How Key West became our happy place, one trip at a time.

From our very first getaway together in 2013 and our engagement in 2016, to our wedding in 2021 and countless memories in between — Key West has become our second home. Here are a few of our favorite places to stay, things to do, and local bites we love most!

Our first time at Latitudes Restaurant, 2013

For us, the journey is part of the fun. We hit the road after dark to avoid traffic, and by dawn, we’re watching the sun rise over the water — the perfect start to any Key West escape.

Our first visit was just a short stay, but I was instantly hooked. We came in March — the perfect time for mild weather and lighter crowds. We explored Fort Zachary Taylor, met the famous Key West chickens, enjoyed some amazing meals, and, of course, had an ice-cold beer at Sloppy Joe’s.

Fort Zach for short, was constructed in 1985 and continued to defend the US through both world wars.

Who thought, we would be dining here for our wedding in 8 years!

Our second visit was just as special, this time in April. Spring is a wonderful time in Key West!

Stone Crab season runs Oct 15th - May 1st. Delicious!

We also visited the Dry Tortugas National Park. This is a US National Park, located 70 miles off Key West. It is great for exploring the fort and snorkeling around the moat walls.

The Dry Tortugas can only be reached by ferry or seaplane, which adds to its remote charm. We chose a day trip, but for the truly adventurous, camping is also available — though it’s considered primitive and requires a bit of planning.

The park is also a critical nesting site for sea turtles and a major stopover for migratory birds

In Key West, seafood isn’t just a meal — it’s a way of life! From the day’s fresh catch to shellfish and local crustaceans, you might just find yourself turning pescatarian.

We wandered through the vibrant streets of Bahama Village, took in a breathtaking sunset cruise, and indulged in even more of the island’s fresh seafood — a perfect end to each sun-soaked day.

Bahama Village is a colorful and historic neighborhood filled with Caribbean flair and laid-back island charm.

In my opinion, Key West sunsets are some of the best!

Marcus would eat his weight in Oysters, if I’d let him.

By our third trip, we were practically Key West pros. We visited in May, and that’s when Marcus proposed — right on the beach at sunrise. Just two days later, we spontaneously took our barefoot engagement photos, and the rest is history.

Over the next few years, we took a few other trips, but Key West has always been the place we return to again and again. Our fourth visit happened during COVID — and honestly, what better place to quarantine than our happy place?

For this trip, we decided to change things up and visit in July. The heat was intense (as expected that time of year!), but the island still had its magic. We took to the skies on a helicopter tour for a new view of paradise and revisited all our favorite local spots for Key West’s best flavors.

DJ’s Clam Shack is always a repeat stop — lobster rolls, cracked conch, and those clams in dreamy broth! No frills, just incredible food right on Duval Street.

Lobster roll and a cold beer, people watching on Duval. Is there anything better?

By our fifth visit, we were ready to experience Key West in a new way. This time, we came in December to see the island decked out for the holidays. The weather was mild and so pleasant.

We added a few new experiences to our list, including touring the Hemingway House and watching the bicycle Christmas parade.

Some of the famous Hemingway cats have six toes — a unique genetic mutation that makes them even more special.

Naturally, we made time for our favorite foodie spots — Latitudes, Blue Heaven, and a few beloved happy hours.

Sunset and a Key Lime Margarita with this view is sublime!

Blue Heaven is a brunch must. The best banana bread EVER!

Nine One Five is a great little spot on Duval St.

Our next trip was the most meaningful of all — our wedding day. We chose May, when the island is at its most beautiful, with warm breezes and endless blue skies.

We reserved a little slice of heaven on For Zach beach

Marcus spent his bachelor weekend out on the water for a deep-sea fishing trip with the guys, while our pre-wedding evening was pure magic — a sunset cruise shared with our closest friends and family.

Our next visit came in October 2023, which turned out to be one of the best times to visit Key West — sunny skies, pleasant temperatures, and that perfect off-season calm.

For this trip, we brought our pups, letting them experience the sunshine, salty air, and Key West’s easygoing charm right alongside us.

Dogs are welcome at Island Dogs Bar… they even have a doggie menu!

Of course, we had to app-hop our way through happy hour — Key West style!

The Waterfront Brewery is one of our favorite spots

The Half Shell Raw Bar is a must for Happy Hour

Our most recent visit, in 2025, marked our four-year anniversary — a chance to revisit the place that holds so many of our favorite memories.

Their Key Lime Martinis are absolutely delicious!

In more than 13 years of visiting, we’ve seen Key West from every angle — as wide-eyed tourists, as familiar friends, and now as part of our story. We’ve found our favorite places, our favorite people, and every time we drive across that bridge, it feels like coming home.
Until next time…

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How Key West became our happy place, one trip at a time.

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