The Friendliest Island in the Atlantic

When I made the decision to go into business for myself, my mom was not only my biggest cheerleader but also my first client. Her own small business, STEPS for Kids, Inc, was in need of some direction on marketing and business development. So one day in March, we met for lunch at Panera to dig into how I might be able to help.

To my surprise and delight, our work meeting went well and my insights and recommendations proved to be helpful enough that I’m still working with her today on social media and email marketing. It’s been a win/win arrangement, as I’ve got the client work to keep busy with and she’s able to move these efforts off her own plate so she can focus on the work of growing the business.

I think it was at that first lunch that she mentioned that she’d been booked to present at a conference in Bermuda in late July. It would be her first trip abroad with the wildly successful class she’s been teaching and touring with for over a year now. I immediately insisted she extend her flights and take a few days to enjoy the beach while she was there. How could you not?!

Not long after mentioning the trip, she messaged me one morning to ask if I might be interested in joining her. YES is be my answer! And with that, we set to booking flights and lodging and learning as much as we could about what to do in Bermuda (which, honestly, I had to look up on a map…).

We booked a room at Greenbank Guest House, a quaint group of private cottages across the harbor from Hamilton, the island’s biggest city. Just down the street from a ferry stop, we had quick access to the rest of the island via public transit – the island’s ferry and bus system is not only affordable, but very easy to navigate. Cars aren’t available to rent, and we opted not to embarrass ourselves on the scooters everyone seems to favor.

Our flight, connected through Miami, arrived at about 9pm; we were treated to a breathtaking view of the island at sunset as we approached for landing. Once on the ground, customs was a smooth check-in and we headed outside the small airport. The woman who’d arranged the conference offered to meet us, and as we waiting no fewer than three different airport attendants checked on us, one even offering to call her on our behalf. This was our first glimpse into the warm and welcoming nature of Bermudians, an island-wide characteristic we’d see exemplified again and again in our five days there.

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In the daylight the next day, we took our time getting going, enjoying the view of the water from our cottage and getting our bearings. Bermuda is just two hours ahead of Chicago, sitting in the Atlantic directly west of the Carolinas, and though their economy is tied to the US dollar, it remains a British territory. Exploring Hamilton that morning, we found brunch at a restaurant on Front Street and spent time wandering the city center.

We found our way to Fort Hamilton, then eventually the Bermuda Botanical Garden. Despite the heat, we wandered the beautiful (and very quiet!) grounds for a bit, even bumping into a local in the gift shop who gave us a friendly primer on the island’s history. That evening, we enjoyed our first round of island drinks (Rum Swizzle for me, Pina Colada for mom) with a view at 1609, a posh outdoor spot attached to the Hamilton Princess hotel. Afterwards, we indulged in a classic pub dinner at The Hog Penny, and yes, I ordered the fish & chips.

On Saturday, my mom had her conference to present, so I was on my own for a bit. I took the opportunity to explore one of the beaches on the island’s south shore. A ferry to Hamilton and then a bus back to the south shore found me at Elbow Beach, where I lay out for a bit at midday until the heat became too much. I was baking under the bright sun, but it didn’t stop me from appreciating the gorgeous view I had essentially to myself. Between two resorts, there’s a public section of Elbow Beach that was much quieter than I expected. Where are all the tourists?

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I stopped for lunch next to the waves, then walked to the bus station to make my way back to the guest house to wait for my mom to return from her day. When she did, we made our way back into Hamilton for dinner at Lobster Pot, where we split a bowl of Bermuda’s famous fish chowder (it was delicious!) and enjoyed heaping plates of fresh seafood.

By Sunday, we were both ready to ramp our exploring into high gear, expanding beyond the city limits of Hamilton. So we took a ferry over to the west end of the island in order to explore the Royal Navy Dockyard, where all the cruise ships dock. (Here, apparently, is where all of Bermuda’s tourists are hiding!) The area boasts shopping and excursions, as well as Bermuda’s National Museum. Both of us were quite fascinated by the settlement and slavery history of the island as we explored the Commissioner’s House, and most impressed by the views from its perch above the docks.

We settled into the pub in town, the Frog & Onion, for lunch and it was a total treat complete with live music and local beer. I decided then and there that my own souvenir from the trip would be a Frog & Onion pilsner glass (which, wonder of wonders, made it home in one piece!). After a bit more wandering, we took a bus all the way down the west side of the island (which really only took about 30 minutes) to Horseshoe Bay, the most popular beach.

Since it was Sunday and our public transit options were limited, we unfortunately didn’t have as much time to explore the beach as we would’ve liked, and I still feel bad that we cut that time short just to make the last bus. But we got the chance to put our feet in the ocean, and I even convinced my mom to wade out to a rock not far from shore for an impromptu photo shoot. That night, we went grocery shopping and enjoyed a home cooked meal in our cottage (easily the cheapest meal of the trip, as the whole island is pricey!).

Our last full day on the island, we went the other direction and found ourselves in historical St. George’s, the first settlement on the island dating to1612. 1612! We took in the history and scenery, enjoying a dockside lunch at Wahoo’s (which is apparently named after a local type of fish that never fails to make me giggle). But St. George’s is a small town, so by mid-afternoon we’d seen everything there was to see and we headed back toward our guest house, stopping halfway to enjoy a pitcher of Rum Swizzle at The Swizzle Inn, watching the island zip by around us. We got home just in time to literally watch a storm roll in across the water; thankfully, the rain only really came at night, leaving our days dry and sunny, if way too hot.

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Our flight home was scheduled to depart at 4pm on Tuesday, and after allowing time to get to the airport and through check-in, we decided to stay in that morning and take our time packing and winding down our trip. We slept in, enjoyed the one last breakfast on our patio as we watched a sailing class in the harbor, and then dipped our feet in the water off the guest house’s private dock. Our taxi to the airport arrived right on time, and as easily as we’d arrived, we were back at the airport this time to leave the island we’d come to love.

I’m so grateful my mom offered to have me join her on this trip, and will forever cherish not only the travel memories, which I love collecting, but the time spent with her, too. We haven’t spent that much time together since she drove out to Utah with me in 2012. Sure, there were a few over-tired, tense moments, but all in all we make good travel companions, and I’m sure we’ll be telling the stories of this latest adventure for years to come.