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If there’s one thing about the BOSSIP staff, you know we love to travel!

Bermuda photos

Source: Janeé Bolden / @janeebolden

This year, BOSSIP’s Sr. Content Director Janeé Bolden traveled to Bermuda for her second Cup Match weekend. The experience was incredible and she was kind enough to put together a list of must-sees from her trip. Bookmark this now to start planning for Cup Match 2024!

Where To Stay In Bermuda

First things first… Where to Stay?

We stayed at The Loren at Pink Sand Beach Club which was incredibly beautiful. The hotel is very close to the airport, so for folks who prefer to be able to walk to restaurants and bars, this is a bit far from town, however, the restaurant was incredible here. We enjoyed delicious meals (especially seafood) and the service was incredible. The staff even were kind enough to keep the kitchen open late for us one night when we were back late from an event. The fresh-pressed juices were really great, I highly recommend them.

One thing I loved about The Loren was the huge balcony outside my room which included a sofa — perfect for napping with the sound of the waves in the background. At night this was especially wonderful to enjoy along with the bright lights from the pool.

Previously I’ve stayed at The Hamilton Princess.

Even if you don’t stay at the Hamilton, be sure to stop by for the incredible collection of modern art. Take a photo with the famous KAWS statue and have dinner at Intrepid Steak, Seafood & Raw Bar. The lobster is incredible. You can also get great cocktails here if you prefer to just have a drink. I got an espresso martini with tequila instead of vodka.

What Is Cup Match?

The actual “Cup Match” is a two-day cricket match for a literal silver cup. The tradition began in 1901, when two “Friendly Societies” began competing for a silver cup. So many Bermudians skipped work for this match that it was made a public holiday in the 1940s. The annual match pits a team from Somerset, the West End of the island, and St. George’s, the East End against one another. Somerset fans wear red and blue, and St. George’s supporters sport dark blue and light blue.

The Cup Match Venue alternates annually between Somerset Cricket Club in Sandy’s Parish and St. George’s Cricket Club, Wellington Slip Road, St. George’s. Match days are really long, but there’s a lot going on there besides cricket. The outdoor venue has different “camps” set up in the rafters where you can sit and watch the game, party and enjoy activities. The Hamilton Princess camp was even offering henna designs at the match I attended. When play is paused, DJ’s play music, there’s food and drinks and it’s just as social as any of your favorite local sporting events, with people going from camp to camp.

There’s also a HUGE tent for Crown and Anchor, which is where Bermudians get to gamble. Crown and Anchor is a dice game that was traditionally played by sailors in the Royal Navy. It reminded us a little of craps! The table is divided into six sections, each marked with a crown, an anchor, a diamond, a club, a heart or a spade. Three dice are marked with the same. Players then place their bets on the symbols that they think will come up when the dice are rolled. Depending on which symbols come up—and how many—you can win up to three times the amount of your bet. If the symbol you bet on does not come up, you lose.

Celebrate Bermudian History

Cup Match weekend is a two-day holiday comprised of Emancipation Day and Mary Prince Day. Many people don’t understand the historical importance of this holiday — but it’s not just about taking a break from work to enjoy a cricket rivalry.

Emancipation Day And Mary Prince Day In Bermuda

Emancipation Day, which coincides with the first day of Cup Match, is a day to recognize the abolition of enslavement on the island on August 1, 1834 — kinda like our Juneteenth in the U.S.! Emancipation Day is followed by a second public holiday, Mary Prince Day, named after a once enslaved Bermudian woman who became a hero of the abolitionist movement in Britain. Her story, “The History of Mary Prince,” was the first biographical account of an enslaved woman published in the U.K. and was instrumental in dismantling slavery in the U.K. and its overseas territories, including Bermuda and the Caribbean.

Bermuda photos

Source: Janeé Bolden / @janeebolden

Kristin White Is A Bermudian Treasure

That said, we highly recommend visiting Kristin White’s bookstore Long Story Short and booking a walking tour with her.

Having the opportunity to visit the East End Mini Yacht Club (Bermuda’s Black yacht club) with Kristin and learning the history of the island was one of the best and most memorable parts of our stay. Kristin is so smart, passionate and intelligent. She was a joy to listen to and her shop is truly an island gem.

Kristin also has one of the most popular camps at Cup Match! Make sure to stop by Sweet Freedom if you come to Cup Match.

Bermuda’s Bacchanal Run Is So Much Fun

Bacchanal Run

Bermudians definitely know how to party and Bacchanal Run aka “The Non-Marathon” is a must do if you love to fete, jouvert, Carnival etc…

Bermuda also has a Carnival as well so if Cup Match isn’t the best time to visit you might want to consider going for Carnival, which is in mid June.

Some things to consider for Bacchanal Run attire include wearing comfy clothes and shoes because it’s a lot of walking and dancing. The powder can be hard to get out of your hair, so you may want to consider wearing a hat, shower cap, turban etc. I recommend having fun with it! Plenty of folks on the road had ski goggles on and masks or cool hats. Feel free to create a costume to your liking and get ready for paint, powder and water to come your way!

Crystal Cave In Bermuda Is A Natural Wonder To Behold

If nature is more your thing, we highly recommend visiting Crystal Caves. It’s a great way to cool off during the hot summer, while also taking in some natural beauty. Crystal Cave is a little easier to navigate, while Fantasy Cave is a little more of a challenge to climb but both are really beautiful and enjoyable ways to enjoy Bermuda. This was another favorite stop of mine that I would put in the top 3 moments for my Cup Match weekend this year.

Bermuda photos

Source: Janeé Bolden / @janeebolden

Get On A Boat For Non-Mariners Day In Bermuda

The grand finale of Cup Match weekend is Non-Mariners day when many Bermudians and tourists set sail for the biggest water raft-up party of the year. While Non-Mariners began as a race, it’s more of a social thing where people pull their boats up beside one another or use smaller rafts or floats (or swim!) socializing on the bay for the day. If you don’t swim, don’t worry, wear a life vest! You can make the day what you like — sun bathe on the boat, get in the water and take a dip or dive off your ship if that’s your vibe.

Bonus: I ran out of time and wasn’t able to list all the places I ate but one spot that I discovered this trip that I didn’t know about on my last visit to Bermuda was Ice Queen. It’s basically a late night fast food spot but it’s the perfect place to soak up your drinking and they have this condiment room that is nothing short of epic!

Hopefully this guide will give a helpful start to your future plans to visit Bermuda. Feel free to hit me up on IG @janeebolden if you have any questions!


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