Back for another year in our favorite place! We’ve spent our last several wedding anniversaries in the Florida Keys, including year three, and it continues to be one of our favorite places to keep visiting.
Days 1-2, Marathon, FL
Monday morning, we flew into Miami, picked up our rental car and made the drive down to the Keys. We typically pick up groceries in Islamorada, head to our condo and relax to open day one in the Keys. We had dinner at The Island (get the Key Lime Colada) in Marathon that evening. Day two, we woke up early, picked up bagel sandwiches at Marathon Bagel Co and drove to Islamorada for a brewery day. If you’re looking for a great way to spend a few hours, Islamorada Brewery & Distillery and Florida Keys Brewing Co are both fantastic breweries with countless options and beautiful outdoor spaces. For dinner that evening, we finally were able to try out Papa Joe’s Waterfront. Fantastic outdoor vibes and the food was excellent (I’ll go back for Papa’s Seafood Pasta).
Days 3-6, Key West, FL
Wednesday morning was our fourth wedding anniversary, so we got on the road early to drive down to Key West. We had lunch at Herbie’s (get the clam chowder) in Marathon and made a stop at Cayo Hueso Brewing on Stock Island. This year we stayed at The Bishop Key West; a cute boutique hotel just blocks from the harbor. Speaking of the harbor, that’s where we headed to check out the happy hour scene! We landed at Boat House Bar & Grill, which is one of our main stays in terms of happy hours in Key West. The food and drink options are unmatched. We watched the sunset at Mallory Square and had a romantic dinner at Mangia Mangia to round out a wonderful fourth anniversary.
Thursday, we grabbed Cubanos at Ana’s Cuban Café and ponied up at Jack Flats to watch some March Madness. We bummed around until happy hour, where we hit up Alonzo’s (another favorite), watched the sunset and had sushi at Misohappy. On Friday we planned to have lobster pizza at the Seaside Cafe at the Mansion, but the wait was so long we walked over to The Lobster Shack for their famous lobster rolls. We spent the day with friends, went to happy hour at Half Shell Raw Bar (Bad Monkey!), watched the sunset and had dinner at Kaya Island Eats (get the Mai Tai). Saturday was our last full day, so we stopped at a few favorites of ours: Rams Head, Dante’s (don’t sleep on their happy hour), and Old Town Mexican Café.
Days 6-9, Marathon, FL
Sunday afternoon we drove back to Marathon and had lunch at The Island. We were on the lookout for a sports bar to watch the NCAA women’s college hockey national championship game, so we tried Marathon Grill and Ale House. If you’re looking for a sports bar while you’re in the Keys, we’d highly recommend this spot. We finished the day with dinner at Keys Fisheries. Monday was fishing day, so we got up early and headed to Hawks Cay for a half-day fishing trip with Tarpon Time. We fish with them every year and it’s always a fun trip. This year we saw a hammerhead shark and a manatee! In the afternoon, we did a beach day at Sombrero Beach and had dinner at Lorelei Restaurant and Cabana Bar. Our final day in paradise consisted of hitting up the breweries one last time as well as our favorite hidden gem, Bongo’s Botanical Beer Garden. We finished another wonderful trip with dinner at Burdine’s Waterfront (get the shrimp sandwich).
I have our whole trip saved on a highlight on Instagram called FL Keys ’25. If you’re interested in other Florida Keys recs, I’ve written about many of our trips to the Keys. If you’re planning a trip, I’d love to help make it your best trip ever!
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