British Virgin Islands Sailing Holiday


British Virgin Islands Sailing Holiday

With over 60 stunning islands and easy line of sight sailing, a BVI sailing holiday offers endless options for exploring.

This 14-day itinerary will give you a flavour of the destination and offer some inspiration. But the joy of a private yacht charter is that you are completely free to follow your own schedule, in your own time.

The BVIs is an unparalleled sailing destination and there are a great range of bareboat, skippered and crewed yachts available.

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  • Day 1: Tortola
  • Day 2: Tortola - The Caves - The Bight (8nm)
  • Day 3: The Bight - The Indians - Jost Van Dyke (12nm)
  • Day 4: Jost Van Dyke - Sandy Cay - Little Jost Van Dyke (4nm)
  • Day 5: Little Jost Van Dyke - Cane Garden Bay (5nm)
  • Day 6: Cane Garden Bay - Guana Island - North Sound (20nm)
  • Day 7: North Sound
  • Day 8: North Sound - Anegada (15nm)
  • Day 9: Anegada - Eustatia Sound (12nm)
  • Day 10: Eustatia Sound - The Baths - Spanish Town (10nm)
  • Day 11: Spanish Town - The Dogs - Scrub Island (6nm)
  • Day 12: Scrub Island - Cooper Island (6nm)
  • Day 13: Cooper Island - Salt Island - Peter Island (5nm)
  • Day 14: Peter Island - Tortola (4nm)

14 day Itinerary


Day 1


Start your yacht charter from Tortola - the largest of the BVIs - where bougainvillea adorned hillsides serve as the backdrop to gorgeous sandy bays, and beach bars serving rum cocktails will help you slip into that famous Caribbean vibe. You’ll likely arrive in the evening so stay put, relax and let the adventure begin tomorrow.

The Caves

Day 2

The Caves, Norman Island

Avast me hearties! Get ye to Norman Island where treasures await. While the doubloons are long since pillaged, this historic island - inspiration for Robert Louis Stevenson’s ‘Treasure Island- - still holds bounty aplenty. Snorkel the famous Caves in Privateer Bay for an exhilarating first taste of what the BVIs have to offer. Take an underwater torch to get a closer look at the mysterious markings on the cave walls and, if you are feeling hardy, find the small room located 70 feet into the darkness of the northernmost cave.


Day 2

The Bight, Norman Island

Spend the night moored in the Bight and swim or dinghy over to Willy T’s floating bar and restaurant where things get real messy real quick. Prepare to party! For something a little more sedate try Pirates Bight restaurant, but be sure to swing by Willy T’s for at least one drink and a gander at the inevitable nudity.


Day 3

The Indians, Pelican Island

Wash away the remnants of the night before with a spectacular morning snorkel at the Indians. Four rocky pinnacles rise 50 feet out of the water, while below lies a cornucopia of aquatic life. Look out for turtles, reef fish, crustaceans, plenty of colourful coral and even an underwater tunnel.

White Bay, Jost Van Dyke

Day 3

White Bay, Jost Van Dyke

Time for a Painkiller Punch! A 12nm sail takes you to the beautiful stretch of white sandy beach known as White Bay where the aptly named Soggy Dollar (named for the customers swimming ashore from their anchored boats) will show you a good time.


Day 3

Great Harbour, Jost Van Dyke

Anchor in bustling Great Harbour, stock up on supplies and enjoy an evening stroll down the beach, taking your pick of the fun, live music beach bars and restaurants. Tucked down the far eastern side of the beach is the legendary Foxy’s, where thirsty sailors have been fed and watered for over 40 years, and you might just catch revered owner Foxy Callwood strumming on his guitar to delighted onlookers. Foxy’s wife, Tessa, runs the next door Foxhole Boutique, touting pretty beachwear and souvenirs. Call ahead for a dinner reservation in high season.

Sandy Cay

Day 4

Sandy Cay, Jost Van Dyke

Sandy Cay, a tiny deserted island off Jost Van Dyke, is an ideal stop for a picnic and some snorkelling. It's sheltered from the prevailing winds and consists of a lush green jungle surrounded by pristine white sands. You'll need shoes if you want to go exploring and watch out for the scores of hermit crabs! Sandy Cay is a dreamy place to spend a few hours and a real favourite of ours at HELM.

Sandy Spit

Day 4

Little Jost Van Dyke

Anchor or collect a mooring buoy off Little Jost Van Dyke and tender over to Foxy's Taboo on Jost Van Dyke. A short trek will take you to the Bubbly Pool, which in the right conditions, is a natural jacuzzi. Check the conditions before you go, as too calm and there are no bubbles, and too rough and the surge is dangerously brutal.

After the excitement make a B-line for B-line Beach Bar on Little JVD or try out Foxy's Taboo (managed by Foxy and Tessa's daughter Justine!) before tendering back to your boat.

Cane Garden Bay

Day 5

Cane Garden Bay

Cane Garden Bay is a lively beach lined with restaurants and shops. Explore the village behind the beach where you can stock up on stock up on provisions from Bobby's Market, visit the family owned 18th Century Callwood Rum Distillery, and watch recycled glass blowing at the not for profit Green VI Glass Studio.

Cane Garden Bay is a special place in the evening when the westerly facing beach provides a spectacular sunset over Jost Van Dyke. There are plenty of restaurants to choose from - Quito's is famous for live music while Myett's has a pretty setting and delicious conch fritters.


Day 6

Guana Island

After breakfast at the Big Banana (be sure to try their banana bread) head round to the stunning Guana Island. Privately owned by the Jarecki family who are passionate conservationists, Guana Island is a wildlife sanctuary, home to flora and fauna extinct in the rest of the BVIs. Snorkelling at Monkey Point is fantastic and White Bay is an idyllic lunch spot.

North Sound

Day 6

Prickly Pear Island (North Sound)

Situated in the North Sound, east of Virgin Gorda, Prickly Pear is named after the large cactus that populated the island. Vixen Point is a great anchorage spot with ten mooring buoys just off a lovely beach. A hiking trail from Vixen Point Beach takes you around salt ponds and over to the north shore where there are two beautiful and quieter beaches. Otherwise kick back and relax at the Sandbox restaurant, play volleyball and enjoy the views of nearby Moskito Island.


Day 7

The North Sound

Spend the day exploring the North Sound. Hop over to The Bitter End Yacht Club where you can rent a dinghy and try your luck in one of the daily sailing races. There is also a kiteboarding school if you want to get the adrenalin pumping! The resort has several restaurants, gift shops and hiking trails and you can easily spend a full day here.

The North Sound

Day 7

The North Sound

Otherwise, head over to Leverick Bay, hail a cab and go up to Hog Heaven for lunch where you'll find the most incredible views of the entire North Sound.

In the evening moor up at tiny Saba Rock. Be sure to arrive in time for happy hour (between 4-6pm) when you can watch the daily tarpon feeding and then enjoy a delicious meal at the restaurant. If you are in need of some land time there is a lovely and inexpensive hotel there too.


Day 8


In the morning stock up on ice and refill your water tanks (included in the Saba Rock mooring fees) and set sail for Anegada.


Day 9

Anegada - Eustatia Sound

In Anegada, watch the flamingos ripple the salt ponds. Here, the dinners consist of huge crustaceans plucked from the water in front of your eyes and grilled on the beach.

It is very different from most other Virgin Islands, which are of volcanic origin and mountainious, while Anegada is flat and low and formed from coral and limestone. Hire scooters or get a taxi over to northern side of the island for gorgeous beaches at Cow Wreck and Loblolly Bay.

Devils Bay

Day 10

Eustatia Sound - The Baths - Spanish Town

On Day 10, sail to Eustatia Sound. Most of the beaches are guarded by rough coral, which make it the perfect place for snorkelling.

Then on to the unmissable Baths on Virgin Gorda. The area is perfect for swimming and snorkeling, but the coolest part is the trail through the Caves to Devil's Bay. During the 20-minute trek, you’ll clamber over boulders, slosh through tidal pools, squeeze into impossibly narrow passages, then drop on to a sugar-sand beach.

In the evening visit Spanish Town where the mix of islanders, yachties and backpackers eating and drinking together in this beautiful place creates a festive vibe.


Day 11

Spanish Town - The Dogs - Scrub Island

In the morning sail to The Dogs islands. This clutch of five little islands is located between Tortola and Virgin Gorda. Protected by the BVI National Parks Trust, the Dogs are sanctuaries for birds and marine animals. The diving and snorkeling here are excellent.

Then, in the afternoon visit Scrub Island, home to the Scrub Island Resort & Spa. This private island is the perfect place for relaxing.

Peter Island

Day 12

Cooper Island - Salt Island - Peter Island

On Day 12, go for a casual lunch at the Cooper Island Beach Club Restaurant. Their curried chicken rotis, jerk pork tenderloin and basil-butter-drizzled mahimahi are exceptional.

Or you may prefer to visit the Salt Island, with its main attraction, the RMS Rhone, which crashed against the rocks off the southwest coast during a hurricane in 1867. An awesome diving spot!

Cooper Island

Day 13

Cooper Island - Salt Island - Peter Island

Peter Island, about 4 miles south of Tortola, remains lush and wild for the most part. There are five pristine beaches, plus excellent snorkeling sites and hiking paths.

Peter Island - Tortola

Day 14

Peter Island - Tortola

On Day 14 return to Tortola, sandier, saltier, hardier and more sun-exposed than when you left and prepare to return home armed with your sea-faring tales of adventure.

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