Insider's Guide to a Perfect Day Off in Tortola

Let's be honest – while Tortola is paradise, its best gems aren't always on the typical tourist map. After years of sailing these waters and countless days exploring the island between courses, we've compiled our instructor-approved guide to making the most of your day off in the BVI's largest island.

First Things First: Rent a Car

If there's one non-negotiable piece of advice for exploring Tortola, it's this: rent a car. The island's winding roads, steep hills, and hidden beaches simply aren't accessible without your own wheels. Most rental companies operate out of Road Town, though you can arrange pickups elsewhere with advance notice.

Pro tip: Book your rental at least a day ahead during high season (December-April). Ask for a vehicle with decent clearance as some roads can be rough.

For the Wave Chasers

Tortola has some of the Caribbean's most underrated surf spots – a perfect playground when you're taking a break from sailing.

Apple Bay

Known as the "Surfing Beach," Apple Bay delivers consistent waves during winter swells (November-March). The reef break works best on a north swell, creating rides that even experienced surfers appreciate.

Josiah's Bay

Our personal favorite for beginners and intermediates. This sandy-bottom beach break has the most consistent waves on the island. If you're looking to learn, Steve at Josiah's offers excellent surf lessons – just ask at the beachfront restaurant, and they'll point you his way. Or click this link to his company: Surf School BVI.

Cane Garden Bay

While primarily known for its pristine beach and restaurants, Cane Garden can offer surprisingly good surf when conditions align. Plus, you can reward your efforts with a cold one at Quito's afterward.

"After a week of teaching sailing, there's nothing better than paddling out at Josiah's. Something about trading one board for another really resets your mind." – John K, Sailing Virgins Photographer

Beach Escapes Away From the Crowds

Long Bay Beach

This gem near the airport remains strangely undiscovered by most visitors. The mile-long stretch of white sand rarely sees more than a handful of people, even during peak season. Pack your own refreshments as there are no facilities here – which is precisely its charm.

Smuggler's Cove

Tucked away on the West End, this perfect crescent bay offers excellent snorkeling and shade from sea grape trees. The road getting there is notoriously rough, but that's why you rented a car with clearance, right?

Cultural & Culinary Stops

Soper's Hole

This colorful little waterfront village on the West End is worth a visit for its picture-perfect Caribbean charm. Grab a coffee from Omar's, browse the boutiques, or simply watch the yachts come and go from the harbor.

Road Town Café Crawl

Start at Island Roots for arguably the island's best coffee in a contemporary space filled with local art. Follow it up with pastries at the French Deli, where the croissants rival anything you'd find in Paris.

Dining Recommendations

For a small island, Tortola punches well above its weight in culinary options. Our top picks for a memorable meal:

The Dove

Located in an old West Indian house in Road Town, The Dove combines Caribbean ingredients with European techniques. Their wine selection is unmatched on the island.

The Dove, Tortola. Thanks Tripbucket for the image

Brandywine Estate Restaurant

Perched on a hillside with stunning views over Sir Francis Drake Channel, Brandywine offers Mediterranean-inspired dishes with a focus on fresh seafood. Reserve a table for sunset.

Sugar Mill Hotel Restaurant

Set in a converted sugar mill dating back to 1640, this restaurant serves elevated Caribbean cuisine in one of the most romantic settings imaginable. Their lobster bisque is legendary.

End Your Day with a Sunset

There's no better way to cap off your Tortola adventure than with a sunset cocktail at Bananakeet Café on the West End. The panoramic views over Jost Van Dyke and the surrounding islands create a sunset spectacle that rivals anywhere in the world.

"We've seen sunsets all over the Caribbean, but there's something special about watching the sun disappear behind Jost from Bananakeet's deck, Dark 'n Stormy in hand." – James, Sailing Virgins Founder

Before You Go

A few final tips to make your day off in Tortola truly memorable:

• Cash is king: Many smaller establishments don't accept cards, especially outside Road Town
• Island time is real: Service may be slower than you're used to – embrace it as part of the experience
• Drive left: Traffic flows on the left side of the road in the BVI
• Respect local customs: While casual, the BVI has a conservative culture – cover up swimwear when not on the beach
• Stay hydrated: The Caribbean sun is stronger than you think, even on cloudy days

Whether you're between sailing courses or simply taking a break from life aboard, these Tortola highlights offer the perfect mix of adventure, relaxation, and local flavor. The best part? You'll be experiencing the island as crew know it – not just as tourists see it.

Have you discovered another hidden gem on Tortola? Share your finds with us on Instagram @sailingvirgins or in the comments below!

Looking to experience the best of Tortola and beyond? Check out our upcoming sailing courses to combine BVI exploration with internationally recognized sailing certification.