There’s something special about the Florida Keys that keeps pulling us back. This year’s trip was extra meaningful because we celebrated our 5-year wedding anniversary there with a group of friends. From March 16–25, we spent 10 days island hopping, eating incredible food, soaking up sunsets and enjoying everything that makes the Keys feel like pure escapism.
We flew into Miami and made the drive south, first stopping in Marathon where we stayed for the first four days. Even the drive down feels like part of the vacation, with endless ocean views and bridges connecting each island. After checking in, we kicked things off with dinner at The Island Fish Company, a relaxed waterfront spot that immediately put us into vacation mode.
Tuesday and Wednesday brought rainy and cool weather, but honestly, the Keys are still fun even when the weather doesn’t cooperate. We headed to Islamorada and turned it into a brewery-and-distillery day, stopping at Florida Keys Brewing Co. and Islamorada Brewery & Distillery. This ended up being one of our favorite rainy day activities of the trip. We wrapped up the day with dinner at Lorelei Restaurant & Cabana Bar, a classic Keys waterfront restaurant with great sunset views even on a cloudy evening.
The next day, we kept things low-key and walked down to Herbie’s Bar & Chowder House, which feels like one of Marathon’s hidden gems. If you love casual local spots with great seafood and zero pretension, this is worth adding to your list.
Thursday was our actual anniversary, and we spent the day doing exactly what we love most in the Keys: eating, drinking and relaxing outdoors. We started with lunch and drinks at Bongos Botanical Beer Garden, followed by one more stop at Florida Keys Brewing. That evening, we celebrated with dinner at Papa Joe’s Waterfront, where we watched a beautiful sunset over the water.
Friday we made the drive down to Key West, dropped off the rental car and immediately grabbed lobster pizza from Seaside Café at the Mansion, which is absolutely worth the hype. We spent the afternoon wandering Duval Street and waiting for our friends to arrive with drinks at The Rum Bar, which has the best rum punch on the island.
Once everyone arrived, the weekend officially began. We had happy hour at Alonzo’s Oyster Bar, watched the sunset at Mallory Square, and ended the night with a late dinner at Mangia Mangia. We stayed at Colors on White this year, a second-time lodging spot for us. We love it for its spacious room, kitchen and private pool.
Saturday was one of the highlights of the trip: a private sandbar boat tour for our entire group. Spending the day out on the water, swimming and relaxing at sandbars is one of the best ways to experience Key West. That night was especially meaningful because we celebrated our anniversary dinner at Blue Heaven, the same place where we had our wedding dinner five years earlier.
Seaside Cafe
The rest of the trip settled into the perfect Key West rhythm: pool days at Dante’s, sushi dinners at Misohappy, live music on Duval Street, and late nights bouncing between iconic spots like Irish Kevin’s and Sloppy Joe’s Bar.
One unexpected highlight was attending Taste of Key West at Truman Waterfront Park. It was crowded but such a fun opportunity to sample food from restaurants across the island all in one place—and I even got to meet Mr. Happy Hour Key West.
On our final day, we watched manatees in the harbor, tried tuna nachos at Schooner Wharf Bar, enjoyed one last happy hour at Dante’s (their stone crab happy hour is elite), and watched the sunset one more time at Mallory Square before dinner at La Te Da.
Celebrating five years of marriage in one of our favorite places with some of our favorite people was everything we hoped it would be. And if you know us, you know this definitely won’t be our last trip to Key West—we’re already planning our return for 2027.
If you’re interested in seeing more, I have our whole trip saved on a highlight on Instagram called FL Keys ’26.
No Comments