St John: Private Sailboat Charter with Snorkeling & Open Bar

Sail St John’s calm bays, swim off Honeymoon Beach, relax on deck

You’ll step onto a classic sailboat in St John with a small group and friendly crew who know these waters by heart. Swim off Honeymoon Beach, try snorkeling with sea life in clear blue coves, enjoy deli sandwiches and an open bar—and maybe take the helm yourself before drifting home salty-haired and sun-warm.

What’s included

Your day includes an easy ferry transfer from St Thomas to Cruz Bay where your local crew greets you; then hop aboard for sailing along St John’s shoreline with stops for swimming or snorkeling at spots like Honeymoon Beach. Enjoy gourmet deli sandwiches or salads from North Shore Deli plus an open bar stocked with beer, spirits and sparkling wine—all with WiFi access and shaded seating if you want it.

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Step-by-step itinerary

Day 1 — Private day sail and snorkeling

• Transfer to Cruz Bay ferry terminal
• Take ferry to St John
• Meet crew near ferry dock
• Board inflatable tender to sailboat
• Sail to calm anchorage
• Relax and sunbathe on sailboat
• Take helm of 40 ft sailboat
• Swim with sea life
• Visit Honeymoon Beach near Caneel Bay
• Snorkel, swim, or sunbathe at beach

The Experience

The first thing I noticed was how the air changed as we left the busy St Thomas port—salty, softer somehow. The ferry to Cruz Bay only took about twelve minutes, but it felt like a little preview of the day: cays sliding by, water flickering blue-green. Our guide, Mark, met us right at the dock (he waved before I even spotted him). He had that easy island way of talking—half stories, half directions. We climbed into the inflatable tender and bounced over gentle waves to where the sailboat waited at anchor. I could smell sunscreen and something citrusy from someone’s drink already.

Once on board, everything slowed down. There’s shade if you want it, or you can stretch out in the sun—my friend immediately claimed a spot up front and didn’t move for an hour. The crew has been sailing here for years; they know every curve of St John’s western shore. We drifted past Trunk Bay and Maho Bay while Mark pointed out turtles surfacing (I missed one because I was distracted by a sandwich—no regrets). Lunch is from North Shore Deli—way better than I expected for a boat picnic. I tried to say “maho” with the right accent; Li laughed and told me to stick to English.

We anchored off Honeymoon Beach for our second stop. The water was so clear it almost looked fake—like someone had turned up the saturation too high. Snorkeling there felt quiet and private; just us and some curious fish darting around my ankles. There’s an open bar on board (rum punch is dangerous if you’re not careful), WiFi if you really need it, even a proper restroom—which is honestly rare on boats this size. At some point I realized I’d stopped checking my phone completely.

I still think about that view back toward Caneel Bay—the light kind of gold and lazy near late afternoon, everyone just stretched out or chatting quietly. It wasn’t flashy or showy; just felt like being let in on something locals love about St John. If you want loud music or crowds, this isn’t your day trip—but if you want calm water, real conversation, maybe steering a 40-foot sailboat for a bit…well, yeah.

Top questions

How do I get to the sailboat from St Thomas?

You’ll take a 12-minute ferry from St Thomas to Cruz Bay in St John; your crew meets you right by the dock.

Is lunch included on this private sailboat charter?

Yes, lunch includes gourmet deli sandwiches or salads from North Shore Deli.

Are drinks provided during the day trip?

An open bar is included with beer, wine, spirits, soda, juice, and water available all day.

What beaches do we visit during the charter?

You’ll sail along Trunk Bay, Maho Bay, and anchor off Honeymoon Beach near Caneel Bay.

Can kids join this private day charter?

Yes—infants and small children are welcome; specialized seats are available if needed.

Is snorkeling equipment provided?

Snorkeling gear is included for all guests at no extra charge.

Is there shade or restroom access on board?

The boat has shaded areas plus a fully functional restroom for comfort during your trip.