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First Year Anniversary Trip to the Florida Keys

It was SO GOOD to be back, you guys. The Florida Keys is our happy place, and we just get so excited for this trip. We have so many traditions that we like to do every year, but we also love to pack in a bunch of new stuff. We had a good mix of old and new this year, so I’m excited to share our trip with you. I think I explained this in a previous blog post I wrote about the Florida Keys, but our trip is usually broken up with the first three days in the middle Keys, three days in Key West and the final three days back in the middle Keys.

First Three Days – Middle Keys

We arrived on Monday and that’s usually our chill day. Make our drive down with our Florida Keys playlist on Spotify, get groceries + booze, relax and enjoy the warm weather. We went out to dinner our first night at The Island in Marathon. It was PACKED! The middle Keys seemed busier than usual this year with lots of families. Day two consisted of hitting up our favorite breweries in Islamorada: Islamorada Brewing & Distillery and Florida Keys Brewing Co. We love both spots and make sure to hit them up multiple times during our trip. That evening we had dinner at Sparky’s Landing in Marathon. Day three consisted of a beach day at Sombrero Beach in Marathon and hitting up our favorite clam chowder spot, Herbie’s Bar and Chowder House. We also tried a new-to-us spot in Marathon, Sunset Grille. They have a unique location with a pool that overlooks the ocean and bridges. We had a couple of drinks and sat by the water for a while.

Sunset at our condo on Conch Key

Middle Three Days – Key West

These three days are our Las Vegas days. We drove down to Key West in the morning on St. Paddy’s Day and immediately wanted to partake in the festivities. We parked our car and began bar hopping down Duval Street, hitting up Willie T’s and Irish Kevin’s and getting Garbo’s shrimp tacos (MUST HAVE!). We had happy hour at Alonzo’s, which is a great tradition for us. They have the best buffalo shrimp. This year I hired a concierge, Kelly Hopkins, to decorate our Airbnb. She dropped off champagne and key lime pie and put candles and flower peddles all around our room. If you need someone to help grocery shop, book excursions or do anything else for your trip Kelly is your girl. We watched the sunset at Mallory Square and then spent the night at Durty Harry’s listening to The Durtbags, a grunge band we’ve been seeing down in Key West for years. Day two we decided to try a new-to-us thing and hit up Dante’s, a Vegas-style pool party. This was really fun, and I’d highly recommend it if you’re going down for a bachelor/bachelorette party or just a friend’s weekend. We stopped off at Seaside Café for lobster pizza, which was to die for and The Rum Bar for rum runners. We had dinner that night at Mangia Mangia, one of our favorite Italian spots we’ve been going to for a long time. Day three was anniversary day! Our one-year wedding anniversary and we started off with a historical sailboat harbor tour. We then did a cocktail tour through Key West Food Tours. I’d highly recommend doing one of their tours just to get an inside perspective of the island. We always learn something new about Key West on these tours. That evening we had dinner at Blue Heaven, the place we had our wedding dinner a year before.

Lobster pizza at Seaside Cafe

Last Three Days – Middle Keys

This is always the most relaxing part of our trip. We usually try to do any last-minute favorite things. We actually had two things planned for this part of the trip, both of which were canceled due to high winds: parasailing and fishing. That left us with two open days, so we decided to check out a new place, Bongo’s at The Lagoon on Grassy Key. What a find! It’s a super cute place with great drinks and food. They’ve been around about eight months and we’re hoping to make this an every year stop. We also made sure to make one last stop at both of the breweries in Islamorada and pick up any last-minute gear. I have an obscene amount of swag from both breweries. We had dinner at Keys Fisheries and were able to see them feed the sharks while we were there. We also hit up Keys Fisheries Upstairs Bar, a 21+ bar that has great drinks and a perfect sunset view. Another new-to-us find this year was Marathon Bagel Co. WOW! If you like New York-style bagels, do not miss this spot in Marathon. We finished our evening with one of our favorite restaurants in Islamorada, Lorelei’s Restaurant and Cabana Bar.

A new find! Bongo’s at The Lagoon

It was a perfect anniversary trip, and I couldn’t have imagined it going any differently. We love it so much in the Keys and we always start picturing what next year’s trip will look like as soon as we leave. If you’re interested in seeing videos of our trip, I’ve saved them all in my highlights under FL Keys ’22. If you have any questions about booking a trip down there, never hesitate to reach out. I love helping to plan a trip down to my favorite place.

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