Your 8-Day / 7-Night Sailing Adventure
PRELIMINARY ITINERARY
Exact itinerary may shift—because sailing’s all about chasing wind, not schedules. We’ll follow the breeze, trust the locals, and aim for maximum fun. Here’s a look at what this epic island-hopping adventure might look like.
DAY ONE | Arrive in Tortola → Cooper Island
Ease into island life as you depart Nanny Cay Marina or Road Town, and enjoy an easy first sail to Cooper Island. Drop anchor in Manchioneel Bay and kick things off with a swim or snorkel in clear Caribbean water. Come ashore to relax at the Cooper Island Beach Club, grab a drink at the Rum Bar, and ease into the laid-back rhythm of the British Virgin Islands.
4 Nautical Miles.
DAY TWO | Cooper Island → The Baths (South Virgin Gorda)
Sail from Cooper Island to the iconic The Baths on the southern tip of Virgin Gorda. Moor nearby and step ashore to explore towering granite boulders, hidden grottoes, and natural tidal pools. After working up an appetite, enjoy a bite and a cold drink at Top of the Baths before swimming through the rock formations into Devil’s Bay or relaxing on the white-sand beach.
5 Nautical Miles.
DAY THREE | The Baths (South Virgin Gorda) → Bitters End (North Virgin Gorda)
Leave the dramatic boulders of The Baths behind as you sail north to North Sound, home to Bitter End Yacht Club. This scenic sail delivers calmer waters and sweeping views before arriving in one of the BVI’s most protected harbors. Go ashore to explore the marina, grab a drink, or unwind dockside as the sun sets over the Sound.
9 Nautical Miles.
DAY FOUR | North Sound → Guana Island
Depart North Sound and enjoy a scenic sail to the untouched shores of Guana Island. Anchor off this privately owned island and soak in its quiet beauty, with clear water perfect for swimming and snorkeling. With limited development and a peaceful atmosphere, Guana Island offers a true escape and a slower pace before the next leg of your journey.
14.5 Nautical Miles.
DAY FIVE | Guana Island → Jost Van Dyke
Sail from the quiet shores of Guana Island to the lively vibes of Jost Van Dyke. Drop anchor in White Bay and wade ashore for powdery sand and turquoise water. Spend the afternoon floating with a Painkiller at Soggy Dollar Bar, or explore the beach before settling in for a fun, laid-back island evening.
11.5 Nautical Miles.
DAY SIX | Jost Van Dyke → Norman Island
Leave the beach bars of Jost Van Dyke behind and sail to legendary Norman Island. Known as the inspiration for Treasure Island, this stop is all about adventure. Snorkel the famous The Caves or The Indians, then head to the floating Willy T for sunset drinks and an unforgettable night on the water.
11 Nautical Miles.
DAY SEVEN | Norman Island (Lay Day)
Start the morning with a hike ashore, where winding trails lead to elevated viewpoints overlooking the Sir Francis Drake Channel, perfect for taking in the sweeping island views before the heat of the day sets in. Later, treat yourself to a massage on Norman Island, surrounded by sea views and the calm of this iconic anchorage.
0 Nautical Miles.
DAY EIGHT | Norman Island → Depart Tortola
Enjoy a final morning sail from Norman Island back to Tortola, taking in last views of the Sir Francis Drake Channel along the way. Arrive at Nanny Cay Marina or Road Town to disembark, wrapping up your island adventure with memories of crystal-clear water, iconic anchorages, and classic BVI sailing.
8 Nautical Miles.
Video taken from our partner: Dream Yacht Charters
ABOUT EACH ISLAND
COOPER ISLAND — BOUTIQUE BVI ESCAPE
WHERE TURQUOISE ANCHORAGES MEET ISLAND-SLOW LIVING
Cooper Island is a laid-back gem in the British Virgin Islands, known for its crystal-clear waters, relaxed beach scene, and eco-minded island culture. Centered around Manchioneel Bay, this stop is all about barefoot afternoons, calm anchorages, and easy island connection. Sailors gather here to unwind, snorkel vibrant reefs just off the beach, and share stories over sunset cocktails. The perfect balance of natural beauty, simplicity, and that unmistakable BVI rhythm.
THINGS TO DO
Snorkel the vibrant reef just steps from Manchioneel Bay
Paddleboard or swim in calm, protected anchorage waters
Grab a drink or dinner at Cooper Island Beach Club
Browse the boutique shops and rum bar at the Beach Club
Relax on the beach with panoramic views of nearby islands
Enjoy a golden-hour sunset with boats gently swinging at anchor
Snorkel the vibrant reef just steps from Manchioneel Bay
Paddleboard or swim in calm, protected anchorage waters
Grab a drink or dinner at Cooper Island Beach Club
Browse the boutique shops and rum bar at the Beach Club
Relax on the beach with panoramic views of nearby islands
Enjoy a golden-hour sunset with boats gently swinging at anchor
THE BATHS — VIRGIN GORDA ICON
WHERE GIANT BOULDERS MEET TURQUOISE POOLS
The Baths is one of the British Virgin Islands’ most iconic natural wonders, located along the southern tip of Virgin Gorda. Towering granite boulders create hidden grottos, tidal pools, and winding passageways that open to crystal-clear water and soft white sand. It’s a place that feels equal parts adventure and relaxation. A must-stop for sailors looking to explore, swim, and experience one of the Caribbean’s most unforgettable landscapes.
THINGS TO DO
Swim through the boulder-lined pools and natural grottoes
Explore the winding stone paths and hidden beach exits
Hike to the top of The Baths for sweeping views over the Sir Francis Drake Channel
Grab a drink or lunch at Top of the Baths Restaurant after the hike
Snorkel in clear, calm water along the rocky edges
Relax on the beach framed by massive granite formations
Swim through the boulder-lined pools and natural grottoes
Explore the winding stone paths and hidden beach exits
Hike to the top of The Baths for sweeping views over the Sir Francis Drake Channel
Grab a drink or lunch at Top of the Baths Restaurant after the hike
Snorkel in clear, calm water along the rocky edges
Relax on the beach framed by massive granite formations
BITTER END — THE SAILORS’ LAST STOP
world-renowned for its sense of adventure
Bitter End sits at the heart of Virgin Gorda’s North Sound, a protected sailing playground known for steady breezes, calm anchorages, and nonstop water activity. This legendary resort hub blends laid-back luxury with high-energy adventure, drawing sailors from across the BVIs for its unbeatable setting and social vibe. With turquoise water stretching in every direction and boats filling the Sound, Bitter End delivers classic island fun with a modern edge.
THINGS TO DO
Paddleboard, kayak, or sail in the calm waters of North Sound
Relax in the calm, protected waters of North Sound with an easy swim off the boat or dock
Grab a drink or dinner at Bitter End’s waterfront restaurants
Explore the resort grounds and soak in the lively marina atmosphere
Watch the sunset as the Sound fills with glowing anchor lights
Enjoy the breeze and social scene that make North Sound legendary
Paddleboard, kayak, or sail in the calm waters of North Sound
Relax in the calm, protected waters of North Sound with an easy swim off the boat or dock
Grab a drink or dinner at Bitter End’s waterfront restaurants
Explore the resort grounds and soak in the lively marina atmosphere
Watch the sunset as the Sound fills with glowing anchor lights
Enjoy the breeze and social scene that make North Sound legendary
GUANA ISLAND — A QUIET BVI ESCAPE
WHERE UNTOUCHED SHORELINES MEET TOTAL SECLUSION
Guana Island is one of the British Virgin Islands’ most peaceful and pristine stops, known for its rugged coastline, protected coves, and private-island feel. With no cruise crowds and minimal development, this stop is all about disconnecting and soaking in the natural beauty of the BVIs. Calm anchorages, clear water, and dramatic landscapes make Guana Island a favorite for sailors looking to slow down and enjoy the islands at their most unspoiled.
THINGS TO DO
Swim in crystal-clear water off quiet, uncrowded beaches
Relax onboard or on shore with uninterrupted island views
Paddleboard or float in calm, protected bays
Take a peaceful shoreline walk along untouched beaches
Enjoy a low-key afternoon anchored far from the crowds
Watch the sunset in near-total silence
Swim in crystal-clear water off quiet, uncrowded beaches
Relax onboard or on shore with uninterrupted island views
Paddleboard or float in calm, protected bays
Take a peaceful shoreline walk along untouched beaches
Enjoy a low-key afternoon anchored far from the crowds
Watch the sunset in near-total silence
JOST VAN DYKE — THE BVI's SOCIAL ANCHORAGE
WHERE SAILORS COME ASHORE TO CELEBRATE
Jost Van Dyke is legendary among sailors for its laid-back beach bars, barefoot energy, and welcoming island spirit. This small, rugged island punches well above its size, drawing boats from across the BVIs for nights that start with a dinghy ride and end under the stars. Equal parts party and pure island charm, Jost is where sailing stories get louder and friendships form fast.
THINGS TO DO
Dinghy ashore for drinks at iconic beach bars
Swim and float in the calm waters of White Bay
Enjoy live music and a lively after-sail atmosphere
Grab a painkiller or two with your feet in the sand
Watch the anchorage come alive as boats roll in
End the night under the stars with the sound of the sea
Dinghy ashore for drinks at iconic beach bars
Swim and float in the calm waters of White Bay
Enjoy live music and a lively after-sail atmosphere
Grab a painkiller or two with your feet in the sand
Watch the anchorage come alive as boats roll in
End the night under the stars with the sound of the sea
NORMAN ISLAND — THE BVI’S PIRATE LEGEND
WHERE STORIES, RUM, AND REEFS COLLIDE
Norman Island is one of the British Virgin Islands’ most famous stops, long associated with pirate lore and rumored to have inspired Treasure Island. By day, sailors explore hidden caves and snorkel vibrant reefs just off the boat; by night, the island transforms into a floating social scene anchored around a legendary floating bar Willy T's. It’s a classic BVI stop that blends adventure, history, and just the right amount of mischief.
THINGS TO DO
Snorkel the famous Caves and Indians just off the island
Dinghy over to the floating bar for drinks and sunset vibes
Swim in clear, calm water straight from the boat
Relax on deck while boats gather in the anchorage
Share stories over rum as the sun goes down and Willy T's
Soak in the lively, after-dark energy on the water
Snorkel the famous Caves and Indians just off the island
Dinghy over to the floating bar for drinks and sunset vibes
Swim in clear, calm water straight from the boat
Relax on deck while boats gather in the anchorage
Share stories over rum as the sun goes down and Willy T's
Soak in the lively, after-dark energy on the water
Tortola — THE BVI’S SAILING HUB
Where your BVI adventure begins and ends
Tortola is the heart of the British Virgin Islands and the starting point for countless sailing adventures. Bustling yet approachable, it blends island culture with the practical side of cruising — marinas, harbors, provisioning, and easy shore access. Whether you’re beginning the journey or winding things down, Tortola offers a grounded pause before heading deeper into the islands or back to shore life.
THINGS TO DO IN LYNYARD CAY
Arrive or depart from Nanny Cay Marina or Road Town
Explore local shops, cafés, and island markets ashore
Enjoy a relaxed meal or drink overlooking the harbor
Take in views of boats coming and going through the channel
Ease into or out of island time at a steady, unhurried pace
Arrive or depart from Nanny Cay Marina or Road Town
Explore local shops, cafés, and island markets ashore
Enjoy a relaxed meal or drink overlooking the harbor
Take in views of boats coming and going through the channel
Ease into or out of island time at a steady, unhurried pace
Island navigator
Explore the British Virgin Islands by sail with the crew of Latitudes & Attitudes.
ABOUT EACH ISLAND
See the world with your
own two eyes
Set sail with the Lats & Atts Crew
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