BVI Sailing Itinerary - Caribbean Spring Break

Enjoy your Spring Break traveling in style on a yacht with your friends! Hop aboard a Caribbean sailing charter to enjoy an amazing week in the BVIs!

Are you looking for a week of fun full of amazing experiences sailing the Caribbean? Join one of our flotilla holidays in 2019 to discover an exotic boating paradise! Spend a week with your friends on a Caribbean sailing charter from Sailo and get ready to meet fun-loving people while island-hopping and partying. Check out the BVI sailing itinerary for Spring Break 2019 to get an idea about what you’re going to be part of when you sign up for one of our BVI flotilla holidays!

BVI Sailing Itinerary Starting Point - Road Town, Tortola


Whether you fly directly to the BVIs or to St Thomas, USVI and then get the ferry to Tortola, do not forget your passport! Once you’ve arrived in Tortola, you’ll go through customs and then head to Sunsail Base in Wickham’s Cay Marina II. Here you’ll meet your captain and your other boatmates for the week. For the rest of the day you’ll get to know each other, relax at the pool, and enjoy the cocktails as you prepare to go sailing the Caribbean in style! We’ll also walk you through how things work onboard of your Caribbean sailing charter, so we are all ready to leave the next morning and start partying.


Norman Island - BVI Sailing Itinerary Day 1


Some say that Norman Island was the inspiration for Robert Louis Stevenson’s pirate novel, “Treasure Island”. What we can tell your for sure is that this little private island is a great place for snorkeling or scuba  - activities that are a must when you go sailing the Caribbean! It’s time to explore the colorful, lively coral reefs and marine life at “The Indians” and then relax on the dreamy white sandy beaches, sipping cocktails. The “Bight” is one of the largest, most scenic protected harbors in the BVI’s and that’s where the captain will moor your Caribbean sailing charter  for the night.


Beef Island - BVI Sailing Itinerary Day 2


The crystal clear water of Beef Island provides a perfect background for plenty of Insta- worthy pictures with your friends. The main town - Trellis Bay - is where you can do some of the best snorkeling, windsurfing, kayaking, kitesurfing, or kiteboarding. Don’t miss your chance to explore the charming streets of Trellis Bay, get a taste of the authentic Caribbean food, and join the happy crowd for an evening of cocktails and dance at the beach bars.


The Baths & Virgin Gorda - BVI Sailing Itinerary Day 3-4


The Baths are must-do for anybody who goes sailing the Caribbeans! We’ll will moor on the north side of the island and spend the afternoon exploring the awe-inspiring granite boulders, which form sheltered sea pools and magical grottoes. On our way to the Bitter End Yacht Club - our anchorage for the night- we’ll pass Sir Richard Branson’s private island - Necker Island.  


Anegada - BVI Sailing Itinerary Day 5


Get ready to swim at Anegada, one of the top beaches in the Caribbean as mentioned by The New York Times. The captain will moor your Caribbean sailing charter at buoys on the south side of the island.  It’s time to have fun in the water and go snorkeling the impressive coral reef.  Then we all reunite at the famous Cow Wreck Beach to enjoy an authentic Caribbean dinner and party on the beach. One of our favorites at Anegada  is to rent scooters from one of the local stores and to ride around the island!


Jost Van Dyke - BVI Sailing Itinerary Day 6


Our next stop is Jost Van Dyke Island - another must on any of Sailo’s flotilla holidays in the BVI’s.  Sit back, relax and enjoy the scenic cruise as we head towards White Bay and the famous Soggy Dollar Bar – original home of the Painkiller, a drink known worldwide. The only way to experience the Painkiller is to jump off the boat and swim to the bar, leaving you with “Soggy Dollars”.

In the afternoon, we sail to Great Harbour, home of the legendary 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


On our way back to Road Town all boats will be part of a race for a sweet and bubbly prize -  a bottle of champagne to celebrate the amazing sailing we had on this trip!  We look forward to welcoming you back aboard a Sailo Caribbean sailing charter!