Bossip Be Trippin’: Bermuda’s Cup Match Weekend Makes For A Vibrant Island Vacation

- By Bossip Staff

Bermuda Is The Island You Have To Visit

In the U.S. a number of African-Americans celebrate Juneteenth, but for most of the former British colonies (including islands like Barbados and Bermuda) Emancipation Dayis August 1, 1834, which is why holidays like Crop Over are celebrated in early August, and also why Cup Match — a two day holiday that is an 116 year tradition — is the perfect time to visit Bermuda. Check out the run down from BOSSIP’s own Janeé Bolden, who travelled to Bermuda for the first time this year for Cup Match 2018 weekend…

We arrived in Bermuda Friday early afternoon just as the afternoon’s Cup Match was getting started. For those not in the know, one of the biggest events of the weekend is a cricket match between St. George’s and Somerset — this tradition has been going on since 1901 and it was started as a friendly rivalry between two Masonic lodges located on opposite ends of the island. It’s supposed to be a friendly rivalry — but the crowd at the Somerset Cricket Club where the match was held was super thick and got rowdy at times. One thing we couldn’t help but notice when we arrived was that Bermudians are OVERWHELMINGLY ATTRACTIVE. Literally everywhere you look you see beautiful people — men, women and especially precious children! Seriously, next time Stella needs to get her groove back, she may want to consider doing it in Bermuda.

Almost as soon as we arrived at Cup Match we were greeted by the country’s young and progressive leader — The Premier of Bermuda, David Burt. We were incredibly touched throughout our stay by his warm personality. His wife Kristin was super friendly as well and a joy to encounter all weekend long.

We traveled to Bermuda as part of the #DreamBermuda group of influencers, which included Power 105.1 The Breakfast Club hosts Angela Yee and DJ Envy, media personality Terrence J and his stunning girlfriend Jasmine Sanders, Chef Roblé, model Olay Noel, Miss Diddy and more.

Being pretty new to the sport, we weren’t following the cricket match too closely, but there was so much going on at the event, including a DJ who played crowd favorites, delicious local cuisine and the national drink — swizzle — basically a kind of rum punch that’s very strong and sweet.

After the match we headed back to our hotel, The Hamilton Princess, to grab dinner and get refreshed before hitting up one of the big local parties going on. The view from Hamilton Princess was amazing and we would highly recommend this resort. Besides being home to some really cool artwork, there’s several great restaurants, including Marcus by Marcus Samuelsson, shops that had some amazing deals on swimwear (we grabbed a fab $150 suit for $30) and our personal favorite, an Exhale spa, where we indulged in an incredible Fusion massage before heading to a special dinner on the beach with the Premier and other government officials on Saturday.

But we’re getting ahead of ourselves. Friday night parties were plentiful. We attended the Soca vs. Reggae bash where we were treated to DJ sets of both styles of music as well as popular U.S. hits.

Chris Mabry's house in Tuckerstown

Janeé Bolden

Saturday proved to be a pretty relaxing day. After enjoying the spa we relaxed at one of the hotel’s pools (yep, there are multiple pools) until it was time to head to Tuckerstown for dinner. The trip required a good amount of travel back and forth between events but the views offered pretty amazing views of both the ocean and the beautiful colorful houses making for some truly enjoyable rides.

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Me and mine… @gia_casey #DreamBermuda

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When we arrived at a private home of one of the island’s most succesful businessmen Saturday everyone received their own bottle of champagne, along with a steel straw. The hosts were extremely hospitable, offering up their backyard to our entire group. They also took a number of guests out on their boat, which was literally docked just below their multi-million dollar home.

We tasted champagne and enjoyed a toast before heading over to a local beach for dinner. One of the perks of this particular event was having the local government officials drive us visitors to the beach. We rode with The Hon. Jamahl S. Simmons, who is the Minister of Economic Development and Tourism. His wife Sherri Johnson-Simmons is a pretty well known radio personality and the couple were straight up HILARIOUS. One thing we learned during the weekend was that Bermudians definitely like to laugh and have a great time. Once we arrived at the beach we were treated to a delicious dinner while a band played in the background. Terrence J did a toast to the Premier and some of the couples danced together on the beach. Things even got a little lively when the lead singer danced with DJ Envy’s manager, making for a pretty memorable night.

But the night didn’t end there. The group opted to continue the evening by visiting some clubs near the hotel on Front Street, where most of the local nightlife is located. Shockingly enough there’s not a lot of photos (listen after all that good food and swizzle and island partying most of our phones were dead), but a great time was had by all.

Sunday we closed out our trip with another Bermudian tradition. Known as Non-Mariners Raft Up, the Sunday following Cup Match usually includes what’s known as the Non-Mariners race, but this year there wasn’t a race. Normally the race is accompanied by what’s called a Raft Up, which basically involves all the boats gathering to watch the race while the people and board go back and forth between each others boats, partying, swimming, jetskiing and having a great time. This is how we spent our Sunday — aboard The Venetian — which is truly a beautiful ship.

The crew spent the whole day eating and drinking, swimming, relaxing on floats and doing a little dancing on the boat. Terrence J even took the mic at one point as the DJ got the crowd going. It was the perfect ending to a beautiful weekend. All we can say is, if you haven’t checked out Bermuda’s Cup Match — what are you waiting for?! Start making your 2019 reservations right NOW!

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