Sample Sailing Itinerary

Lagoon 450 YOLO | Caribbean Crewed Catamaran Charters BVI | Sample Itinerary 
British Virgin Islands Sample Sailing Itinerary              Inquire Now

The BVI’s are the “Sailing Capital of the World” and have been called “Natures Little Secret” as their beauty is stunning. You can fly into Beef Island on Tortola or the more popular St Thomas Airport and hop aboard the Charlotte Amalie ferry for a scenic ride over to Tortola.We have created a seven night sample sailing itinerary encompassing some of the most notable places in the British Virgin Islands. Please keep in mind that this is a sample only and your itinerary can be specifically tailored for you by your charter captain.There are many more incredible places to visit than can be included in a single 7 day sailing vacation, so we have included just a few in this sample. Of course, if you can spend more time on this Caribbean Sailing Vacation or plan on coming back for more in the future, you will never cease to be in awe of your surroundings and discoveries.

Day 1    

Your Luxury Caribbean Sailing Vacation begins aboard YOLO, a brand new Lagoon 450 catamaran, at the nanny Cay Marina, Tortola. You will be greeted by your Captain and given time to get settled on board YOLO. Before heading out into the beauty of the BVI’s, you will receive a briefing by the Captain and base crew.

Your first sailing day is a short trip across the sheltered Sir Francis Drake Channel to Norman Island, the home of The Caves and reportedly the site of the famous Treasure Island. The Caves on Norman Island brings you to your first experience of the beauty and splendor of the BVI, both above and below the surface. Snorkeling in what seems like an aquarium teaming with thousands of the most colorful fish. A five minute motor around the headland brings us into “The Bight”

on Norman Island, home of the famous “William Thornton”, a floating bar and restaurant known to many as the “Willy T”.


Day 2

After a leisurely morning we will head down the Channel past Sopers Hole (where a stop for fresh baked bread may be in order) and through to Jost Van Dyke, home to the famous Foxy’s in Great Harbor, as well as the Soggy Dollar Bar on White Bay. We will either anchor in Great Harbor or at White Bay, one of the most beautiful white sand beaches in the world. Here you can choose to hang out on the lightly used beach in front of Ivan’s Stress Free Bar, or head further down the Bay to the popular



Soggy Dollar Bar, where the original “Painkiller” cocktail was conceived.




Day 3

A dip in the “Bubbly Pool”, just a short walk from our first stop in Diamond Cay,  Jost Van Dyke. This unbelievable spot is nature’s version of a Jacuzzi.  The rock formation located on the rugged northern coast of Jost Van Dyke funnels waves through a very narrow passage into this small, natural pool. If you visit while the tide is up, it can be quite invigorating!

Then it’s on to beautiful Sandy Spit for some leisurely fun. This tiny little island lights up the aqua marine Caribbean Sea like a beacon in the sun. The perfect beach is punctuated by a cluster of rocks with green vegetation and two lonely coconut palms. Absolutely Stunning!

After lunch we head to Cane Garden Bay, another exquisite bay in paradise. The beach along the bay is surrounded by beach bars and eating establishments like Quito’s Gazebo. Quito is a well known BVI recording artist, famous for his soulful reggae tunes, soft voice and warm smile. He owns Quito’s Gazebo Bar, restaurant and night club, where he sings for the after dinner crowd several nights a week.

Day 4

After breakfast we head out for a nice sail north to Marina Cay. Along the way we will stop at Monkey Point on Guana Island. A snorkel around the unusual coral outcroppings will reveal some strange marine creatures not often encountered. Then onward through the passage between Great and Little Camano Islands to Marina Cay. Here you have the option of dining ashore either at the Marina Cay Pussers restaurant, or at the 5 star Scrub Island Resort, or across the bay at The Last Resort in Trellis Bay.

Day 5

An early start get’s us to Virgin Gorda where The Baths for some of the most incredible snorkeling amongst enormous granite boulders and turquoise blue sea. The beaches are also incredibly beautiful around the baths. From here we sail north to Gorda Sound, home of the Bitter End Resort, Saba Rock and Biras Creek, all of which boast first class restaurants and bars.

Day 6

After the morning exploring Gorda Sound, a leisurely sail down to Manchioneel Bay with it’s gorgeous sweeping arc of beach at the Cooper Island Beach Club.  The gorgeous and accessible Cooper Island Beach Club, with a restaurant, bar and the charming Sea Grape Boutique will keep you busy if you’re not splayed out on that fantastic stretch of sand. Don’t miss the sunset staring right down the length of the Sir Francis Drake Channel. St. John is in the distance, and your view is rimmed by a continuous line of green gems. The lights of Road Town begin to blink to the north, and the sun dips lower creating a rich, orange light perfect for photos of Cooper Island, your crew, and this ethereal setting.

Day 7

Unfortunately we are nearing the end of this YOLO sailing vacation. However, not before another swim in the beautiful waters or a walk along the beach. Then we sail across the channel back to base to ready for your return home.