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2nd Anniversary Trip to the Florida Keys

…and we’re back! We spent our 2nd wedding anniversary in the Florida Keys and despite windier and cooler weather than normal, we had such a fun and relaxing trip. It’s so fun to get to spend our anniversaries here. After getting married in Key West in 2021 and spending our first wedding anniversary in the Florida Keys in 2022, we felt so lucky to be back again in 2023. This year we flew into Fort Lauderdale as the rates were a little better than our usual Miami flight.

First Three Days – Marathon & Islamorada

After what has felt like the longest winter in Minnesota history, it felt SO GOOD to get into shorts again and get a little sun on our skin. Our first full day of vacation we went parasailing out of Robbie’s of Islamorada. This was our second time parasailing with Robbie’s and we have enjoyed it each time. The price is really reasonable and you can add on a photo package if you want the boat captain to take some great high-res images of your flight. Since we were already in Islamorada we also hit up our two favorite breweries: Florida Keys Brewing Company and Islamorada Brewery & Distillery. Both are must-stop spots if you’re in this area. On day two we did a half-day fishing charter with Tarpon Time. We’ve fished with them several times and it is such a good experience.

A few extra favorite stops: Herbie’s Chowder House, The Island Fish Company, Keys Fisheries

Parasailing at Robbie’s

Middle Three Days – Key West

We drove down to Key West bright and early from Marathon on Thursday and did another tour with Key West Food Tours. This is one of our favorite things to do in Key West! We’ve done them multiple times and each time we try a new restaurant or learn something new about Key West. We also hit up our favorite happy hour spot on the water: Alonzo’s Oyster Bar. We topped off the day with a sunset in Mallory Square. Friday was St. Paddy’s Day and it was HOT so we went to Dante’s pool for the day. We tried a new spot for dinner on Friday, Louie’s Backyard. I’d recommend getting a reservation (we didn’t have one) if you want to sit on the patio by the water. We were able to sit on the upstairs porch and had a beautiful view of the Atlantic and the most delicious food. On our final day we walked around Fort Zachary State Park and Beach. We’d never been back on the beach and it’s a great hidden gem if you’re looking for something off the beaten path in Key West.

A few extra favorite stops: Garbo’s Grill, First Flight Brewery, General Horseplay, Sunset Pier, Misohappy, Durty Harry’s

Sunset at Mallory Square

Final Three Days – Marathon & Islamorada

After our three nights in Key West, we drove back to Marathon to celebrate our second wedding anniversary! Because we weren’t down in Key West, I made reservations at Pierre’s Restaurant in Islamorada. A spectacular spot! We had never been here but were interested in a more romantic, elegant setting and Pierre’s did not disappoint. Our final two days were very relaxing. We spent a lot of time by the pool and checked out a few of our favorite bars and restaurants including Lorelei, Sunset Grille and Bongo’s Botanical Beer Garden.

A few extra favorite stops: Sparky’s Landing, Hog Heaven, Sombrero Beach

Dinner at Lorelei

I have our whole trip saved on a highlight on Instagram called FL Keys ’23. If you’re interested in reading more about our favorite things to do in the Florida Keys, I’ve written several posts previously on our favorite restaurants, bars and activities. If you’re planning on a trip, I’d love to help make it your best trip ever!

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