Day 1 | Find your sea legs in the protected anchorages at Peter Island

To start off your British Virgin Island sailing charter, you’ll enjoy a relaxing sail from Road Town to Peter Island. After testing out your new sea legs, we’ll drop anchor in Great Harbour for the night. This anchorage is a short walk from the Peter Island Resort, which has great beachside restaurants to enjoy a delicious lunch/dinner with beautiful views of the Caribbean Sea.

Great Harbour is a protected bay, making it a perfect spot for a restful night’s sleep on your sailing charter in the BVIs. Explore the crystal blue waters of Peter Island with kayaks, paddleboards, or snorkel gear, which we provide onboard during your Caribbean sailing vacation.

Day 2 | Search for treasure in the pirate caves at Norman Island. And get into the Caribbean vibe at Willy T’s!

Wake-up for your first morning in the BVI surrounded by the pristine waters of the Caribbean Sea – one of the best feelings in the world. Breathe in the salty air and get ready for an awesome sailing day. We’ll head south for a short sail to Norman Island.

Norman Island is locally known as Treasure Island because of the rampant trafficking by pirates in the 1800s. The caves located around Norman Island are accessible by snorkeling, kayaking, or paddleboarding. These caves are not only home to hundreds of reef fish but are also steeped with fantasy tales of buried pirate treasure! Don’t forget to stop at Pirate Beach Bar for the full experience of pirate life in the Caribbean.

After an active day looking for pirate treasure, finish it with a cocktail (or a few) at the infamous Willy T’s. You’ll get right into the Caribbean vibe at this floating bar, where everyone is sure to make a stop here on their BVI yacht charters!

Day 3 | Dive on the wreck of the Rhone under the waters of Salt Island

Salt Island contains one of the most spectacular scuba dives in the British Virgin Islands. The Royal Mail Steamship “Rhone” was a UK mail ship which sunk after a powerful hurricane struck the islands in 1867. The RMS Rhone is a 310x41 foot long shipwreck encapsulated in red coral and bustling sea life including sea turtles, stingrays, angelfish, yellow snapper, and more!

If your party has a mixed crowd of snorkelers and scuba divers– no worries. Salt Island has activities for everyone on your British Virgin Island sailing vacation. Snorkel, scuba, kayak, paddleboard, or relax – no one will be left out.

Day 4 | Explore the cracks and crevices of the Baths on Virgin Gorda

There’s an early wake up call on Day 4 for those who want to arrive at The Baths in Virgin Gorda before the bustling tourists. These stunning 50 million year old rock formations are busy during high season with the charter boats, which is why we want to sail you there early to enjoy the serenity.

You can spend a full-day wandering in and out of the crevices and grottos of these rocks. It’s no wonder some consider them the eighth wonder of the world.

At the end of the day, we’ll take a short sail over to Scrub Island or Marina Cay for the night. After choosing your evening anchorage between dinner at Pusser’s or a more fine dining option at Scrub Island Resort – it’s time for sundowners in the Caribbean!

Day 5 | Your playground awaits in the beautiful waters of the North Sound

On Day 5 of your BVI yacht charter, we’ll sail to the North Sound. You’ll have the option to stop at Dog Island for some remarkable snorkeling or scuba diving activities. These dives in the BVI are notorious for being discovered by the legendary Jacques Cousteau – the undersea explorer famous for inventing many of the scuba devices we use today.

Leverick Bay is bustling with Caribbean island entertainment during your sailing charter. From dinghy sailing, kiteboarding, hiking lookouts, BBQ pig roast, and Jumbie performers – this spot is a one-stop shop Caribbean playground.

BVI sailing update October 2019: The infamous Bitter End Yacht Club & Saba Rock Restaurant are still under reconstruction after Hurricane Irma. The plan is to open at the end of the 2019 year – just in time for charter season in the BVI!

Day 6 | Feast on lobsters after paddleboarding the reefs of Anegada

The sail to Anegada will take a couple of hours since it lies 12 miles due north of the North Sound. It’s one of the most secluded BVI islands you can sail to. You will be rewarded by some of the bluest and most pristine waters in the British Virgin Islands along with some of THE tastiest lobster in the Caribbean Sea.

This flat and lightly inhabited island has stunning beaches on the north coast, such as Loblolly Beach. These waters are ideal for any and all recreational water activities. If you've seen pictures of the atolls in the Pacific – this is the Caribbean version. Anegada will be sure to at a little culture flare to your BVI charter.

Anegada is another incredible spot for kiteboarding, windsurfing, and even bonefishing with the locals. Let the friendly locals treat you to their fresh seafood alongside an amazing Caribbean sunset on your vacation.

Day 7 | Jost Van Dyke is stunning and gets even better with their local Painkiller drinks

This is the longest sail of your BVI sailing charter – it takes four to five hours to get from Anegada to Jost Van Dyke. This sail can be broken up with a lunch break for you at Guana Island if you prefer. If not, we’ll head straight to the watering hole of Jost Van Dyke – Great Harbour.

Sandy Spit is also along the way, which is one of our favorite stops on this sailing itinerary! This charming 360 degrees of white sandy beach surrounded by deep turquoise blue waters will have you feeling relaxed in no time.

The infamous Foxy’s is also easily accessible from the Great Harbour anchor. This bar is “island vibe” at its finest with the sweet sounds of the owner Foxy Callwood. He also hosts a delicious Thanksgiving dinner here if you plan on chartering during the holidays!

Soggy Dollar Bar is another go-to spot on Jost Van Dyke during your sailing charter specifically known for their famous Painkiller drinks. Made with the local Pusser’s rum, it's the best way to finish a long day sailing on the Caribbean Sea.

Day 8 | After a morning swim, chow down on BBQ and sip your last cocktail in Cane Garden Bay

Day 8 wraps up the end of your British Virgin Island sailing vacation. Depending on your departure time, you can spend your morning exploring Jost Van Dyke a bit more. We’ll then take an easy cruise over to the mainland in Cane Garden Bay for a bite to eat before you fly. 


The sailing itinerary is only a glimpse into what the British Virgin Islands offer for you sailing charter. Remember that all sailing charters are fully personalized to your schedule, desired activities and destinations. Contact us today to talk about ideas of what your sailing charter could look like in the Caribbean.