“You Make the Memories, We’ll Make the Arrangements”

Experience a BVI Sailing Itinerary 14-day adventure. Whether it’s your first sailing vacation to the British Virgin Islands or if you are a frequent visitor, one week is not enough. This allows you to visit (or re-visit) the best of the BVI. Each island has its personality and vibe.

If you’ve sailed before, you’ll know that flexibility is vital as the winds often dictate the route. If you’ve never sailed before, get ready for an incredible adventure.

This sample itinerary gives you an idea of what to expect, from secluded anchorages to lively beach bars.

Day 1 Road Town, Tortola – The Bight, Norman Island

After arriving at your yacht, you will meet the crew you’ve probably already met virtually in person. They will greet you with a chilled beverage, and after a brief safety meeting, you’ll set sail on your 14-day BVI sailing itinerary. Your first destination is the Indians for snorkeling, and then to Norman Island, where you’ll anchor at Bight Bay for the night.

14-night BVI sailing itinerary Norman Island
Norman Island

Dinghy to shore and explore the hiking trails on Norman Island. Keep an eye out for pirate booty. This island is the inspiration for Treasure Island by Robert Louis Stevenson.

Enjoy your first dinner aboard, tailored just for you by your chef. Or, if you prefer, go ashore and have dinner at the Pirate’s Bight Restaurant. And whether you dine aboard or ashore, make sure to tender over to Willy T’s for a tropical cocktail and some island-style fun.

Activities | BVI Sailing Itinerary 14-Day

  • Hike
  • Dine
  • Cocktails
  • Beach

Day 2 Norman Island – Cooper Island

Sleep in or wake early; it’s up to you. While starting your day with a made-to-order breakfast, discuss your plans for the day.

The first stop could be the Treasure Point Caves at Norman Island for snorkeling before heading to Cooper Island. On the way, stop snorkeling at the Wreck of the Rhone, just off Salt Island. Besides offering a beach, Cooper Island has a Rum Bar, restaurant, coffee shop, and boutique. Beachfront cottages also boast captivating views of the Sir Francis Drake Channel and nearby islands.

14-night BVI sailing itinerary coral reef
Colorful coral reefs

Activities | BVI Sailing Itinerary 14-Day

  • Snorkel
  • Dive Cistern Point
  • Beach
  • Cooper Island Beach Club

Day 3 Cooper Island – Spanish Town, Virgin Gorda, via The Baths

Another day of adventure awaits as you make your way to Virgin Gorda. It’s a short sail to the Baths, where if the conditions are right, the captain will tender you to the drop-off point, or you can snorkel ashore.

14-night BVI sailing itinerary the baths
The Baths, Virgin Gorda

Explore the Baths and snorkel at Devil’s Bay National Park. While there, visit the Top of the Baths for a snack and some shopping. Try a Pina Colada at Mad Dogs.

From the Baths, it is a short sail to Spanish Town. Your yacht will use either anchor off Spanish Town or dock per your request at the Marina in Virgin Gorda Yacht Harbour. Here there are many things to see and do, such as

  • Dining at CocoMaya
  • Shopping at Yacht Harbour
  • Taking a taxi to the Copper Mines

Day 4 Spanish Town – Leverick Bay, North Sound

On the way to Leverick Bay this morning, stop at the Dog Islands for snorkeling, swimming, and paddle boarding. Afterward, continue to Leverick Bay. There’s a lot to see and do in this area, such as

  • The Spa at Leverick Bay. Treat yourself to a massage, mani/Pedi, or a complete spa package.
  • Watersports. The North Sound is a protected area that’s great for watersports. Besides snorkeling, there’s kiteboarding, windsurfing, and jet skiing. Or, rent a flyboard. You don’t need any experience.
  • Fish.
  • Rent a car or taxi. Then, check out some local eateries like Hog Heaven Restaurant or the Restaurant at Leverick Bay.

Day 5 Leverick Bay – Bitter End Yacht Club | BVI Sailing Itinerary 14-Day

Depart mid-morning from Leverick Bay to Prickly Pear Island for some beach and water sports action. Optionally, you can snorkel the reefs that are close to Moskito Island.

  • Enjoy lunch on board before heading over to the anchorage off Bitter End Yacht Club.
  • Take the tender to Saba Rock. Saba Rock is a tiny island — about an acre and a half in size. The island has a small hotel, restaurant, bar, and gift shop. Snorkeling is good around the island — keep an eye out for old sunken cannons.
  • Take the tender to the Fat Virgin Cafe or Oil Nut Bay Marina Village. Or, instead of anchoring off Bitter End Yacht Club, your yacht can dock at the Oil Nut Bay Marina Village. The marina has a pool, shopping, and a restaurant and bar.

Day 6 North Sound – Anegada

By day six, you’ve probably mastered the fine art of doing nothing. This morning you’ll set out on a 2-hour sail from North Sound to Anegada. Once you arrive, you might spend the day exploring Anegada’s unique flat landscape. It stands in contrast to the other mountainous islands in the BVI.

Activities | BVI Sailing Itinerary 14-Day

  • Look for the endangered Anegada rock iguana, turtles, wild orchids, and frangipani. Journey to the salt ponds on the island’s western end to catch a glimpse of local pink flamingos.
  • Loblolly Bay. Relax on the soft sand, swim in the turquoise water, and dine on local Anegada lobster.
  • Visit the largest town in Anegada, The Settlement. It has a year-round population of about 200.
  • Snorkel Horseshoe Reef. The largest coral reef in the Caribbean will keep you busy for hours. Just remember to reapply your sunscreen.
  • Kiteboard.
  • Rent a scooter or take a taxi tour.

Days 7 & 8 Anegada – Marina Cay or Trellis Bay, Beef Island

Although you may fall in love with Anegada and not want to leave, your captain will set sail for Marina Cay on day eight. Don’t worry, however, because there’s still plenty to see and do in the British Virgin Islands. Activities around Marina Cay include:

  • Snorkeling. The shallow waters here make for superb snorkeling.
  • Take the dinghy to nearby islands such as Scrub Island, Great Camanoe, and Little Camanoe.
  • Shop. Aragorn’s studio is well-known for hand-crafted art.
  • Party. Monthly Full Moon parties are a blast where locals and visitors mingle and celebrate.
  • Rent a car and explore.
  • Snorkel Bellamy Cay.

Day 9 Marina Cay or Trellis Bay, – Cane Garden Bay

Leave Trellis Bay for a short sail to Cane Garden Bay, stopping at Guana Island to snorkel Monkey Point if you choose. Pick up a mooring at Cane Garden Bay and throw the water toys overboard for a fun afternoon. In the evening, have dinner on your yacht or go ashore to sample the menus at the many restaurants and bars.

Cane Garden Bay, Tortola, BVI
Cane Garden Bay, Tortola, BVI

Day 10 Cane Garden Bay – Diamond Cay, Jost van Dyke

Today you sail to Diamond Cay, Jost van Dyke. On the way, stop at Green Cay and Sandy Cay to snorkel. This gorgeous area is where you may see manta rays, sharks, and sometimes dolphins. Other BVI Sailing Itinerary 14-Day activities include:

  • Exploring Diamond Cay National Park
  • Enjoying the Bubbly pool, a natural jacuzzi created by ocean waves and rock formations
  • Eating and drinking at Foxy’s Taboo

Day 11 Diamond Cay, Jost van Dyke – Great Harbour, Jost van Dyke

Leave Diamond Cay and sail to Great Harbour. Great Harbour and nearby White Bay have some excellent bars and upbeat nightlife.

  • Visit the famous Foxy’s at Great Harbor for a cocktail or two.
  • You can sail or take the dinghy to White Bay. Hike, explore, and stop by the Soggy Dollar Bar.

Day 12 Jost van Dyke – Soper’s Hole, West End, Tortola

Say goodbye to Jost van Dyke and travel to Soper’s Hole. This is an excellent anchorage with several restaurants.

Activities | BVI Sailing Itinerary 14-Day

  • Shop at Soper’s Hole Wharf and Marina.
  • Arrange for a dive trip at Island Surf & Sail (located in the marina).
  • Take a taxi to Smuggler’s Cove beach.

Day 13 Soper’s Hole – Peter Island during

On the last full day on your yacht, journey from Soper’s Hole to Peter Island. Visiting this island is the perfect way to bring your BVI Sailing Itinerary 14-day Adventure to a close. Put off packing your bags until later because there’s still much to do.

  • Lounge in a hammock on Deadman’s Bay beach.
  • Snorkel.
  • Have a picnic.
  • Take selfies with the tropical paradise as your background.
  • Begin dreaming of your next BVI vacation.

14 Day Sailing Itinerary BVI| Peter Island – Road Town, Tortola

As you awake to the last day of your BVI Sailing Itinerary 14-day adventure, take some time to breathe in the salty air and reflect on your memories. Enjoy breakfast and sail back to Road Town.

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Contact us at 1-321-777-1707 or complete this form to discuss your vacation plans.