British Virgin Islands Sailing Itinerary

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British Virgin Islands Sailing Itinerary & Guide. Located in the Caribbean’s Leeward islands, this former haunt of pirates, including the infamous Blackbeard, is now host to one of the world’s premier sailing destinations.

The Two Best Reasons To Bareboat Charter in the BVI

Steady Trade Winds. The alluring promise of steady trade wind sailing a limited development  of restaurants and marinas, plus line-of-sight navigation between the 33-odd islands still make the British Virgin Islands Sailing Itinerary (BVI) a true sailor’s favorite; windy, but not too windy, and never far from a rum punch. This is quintessential chartering territory, a playground where you can expect a certain laid-back ‘Britishness’.

Easy Navigation. The small tidal range – a mere 12in (30cm) – and the sheltered waters mean that even novice sailors can enjoy island hopping from Tortola, although many more experienced sailors also travel to the islands each year to relax and lazily crisscross the Sir Francis Drake Channel without the hassles of customs clearance. Passages between the islands can take as little as half an hour and rarely more than three hours.

… British Virgin Islands Sailing Itinerary (BVI) a true sailor’s favorite; windy, but not too windy, and never far from a rum punch.

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Ensure White Bay, Jost Van Dyke is On Your British Virgin Islands Sailing Itinerary

British Virgin Islands Sailing Itinerary

Our Aim. This British Virgin Islands Sailing Itinerary highlights is designed to ensure that you will discover secluded bights, the very best snorkelling spots, and impossibly gorgeous cays. Designed to give you a flavour of the islands, with so much to do, we create tailored itineraries for all our guests.

Locals Choice. What to squeeze in 7 days in these wonderful islands for your British Virgin Islands Sailing Itinerary. To assist us, we used the helpful  guidance of our local partners combined with the help of our experienced team. We think we have chosen some amazing spots for you to consider. 

We love to Hear From You. Why not leave us a comment at the bottom of this blog.

Typical Prices. You can sail for $365 USD/ €345 EUR/ £305 GBP/  $495 AUD per person*

  • Family (2 adults, 2 children) (01 Jan and 31 Mar)*

Day 1 – BVI Sailing Itinerary – Tortola

Home Marina → Cooper Island/Peter Island (3.53 NM)

Day 1 – Tortola

Home Marina. Most marinas are on the main Island of Tortola, this is where most adventures will begin. You will, on your cruise, not doubt be heading back to the island on more than one occasion, yet you are unlikely to see it’s capital Road Town. You may end up there provisioning, or just to sightsee, but it is worth it.

Road Town. The British Virgin Islands Sailing Itinerary’s largest and most developed island includes the chain’s airport (strictly on Beef Island) and is home to a bustling capital Road Town. Here you will find plenty of well-stocked shops selling provisions and souvenirs.

Many choose to leave the marina and head for Cooper Island or Peter Island, a short hop over the Sir Francis Drake Channel.

As darkness falls the sound of steel bands fill the evening air.

Day 2 – BVI Sailing Itinerary – Marina Cay

Cooper Island/Peter Island → Marina Cay/Trellis Bay  (3.2 NM)

Design your own fun packed day. This could be one of your busiest days with so many great sights to see or activities to participate in. Whatever options you select – don’t miss out on the Baths – Think about a pleasant walk up to the restaurant “Top of the Baths” for a great lunch and a dip in the pool.

Snorkel the Rhone. If you are anchored at Little Harbour, it’s a short passage over to Pelican island and the Indians for a morning snorkel. From Cooper Island, nip across to Salt Island and snorkel over the amazing wreck of the RMS Rhone.

The Baths. Sail on up the channel to Virgin Gorda and the Baths. Explore and snorkel before sailing across the channel to Marina Cay or Trellis Bay for the evening.

Marina Cay. The tiny popular island protected by a crescent-shaped reef. There is a Pusser’s restaurant and ship’s store ashore and evening happy hour at the top of the hill.

Trellis Bay and the Last Resort. The community of Trellis Bay offers an interesting and fun combination of restaurants, water sports, entertainment, local artists and local crafts. And now organic fruits and vegetables are cultivated by Aragorn from his Good Moon Farm on the fertile north side of Tortola.

The Last Resort. On Bellamy Cay, a tiny tropical island in the centre of Trellis Bay, the Last Resort is an absolute must on a cruise around the BVI. The Last Resort has had several donkeys although the last, Mary had past-on last we were there.

Day 3 – BVI Sailing Itinerary – North Virgin Gorda Sound or Diving in the BVI

Marina Cay/Trellis Bay → Bitter End Yacht Club or Leverick Bay (3.2 NM)

Spoilt for choice. We have given you two options today. you could either head for a resort in North Virgin Gorda Sound or dive in one of the world’s diving hotspots.

Diving. The BVI is a great place to dive. You can easily accomplish a ‘try-dive’ as part of a sailing holiday, training on the beach in the morning followed by the main event in the afternoon.

North Virgin Gorda Sound. You could quite easily spend all 7 days in North Virgin Gorda Sound still have places there left to visit:

  • Colquhoun Reef
  • Vixen Point
  • Saba Rock
  • Eustatia Sound
  • Biras Creek

On our 7-Day Itinerary, see this as a day to kick back and relax. We recommend either picking up a bouy at Saba Rock or Bitter End, or visiting Leverick Bay (Pussers Franchise) at the end of the sound. For those looking for even more chill – head for Drake’s Anchorage.

  • Bitter End
  • Leverick Bay
  • Drake’s Anchorage

Wreck of the Rhone

Divers’ Dream. For  slightly  more experienced divers the wreck of the Royal Mail steamer Rhone, the setting for the movie The Deep, starring Nick Nolte and Jacqueline Bissett, is an absolute must. Bear in mind, you can still get a great view of the old steamer with basic snorkeling gear.

British Virgin Islands 7 & 14 Day Sailing Itinerary

Enjoy learning all about the highlights and must-sees of any British Virgin Island Sailing Itinerary. Use the links below to see our 7 and 14 Day Itinerary.

The Soggy Dollar Bar - Great Spot to Swim Ashore for a Painkiller

While away the afternoon in a hammock under a palm tree.

Day 4 – Choice 1 – BVI Sailing Itinerary – White Bay 18°26’30 N 64°45’80 W

North Gorda Sound or Leverick Bay → Jost Van Dyke (5.2 NM)

More Choices! Here you have a difficult choice (which is why you really need two weeks to explore these islands properly). Do you sail out and visit the more remote island of Anegada, visit the pink coral sand beaches and eat lobster cooked over a flaming grill on the beach. Or do you head for Jost Van Dyke and White Bay.

Soggy Dollar Bar. One of the most famous spots in our British Virgin Islands Sailing Itinerary, so arrive early for the chance of a mooring buoy. It is a great spot to swim ashore for a Painkiller and to while away the afternoon in a hammock under a palm tree. The Painkiller, a delicious but potent rum drink was originally invented at the Soggy Dollar Bar (named for the soggy state of dollar bills used to pay for drinks after swimming ashore from an anchored vessel). To the west down the beach is One Love Bar & Grill serving lunch and cold drinks daily.

Provisions. Jewel’s Snack Shop serves light bites during the day, White Bay Superette is a small super-market where you can pick up a few essentials. Ivan’s Stress Free Bar and Restaurant, lavishly decorated with shells from the beach, is on the eastern end of the bay and is where you pay for your moorings.

Day 4 – Choice 2 – BVI Sailing Itinerary – Anegada – The Sunken Island

North Gorda Sound → Anegada Reef Hotel (15.2 NM)

The Best Place to Eat Lobster. Mysterious Anegada lies low on the horizon for those who enjoy line-of-sight navigation.Should you choose this for your British Virgin Islands Sailing Itinerary, enjoy calling ahead to order your lobster from one of the many seafront restaurants and hotels including Potters by the Sea.

Navigation Caution. Don’t leave it too late in the day: dark blue water is deep, powder blue shallow and if you find yourself in brown water, the coral heads are just below the surface, so it’s time to retrace your course to safety. Read our informative blog on how to navigate coral safely.

The Painkiller Cocktail

“Originated and Perfected at Sandcastle’s Soggy Dollar Bar in the 1970’s this smooth, full flavoured run cocktail has become the essence of Caribbean imbibing.

The perfect concoction of premium dark Rum, Cream of Coconut, pineapple, and orange juice (proportions are secret, topped with fresh Grenadian Nutmeg makes the swim (no dock) to the Soggy Dollar worth the effort.

Perhaps it’s the setting of White Bay, the thirst from the swim, the perfect blend, or just because of the tradition of the ‘original’ painkiller at the Soggy Dollar Bar…

… whatever the reason, Welcome and Enjoy!

Tish and Jerry”

The Secret Painkiller Recipe

  •  2-4 oz Pussers’ Dark Navy Rum

  •  4 oz pineapple juice

  •  l oz cream of coconut

Blend or shake vigorously and serve on the rocks.

Grate fresh nutmeg.

Day 5 – BVI Sailing Itinerary – Cane Garden Bay

Callwood’s Distillery. Mr. Callwood’s rum distillery affords visiting yachts a glimpse back into history.

Panty Dropper. White and gold rum is still produced from the cane grown on the hillsides and bears the label Arundel from the name of the estate purchased by the Callwood family in the late 1800’s. Rums available include the famous Panty Dropper, who could resist a Rum with such an alluring name!

It is recommended that you ask permission prior to wandering through the distillery, and the purchase of a bottle or two is expected.

BVI Sailing Itinerary – Callwood Distillery

Callwood’s Distillery. Mr. Callwood’s rum distillery affords visiting yachts a glimpse back into history.

Panty Dropper. White and gold rum is still produced from the cane grown on the hillsides and bears the label Arundel from the name of the estate purchased by the Callwood family in the late 1800’s. Rums available include the famous Panty Dropper, who could resist a Rum with such an alluring name!

It is recommended that you ask permission prior to wandering through the distillery, and the purchase of a bottle or two is expected.

Norman Island

Norman Island Bight. Just seven miles (11km) south of Road Town, Norman Island is within easy reach. A world-renowned site for snorkeling, the sea here teems with life, including turtles, exotic sponges and corals. The island was a favourite haunt of legendary pirates and is said to have inspired Robert Louis Stevenson’s Treasure Island.

William Thornton. Historical home (Update: now on Peter Island) To the west of Norman Island is a safe, sheltered anchorage if you decide to drop anchor for the night and party, Caribbean style, aboard the famous ‘Willy T‘, a converted 1915 schooner.

Norman Island Bight. Just seven miles (11km) south of Road Town, Norman Island is within easy reach. A world-renowned site for snorkeling, the sea here teems with life, including turtles, exotic sponges and corals. The island was a favourite haunt of legendary pirates and is said to have inspired Robert Louis Stevenson’s Treasure Island.

William Thornton. Historical home (Update: now on Peter Island) To the west of Norman Island is a safe, sheltered anchorage if you decide to drop anchor for the night and party, Caribbean style, aboard the famous ‘Willy T‘, a converted 1915 schooner.

The Classic CRUISING GUIDE TO THE VIRGIN ISLANDS by Simon Scott is the post-hurricane edition. As we all know, September 2017 saw  Irma, a category 5 hurricane, passed directly through the Virgin Islands bringing untold devastation.

Two years on, the windward island chain continues to recover with a renewed spirit, strength and hope for the future. There are businesses that are still closed, yet the majority have rebuilt and reopened.

This 2020 edition will mark the 38th year of helping cruisers cruise the tropical waters of the British and US Virgin Islands. The edition, completely updated, is packed with the latest information on navigation (including key GPS coordinates), customs and immigration regulations, weather, communications, marinas, haul-out facilities, chandleries, dive services, shore-side services, shopping and an indispensable wealth of other valuable information.

Get Our Downloadable Guide to British Virgin Islands

Download a PDF Version of Our British Virgin Sailing Itinerary and Guide:

Click here to view or download

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Jost Van Dyke

Jost Van Dyke. Named after a Dutch pirate this is another must-see islands group . This island, three miles northwest of Tortola, is worth exploring on foot and rewards with many stunning views.

The Soggy Dollar. The island’s notorious “painkiller” cocktail originated at the Soggy Dollar, a bar so-named because sailors would dive from their boats to swim ashore from its perfect anchorages and hang up their wet dollars to pay for their drinks.

The Fat Virgin

The Baths & Virgin Gorda. Seven miles southeast of Tortola is Virgin Gorda, or the “fat virgin” from the Spanish, with its labyrinth of boulders, caves and natural pools, known as “The Baths”.

Swim ashore, wade between the huge boulders and you may chance upon one of the Caribbean’s finest beaches while round the corner – passing the extraordinary island they call Fallen Jerusalem – and through into Gorda Sound at the Bitter End Yacht Club.

Soper's Hole Wharf

Great Place to Shop & Get a Bite to Eat

Necker Island

Richard Branson & Neckar island. Celebrity Spotters will know that Sir Richard Branson’s Neckar Island is a boat hop away, but well protected from prying eyes behind fringed reefs.

British Virgin Islands 7 & 14 Day Sailing Itinerary

Enjoy learning all about the highlights and must-sees of any British Virgin Island Sailing Itinerary. Use the links below to see our 7 and 14 Day Itinerary.

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