Jost Van Dyke: Sandy Spit & Soggy Dollar Sailing Tour

Summary

Sail to sandy spit swim up to soggy dollar bar taste painkiller bvi style

You’ll sail across turquoise waters to Jost Van Dyke, wade ashore at Sandy Spit, swim up to the Soggy Dollar Bar for their famous Painkiller cocktail, and float in the Bubble Pool if weather allows. Expect laughter with locals and guides, buffet lunch on board with drinks included—and moments you’ll remember long after you shake off the sand.

What’s the experience like?

The first thing I remember is the slap of salt spray on my face—somehow colder than I expected, even in the BVI sun. We’d just left Tortola behind and already you could see Jost Van Dyke in that hazy blue distance. Our captain, Marcus (he’s from Road Town—tells stories like he’s been at sea forever), pointed out Sandy Spit. It’s honestly just a bright little swirl of sand with two palm trees, but when we dropped anchor there, it felt like we’d landed somewhere nobody else had ever seen. The sand was almost too white to look at straight on. I waded out and lost track of time watching tiny fish dart around my ankles.

Getting to the Soggy Dollar Bar isn’t what I pictured—you really do have to jump off the boat and swim for it. My shorts were soaked before I even hit the beach (so yeah, “soggy dollar” makes sense). There was music drifting from the bar—reggae or maybe soca—and people laughing in that easy way you only hear near water. Li behind the bar handed me a Painkiller (I tried ordering it in my best Caribbean accent; she laughed and said I sounded like her cousin from London). The drink tasted like nutmeg and coconut and something else I still can’t name. Honestly, I could’ve stayed there all afternoon just listening to that low hum of voices and feeling the sun dry my skin.

We stopped at the Bubble Pool next—Marcus said it’s better when the swell is up, but even on a calm day it was strange and kind of magical: foamy water swirling around your legs while you stand between rocks that look like they’ve been there forever. Lunch was back on board—a buffet with veggie options (I grabbed more than my share of plantains). Someone started up a game with paddle boards off the stern; I mostly watched, not brave enough after two Painkillers. The sail back felt slower somehow, maybe because nobody wanted it to end. The light was softer by then, everyone a bit quieter.

Step-by-step itinerary

Day 1 — Sail to Jost Van Dyke and beach stops

• Set sail to Jost Van Dyke
• Swim ashore to Soggy Dollar Bar
• Enjoy a Painkiller cocktail
• Visit Sandy Spit beach
• Explore the Bubble Pool
• Relax on stunning beaches
• Enjoy buffet lunch and open bar

Top questions

Do you really have to swim ashore at Soggy Dollar Bar?

Yes, you need to swim from the boat to reach Soggy Dollar Bar—that’s how it got its name.

Is lunch included on this Jost Van Dyke sailing tour?

Yes, a buffet lunch is served on board with vegetarian options available.

What stops are included besides Soggy Dollar Bar?

The tour usually includes Sandy Spit and the Bubble Pool if weather permits.

Are drinks provided during the sailing tour?

Yes, both alcoholic and non-alcoholic drinks are included throughout your trip.

Is snorkeling good near Jost Van Dyke?

The area is mostly sandy bottom; snorkeling gear is provided but Norman Island offers better snorkeling.

How do I get from the cruise pier to the boat?

A taxi transfer from the cruise pier is included in your booking price.

Are paddle boards available during this tour?

Paddle boards are available for guests to use off the boat.

Is this sailing tour suitable for children or infants?

Yes, infants and small children can join—the boat accommodates prams or strollers and has child life vests.

What’s included

Your day includes taxi pickup from the cruise pier about an hour before departure, all sailing between Tortola and Jost Van Dyke with stops at Sandy Spit and (if weather allows) Bubble Pool. On board there’s a buffet lunch with vegetarian options plus an open bar serving both alcoholic and non-alcoholic drinks. Paddle boards are ready for anyone feeling adventurous—and yes, there’s a restroom on board too before heading back in the afternoon.