This 14-day BVI sailing itinerary is for travelers planning a two-week charter with time for more stops and longer stays at anchor. It is a sample route, not a fixed sailing schedule; actual passages depend on conditions and the yacht. For a broader introduction to sailing destinations and charter choices, see our British Virgin Islands yacht charter destination guide. 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.
Share your dates and guest count to start planning. Add your preferred island stops, sailing pace, cabin needs, and budget on the next step.
Share your dates, guest count, cabin needs and preferences using our charter inquiry form. BVISAIL will check suitable yachts and crews for your group.
No obligation to book. Advisory services are free.
For those with extra time, a 14-day sailing itinerary in the British Virgin Islands gives you a chance to fully experience the islands’ culture, beautiful landscapes, and clear waters.
Short on time? Try our 10-night BVI island-hopping itinerary.
Plan the Top 10 Stops on a BVI Yacht Charter.
🤿 The Indians • Treasure Caves • The Baths
🥾 Hiking Trails • 🦩 Anegada Trips • 🐢 Wildlife Spotting
🏖️ Sunny Beaches • 🌊 Water Sports • 🌅 Hammocks & Sunsets
🍽️ Waterfront Dining • 🍹 Rum Bars • 🎉 Willy T’s Party Boat
Treasure Island Inspiration • Pirate’s Bight & Willy T’s
The Baths & Devil’s Bay • CocoMaya Restaurant
Loblolly Bay • Horseshoe Reef • Pink Flamingos & Lobster
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.
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.
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.
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.
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
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
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.
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.
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:
Explore BVI wind patterns for longer charters.
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.
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:
Leave Diamond Cay and sail to Great Harbour. Great Harbour and nearby White Bay have some excellent bars and upbeat nightlife.
Say goodbye to Jost van Dyke and travel to Soper’s Hole. This is an excellent anchorage with several restaurants.
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.
As you awake to the last day of the British Virgin Islands 2-week itinerary, take some time to breathe in the salty air and reflect on your memories. Enjoy breakfast and sail back to Road Town.
⬇️ Download 14-Day BVI Charter Itinerary (PDF)If this is your first charter, BVISAIL can also help you understand how chartering works, what is included, how pricing works, and how to prepare for your week aboard.
Discover why yacht charters offer more freedom, privacy, and value than resorts and cruises.
Discover the Benefits →Share your travel dates, group details, and preferences to get matched with the perfect yacht.
Plan Your Yacht Escape →Step‑by‑Step Process
A. Share your details with BVISAIL:
Preferred charter dates
Destination, including BVI, USVI, Bahamas, or wider Caribbean
Special occasions, such as a honeymoon, anniversary, or corporate retreat
Interests and activities, such as diving, island-hopping, and cultural tours
B. Who will be traveling with you?
Family
Friends
Business associates
C. What’s your charter budget range?
$150,000+ per week plus expenses
$100,000+
$75,000+
$50,000+
$35,000+
D. What type of yacht do you prefer?
Motor Yacht
Power Catamaran
Sailing Catamaran
Sailboat
E. What’s your group’s charter history?
Tip: Book at least 9–12 months in advance to secure the best yachts and destinations. This is one of the reasons why chartering with a U.S.-based brokerage helps you plan with confidence.
Discuss preferences with a BVISAIL charter expert. Then, we’ll review destination options, yacht types, and finally recommend travel insurance.
Tailored proposal with sample itineraries, rates, and testimonials.
To begin, review the proposal. Then, select your yacht. Afterward, talk through upgrades or excursions.
Review agreements, hold dates, and make payments securely.
Start by completing preference forms. After that, schedule a captain’s call. In the end, review your itinerary.
7–10 days before departure, review final details with your group.
Finally, board the yacht, meet the crew, and begin your charter.
The crew provides daily briefings and support.
Final settlements, farewell to crew.
Afterward, a feedback survey and follow‑up call help plan future charters.
Contact us at 1-321-777-1707 or complete this form to discuss your vacation plans.
