British Virgin Islands Sail Trip // Winter 2026
Escape with Sail Rockaway for an epic 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, fine 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.
3 Double Cabins Available
Dates & Availability:
Trip 1: February 15-21, 2026
Trip 2: February 23-March 1, 2026
Trip 3: March 4-11, 2026
Price: $4,500 per double cabin.
UPDATE: Fully booked for Winter 2026 trip!
Check back with us for the next Caribbean voyage later in 2026.
Escape with Sail Rockaway for an epic 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, fine 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.
3 Double Cabins Available
Dates & Availability:
Trip 1: February 15-21, 2026
Trip 2: February 23-March 1, 2026
Trip 3: March 4-11, 2026
Price: $4,500 per double cabin.
UPDATE: Fully booked for Winter 2026 trip!
Check back with us for the next Caribbean voyage later in 2026.
The Voyage: What to Expect
Your floating getaway will take you through the main islands of Tortola, Virgin Gorda, and Jost van Dyke, with many smaller islets 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 swim off the boat 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 over the Caribbean Sea. All nights are spent in a harbor at mooring or 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
We also offer an alternative U.S. Virgin Islands itinerary that includes Saint John, an island where over 60% of the land is protected as the Virgin Island National Park.
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Life Onboard
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 at the stern with a freshwater rinse makes swimming off the boat easy. Onboard amenities include Wi-Fi, electrical outlets, and a Bluetooth stereo. Your private cabin sleeps two people and comes with fresh linens, pillows, and a fan. |
Meals
The cost of your trip includes 7 breakfasts, 5 lunches, and 3 dinners.
We also provide snacks, coffee, tea, water, and ice.
Most anchorages have open-air beachside restaurants where you can enjoy West Indian favorites along the day's catch.
Onshore dining is not included in the trip cost, but advance reservations can be made for the group upon request.
We can accommodate most dietary restrictions and food allergies.
Please let us know in advance by filling out the Guest Form.
Activities & Learning
Besides sailing, you can enjoy a multitude of activities including:
~Snorkeling (masks and fins included)
~Paddle boarding, surfing, and kiteboarding
~Beach combing and exploring the islands in the dinghy
~Hiking scenic trails
Learning to Sail
The captain is happy to teach you the daily ins and outs of cruising.
You can participate as much or as little as you'd like, keeping the trip casual.
The captain will occasionally enlist crew members to help with basic tasks
like picking up a mooring ball or throwing a dock line.
Besides sailing, you can enjoy a multitude of activities including:
~Snorkeling (masks and fins included)
~Paddle boarding, surfing, and kiteboarding
~Beach combing and exploring the islands in the dinghy
~Hiking scenic trails
Learning to Sail
The captain is happy to teach you the daily ins and outs of cruising.
You can participate as much or as little as you'd like, keeping the trip casual.
The captain will occasionally enlist crew members to help with basic tasks
like picking up a mooring ball or throwing a dock line.
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 30 minute taxi ride to the marina.
Theres also a local ferry service from trellis bay (5 minute walk from EIS airport) to Roadtown that is an option if your timing allows. Fort Burt Marina is very close to the Roadtown ferry terminal; 2 minutes by car and 12 minutes on foot.
Most BVI bound travelers end up flying into Charlotte Amalie, St. Thomas, USVI (STT), and taking a ferry to Roadtown, BVI. The ferry terminal is a quick 5-minute taxi ride from the airport. The ferry ride lasts 45-60 minutes. Allow at least a 60-minute buffer between your flight landing and the ferry departure.
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. .
The schedule remains the same every week, but the different ferry companies alternate service with each other, so just ask one of the clerks at the ferry terminal which company is operating that day and buy your tickets there..
Pro Tip: There is a great bar/restaurant on the top floor of the ferry office with views of the harbor.
Ending the Trip
We aim to end our trip docked back at the Fort Burt Marina in Roadtown, before noon on the last day of the trip. There is flexibility in the sailing schedule for arriving back at the marina earlier or later depending on guests specific travel arrangements. If you plan to fly home from Charlotte Amalie USVI the same day that the sailing trip ends, we recommend you book a flight departing after 12pm, 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.
If you have any questions, please contact your embassy for full details.
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 30 minute taxi ride to the marina.
Theres also a local ferry service from trellis bay (5 minute walk from EIS airport) to Roadtown that is an option if your timing allows. Fort Burt Marina is very close to the Roadtown ferry terminal; 2 minutes by car and 12 minutes on foot.
Most BVI bound travelers end up flying into Charlotte Amalie, St. Thomas, USVI (STT), and taking a ferry to Roadtown, BVI. The ferry terminal is a quick 5-minute taxi ride from the airport. The ferry ride lasts 45-60 minutes. Allow at least a 60-minute buffer between your flight landing and the ferry departure.
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. .
The schedule remains the same every week, but the different ferry companies alternate service with each other, so just ask one of the clerks at the ferry terminal which company is operating that day and buy your tickets there..
Pro Tip: There is a great bar/restaurant on the top floor of the ferry office with views of the harbor.
Ending the Trip
We aim to end our trip docked back at the Fort Burt Marina in Roadtown, before noon on the last day of the trip. There is flexibility in the sailing schedule for arriving back at the marina earlier or later depending on guests specific travel arrangements. If you plan to fly home from Charlotte Amalie USVI the same day that the sailing trip ends, we recommend you book a flight departing after 12pm, 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.
If you have any questions, please contact your embassy for full details.
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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)
Packing Tips:
We recommend using collapsible bags instead of rigid suitcases for easy storage on the boat. Bring a light raincoat, a sun hat, and a warm layer. Since dinghy landings can be wet, bring shoes you don't mind getting soaked. A headlamp is good to have as well.
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.
Payment
We require a 50% deposit to reserve your cabin. The full balance is due 30 days before trip starts. There are no refunds.
Payment can be made via Cash, Check, Zelle, Venmo, Bank Transfer. Credit card or Paypal (3% surcharge)
Please contact Sail Rockaway for payment arrangements.
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)
Packing Tips:
We recommend using collapsible bags instead of rigid suitcases for easy storage on the boat. Bring a light raincoat, a sun hat, and a warm layer. Since dinghy landings can be wet, bring shoes you don't mind getting soaked. A headlamp is good to have as well.
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.
Payment
We require a 50% deposit to reserve your cabin. The full balance is due 30 days before trip starts. There are no refunds.
Payment can be made via Cash, Check, Zelle, Venmo, Bank Transfer. Credit card or Paypal (3% surcharge)
Please contact Sail Rockaway for payment arrangements.
