Cup Match in Bermuda

Today I want to share my guide to Cup Match in Bermuda. This annual cricket match sees the whole island erupt into one big party, bringing Bermudians who live overseas home and attracting visitors who want to experience the festivities for the first time (or in my case, the second).

I wasn’t planning to go back to Cup Match in Bermuda this year.

Having just taken an impromptu weekend trip to Jamaica in June and a vacation to Colombia in mid-July, it seemed a bit over-the-top to go west on another long-haul flight.

But after the epic adventure of last year’s trip, I couldn’t turn down my friend’s invitation to return to Bermuda for Cup Match, which takes place at the end of the last week of July each year.

Aside from arriving one day later, the trip was a fabulous reenactment of last year’s Bermudian epic.

My boyfriend and I saw the same friends from the prior year, and it felt somewhat like returning to a members-only weekend retreat at an island club.

Cup Match Friday in Bermuda

We touched down in Bermuda on Friday. Our taxi arrived at the Hamilton Princess & Beach Club just in time for us to get a text from our friend that this year’s Friday night party for Cup Match in Bermuda was right down the street.

At a house with a private peninsula right on the water, the party was complete with volleyball, a slip n’ slide, croquet, and American frat party drinking games.

It was the epitome of Bermuda: a little bit English, a little bit American, and all laid-back island goodness.

Cup Match Saturday in Bermuda

On Saturday our friend picked us up from the Hamilton Princess & Beach Club in his boat and took us out to his island for lunch with his family.

Afterwards we boated over to a sandbar that extends from one side of Bermuda for about a mile.

We met up with two boats full of friends, and spent the afternoon hanging out in the gorgeous crystalline water about a quarter of a mile out into the ocean. When we’d had our fill of swimming, we went wakeboarding until sunset.

Saturday night featured a great dinner on our friend’s island in honor of Cup Match in Bermuda. Rather than the traditional Thanksgiving-style dinner party from last year, this was a family dinner.

That said, the meal featured the same turkey, stuffing, and fixings that we loved so much.

Along with some tasty Bollinger, the ’76 Chateau Margaux made another guest appearance and we wafted home on the waves happy and full.

Cup Match Sunday in Bermuda

Sunday once again stepped things up a bit. With all the fun of last year but none of the horrible sunburn, the Non-Mariners Water Raft-Up was the highlight of Cup Match in Bermuda.

After anchoring our friend’s boat in the cove, over 30 other boats tied up alongside ours.

We witnessed every kind of craziness from a $900 double-magnum of red wine being funneled by a guy who won the bottle in a golf tournament, to people diving off boats to catch drinks in mid-air.

Beach in Bermuda

Monday was our final day in Bermuda. I woke up with a massive allergy attack, so we decided to take it easy.

Camped out under an umbrella at the beach at the Fairmont Southampton, our hotel’s sister property, we spent the day reading and sipping tropical drinks.