My First Solo Trip to Bermuda: What I Wish I Knew Before Going

Four nights in Bermuda over Thanksgiving weekend — from Hamilton, food tours and a spa day to the experiences that made me decide I wouldn't return.

Why I chose Bermuda

There wasn't some deep reason behind choosing Bermuda. I was shopping for cheap flights — as I often do — and found a nonstop flight from JFK for somewhere in the $300 range.

At the time, I really wanted to start my solo travel journey, but I knew that meant I actually had to stop thinking about traveling and book something. So I made myself buy the ticket. Bermuda became my first trip.

I traveled over Thanksgiving weekend, November 23–27, 2023. My Delta flight left JFK around 8:30 a.m. and arrived in Bermuda around 11:50 a.m. The flight itself was relaxing. I'm a sleeper when I fly, so I put on my iPod and slept for most of it.

Getting from the airport

One thing I did before the trip was research transportation. I'd read complaints about taxis in Bermuda, so I didn't want to arrive and have to figure everything out on the spot.

I booked my airport transportation in advance with CEO Transport. I also purchased travel insurance through World Nomads, something I make a point of doing when I travel.

Staying at the Hamilton Princess

I chose the Hamilton Princess & Beach Club after reading so many great reviews. Unfortunately, my experience didn't live up to them.

The positive: my room was clean. That's extremely important to me.

But I'm also a view person, and my view wasn't impressive. Instead of the beautiful Bermuda water I had imagined, I was looking toward what reminded me of swampy water with fishermen and boats.

The service was an even bigger disappointment. When I arrived, I wasn't escorted to my room or really shown where to go — I had to find the room myself. Some of my interactions with male staff also made me uncomfortable rather than welcomed.

The hotel's biggest advantage for me was its location. I could walk to Front Street, which made meeting my tour guides easy, and I had convenient access to the ferry.

Looking back, though, I learned something important about myself as a traveler: I want to be on the beach. If I were planning that trip again, I would have looked much more seriously at a beachfront resort such as the St. Regis instead of prioritizing being in Hamilton.

My first day: pool + my first Bermuda fish sandwich

My first day was intentionally easy. I hung out by the pool, ate and started settling into being in Bermuda by myself.

Of course, I had to try a Bermuda fish sandwich. I actually liked it — and because honey mustard is my favorite condiment, I added some. Even better.

And you can't go to Bermuda without hearing about the Rum Swizzle, Bermuda's signature cocktail. I spent the afternoon sitting outside by the pool, enjoying the sun with a Rum Swizzle in hand.

Day two: my day of zen

My second day was my relaxation day.

I started with a power yoga class at Exhale Bermuda from 10:30–11:30 a.m., and later had a Flow Massage at the hotel at 1:15 p.m. This was much more my speed: yoga, massage, relaxation and no rushing around.

Food in Bermuda — and a bad experience at Pickled Onion

Food is a big part of traveling for me, but Bermuda was mixed. I ate quite a bit at the hotel, and overall I'd describe the food as okay — not terrible, but nothing that made the hotel a destination for me.

My experience at Pickled Onion was very different.

I ordered empanadas and pizza as my entrée. The pizza was horrible, and I eventually asked for a refund. But the food wasn't what ultimately bothered me most — it was how the situation was handled.

There was a white couple in front of me, and I noticed a clear difference between the way they were treated and the way I was treated. After observing their interactions with both the waitress and the manager and then experiencing my own interaction with them, I personally felt that race played a role in the difference in treatment.

The manager's response to my concerns also felt unprofessional, and unfortunately, the poor customer service continued until I walked out the door. As I was leaving, another waitress was standing at the bar near the entrance. She saw me leaving but didn't acknowledge me or say anything.

Overall, the customer service was horrible, and the experience made me feel unwelcome. Between what happened at the restaurant and what my guide had already told me, I honestly wish I had never gone there.

Interestingly, Pickled Onion was one of the restaurants on my original Bermuda research list.

Exploring Bermuda through food

I booked a food tour because I wanted to experience some of Bermuda beyond my hotel and try some of the local food.

During the tour, I tried a traditional Bermuda breakfast, learned more about the island's history, and sampled local beer and cocktails. I'm glad I included a food tour because food is always a big part of how I experience a destination.

My favorite stop on the food tour was Meltdown Ice Cream, tucked into Old Cellar Lane just off Front Street. I tried their Bermuda Triangle, which included Black Rum & Raisin, Dark 'n' Stormy, and Coconut. I loved it! One thing I learned on this trip — Bermuda really loves raisins. 😂 I found them in the ice cream and even in the traditional Bermuda fish sandwich. Definitely something I wasn't expecting!

The island tour I REALLY wish I'd done first

On my last day, I finally did a full-island tour booked through Viator — and this ended up teaching me one of my biggest travel lessons.

Do the island tour at the beginning of the trip, not the end.

I had an amazing conversation with my tour guide. We talked about my experiences during the trip, including what happened to me at Pickled Onion. His response stuck with me: he wouldn't have recommended that I go there in the first place.

I remember thinking, Where were you on Day One?! Had I met him at the beginning of my trip, I might have avoided that entire experience.

And that's exactly why I now see the value in doing a good local tour early. A knowledgeable local guide can give you information that hours of Googling and reading reviews won't necessarily give you — where to go, what to skip, what might be overrated, and places that may be a better fit for you.

Because I visited over Thanksgiving weekend, some attractions weren't operating every day and others were closed. My tour group was mostly people coming from a cruise ship, so we all met at the dock at 9:30 on Sunday morning before heading out.

By the time I got this great introduction to the island, my trip was basically over. If I could redo Bermuda, the full-island tour would be one of the first things on my itinerary.

What it was like traveling solo as a Black woman in Bermuda

This is the part of the trip that ultimately determines whether I would recommend Bermuda — and for me, the answer is no.

I did not feel welcomed.

There were comments made around me that I found disturbing, including a comment along the lines of, "How are they able to come here?"

There were also interactions with some Black men that made me particularly uncomfortable — gawking, loud remarks directed toward me and behavior that I didn't experience as respectful.

Traveling alone already makes you more aware of your surroundings. I don't expect everyone in a destination to cater to me, but I do expect to be able to walk around, eat, stay at my hotel and explore without repeatedly feeling uncomfortable or unwelcome. That wasn't my experience in Bermuda.

I can only speak about my trip and the interactions I personally had, but they affected my perception of the destination enough that I would not return.

What Bermuda taught me about solo travel

Even though Bermuda isn't somewhere I'd return to, I'm glad it was the trip that finally got me started. It taught me a lot about how I like to travel.

I learned that I want the beach outside my hotel — not a shuttle ride away. I learned that a beautiful or highly rated hotel means very little to me if the service doesn't make me feel comfortable. And I learned that wellness experiences, great food and having time to simply relax are as important to me as sightseeing.

Bermuda also taught me not to wait until the end of a trip to get the local perspective. My island tour guide gave me some of the most useful insight I received during my entire stay — but unfortunately, I met him on my last day. Now, when possible, I'd rather take an overview tour toward the beginning of a trip and use what I learn to shape the rest of my itinerary.

Most importantly, I bought the ticket and went.

Bermuda may not have turned into a destination I loved, but it accomplished exactly what I needed that $300 flight to accomplish: it started my solo travel journey.