14-Day Sailing Itinerary in the BVI

Explore the magnificent British Virgin Isles

Visit treasure islands and tropical bars, enjoy a 2-week BVI sailing itinerary, known as one of the Caribbean’s most desirable sailing destinations. The British Virgin Islands are made up of 4 main archipelagos, amongst many smaller, uninhabited ones. They really are any island hopper’s dream, as there is the opportunity to experience breathtaking islands without much mainland development. In contrast to this, there is also the opportunity to party the night away with your crew and others.

The best BVI boat charter

Discover the stunning British Virgin Isles


Each island has its own unique characteristics and charm, therefore, you can snorkel around one and hike through another. Tell me another destination where you can experience this pure bliss? During your sailing experience, you will encounter many out of this world adventures, including the discovery of the island which inspired Robert Louis Stevenson’s Treasure Island! In addition to this, you will have many many chances to soak up glorious sun rays, whilst breathing in that sweet island atmosphere. Sailing around the British Virgin Islands is for anyone at any level or sailing experience. This particular route planned focuses on intermediate sailors. The suggested activities are largely aimed at groups of friends or couples. However, there are also many activities that are perfect for families along the way.

Start your 2-week itinerary in the BVI from Road Town

Start your BVI sailing itinerary in Road Town

Map of your 2-week sailing itinerary around the British Virgin Islands


Day 1: Road Town, Tortola to the Bight, Norman Island (8 nm)

Things to do:

  • Hiking Trails on Norman.

Day 1 of your BVI sailing route will start in Road Town where you can begin your charter. After a morning at base preparing for your voyage, we recommend that you head across the Sir Frances Drake Channel to Norman Island where you will eventually spend the night time on Bight Bay at the Northern shores. All together this distance is around 8 nautical miles. But first, there is lots of exploring to do! Throughout the afternoon spend your time wisely and be sure to take the dinghy and your snorkelling equipment to Treasure Point where you can delve into and discover the magical caves.

This island is thought to have provided inspiration for Robert Louis Stevenson’s Treasure island, and you will feel that a palpable sense of adventure still remains here to this day. Bight Bay is a forest of mooring balls all year round, so don’t worry about not getting a spot. They are maintained by Pirates Restaurant and Bar ashore and they charge around $25.

As the evening approaches and you hear that growling in your hungry tummies you will be happy to know that you can then eat ashore at Pirates Bight, then head over to Willy T to enjoy some cocktails!

Start your sailing adventure in the British Virgin Islands

Go snorkelling and explore the sunken RMS Rhone


Day 2: Norman Island to Cooper Island (6.76 nm)

Things to do:

  • Kayaking
  • Stand Up Paddle Boarding

Day 2 of your sailing experience is a fun one. Set out as early as you can manage and motor over to the Indians for a morning snorkel. After this, it would be a good idea to enjoy the upwind sail to Cooper island. At the halfway point, you should stop off at the Wreck of RMS Rhone, which is located just off Salt Island.

Here, you will find a UK Royal Mail Ship which was wrecked here in 1867 during a hurricane, killing 123 people. This is the ideal stop for snorkelling, or even better, it is one of the top locations in the world to dive. It is also where the 1977 film classic “The Deep” was shot. So take the plunge and discover the hidden depths of the earth, you won’t regret it! This could be a great family activity as there are fantastic certified diving instructors to help with all levels, or snorkelling for the little ones.

Start your sailing itinerary in the BVI

Have an adventurous time snorkelling


Spend the night at Manchioneel Bay, again sprinkled with mooring balls, where you should seize the opportunity to kayak or dinghy over to Cistern Point for the last snorkel of the afternoon. The perfect way to end such a perfect day is by heading ashore for happy hour drinks and dinner at the Cooper Island Beach Club. This relaxed eco-resort built with recycled materials and flanked by palm trees is only accessible by boat, and therefore a great place to cheers and share tales of the sea with your fellow sailors.

the best adventurous sailing route in the British Virgin Islands

To have a drink you need to take a boat to the shore


Day 3: Cooper Island

Day 3 is a day to relax and enjoy the phenomenal island paradise that is Cooper Island. From its brilliant beaches, to great rum shacks and fantastic fishing spots, whatever you do, it is bound to be a great day. Here, you can recharge not only your batteries, but your boats. Take the opportunity to fill up your water too.

Sailing British Virgin Islands - a dream come true

Explore the marine life around Cooper Island


Day 4: Cooper Island to Leverick Bay, North Sound, Virgin Gorda (10.34 nm)

Day 4 of your BVI sailing route consists of a set course to the Baths located on the southern end of Virgin Gorda. Mooring buoys and a dinghy dock allow you to conveniently moor here and access the beach.

Once you have moored, swim over to the tranquilest of beaches, then begin the trail through the boulders to the picturesque Devils Bay National Park. After you have explored this mesmerising place, head back to your boat and begin your way up to the North Sound.

You can then moor your boat at Leverick Bay for a very pleasant evening ahead. If you’re up for some entertainment, try and catch the Michael Beans Pirate show! This is a great family fun activity, early in the evening, take pirate gear if you are into dressing up. The kids will love it and the adults with love it more. We would advise that you call ahead and make a reservation in busy periods of the year. Pirates and rum after a day of sailing, who can complain? You’re as good as Captain Jack Sparrow.


Day 5: A Day To Enjoy The North Sound

Things to do:

  • Fish feeding at Saba
  • Watersports
  • Hiking
  • Hire a car  

Day 5 is going to be full of adventure. Take your dinghy over to Saba Rock, better known as a jewel in the heart of the North Sound. Here you can indulge in Caribbean inspired cuisine and expertly crafted cocktails. If you don’t already feel it, then this is the beginning of your love affair with the British Virgin Islands.

Close to Saba Rock, you will find Eustatia Reef. Be sure to only visit this area with your dinghy, and make your way slowly as it is very shallow in many places. This area is best explored on calm days with good visibility unless you are well acquainted with it already.

Start your boat charter in the British Virgin Islands

The stunning Eustatia Reef


In the afternoon we highly suggest Leverick Bay. Here you will find quaint trinket shops in the marina. Or if you feel like swimming, take a dip in the pool. If you love 360 views and food (who doesn’t?) then be sure to organise a taxi in the late afternoon to take you to Hogs Haven restaurant. Believe us, the sunset is unlike anything that you have ever seen. Enjoy your dinner with the lights of the island glimmering and twinkling in the distance.

Your yacht charter in the BVI is waiting for you

Enjoy the view from Hog Heaven


Day 6: Leverick Bay, North Sound, Virgin Gorda to Anegada (13 nm)

Things to do:

  • Eco Tour

Day 6  let’s go! As they say, the early bird catches the worm. Rise and shine guys and depart in the morning for the 13 nautical miles passage to the Setting point harbor on Anegada. This destination is a truly unique within the British Virgin Islands. This is because it is entirely flat and therefore cannot be seen from the other islands.

The anchorage lies between Setting Point and Pomato Point and the entract through the reef is well marked and lit. There are overnight mooring buoys available here with hard sand and a good holding. Just contact the Anegada reef Hotel or Neptune’s Treasure for availability. Anegada is 11 miles long in total and has miles of some of the most wonderful beaches (Loblolly Bay and Cow Wreck) in the British Virgin Islands, or anywhere for that matter. Catching an eco tours to see the salt ponds, home of a flock of pink flamingos and keeping a lookout for the islands protected giant iguana would be an afternoon well spent here.

BVI sailing route

The breathtaking Loblolly Bay


If you are a lobster lover, then your evening is very much set! The lobster dinner is the main attraction here. It is advised that you call ahead the day before if possible to be sure they get enough lobsters in the daily catch. It isn’t a realistic expectation to show up here without a reservation, which is a good sign of excellent food if you ask me!


Day 7: Anegada Beach Day

Things to do:

  • Rent a scooter
  • Take a taxi tour

Day 7 is the beach kinda day of your BVI sailing route. Top up that tan you bronzed god/goddess. As previously mentioned, Anegada is home to the most fabulous beaches you ever did see. It is advised to get a taxi to these islands. I use the phrase ‘taxi’ lightly as it is more like seats attached to the back of a pickup truck which happens to be a very fun (if not exhilarating) experience! It is also possible to hire cars/ jeeps and motorbikes ashore! Spend your evening barbecuing followed by a beach party. You can also get involved in pool games and watersports at Bitter End yacht club, ideal!

Rent the best boats in the BVI

Enjoy your evening with a barbecue on the beach


Day 8: Anegada to Marina Cay (19 nm)

Things to do:

  • Marina Cay
  • Diamond Reef

Day 8 you will set sail to Marina Cay! You may have heard of the famous telephone box. Well here you can see it first hand, reminding you that the islands are British. Cameras take new photos here every 15 seconds so make sure you get yourself in on the action. Another iconic part of this island is “Pussers”. Founded by Charles Tobias, Pussers started out as a shop and quickly expanded into several chains throughout the island covering clothing, cigars gifts and rum cakes. Their large menu includes seafood, Caribbean specialities as well as typical North American fare. You may also top up your fresh water and ice at the same time. Around this area you can take your dinghy and will also find “Diamond Reef”, this is a great spot for snorkeling. Be sure to try out Pusser’s famous “pain killer club cocktails” (the name says it all)!

Start your BVI boat charter

The amazing Marina Cay is waiting for you


Day 9: Marina Cay and Trellis Bay

Day 9 will start with a relaxing morning snorkelling at Marina Kay and again at Diamond Reef. In the afternoon it would be a nice idea to take the Marina Kay ferry over to Trellis Bay on Tortola and explore Aragorn’s spectacular art studio. Here you will see that they make beautiful pottery and ceramics on site. Have an early dinner and cocktails at De Loose Mongoose in Trellis Bay, and if you take one thing from this blog then ORDER THE RIBS! They are simply delicious.

Sailing British Virgin Islands

Order ribs and a cocktail in Trellis Bay – you won’t regret it!


Day 10: Marina Cay to Cane Garden Bay (8 nm)

Things to do:

  • Beach
  • Watersports
  • Tree Top Zipline
  • Callwood Rum Distillery

Day 10 will start with a cruise down the Northern shore of Tortula, keeping an eye out for leaping dolphins by your boat on the way to Cane Garden Bay. We highly recommend that you stop at Monkey Point on Guana Island for some great snorkelling on the way!

Start your BVI sailing route and visit Tortula

The fabulous beach on Tortula


I hope you packed your dancing shoes because tonight, you will be partying the night away. Cane Garden Bay is renowned for its crazy night life, so make sure you check out the local scene here. The main place to party is Bomba’s Surfside Shack. It is a little more than a colourful shack in the sand, this bar is known for its “herbal” tea and Bomba Punch for which it is named. Make sure to stop by for the Full Moon Party! Alternatively, spend a night in peace laid underneath the twinkling night sky and enjoy your beautiful surroundings. You might be able to hear the satisfyingly quiet splashes of water around you and perhaps the muffled sound of reggae music distantly floating across the water.


Day 11: Cane Garden Bay to Diamond Cay, Jost Van Dyke (4.29 nm)

Things to do:

  • Snorkelling
  • Bubbly Pools

Day 11 is all about Diamond Cay on Jost Van Dyke. Moor your boat here and in a short distance from Foxy’s Taboo, you will find the trail that leads to a real geological delight, the Bubbly pool. The bubbly pool is akin to a natural Jacuzzi and if visited at the right time, can be quite invigorating and a lot of fun. This is an experience not to be missed! Get yourselves to Foxy’s Taboo for a scrumptious lunch and then go across to Sandy Cay to explore. Both Sandy Cay and Sandy Split are great sites for snorkelling.

The best itinerary for your BVI sailing vacation

Maybe you can even spot some dolphins in Sandy Cay or Sandy Split


Day 12: Diamond Cay, Jost Van Dyke to Great Harbour, Jost Van Dyke (3 nm)

Day 12 provides the perfect opportunity to explore Jost Van Dyke! After breakfast motor sail around to Great Harbour. Pick up your overnight mooring, then jump in the dinghy and head around the point into White Bay.

Start your BVI yacht charter and sail in the Caribbean

Enjoy the view of the superb White Bay


Go spend your soggy dollars in the Soggy Dollar Bar before heading back round to the beautiful Great Harbour where you can enjoy dinner in any of the restaurants. If you happen to approach this area on a weekend then you’re in luck! There is live music and BBQs which makes a great stop for all the family. It is okay to have ribs two nights in a row by the way.


Day 13: Jost Van Dyke to Soper’s Hole, West End Tortola (5 nm)

Things to do:

  • Shopping at Soper’s Hole

Day 13 will be spent enjoying a leisurely morning exploring Great Harbour on Jost Van Dyke, before setting out on your new voyage to Soper Hol on the Western End of Tortola. Here you will find a choice of shops, bars and restaurants to explore in the afternoon. The Fish’n Lime restaurant, located right next to the ferry terminal, serves a great lobster dinner as well as other specialities including fresh fish dishes. The best part about this place is the spectacular decking where you can enjoy even more spectacular sunsets.

The best 2-week sailing route in the British Virgin Islands

The sunsets on Jost Van Dyke will take your breath away


Day 14: Soper’s Hole to Great Harbour, Peter Island (5 nm)

On day 14 set out for a great upwind sail from Soper’s Hole, to Deadman’s Bay on Peter Island. Here you can sink your toes into those white sandy beaches before climbing the trail up to view the islands from above.

Be sure to motor round to Great Harbour for a night under the stars. This is the ideal spot for your final evening as it is picturesque and has a unique tranquility about it. It is also only a short sail from here back to base the following morning. There is a small bar and restaurant located on the beach called Oceans Seven where you can enjoy a final drink and reminisce and toast to the last two unforgettable weeks.

Charter a boat in the British Virgin Islands

The stunning coastline of Peter Island


Day 15: Peter Island to Road Town, Tortula (6 nm)

Day 15 is your last sail of the holiday. Absorb the views and take mental pictures as you come back the Sir Frances Drake Channel into Road Harbour. Arrive here mid-morning so that you have plenty of time to catch your afternoon flights or ferry back to St. Thomas. We hope you enjoyed your trip and have taken away magical memories to last a lifetime! Would you like to see which types of boats you can charter in the British Virgin Islands? Take a look at our vast choice of boats for your sailing adventure. Until your next voyage…


If you would like to sail for a shorter period than two weeks, take a look at our BVI sailing route for 10 days or for a compact 7 days. 

Did you already plan an itinerary for sailing in the Virgin Isles? Share your sailing vacation experience!