“All Caribbean islands are the same – just sun, sea and sand with nothing to see or do.” We hear that a lot at Winnow. But Bermuda isn’t a Caribbean island and while it’s certainly got plenty of sun, sea and sand, venture a little further and you'll find that there’s a lot more to this exotic overseas British territory than you might think. If you’re looking for a vacation to take you far from your everyday, then get ready to roll onto island time for the ultimate disconnection.
Dig deeper into a spectacular archipelago and make real connections with Bermudians who are looking forward to sharing their favorite island spots. Whether you want to, or , our local experts will take care of everything, leaving you free to sit back and enjoy the island. We’ve done all the research so you don’t have to; just scroll through our Bermuda experiences online or on the app and book the one you’d like to try in a couple of clicks.
1. Learn About Bermuda’s History in St George
Explore the 400-year-old UNESCO World Heritage sites of Bermuda’s unofficial capital with, our local expert who knows St George and its history inside out and can share anecdotes that most tour guides can't. Starting your vacation with St George will give you a grounding in the Bermuda's heritage and help you understand the local culture for the rest of your trip. Highlights include the town’s finest examples of British colonial architecture, the 1699 Globe Hotel and 18th-century Tucker House museum showcasing Bermudan life through the ages.
2. Jam with Local Celebrity Heather Nova
Settle in for afternoon tea looking out to the ocean to the uplifting pop sounds of the archipelago’s most famous singer/songwriter. Bermudianhas played over 600 concerts and sold more than two million albums over her 20-year career and Winnow travelers can enjoy an intimate private concert with her and learn more about how Bermuda’s spectacular natural beauty has influenced her music over the years.
3. Swim With the Friendly Green Turtle
Easily one of the coolest characters on the island,loves to share his passion for the ocean with the travelers he takes out on his boat to explore Bermuda’s most beautiful bays. He loves to stop off at his favorite places for spotting the famous green turtle and teach guests to swim with them in a way that is respectful of both the animals and their environment.
4. Cycle or Run Bermuda’s Abandoned Railway
Named after the route that once circled the island, the Railway Trail is one of Bermuda’s top outdoor draws, offering no less than 22 miles of spectacular shoreline views. Explore the trail on foot, running with fitness expert, or cycling with , both of whom know their way around the route and its story. The clincher here, is that no motorized vehicles are allowed on the trail leaving you to enjoy the high-angle vistas in delightful peace and quiet.
5. Explore the Mangrove Forests of Hungry Bay
Lose yourself in the shade and tranquility of the reserve’s mangrove and sub-tropical forests on a paddleboard with, our local Bermudian paddleboard guide who takes travelers through the forest for a one-of-a-kind adventure peppered with his favorite stops. Thrill-seekers will be pleased to hear that he can wrap the day up with surf time in the bay.