling time with less hassle than booking separate activities
• If you care about being on a sailboat specifically, not just any boat

If you are traveling solo or as a couple and you are not focused on the included lunch and open bar, you might decide to book a different format. But if you want one standout day that feels custom, this price structure can work in your favor.

One more value note: this is timed well. A 4 to 5 hour window is long enough to justify a full-day charter cost, but short enough that you are not losing your entire vacation day.

Who this charter fits best, and who might want a different plan

This charter is a great fit if you want:

• A private experience on the water, not a shared party boat
• A day built around snorkeling with equipment handled for you
• Comfort features like restroom access and shaded seating
• A simple food plan, with lunch included
• A fun social setup, with a broad open bar included

It is also a good choice if you like the idea of learning something small. The sailing lesson is a real perk when you are on a private boat.

You might want to think twice if:

• You do not like the idea of sailing and tender transfers
• Your group wants a long, walkable onshore program instead of time at sea and at anchor

Also, because the day requires good weather, build flexibility into your schedule. If you are planning around only one tight window for St John water time, it can feel risky. If you have a buffer day, you will feel more relaxed.

Quick checklist so your day stays smooth

This is how I would prepare, based on what matters on a sailing snorkeling charter:

• Wear comfortable swimwear and grippy footwear for tender boarding
• Bring sunscreen and a hat, even if you plan to spend time in the shaded cockpit
• Pack a swimsuit cover-up for after snorkeling sessions
• Bring a small waterproof bag if you want to protect your phone while you are in and out

Since snorkeling equipment is provided, you do not need to pack gear. That is part of why this is such an easy day to enjoy.

Should you book Morningstar Sailing and Power Charters?

I would book this charter if your priority is one standout St John day where you get a private sailboat experience plus real snorkeling time, with lunch and drinks handled for you. Captain Mike’s style shows up in the details: safe handling, clear communication, and a crew that keeps the day organized.

Where I might hesitate is when your schedule is rigid and weather would leave you with no backup. This is sailing, so good conditions are part of the deal. Also, if your group is small and you are paying per person without filling most of the six spots, you may decide the value math is not for you.

If you can align a good weather day and you are traveling with a group that can share the cost, this is the kind of outing that tends to stick in your memory long after the beach stops blur together.

FAQ

How long is the Private Day Charter Classic Sailboat?

The charter lasts about 4 to 5 hours.

What is the price and group size?

It costs $1,395 per group and can host up to 6 people.

Where does the tour start and end?

It starts at the Saint John Ferry Terminal in Cruz Bay, St John 00830, USVI, and ends back at the same meeting point.

What is included with snorkeling?

Snorkeling equipment is provided for all passengers.

Is lunch and drinks included?

Yes. Lunch is included, and alcoholic beverages and non-alcoholic drinks are included as part of the open bar.

Do I need my own transportation to the meeting point?

Private transportation is not included, but pickup is offered.