Island hopping, hidden gems, and why the BVI is best experienced by boat

Why the BVI is Made for Sailing

If there’s one trip that truly lets you unplug, slow down, and live fully in the moment—it’s sailing through the British Virgin Islands.

The beauty of the BVI is that every stop feels completely different:

• quiet coves and turquoise water
• lively beach bars and yacht clubs
• hidden snorkeling spots and sunset dinners

And the best way to experience it all? By boat.

We chartered with Voyage Charters and spent our days island hopping through some of the most beautiful water we’ve ever seen—with Captain Sebastian and Jess making the entire experience feel seamless from start to finish.

Think of it as a floating boutique hotel:

• wake up somewhere new every morning
• jump straight into the water from the boat
• and let someone else handle the logistics for once

For families especially, a crewed catamaran is the move. Spacious, relaxed, and surprisingly easy with kids.

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Our BVI Itinerary

Day One: Virgin Gorda + The Baths

We started the morning sailing to Long Bay, Virgin Gorda for snorkeling, paddleboarding, and watersports.

From there, we headed into Spanish Town where we met the iconic Sweet Ice Willy for a taxi ride over to The Baths—one of the most famous spots in the Caribbean for good reason.

Massive granite boulders, hidden caves, turquoise pools—it truly feels like another world.

BVI Tip:

Go early to The Baths if possible. It gets crowded quickly, especially with day charters and cruise visitors.

That evening, we sailed into Leverick Bay before heading to dinner at Cocomaya, which felt like the perfect blend of chic beach dinner and island ease.

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Day Two: Bitter End Yacht Club + Saba Rock

Our second day started with a short sail over to Bitter End Yacht Club, one of those iconic BVI destinations that somehow still feels relaxed and understated.

We spent the morning:

• swimming
• lounging on the boat
• ordering drinks from the Rum Runner
• and fully embracing island time

We also met Drake, the BVI’s most famous dog—which honestly deserves its own moment.

As the sun started to set, we watched the tarpon feeding before dinner at Saba Rock, another must if you’re sailing through the islands.

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Tips for Planning a BVI Sailing Trip

Book a Crewed Charter

This changes everything.

No navigating, no cooking, no over-planning—just time together and the freedom to enjoy the experience.

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Don’t Over-Schedule

The best parts of the BVI happen in between:

• floating off the boat
• stopping somewhere unexpectedly beautiful
• lingering longer than planned

Leave room for that.

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Pack Light (But Smart)

Bring:

• multiple swimsuits
• easy coverups
• non-slip sandals
• a waterproof tote or dry bag
• light layers for breezy evenings on the water

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Bring Cash

You’ll want it for:

• taxis
• beach bars
• small local stops throughout the islands

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Before You Go

Best Time to Visit

December through May offers some of the calmest waters and best sailing conditions.

How Long to Stay

We’d recommend at least 4–7 days if you’re chartering so you can fully settle into the pace of the islands.

Is the BVI Kid-Friendly?

Absolutely. Calm waters, short sail times, endless swim stops, and laid-back island culture make it surprisingly ideal for families.

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If You Have More Time…

Add:

• Jost Van Dyke
• Norman Island caves
• Anegada for lobster + quieter beaches

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Final Thought

The BVI is one of those rare trips that feels adventurous and relaxing at the same time.

The days are slower.
The water is always within reach.
And somehow, life feels wonderfully uncomplicated out there.

It’s the kind of trip you talk about long after you come home.