Explore Bermuda's 500 years of history

Perhaps best known for the lore behind the Bermuda Triangle, the 21-square-mile slice of paradise falls victim to many misconceptions: one being that it’s in the Caribbean Sea (it’s actually in the Atlantic Ocean), and another being that it’s a single island (it’s actually a chain of 181). But no one will dispute Bermuda’s vast and varied history that reaches back to the 16th century, nor the country's significance to maritime exploration.

The Commissioner's house in King's Wharf, Bermuda © Pr3t3nd3r / Getty Images

Start in St George

To get an idea of how it all began, start in the eastern city of St George, a UNESCO World Heritage Site. While Bermuda was first discovered by a Spanish conquistador named Juan de Bermudez in the early 1500s, it’s most influential and permanent settlers were the British who moored here while sailing for Jamestown, Virginia. St George, settled in 1609, is a goldmine for history aficionados looking to learn about life in colonial Bermuda. A good starting point is the UNESCO World Heritage Centre, where you can get a general overview; don’t miss the quirky consignment shop attached to it called Second-Hand Rose (facebook.com/Second-Hand-Rose), which exemplifies the juxtaposition of old and new and Bermuda's slightly oddball traditions.

The Unfinished Church on St George's Island © DEA / G. SOSIO / Getty Images

Also on the Don’t Miss list: stunning St. Peter’s Church, built in 1612; the Unfinished Church, a gorgeous, haunting byproduct of a feud within the St. Peter’s congregation; Fort St. Catherine, the largest fort on the island, built in 1614; and Tucker House Museum, where you can get a glimpse of life in the 1750s in St George (bermuda.com). Of equal importance is Barber’s Alley, right off Tucker House, where a freed black slave named Joseph Rainey ran a barbershop during the American Civil War; Rainey went on to become the first African-American in the US House of Representatives. While you’re in St George, keep an eye out for Bermuda’s African Diaspora Heritage Trail, which highlights the history of those of African descent in the Americas and the Caribbean. Landmarks are marked clearly with a seal.

You’ll also want to stop by the Bermuda Perfumery (lilibermuda.com), whose facilities and boutique are housed in an historically preserved house. Next, mill around the colorfully painted town and meander through its lovely English-style alleyways -- there’s Petticoat Lane, Printer’s Alley, Somers Garden and more. If you’re looking for a little spookiness with your history, you can also try a ghost tour through St George’s Haunted History (hauntedhistorybda.com).

Colorful streets and shops in St George © John Greim / Getty Images

Stop by St David

Near to St George is the island of St David, whose cultural mishmash represents the diversity of Bermudian culture. The Carter House is a testament to the varied groups of people who settled here, exploring the history of the English, black West Indians, Spaniards, Portuguese, Native Americans and even Scottish and Irish prisoners of war (carterhousemuseum.org).

For most of the 20th century, nearby Cooper Island was occupied by NASA and the US military, and it’s only recently been reopened to the public as a pristine 12 acre nature reserve.

Check out bustling Hamilton

Hamilton, the capital of Bermuda since the early 19th century, is where most of the commerce happens these days, and it’s still home to many historic relics that are worthy of exploration. On your way into town from St George, stop at the millions-of-years-old Crystal Caves, a subterranean marvel discovered in 1907 when two little boys lost their cricket ball. From there, it’s easy to pop across the road to the Swizzle Inn, where potent rum swizzle punches are served up in a 17th-century abode. (Their motto is “Swizzle Inn, Swagger Out” – you’ve been warned.)

Impressive stalagmites and stalactites in the Crystal Caves © Michael Runkel / Getty Images

There’s plenty to discover in Hamilton proper, such as the National Library and City Hall and Arts Centre, also home to the Bermuda National Gallery. Within walking distance are the Cathedral of the Most Holy Trinity, Bermuda’s most revered Anglican church, and Fort Hamilton, both of which afford excellent views of Hamilton and the surrounding waters.

For art lovers, Masterworks Museum of Bermuda Art and the Bermuda Botanical Gardens are a must-see. All the art within the permanent and loaned collections has some connection to the islands; you’ll recognize names like Winslow Homer and Georgia O’Keefe, but the museum features locally-based, lesser-known artists, too. A John Lennon sculpture created by local artist Graham Foster stands out front, commemorating Lennon’s inspirational time spent in Bermuda in 1980. The museum sits among 36 lush, manicured acres of the botanical gardens, perfect for a mid-day stroll.

Surprisingly, some of the best modern art in Bermuda can be found at the newly redone Hamilton Princess (thehamiltonprincess.com), where a $90 million renovation showcases artwork from Andy Warhol, Damien Hirst, and Nelson Mandela, among others.

Explore the Royal Navy Dockyard

While making your way to the other end of the island chain, stop by Gibbs Lighthouse in Southampton, one of oldest cast-iron lighthouses in the world. There’s also Somerset Bridge, pegged as ‘The World’s Smallest Working Drawbridge’, that connects Somerset Parish with Sandys Parish, and measures only 32 inches across. Once in the Royal Navy Dockyard proper, you’ll notice tons of construction work as Bermuda gears up to host the America’s Cup in 2017. The Village will be home to the moored boats, as well as spectator zones.

West End and Pier 41 Marina at the Royal Naval Dockyard in Sandys Parish © M. Timothy O' Keefe / Getty Images

The Royal Navy Dockyard has long been a bastion of safety and a place for ships to refuel and restock before making the trip across the Atlantic. There are tons of touristy shops catering to the cruise ships that come into port here, but the real draw is the National Museum of Bermuda, which also includes the Commissioner’s House. The limestone buildings, which date back to the 19th century, are fascinating on their own, but within their walls you’ll find various exhibits explaining Bermuda’s cultural relevance on a global scale. A mural by aforementioned Bermudian artist Graham Foster adorns a back stairwell of the Commissioner’s House and provides an excellent and moving tribute to Bermuda’s centuries of history.

Where to Stay

If you fancy staying in historic St George, Aunt Nea’s Inn is an excellent B&B-style choice (auntneasinn.com). The structure dates from the 1700s, but the rooms are updated with modern amenities. In centrally located Hamilton, try the Rosedon Hotel (rosedon.com), where the verdant grounds include a pool, and afternoon tea is served on the veranda. Built at the turn of the last century, it used to be a private home that was turned into a bed and breakfast during World War II. Looking for something a little more geological? Try the Grotto Bay Beach Hotel (grottobay.com), where you can book spa treatments in their millions-of-years-old private limestone cave enclosures.

Lauren Finney traveled to Bermuda with support from the Bermuda Tourism Authority (gotobermuda.com). Lonely Planet contributors do not accept freebies in exchange for positive coverage.