A day on a sailboat beats most shore plans. This private 40-foot classic sailboat charter takes you out of Cruz Bay, adds two snorkeling chances in clear Virgin Islands water, and keeps things easy with onboard comfort, lunch, and an open bar.

I like that it feels truly private, you and your group only, not a mixed crowd. I also love the way the day is set up for “in-water time,” not just drifting past views, with snorkeling gear included and a stop off Honeymoon Beach near Caneel Bay for a second swim.

One thing to consider is timing and weather. This charter runs only when conditions are good, so you should plan for the day to shift if the sea is cranky.

Key Points to Know Before You Go

• Private charter for up to 6 people, so the vibe stays relaxed and personal
• Inflatable tender transfer from Cruz Bay to the sailboat, which adds a fun start and a bit of movement
• Snorkeling gear included for everyone, plus two water-focused stops
• Lunch from North Shore Deli with a deli-sandwich and salad menu onboard
• Very Open Bar with beer, soda, juice, water, and spirits like vodka, rum, gin, tequila
• Onboard comfort: restroom, shaded cockpit, and WiFi

A 40-Foot Private Sail That Feels Like Your Own Day at Sea

This is the kind of St John trip that lets you treat the day like it belongs to you. You book a private classic sailboat day for up to six people, so you are not sharing your itinerary with strangers or waiting on a slow group. The boat size also helps. A 40-foot sailboat feels spacious enough for comfort, but still intimate enough that the crew can pay attention to how everyone is doing.

The flow matters. You start at the Saint John Ferry Terminal in Cruz Bay and then move out from there. Instead of spending your time ferrying between stops, you are on the water doing the main event: sailing, snorkeling, and relaxing.

And yes, the food and drinks are part of the plan, not a side note. Lunch is included, and a bar is part of the experience, which makes a big difference when you are out for about half a day.

Getting to the Sailboat: Ferry Terminal to Cruz Bay Tender Ride

Your day starts back at the Saint John Ferry Terminal in Cruz Bay and ends there too. A lot of St John boat trips involve some kind of transfer, and here you will go to Cruz Bay first, then take an inflatable tender out to the sailboat.

That matters for two reasons:

1. You get that “arrival into the waters” feeling early. It is part of the fun of being on the water.
2. The tender ride can feel bouncy if you are prone to motion sickness. If that is you, consider eating lightly beforehand, staying hydrated, and choosing a spot where you face forward.

If you are staying elsewhere on the island, pickup is offered, but the listing also notes private transportation is not included. So I would treat this as, you may have help getting to the meeting point, but do not assume someone will pick you up from your exact door without confirmation.

Sailing Time Plus Snorkeling Stops You Can Actually Use

The charter runs about 4 to 5 hours. In that time, the schedule balances sailing and water time. You head out to sea with a couple of snorkeling stops, and you also get downtime where you can swim or sunbathe.

Snorkeling gear is included for all passengers. That is one of those details that makes the day smoother. You do not have to track down rentals, rinse equipment, or hope you brought the right size mask. If you have never snorkeled before, it helps to know you are not showing up with only goodwill.

Stop near Honeymoon Beach and Caneel Bay

Your second stop is at a secluded anchorage off the shoreline of Honeymoon Beach near Caneel Bay. This is the kind of location where the water clarity is a big part of the experience, and where you can do more than just float at the surface.

Here is what you can plan to do during that stop:

• Swim at your pace
• Snorkel with the provided equipment
• Hang out and sunbathe if you prefer a slower rhythm

A secluded anchorage is also practical. It usually means fewer crowds around you compared with the most obvious beach areas, which makes the whole stop feel more like a retreat.

Other snorkeling time during the trip

You will have additional sailing plus a couple of snorkeling stops total. The day is designed so you are not snorkeling once and then just watching the rest of the time. You are given more than one chance to get in the water and enjoy it.

Onboard Comfort: Restroom, Shaded Cockpit, and WiFi

On a boat, comfort is not fancy. It is functional. This charter includes a fully functional restroom on board and a shaded cockpit, which is exactly what you want in the heat. Even on a “fun” day, you will notice the difference when you are not constantly trying to hide from the sun or time your hydration.

WiFi is also available on board. I would not expect it to work like home internet, but it is still a nice touch for quick messages, maps, or sharing a photo after the swim.

Lunch From North Shore Deli, Not a Sad Boat Snack

Lunch is included, and that is a big reason this feels like a real day out rather than a short excursion with a snack. The onboard menu is built around deli favorites, with 9 gourmet deli sandwiches and 5 gourmet salads, using the North Shore Deli menu.

That sandwich-and-salad approach is smart for a sailing day. It is easy to eat without needing cutlery you do not have, and it works whether you feel hungry after snorkeling or you just want something simple.

If you are picky, you will still be fine, but you should plan to eat at a normal pace. On a moving boat, swallowing fast is not your friend.

The Very Open Bar: Drinks Built Into the Experience

This charter makes drinking part of the day, not a separate purchase. Alcoholic beverages are served, and the bar is described as a very open bar with a wide range of options.

From the included list, you can expect:

• Beer
• Soda and juice
• Water
• Vodka, rum, gin, tequila
• Sparkling wine and more

I like how this changes the “math” of the day. You are not trying to estimate what the drink tab might be once you are already out on the water. It also means you can keep the mood celebratory if you are on a birthday, anniversary, or just a “we made it through the work week” kind of trip.

That said, you still need to be smart. You are snorkeling and swimming, so keep a steady pace with water and sunscreen. You do not want to be the person who calls it “fun” while feeling seasick.

Captain Mike and Beau: Clear Communication and Extra Personal Touches

The crew is a huge part of why this charter lands at the top of the experience list. You will likely sail with Captain Mike, and many groups also mention his nephew, Beau.

What stands out from the tone of the experience is attentiveness and communication. People mention that Captain Mike is thoughtful, safety-minded, and clear about what passengers need to do. That kind of briefing matters on a boat, especially when there is snorkeling involved and you need to know where to go, how to handle gear, and what to do when the boat moves.

There is also a hands-on side. Some groups mention that Captain Mike gives sailing lessons, even teaching people how to sail during the day. If you like learning how things work, that can turn a relaxing charter into something memorable and genuinely educational.

Dolphins and Wildlife: When Conditions Let Nature Join In

One of the most exciting moments people talk about is a chance to swim with dolphins in Scotts Bay. That is not guaranteed based on the core charter description, but it tells you something important.

This is not an itinerary that feels rigid from start to finish. If conditions allow and wildlife shows up, you might get an extra special moment beyond snorkeling and swimming.

So go with the right mindset. Plan for what is clearly included: sailing time, snorkeling stops, lunch, and the open bar. Then stay open to the possibility of a bonus wildlife encounter.

Price and Value for a Private Group Up to 6

The price is $1,395 per group, up to six people. That means your real cost depends on whether you fill the boat. If you book for two, it is a premium outing. If you book for a full group, the per-person math starts to look more reasonable.

What makes it feel like good value is the bundle:

• Private charter (just your group)
• Two snorkeling stops with gear included
• Lunch included
• A wide open bar
• Restroom and shaded cockpit
• WiFi on board

A lot of tours only include “one or two of those things.” Here, you are paying for a whole half-day package that covers the basics and the extras that make it comfortable.

If you are traveling with friends or a mixed group of ages, this also becomes easier. You can split attention: some people snorkel, some people relax, and everyone still shares the same private plan.

Who Should Book This Charter, and Who Might Want Something Else

This is a great fit if you:

• Want a true private experience for up to six people
• Care about comfort on the water, including a restroom and shade
• Plan to spend real time snorkeling
• Want lunch and drinks included so the day feels effortless

It might be less ideal if you:

• Are on a very tight schedule and cannot be flexible, because the experience requires good weather
• Prefer a purely non-alcohol outing, since the bar is a core part of the charter
• Get motion sick easily during tender transfers

Final Call: Should You Book the Private Day Charter Classic Sailboat?

If your ideal St John day is sailing plus snorkeling plus comfort, I would book it. The private setup for up to six, combined with included snorkeling gear, lunch, a restroom, and a shaded cockpit, makes it feel like a well-built half-day plan rather than a “maybe we do a swim” kind of excursion.

Book it especially if you are traveling with the right group size and want the day to feel curated for you, not for a crowd. If you have flexible weather tolerance and you like the idea of a captain who keeps things safe and organized, this is the kind of charter that earns its high rating fast.

FAQ

How much does the private sailboat charter cost?

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

How many people can be on the charter?

The charter is for up to 6 passengers in your private group.

How long is the experience?

It runs about 4 to 5 hours.

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.

Is snorkeling equipment included?

Yes. Snorkeling equipment is available to all passengers.

Is lunch included?

Yes. Lunch is included, with a menu of gourmet deli sandwiches and gourmet salads from North Shore Deli.

Are alcoholic beverages included?

Yes. Alcoholic beverages are served, and the itinerary includes a Very Open Bar with options listed such as beer, soda, juice, water, vodka, rum, gin, tequila, and sparkling wine.

Is there a restroom onboard?

Yes. There is a fully functional restroom on board, and there is also a restroom on board mentioned in the details.

Is WiFi available during the trip?

Yes. WiFi is available on board.

Can I get a full refund if plans change?

Free cancellation is available. You can cancel up to 24 hours in advance for a full refund. If you cancel less than 24 hours before the experience starts, the amount paid is not refunded.