Top BVI Sailing Itinerary - A Dream Vacation with Sailo

Hop aboard one of our Tortola sailing charters to enjoy a fun week at sea!

Are you looking for a week of fun and amazing experiences in the Caribbean? Book a private BVI catamaran charter on Sailo for your sailing vacation to discover an amazing winter boating paradise in the Caribbean! Spend a week with your friends on one of our Tortola sailing charters and get ready to meet new fun-loving people while going island-hopping in the BVI.

Check out the BVI sailing itinerary our captains put together to get an idea about the great experiences you’re going to have on a Sailo BVI sailing vacation!

Manual Reef Marina

Nanny Cay Resort & Marina

Soper's Hole Wharf & Marina

Road Town, Tortola

Fort Burt Marina

BVI Sailing Itinerary Starting Point - Road Town, Tortola


Once you arrive in Tortola, your next stop is our Tortola yacht charters base -  Sunsail Base (in Wickham’s Cay Marina II) and meet your captain for the week. This day is about getting confortable on your boat, relax at the pool,  and enjoy cocktails as you get ready for one of the most exciting BVI sailing vacations of your life!

Norman Island - BVI Sailing Itinerary Day 1


Norman Island - a must stop on all of our BVI sailing vacations - is a yachtie dream destination. Believed to be the inspiration for Robert Louis Stevenson’s pirate novel, “Treasure Island”,  this little private with no permanent residents is a great scuba and snorkeling place. You can spend the day exploring the amazing coral reefs  and marine life at “The Caves” or “The Indians” or just laying on the beautiful white sandy beaches, sipping cocktails and dipping your toes in the crystal clear waters of the bay. The “Bight” is one of the largest, most scenic protected harbors in the BVI’s and that’s where we will moor our boats for the night.

Beef Island - BVI Sailing Itinerary Day 2


Beef Island, home of the only airport in the BVI’s, is one of the hidden treasures we like to always include in our BVI sailing itinerary. Get ready to soak up the sun on one of the beautiful secluded beaches, go swimming and snorkeling the turquoise calm waters. The coast is lined with picturesque little restaurants, bars, shops and discos that make it a great afternoon, dinner, and evening stop.  Get a taste of the authentic Caribbean food and join the happy crowd for an evening of cocktails and dance.

Virgin Gorda - BVI Sailing Itinerary Day 3-4


The Baths are Virgin Gorda’s most famous attraction and a must-do for anybody who decides to go for one of our BVI sailing vacations. We’ll moor and spend the afternoon exploring the huge boulders scattered across beaches, shaping up an unique exotic landscape of magical grottos. Next we will sail Virgin Gorda and slow down to stop outside Necker Island - Sir Richard Branson’s private island. Our anchorage for the night is the Bitter End Yacht Club. Despite being hit hard by hurricane Irma, this well-known resort is being rebuilt and soon it will be ready to welcome again boating enthusiasts from all over the world.

Anegada - BVI Sailing Itinerary Day 5


The New York Times has called Anegada one of the top beaches in the Caribbean. We will moor our Tortola catamaran charters on the south side of the island, as the rest is surrounded by a massive coral reef, making it great for snorkeling or having fun in the water. We will surely not miss the Cow Wreck Beach - another landmark of BVI sailing vacations - where we can enjoy a delicious Caribbean dinner and party at one of the islands’ favorite beach bars. You can also rent scooters to ride around Anegada from one of the local stores on the island.

Jost Van Dyke - BVI Sailing Itinerary Day 6


Today we will enjoy a scenic day aboard our Tortola sailing charters, heading  towards Jost van Dyke and White Bay. The island has been affected by 2017 hurricanes but quickly bounced back and it is now ready to welcome its thirsty visitors at the famous Soggy Dollar Bar – original home of the Painkiller. In the afternoon we move to Great Harbour, home of another staple of any of our BVI sailing vacations - Foxy’s Bar. This is our mooring spot for the night, giving you the chance to enjoy Foxy’s live Caribbean music and wild parties.

Back to Road Town, Tortola - BVI Sailing Itinerary Day 7


As we are getting back to base, we  will have a race among our Tortola sailing charters to return to Road Town where the winning team will win a bottle of champagne. From here, we will disembark the boats, saying goodbye to hopefully one of your most amazing BVI sailing vacations so far.  We look forward to welcoming you back soon aboard on one of our sailing charters around the world!