20 of My Most Memorable Travel Moments

20 of My Most Memorable Travel Moments

This article was updated on January 5, 2026.

Taking pleasure in travel is a given, but the intimate experiences when visiting a new place –– be it a major metropolitan city or small town –– make each journey unforgettable. I’ve experienced many memorable travel moments over the years. Here, I rounded up some favorite places and travel memories.

Boston, MA

Roaming the Harvard campus with my dog. I think Bogey loved the vastness and lush grounds as much as I did.

Palm Springs, CA

Basking on old Hollywood glam while listening to standards at Melvyn’s Lounge. I felt as if I was living in the days of the Rat Pack. Fly me to the moon!

Paris, France

I recall one evening, sipping way-too-expensive champagne near the Eiffel Tower, and galavanting the city streets into the night. I don’t remember a headache after all that bubbly, but then again, I don’t remember much else either.

St. Louis, MO

Eating probably the most amazing filet mignon of my life at Sidney Street Cafe. I loved everything about this restaurant –– the food, wine, vibe, neighborhood….that meal will always be one of my favorites while traveling.

Sedona, AZ

My first sight of Sedona red rock. Driving into town I witnessed one of the most raw yet beautiful landscapes I’d ever laid eyes on. I still smile to myself each time I think of that moment.

London, England

Bohemian Camden Town in the ’90s, when I purchased a black leather biker jacket for about $75. I wore that jacket for years and got more than my money’s worth and thought of that neighborhood every time I wore it.

Quito, Ecuador

The afternoon I spent wandering La Ronda. I became immersed and involved in local culture my very first day in the country as I window shopped on this quaint, cobblestone street.

Newport, RI

The juxtaposition of the mansions and the cliffs along the famed Cliff Walk…amazing.

Florence, Italy

An absolute perfect dinner at Ristorante La Giostra. Every bite, every sip of wine, and the service ––all were impeccable. The owner was charming, friendly and engaging. A night to remember!

Bathsheba, Barbados

On my first night here, I discovered that my phone was missing when I arrived to dinner at The Atlantis Hotel. Carol was working the front desk and made a few phone calls, and unbelievably, my phone turned up. I had left it outside on a table by the pool of my hotel. The security guard had found it and kept it for me until I returned later that evening. I knew then that I loved Barbados.

Napa Valley, CA

Tasting wine at Clos de Val. I visited eight or nine wineries that day, but Clos de Val’s wines were a stand-out. The Carneros Pinot Noir is still one of my favorite reds.

Charleston, South Carolina

Riding all over town in a rickshaw. I mean –– everywhere. That was the only time I’ve ever been in a rickshaw, and Charleston is the ideal city to have someone pedal you around town. Try it!

Boothbay Harbor, Maine

This town feels quintessentially Maine. I was in Boothbay twice and adored both of my visits, but walking into Kaler’s and saying that my name was Kaler too is a moment I can’t forget.

Venice, Italy

As touristy as it was, the gondola ride was romantic and spectacular, and I would do it again in a heartbeat.

Newcastle Upon Tyne, England

The Geordie accent isn’t the easiest to understand at times, but by the end of my two-week stay, I became fond of the dialect and found it endearing. I can still recognize that accent when I hear it.

Savannah, Georgia

Forsyth Park and the countless squares with statues and stately trees were the highlights of my trip. I recall walking through a square what seemed like every few blocks. Savannah is a dreamy town.

West Hollywood, California

Checking into a spacious, stylish room at the Mondrian, and looking outside the window for a fantastic view of Sunset Blvd. The hotel gods were on my side––the room was a complimentary upgrade.

Rome, Italy

The pilgrimage to the Sistine Chapel is a memorable one. I say pilgrimage because I walked miles (or so I thought) until I reached the chapel, but every moment of the journey was special. I was surprised at the size, but then again, it’s not called a chapel because it’s a huge building. Although magnificent, there was nothing large about it.

Cuenca, Ecuador

I had never ridden a mountain bike before I went to Cuenca. Let’s just say that the altitude took its toll on me. I was a little breathy by the end of the 12K ride, but I was proud that I finished considering the height was 8,000-plus feet.

Brooklyn, New York

I’ve visited Brooklyn countless times, but one of the most noteworthy trips was the day I spent at Coney Island. In particular, when riding the Cyclone, I was gripping the lap bar for dear life and screaming like a child riding the big roller coaster for the first time.