Lady’s Guide to Visiting Bermuda for Cup Match

Today I want to share my guide to visiting Bermuda for Cup Match. This annual event is a great one to be on the island for, and it’s even better when you can experience it with locals.

Visiting Bermuda for Cup Match

This morning I woke up at 6am and stumbled off the red-eye from Bermuda at Gatwick Airport.

Normally that would be cause for a bad day, but having just returned from an epic journey to the island in the Atlantic Ocean, I rode the wave of my holiday high until it crashed sometime around 3pm.

Let me back up a bit. My boyfriend and I touched down in Bermuda on Thursday evening.

We’d hardly checked into our hotel room at the Hamilton Princess & Beach Club before our Bermudian friends came to pick us up and take us to a party.

The best part was that they picked us up in a boat and took us to a party on our friend’s island. This was just the beginning of what turned out to be an epic weekend.

Cup Match in Bermuda

We were visiting Bermuda for Cup Match, the annual island cricket game for which all of our Bermudian friends return home each summer.

As such, on Friday my boyfriend and I spent the day enjoying the festivities and watching people try their luck at Crown & Anchor, a dice game that’s traditionally played during Cup Match.

In the evening we met up with friends for another big party. Instead of an island, this one was at the top of a hill with amazing views of the ocean from the pool area.

We woke up late on Saturday and spent a lazy day by the pool, followed by a great dinner party back on our friend’s island.

The tradition is that every year they serve a Thanksgiving-style dinner, complete with turkey, stuffing, and all the fixings.

Washed down with plenty of 1976 Chateau Margaux under the setting sun, and, well, it made for a pretty amazing evening.

Non-Mariners in Bermuda

If the preceding three days were full of partying and amazing dinners, then Sunday stepped things up a notch to be the pinnacle of the weekend’s madness.

We met at a dock at 10am and rode in our friend’s fishing boat to a cove where the annual Non-Mariners Race takes place. It’s another highlight of visiting Bermuda for Cup Match.

Non-Mariners is a boat race in which only non-seaworthy vessels are allowed to compete. But the highlight of the day isn’t the race. In fact, we didn’t even see it happen.

What we did see happen was that within two hours of our anchoring in the cove, there were over 45 other boats tied up alongside ours. We spent the entire day hopping from boat to boat in one giant raft-up.

When the sun went down, there erupted an impromptu ’80s dance party. It lasted until it was dark enough that we had to call it a night.

Beach in Bermuda

Monday was our final day of visiting Bermuda for Cup Match, and as such it was a day of detox. We headed to the beach with friends to enjoy what was left of our time on the island.

Having eschewed my usual good judgment when it comes to keeping my pasty-white skin out of the hot island sun, I spent Monday lying on the beach fully clothed under an immense sun umbrella while nursing the worst sunburn of my life.

Beyond Cup Match

The sunburn meant the red-eye flight back to London was painful in more than just the usual sleep-deprived, baby-next-to-me-won’t-stop-crying kind of way. My boyfriend and I took it easy after work today, ordering pizza for dinner.

We would feel worse about doing such a thing except for the fact that this weekend we head to San Sebastian, Spain, the Michelin-star capital of the world.

We’ll more than make up for this evening’s culinary lapse with all the pintxos and nine-course tasting menus that await us in Basque Country. Until then, we’ll survive on memories of our amazing weekend of visiting Bermuda for Cup Match.

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