St. George's & St. David’s Islands, Bermuda

In 1609, a fleet of nine ships owned by the Virginia Company of London set sail for Jamestown, Virginia. En route, there was a terrible storm and one vessel, the Sea Venture, crashed into one of Bermuda's treacherous reefs. The Virginia Company laid claim to the island, originally calling it New London, the Town of St. George. Bermuda was first settled in 1612 and St. George's was the capital until 1815. The survivors built two new ships, and most continued their voyage to Jamestown.

St. George's Island & The Town of St. George

On St. George's Island, the Town of St. George is the oldest continuously occupied town of English origin in the New World. A UNESCO World Heritage Site, it's full of picturesque 18th-century cottages, cobblestoned lanes and historic architecture that attracts visitors from all over the world. Though it teems with centuries-old buildings, the town handily blends the colonial and modern worlds.

Take a stroll through town, starting at the circa-1612 St. Peter's Church, the oldest Anglican Church in continuous use outside of the UK. It's also known as Their Majesties Chappell in a nod to its long history. Next, stop in at Lili Bermuda Perfumery, which has been distilling island elements like flowers and herbs into distinctive scents since 1928. It's housed in a traditional cottage with a garden.

The Ducking Stool

In the 17th and 18th century, "misbehaving" Bermudians (aka gossips, nagging wives or drunks) were subject to punishment by a forced plunge into the water. On King's Square in downtown St. George, a replica of a ducking stool – a chair attached to the end of a pole that can be lowered into the harbour – is used for lighthearted historical reenactments of the practice. Joke-cracking actors in historic garb lead the charge, and they'll often ask for volunteers.

Tucker House Museum

An elegant example of how colonial Bermudians lived, this 1750s house in St. George's has ties with Colonial Williamsburg. Tucker House offers a fascinating archaeological exhibit as well as antique furniture from the family that inhabited the property until 1809.

Fort St. Catherine

Nearby, visit the sprawling Fort St. Catherine & Museum, a former military stronghold dating to 1614. The largest fort in Bermuda, it boasts an impressive collection of antique swords and muskets plus views of the beach and bay beyond. Neighboring St. David's Island also holds historic buildings and a notable lighthouse.

St. David's Lighthouse

Constructed of Bermuda stone and lit for the first time in 1879, this 55-foot landmark has enabled navigators safe passage for more than a century. The distinctive red-and-white painted structure also serves as a finishing-line marker for sailing contests like the Newport Bermuda Race.

Carter House Museum

At this traditional Bermuda cottage on neighboring St. David's Island, exhibits help you travel back to the 17th century and see what life was like for first settlers. Sitting in a bucolic location with views of Nonsuch Island, Carter House Museum features displays of early locks and tools. Also on site is a replica of a 1612-style dwelling with a palm-thatched roof and a primitive cooking fireplace.

Clearwater Beach & Cooper's Island

Explore the shores of Clearwater Beach & Turtle Bay, two spacious, sandy beaches that are perfect for families and group gatherings. The 36-acre public park features nature trails, playground equipment and views of some outer islands reserved for wildlife. Right next door, check out the scenic trails and idyllic views from Cooper's Island Nature Reserve.

For more incredible nature, head west and then south to explore the Crystal Caves, known for otherworldly formations framing blue subterranean lakes, and scenic Blue Hole Park.