Sample Itinerary

Day 1. Arrival in the beautiful British Virgin Islands!

Gypsy Princess and her crew will pick you up as close to your arrival port in BVI as they can. Whether meeting you at Trellis Bay on Beef Island, close to the BVI Airport or at Village or Nanny Cay Marinas near to Road Town Ferry Dock they will ensure your transition from journey to vacation is smooth!

Upon arrival at Gypsy Princess your crew will offer a brief introduction to the Yacht and the Islands, the dock lines shall be released and the sailing will begin. 

Just a short sail across the Sir Francis Drake Chanel is the idyllic Cooper Island. The afternoon will be spent here testing the snorkelling gear, taking to the water on a SUP or Kayak and relaxing aboard or on the beach of the Cooper Island Beach Club. After sunset cocktails aboard and a delicious fresh dinner there will be time to relax aboard or explore the Cooper Island Rum Bar & Brewery. 

Day 2. Exploring on Virgin Gorda

After waking up to the aroma of coffee, bacon and eggs, you’ll enjoy a delicious breakfast with the freshest of local tropical fruits. A short sail to the east and we discover The Baths on the island of Virgin Gorda; a maze of building-sized boulders. Lose yourself in the shallow pools hidden inside the naturally formed caves or release your inner adventurer and clamber to the rocky peaks into the sunshine. Hungry from a morning of exploring enjoy a delicious lunch aboard before an exhilarating sail to The North Sound. Depending on your preference we can moor at Leverick Bay to enjoy some fabulous live entertainment after dinner or to a secluded bay to watch the flamingos circle the salt ponds before roosting for the night. 



Day 3. Anegada Bound

After a fresh & energising breakfast you will be able to snorkel the Eustacia Reef which encloses the Eustacia Sound of Virgin Gorda. Hopefully you’ll enjoy seeing the corals, turtles & even pirate canons in this area! Once back aboard Gypsy Princess we’ll quickly hoist the sails & set off for Anegada; a lovely sail skipping towards the horizon but arriving at our anchorage in time for lunch aboard. The afternoon is spent exploring the ‘Drowned Island’ by Safari Bus, visiting the north shore with it’s famous never ending white sandy beach & tiki bars. Returning to the boat, cocktails & canopies will be prepared in time to see the stunning sunset. Should you wish to try local Lobster, Anegada is the place to do it & there is the opportunity to eat freshly caught seafood on the beach for dinner with the locals. Alternatively dine aboard for a feast prepared by your chef.



Day 4. Snorkelers Delight

Wake up to another tasty fresh breakast and then relax and enjoy your book or join the Captain for a spot of helming as we sail down-wind towards the uninhabited Dog Islands. We moor at this National Park next to a lovely coral reef which offers fantastic snorkeling and kayaking.  After lunch we sail down wind again to out final stop of the day.  Either Trellis Bay, famous for its full moon parties and some local crafts and culture or a secluded bay where we can enjoy the sunset as a solitary boat in a beautiful bay and watch the stars after dinner.



Day 5. Guana Island to Little Jost

After Breakfast we set off for beautiful White Bay on Guana Island. A nice flat anchorage, perfect for getting out the water toys and having a go at wakeboarding or waterskiing. If you prefer a quieter life then the beach is perfect for beach combing and there is excellent snorkelling nearby. After another delicious lunch we leave the mooring and sail down to Little Jost Van Dyke. Time for sunset cocktails at our favourite bar, B-Line right on the beach or on board if you prefer, followed by dinner served on the aft deck.


Day 6. Jost Van Dyke

Before Breakfast the crew will rise early & move Gypsy Princess to your own deserted island! Sandy Cay. Famous for the Corona Adverts is just as it is named, a small sand atoll accessible by swimming or kayak. Breakfast will be served on the top deck if you prefer so you can enjoy the view of this delightful little piece of paradise!

When ready we’ll sail down to the western end of Jost Van Dyke to visit another White Bay & the famous Soggy Dollar Bar, home of the BVI cocktail the Painkiller! You can spend the rest of the morning here, tasting the cocktails, enjoying the beach games or relaxing in the hammocks and people watching! After lunch we’ll hop around to Great Harbour, a sleepy but sheltered bay where we can anchor away from the crowd next to the beach. Enjoy dinner aboard and then if you have the energy check out the famous bar ‘Foxy’s’ that often has live music and a fabulous shop for souvenirs. Alternatively enjoy relaxing on board in peace with a crisp glass on wine!



Day 7. Snorkeling at Norman Island

After breakfast we’ll up anchor and sail around the western most point of Tortola and head up to Norman Island, famously the inspiration for Robert Louis Stevensons ‘Treasure Island’. With a number of mooring spots depending on whether you prefer a crowd and a bar or star gazing in solitude, Norman Island has a lot to offer! We’ll pick our resting place and enjoy lunch aboard.  Once our meal has settled we can explore some of the underwater gems nearby, including The Caves & The Indians. If you prefer to stay dry you can take the trail map & hike the island to the top of Spy Glass Hill which offers fabulous views of the BVI & USVI.
Back on board for cocktails & nibbles, followed by dinner, you know you’ll be in for a treat from the grill on your last night!



Day 8. Drop off on Tortola or Beef Island

We hoist the sails and draw the anchor for the very last time head back to Tortola and your preferred drop off point for ferry or airport. This day is always a tough one as goodbyes are never easy, so we prefer to say ‘until we meet again’.


The BVI has so much to offer, whether you want to party every night or enjoy the peace and quiet and never see another soul all week. We can tailor make your itinerary to your groups requirements of course taking into consideration the all important weather! This is a suggested itinerary taking in some of the highlights the BVI has to offer but from one week to the next we take our guests to the spots they will enjoy. If you want to join us for a vacation of more than 7 days we can still easily make sure you won’t see the same beach, bar, hiking trail or sunset twice!

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