British Virgin Islands Sail Trip // Winter 2026
Escape with Sail Rockaway for a once-in-a-lifetime sailing trip in the Caribbean! The British Virgin Islands (BVIs) are a world-class sailing destination, offering ideal conditions with steady trade winds, calm waters, and simple, line-of-sight navigation. The islands' close proximity allows for easy island-hopping, and with an abundance of sheltered anchorages, white-sand beaches, and vibrant marine life, it’s a paradise for both novice and experienced sailors.
Trip Details
- Duration: 7 days and 6 nights aboard our 41 ft. sailboat.
- Capacity: Our sailboat accommodates up to six guests, ensuring a personalized and casual experience.
- Dates & Availability:
- Trip 1: February 15-21, 2026 (3 Double Cabins Available)
- Trip 2: February 23-March 1, 2026
- Trip 3: March 4-11, 2026
- Price: $4,500 per double cabin.
*Contact us for a private charter
The Voyage: What to Expect
Your floating getaway will take you through the stunning islands of Tortola, Virgin Gorda, and Jost van Dyke, with many more places to discover along the way. Your days will be filled with white-sand beaches, incredible snorkeling, and iconic beach bars.
A Typical Day:
Each day begins with morning beverages and breakfast, followed by a chance for a quick swim or walk on the land. We’ll then set sail for 2-4 hours, arriving at a new beach or snorkel spot for a mid-day break and lunch. The afternoon is yours to enjoy an activity—like swimming, exploring, or simply lounging on the boat—before we hoist the sails again.
Our final destination for the day is a sheltered anchorage where we’ll drop anchor and prepare for a spectacular sunset with drinks and snacks. All nights are spent at a mooring or at anchor, providing a true escape from the mainland.
Sample Itinerary Stops:
- Peter Island
- Cooper Island
- The Baths
- North Sound
- Anegada
- Cane Garden Bay
- Green Cay
- Little Jost
- Bubbly Pool
- Sandy Spit
- White Bay
- Great Harbor
Life Onboard
The Boat: Our sailboat is a Jeanneau Sun Odyssey 409 (2015), designed for comfort and speed. It features three double cabins, two heads (bathrooms), and a fully stocked galley with refrigeration. The roomy cockpit has a bimini top for shade, and the foredeck is perfect for sunbathing. A swim deck on the stern with a freshwater rinse makes swimming off the boat irresistible. Onboard amenities include Wi-Fi, electrical outlets, and a Bluetooth stereo.
Cabins: Your private cabin sleeps two people and comes with fresh linens, pillows, and a fan.
Meals:
- Included: The cost of your trip includes 7 breakfasts, 5 lunches, and 3 dinners. We also provide snacks, coffee, tea, water, and ice.
- Onshore Dining: Most anchorages have open-air beachside restaurants where you can enjoy the day's catch. Onshore dining is not included in the trip cost, and reservations will be made for the group.
- Dietary Needs: We can accommodate most dietary restrictions and food allergies. Please let us know in advance by filling out the Guest Form.
Activities & Learning
Activities: Besides sailing, you can enjoy a multitude of activities including:
- Snorkeling (masks and fins included)
- Paddleboarding, surfing, and kiteboarding
- Beachcombing and exploring the islands in the dinghy
- Hiking scenic trails
Getting to the BVIs
You will meet the boat at Fort Burt Marina in Roadtown, Tortola. The easiest way to get there is to fly directly into Terrence B. Lettsome International Airport (EIS) and take a short taxi ride to the marina.
For a more affordable option, you can fly into Charlotte Amalie, St. Thomas, USVI (STT), and take a ferry to Roadtown. The ferry terminal is a quick 5-minute taxi ride from the airport.
- Ferry Schedule: Daily ferries run from St. Thomas to Tortola at 9:00 a.m., 2:00 p.m., 4:00 p.m., and 5:30 p.m. Allow at least a 45-minute buffer between your flight landing and the ferry departure.
- Pro Tip: There is a great bar/restaurant on the top floor of the ferry office with views of the harbor.
Ending the Trip
Whether you you depart for home on the last day of sailing, the day after sailing, or even a day before sailing ends, we can get you to the proper location for making your way to the airport in time. If you plan to fly home the same day that the sailing trip ends (Day 7) we recomend you book a flight after 12pm IF flying out from Charlotte Amalie USVI, to allot for ferry travel time from Tortola to St. Thomas.
Extra Nights Aboard:
Arriving to the island a day before the sail begins? Or need an extra night on the boat after the sail ends? You can spend an extra night aboard, before and after the trip for just $100 per cabin, per night. Checkout is 10am the following morning.
Passports & Visas
Please ensure your passport is valid for the period of travel and for at least six months after you return. It is the traveler's responsibility to confirm visa requirements for their country of origin. Sail Rockaway cannot be held responsible for refusal of entry or travel due to a lack of proper documentation. If you have any questions, please contact your embassy for full details.
Additional Costs & Info
What's Not Included:
- Flights and land transportation to/from the marina
- Onshore meals and drinks
- Alcoholic beverages and soft drinks on the boat
- Crew gratuity (15-20% is standard)
Travel Insurance: We strongly recommend purchasing a travel insurance policy to protect against trip interruptions.
Terms & Conditions: By booking, you agree to the Terms & Conditions available on our website.
