Bermuda: Trip Overview

Bermuda has one of the highest concentrations of (now decommissioned) British forts due to its strategic location in the Atlantic.

UPDATED: 2/5/2023

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Planning our Bermuda Trip

In case you haven’t noticed or are new to reading about our travels, we are active travelers and so usually steer clear of beachy and resort-filled destinations, which is why we have not visited Caribbean islands, which are relatively close to us geographically speaking and are a popular destination from our area. We know many places have a whole lot more to offer beyond laying on the beach, but making sure that is absolutely the case is important to us.

For some reason, Bermuda has always piqued my interest. Maybe it goes back to my childhood and watching Bermuda’s Olympians marching in during the Olympic Opening Ceremonies in their Bermuda shorts. Maybe it’s that an island isolated in the middle of the Atlantic Ocean hundreds of miles from any other land mass seems like such a different way to live.

When we found ourselves with enough airline points to be able to book a free set of plane tickets (yay and very rare for us), we searched for various destinations that would be within our allotment of points and have warm enough weather for our long weekend during Thanksgiving (which the US celebrates in late November). Bermuda fit the bill, and so we booked it for a four-day trip. But first, of course, we checked to ensure there would be enough to explore on the island to meet our interests, and there was.

We booked a place to stay through Homeaway.com across the bay from Hamilton, Bermuda’s capital. A week before our trip, when looking to confirm our details, we discovered that the place was no longer an active listing and reached out to the owner, who had since converted the house into more of a B&B and had totally forgotten we had booked with her. She offered us a room that was worth more per night at her B&B in Hamilton but for the same cost. After doing our own research, we decided to leverage points we had accrued through our Chase Sapphire credit card and booked a stay entirely on points at Hamilton Princess, a landmark hotel right in Hamilton and walkable to its restaurants and shopping and situated along the water. While at the time this last minute accommodation issue was a pain, we ultimately were happy that we ended up in Hamilton instead of our original rental because Bermuda is not the easiest place to get around, and Hamilton has the best transportation options.

Looking back as the ferry pulled away from the dock and Hamilton slipped away behind us.

On this gray and stormy day Lindsey nearly got blown off the patio of the National Museum of Bermuda. (Ok, not really)

Would we recommend Bermuda in the late fall/early winter?

It depends.

If you like the standard beach activities - sunbathing, snorkling or diving, or boating, if you like a hopping night life, and if you don’t mind crowds, then this is probably not the best time for you to visit.

If you like a quieter setting (it is a populated island that is very built up regardless of the season - it’s just a matter of relative quiet!), aren’t keen to sunbathe or frolic on the beaches but are perhaps interested in walking along them bundled up, and if you like exploring cultural locations and having them basically all to yourself, then off-season Bermuda is a good bet.

In terms of the weather, this is a tough one since we can’t extrapolate all Bermuda’s off-season weather from our weekend visit. For us, the temperatures were warmer on Bermuda just before and just after our visit. It was in the 60s (Fahrenheit) for the most part during the day when we were there, which in late November, was significantly warmer than the 30s-40s back home in Virginia. What really took us by surprise was the really, really strong winds that made it feel much colder and made walking uncomfortable. Strong windy days are also a good time to avoid walking on the sandy beaches unless you enjoy sand pelting your eyes. Again, the wind happened to hit on the second day of our visit but hadn’t been a prime feature in the forecast before or after, since this can vary. The weather in general in Bermuda shuffles between sun and occasional rain regardless of the season. I think as long as you have a rain coat and warmer clothes, the late fall/winter can still be a good time to visit.

Sitting on a bench. Looking out at the ocean while relaxing. …Yes please!

Highlights of Our Long Weekend Trip to Bermuda

We know there is a lot more to do and see than what we were able to do in our 4 days, though only 3 of which were really usable since Dustin got sick on the last day.

We enjoyed everything we did while we were on the island, which included a tour of water-filled Crystal Cave, a visit to the National Museum of Bermuda in the fortress of the Royal Naval Dockyard, explorations of the UNESCO World Heritage Site of St. George’s and surrounding sites, and more.

We had a number of truly phenomenal meals and were pleasantly surprised by the variety and various culinary influences throughout the island. And we found all the local people we interacted with to be incredibly friendly, though it was also clear that most people in the tourism industry from restaurants to hotels are not native Bermudians and have mostly emigrated for the jobs.

Would we return to Bermuda?

Yes, if we are looking for another short getaway, we would absolutely return to Bermuda to continue exploring spots we didn’t get to but were on our list during the first visit. Having gone in cooler weather, we would probably try to return in a shoulder season but closer to the warmer weather to enjoy the beaches more or get out in the water.

It probably wouldn’t be at the top of our list given the way we tend to travel but that is merely a personal preference for us, and we absolutely loved our time in Bermuda.

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