Six days, one Lagoon 40, and a route that took us through some of the best-known islands and anchorages in the British Virgin Islands. Our first major Live the Fresh Life journey began and ended at Nanny Cay, with stops at Norman Island, Cooper Island, Virgin Gorda, Anegada, Cane Garden Bay, Sandy Spit, Jost Van Dyke, and Soper's Hole.
Our BVI Bareboat Route
Nanny Cay → Norman Island → Cooper Island → Virgin Gorda → Anegada → Cane Garden Bay → Sandy Spit → Jost Van Dyke → Soper's Hole → Nanny Cay
We chartered a Lagoon 40 through Navigare Yachting and built the trip around a mix of sailing, island stops, beaches, restaurants, and time ashore. The appeal of the BVI is how much variety you can fit into a relatively compact sailing area. Most days gave us meaningful time under sail without turning the trip into a series of long passages.
Norman Island and The Willy T
Our first major stop was Norman Island, where we visited The Willy T. It was a fitting start to the trip: an iconic BVI stop, a lively atmosphere, and an easy introduction to the rhythm of moving from island to island by boat.
Cooper Island
From Norman Island we continued to Cooper Island. The stop gave us another side of the BVI: a more relaxed pace, beautiful water, and one of those places that makes the trip feel less like transportation between destinations and more like a series of distinct experiences.
Virgin Gorda: Bitter End and Saba Rock
On Virgin Gorda, our focus was the North Sound area, including Bitter End Yacht Club and Saba Rock. One of the most memorable moments was watching the tarpon feeding at Saba Rock. It was the kind of small experience that becomes one of the things you remember most from the trip.
We did not build this itinerary around The Baths. For this trip, the North Sound fit the route and the pace we wanted better.
Anegada by Jeep
Anegada was the biggest change of pace. Instead of staying close to the boat all day, we rented a Jeep and explored the island from shore. The longer sail to Anegada also made it feel distinctly different from the shorter hops between the other islands.
Cane Garden Bay and Sandy Spit
After Anegada, we worked our way back toward Tortola and stopped at Cane Garden Bay before continuing to Sandy Spit. Sandy Spit is tiny, but that is part of the appeal. It feels like the classic image of a Caribbean sailing trip: a small patch of sand, clear water, and boats scattered nearby.
Jost Van Dyke and Foxy's
Jost Van Dyke was another essential stop for us, including time at Foxy's. By this point the trip had settled into a rhythm: sail, anchor or moor, get ashore, explore, and then move again the next day.
Soper's Hole and Back to Nanny Cay
Our final stop before returning the boat was Soper's Hole. From there we completed the loop back to Nanny Cay, ending almost exactly where the trip began, but with a very different sense of the islands.
Why the BVI Works So Well for a Bareboat Trip
The BVI works especially well for a sailing itinerary because the islands are close enough together to give you flexibility. You can spend meaningful time sailing, but you do not have to give up the rest of the day to do it. That balance matters if the goal is not simply to cover distance, but to actually experience the places along the route.
For us, the strongest parts of the trip were the mix: Norman Island and The Willy T, Cooper Island, Bitter End and Saba Rock, Anegada by Jeep, Cane Garden Bay, Sandy Spit, Jost Van Dyke, and Soper's Hole. No single stop defined the trip. The route did.
Watch the Full Journey
We put the full trip together as the first major Live the Fresh Life sailing video. Watch Live the Fresh Life on YouTube.
More routes, destinations, and time on the water are coming. You can also visit our Journeys page for the latest trips.