Pink sand beaches, rum swizzles, a much-needed history lesson, and a Gombey sighting or two are just a handful of what awaits you when you touch down in beautiful Bermuda. Accessing the island is simple, board a direct flight from New York City to L.F. Wade International Airport and you’re on the island in two hours flat.
All major airlines offer the quick trip from JFK at least once a day, which means if you leave by 8 AM you’ll be on a beach by noon.
From the average tourists’ perspective, the best time to travel to Bermuda is between May and October, but as a native, trust me when I tell you, you really don’t want to miss Cupmatch weekend, held annually on the weekend nearest to August 1st. Cupmatch is the celebration of the 1834 emancipation of Black slaves in Bermuda and during this weekend, Bermuda is in full party mode. Bermudians come together for community events that mark and commemorate their pride and freedom, including a friendly cricket game between rival teams, Somerset and St. George’s (more on that later) and Non-Mariners boat day.
Day 1: Welcome to Beautiful Bermuda
Before you land, schedule an easy 15-minute taxi from L.F. Wade International Airport to The Loren, Bermuda’s newest beachfront boutique hotel, offering a mix of gorgeous villas and hotel rooms boasting impressive views, and direct access to the infinity pool.
After dropping your bags off at The Loren, it’s off to St George’s Cricket Field to watch the game. Bermuda’s various transportation options offer easy and fun solutions for getting around the island. Hit up Current Vehicles for a two-seater electric rental car (aka a twizzy) or Rugged Rentals for an electric mini Hummer that is guaranteed to turn heads. A classic scooter is also an option to bop around with ease.
Once you hit the cricket field, get ready for a serious turn up. St. George’s fans are decked out in blue, while Somerset fans wear red and blue. Choose your allegiance wisely—the spirit and team-pride run deep. No matter who you pick, game-goers can at least agree on two things: you MUST have a Swizzle (or four), Bermuda’s national rum cocktail, and hit the Crown & Anchor tent to get in on the gambling action.
As for food, Country Kitchen offers mouthwatering fried fish and shrimp that will leave you going back for seconds. Cool down with a Henny Pop from Duchess Pops, which is exactly what it sounds like: a popsicle laced with Hennessy.
Stay until the very end, leaving the field at around 7 pm (and not a second sooner or Bermudians will give you the side-eye) for a post-game and pre-night flex, then head to dinner at nearby Wahoo’s Bistro. The pasta du jour will soak up all that rum you consumed.
Day 2: Get to Know Black Bermuda
I know you’ll be tired after a full day of Cupmatching, but drag yourself out of bed for breakfast at The Loren’s Pink Beach Club. Whether you choose The Loren Eggs Benedict, Fried Egg and Lobster Hash or Brioche French Toast, you’ll find several delicious options to satisfy your palette.
After breakfast, explore the nearby town of St. George with Kristin White, resident tour guide and “Long Story Short” bookstore owner. On White’s enlightening tour you’ll learn about Bermuda’s past and present, specifically through a Black historical lens, and if you’re lucky, bump into a Gombey dance troupe performing.
Of the many stops on the tour, the following are especially can’t-miss destinations: St. Peter’s Church, which has a page from their Black Baptism Register on display that lists the names of people baptized the weekend of Emancipation. Gravesite of Pilot James ‘Jemmy’ Darrell, who was an enslaved pilot who went on to buy his freedom and became the first Black person to own property on the island. Barber’s Ally, named after Joseph Rainey, who was born into slavery in South Carolina. When conscription forced him to serve for the Confederacy, he escaped to Bermuda, became a barber and after the war ended, returned to South Carolina and became the first Black man elected to the U.S. House of Representatives, and the second man in congress.
Additionally, visit places like Bermuda’s most famous architectural site, the Unfinished Church and Kristin’s carefully curated bookstore, with adjoining handmade soap shop, Salt Spray Soap Co. If you’re feeling a little hungry, head to Sweet SAAK bakery for a snack; good luck choosing which pastry to try.
Once the sun sets, head to Marcus at The Hamilton Princess for a dinner of Bermudian fusion delights. Founded by chef Marcus Samuelsson, the force behind New York’s beloved Red Rooster Harlem, this new restaurant is changing the rules of Bermuda cuisine. After dinner, be sure to stroll through the lobby of the Hamilton Princess. The hotel is home to the most culturally robust collection of art on the island, including pieces from Keith Haring, Banksy, and Andy Warhol.
Later that evening, once you’re all fueled up, it’ll be time for one of the island’s newest cultural explosions, Bacchanal Run. For all you non-runners out there, don’t fear, it’s actually a two-mile walk/party with Soca and Reggae tunes blasting as your soundtrack. Participants fling water and colorful powder, and neon paint is thrown into the crowd; every wall and fence along the way is used as a dancing prop. It’s truly an unforgettable experience. Tuck your favorite threads away for this—as the wise Shal Marshall put it, ‘can’t play mass if you ‘fraid powda.’
Once the walk is over (and you’re hosed off by Bacchanal Run participants) head into an open field where the music continues, and treat yourself to an assortment of vendor treats. The wahoo nuggets are non-negotiable.
Day 3: The Party’s Just Getting Started
Ease into the day with a traditional Bermudian Breakfast: Codfish and potatoes. For the authentic experience, mash the codfish, potatoes, hard-boiled eggs, plantain, avocado, and tomato sauce together with mounds of mayo. If you’re not lucky enough to have a local host for this breakfast, Bouchée in Hamilton offers it as close to home-cooked as you can get on the island.
Mid-day and into the evening is when the weekend celebration climaxes with Non-Mariner’s Water Raft-Up, a conjoining boat party at Mangrove Bay located on the west end of the island. The waters aren’t shallow enough to stand in, so when boats park, swimming and floats are the modes of transportation du jour.
It’s not a true raft-up if you haven’t stepped foot on to another boat to bus’ it down to a different playlist or try someone else’s take on Bermudian Swizzle. For lunch, pull straight up to Woody’s Sports Bar to catch heaven in a bite with a traditional fish sandwich: fried Wahoo fish fillets, tomato, lettuce, coleslaw and most importantly, tartar sauce pressed between two toasted slices of raisin bread.
By the time your flight home arrives, you’ll leave Bermuda feeling more like family than a visitor, which means it’s never goodbye, its see you soon!
Additional reporting by Nikki Ogunnaike.
