Celebrate Bermuda’s Cup Match & Island Culture: A 5-Day Itinerary

More than a game, Bermuda’s annual Cup Match is a cultural experience packed with sports action, island pride, delicious food, and plenty of revelry. Visit during Cup Match in early August to enjoy the best of Bermuda like a local.

  • People & Culture,
  • Travel Tips
Cup match in Bermuda

One of the year’s biggest events, Cup Match takes place August 1-2, 2024, at Somerset Cricket Club on the island’s West End (the location alternates yearly between the West End and East End). The two-day cricket match between rival teams – Somerset Cricket Club and St. George's Cricket Club – brings the entire island together in celebration of Emancipation, sport, and Bermuda pride.

The Cup Match Cricket Festival coincides with two national holidays – Emancipation Day, commemorating Bermuda’s abolition of slavery on August 1, 1834, and Mary Prince Day, honouring the once enslaved Bermudian turned author and abolitionist hero. The momentous match is followed by a full weekend of festivities, setting up one of most energised, exciting, and important holiday weekends of the year. You’re invited to celebrate freedom and island life right alongside the locals. 

See what it’s like! Watch our Cup Match video.

Plan to spend about a week in Bermuda to fully experience the events surrounding Cup Match and other island highlights. Let this 5-day itinerary be your guide.


Stay on the West End close to all the Cup Match fun. A boutique retreat on Bermuda’s famous South Shore, The Reefs Resort & Club is perched on cliffs overlooking the Atlantic Ocean. Take in the view from the infinity-edge pool, restaurants, or private pink-sand beach. Amenities include complimentary watersports rentals, tennis and pickleball courts, and a full-service spa.

Exterior view of The Reefs Resort

Also on the West End, Willowbank Resort is another oceanfront gem to consider. Relax on two private pink-sand beaches or poolside with complimentary chaise lounges, umbrellas, and towels. You’ll also find tennis and basketball courts (balls and rackets are complimentary) and a couple of great options for onsite dining.

DAY 1 


Check in, get settled, and dip into the resort amenities. Take a swim or grab a refreshing beverage – the Dark ‘n Stormy® and Rum Swizzle are two signature cocktails to try.

Then savour dinner at a West End favourite. For a laidback vibe, head to the waterfront Woody's Sports Bar, known for its stellar fish sandwich, or Bone Fish Bar & Grill, offering a mix of choices from land and sea at the popular Royal Naval Dockyard. For a more formal setting and sunset views, enjoy elevated island fare at Sunken Harbour Club at Cambridge Beaches (reservations required), or feast on Bermuda classics at The Ocean Restaurant at Willowbank.

Sunken Harbor Club – Sunken Harbor Club

Come Cup Match eve, the Collie Buddz concert at Snorkel Park Beach Club will be the hottest spot on the island. Buddz was nominated for a 2023 GRAMMY for Best Reggae Album alongside Julian Marley and Buju Banton, legends in the genre, and is best known for his hit single “Come Around." The concert is selling out fast, so don’t wait to purchase tickets.

DAY 2 


Start the day with some blissful beach time right at your resort. Lounge on the powdery pink sand or go for an invigorating swim. If you’re an early riser, consider visiting one of Bermuda’s most famous stretches of coastline, Horseshoe Bay Beach, and its neighboring beaches and coves.

Then it’s time for the main event: the Cup Match Cricket Classic. This tradition dates back over 100 years and comes with a storied rivalry. You’ll want to pick a side – East or West – and sport your colours accordingly. On the East is St. George’s (light blue and dark blue), and on the West is Somerset (red and dark blue). Bermudians show off their colours from head to toe, so get ready for some spirited fashion!

A group are posing at Cup Match in their team colours.

The match starts at 10 AM on both days. Want to learn how cricket works or need to brush up? See our Beginner’s Guide to Cricket in Bermuda. Beyond the action on the field, there’s the food, drinks, and nonstop entertainment. Try traditional dishes like fish cakes, mussel and beef pies, Bermuda-style potato salad, and peas and rice. Stay cool with ginger beer and rum swizzles. Locals celebrate in camps as they cheer on their teams – make some Bermudian friends and you may score some free bites and swizzles! 

Outside the venue, camping for Cup Match is a key part of the experience. Elaborate overnight camps pop up in nearby parks days before the event – think roomy tents with air mattresses, seating areas, barbecue grills, and generators powering electric fans and mini refrigerators. The camps are decked-out with the comforts of home and fully stocked with food and drinks. 

After the match, do dinner “in town,” otherwise known as the City of Hamilton. Here you’ll find a mix of options at various price points, from Front Street favourites like The Pickled Onion to the inventive Devil's Isle Cafe and the elegant Intrepid at the Hamilton Princess hotel.

DAY 3 


Come back for the second day of Cup Match and see which team takes home the coveted cup. It’s another great day of cricket, spirited celebrating, and soaking up the local culture. 

If you haven’t already, check out the Crown and Anchor tent, where another beloved game is being played. This simple dice game was traditionally played by sailors in the British Royal Navy. Cup Match is the only time when you can officially gamble on the island, so now is the time to get in on the game. Try your luck and you could win some cash!

A man is managing the Crown & Anchor table at cup match.

Whether or not your team is victorious, you’ll be ready for a relaxing sit-down dinner when the match is done. Head back to your hotel and refuel with Bermudian favourites at one of the onsite restaurants. Then head out for the evening entertainment – go to the Cup Match Fever After Party at Snorkel Park or enjoy music and dancing at Henry VIII Restaurant, Sushi Bar & Pub.

DAY 4 


After the excitement of Cup Match, the island’s peaceful East End may seem like another world. Go underground on the Crystal & Fantasy Caves Tour, where you’ll see surreal limestone rock formations and a crystal-clear subterranean lake. 

Then head to the historic Town of St. George, a UNESCO World Heritage Site. Have lunch at Wahoo's Bistro & Patio, a waterfront spot with an eclectic, seafood-forward menu. Then do some cultural immersion with the Lili Bermuda Perfumery Experience, where you can create your own fragrance, or a walking tour with Long Story Short, where a Bermudian guide illuminates local history and hidden gems.

In the evening, experience the Bacchanal Run, a.k.a. the “Non Marathon.” This exhilarating event involves soca music, paint, powder, and water. Nothing says island party vibes like this explosion of colour and sound, but you’ll want to be prepared – wear comfortable clothes and shoes (preferably shorts and a T-Shirt) that you don’t mind throwing away after. Ladies should wrap their hair tightly to avoid damage. Everyone goes home with a swag bag.

A group of people are smiling while paint is being thrown every where.

DAY 5 


On your last full day, indulge in an authentic Bermuda codfish breakfast, a Sunday staple. It’s a delightful plate of salted cod, boiled potatoes, a boiled egg, and slices of banana and avocado, and The Paraquet Restaurant serves one of the best.

Then hit the water for the final celebration of the trip. The Non-Mariner’s Raft-Up began as a race for DIY boats and evolved into Bermuda’s biggest party on the water. While Bermuda takes its sailing legacy quite seriously, the race made its mark by flipping convention for humour and entertainment. Today, Bermudians celebrate by gathering in hundreds of boats and tying up together to form large “raft-ups” under the sun. To get to the event, you can charter or rent a boat or hop on a larger boat with companies like UberVida. No matter how you get there, it’s sure to be unforgettable.

Non mariners event with lots of boats rafted up together.

DAY 6 


It’s time to say farewell to paradise. But if you’re staying at The Reefs, considering springing for one last hurrah at the La Serena Spa – a soothing massage or Ayurvedic treatment to complete your island escape.



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