Spring break is here and that means we’re back in the Florida Keys! We realized this year that we’ve been traveling down to the Keys for a decade now. It truly is one of our favorite places on earth. We get asked a lot why we travel to the same place every year and our answer is always the same: we just absolutely love it there! Being able to celebrate our wedding anniversary in the place we got married is just the cherry on top.
First Three Days – Marathon
We flew into Miami, grabbed our rental car and took off for the Keys. The drive down is always exciting and it’s so beautiful. I recommend getting an island playlist set up beforehand to really make the drive special. We got groceries and stocked up on beverages and headed to our condo on Key Colony Beach. This is such a cute and walkable community. Their sunset celebration is something out of a movie (IYKYK). We relaxed that afternoon with cocktails by the water and had dinner at The Island – one of our must-stop favorites. Day two consisted of brewery day in Islamorada, hitting up Islamorada Brewery and Distillery and Florida Keys Brewing. These are two of our favorite spots in Islamorada and we try to go every year. We also stopped at newly opened Papa Joe’s Waterfront. They had just opened days before our arrival, so everything was a bit new, but this is going to be an every-year stop for us. The outdoor tiki bar is great with a huge lawn area to play bags overlooking the water. For dinner, we finally got to check out Burdine’s Waterfront. We’ve had this recommended to us a bunch and we finally got here! Beautiful spot right on the water and oh my gosh – get the shrimp sandwich + fries. Wednesday was a beach day at Sombrero Beach and clam chowder and fish dip at Herbie’s Bar & Chowder House. We also grabbed cocktails at Sunset Grille. We ended the night with lobster rolls and popcorn shrimp at Keys Fisheries.
Middle Three Days – Key West
On Thursday, we got on the road early and headed south to Key West. We stayed at the Caribbean House this year. We typically don’t stay in the same place year-to-year in Key West, but this is a place we’d stay again. Great location, great price and clean rooms. Lodging in Key West can sometimes give New York hotels a run for their money in terms of small sizes, but we don’t mind – we’re just looking for a place to rest our heads. We grabbed lunch at Garbo’s Grill (must stop) and just bar hopped the rest of the afternoon. We had happy hour at Alonzo’s (we stop here every year) and at Dante’s (first time). We bar hopped a little more and did late-night at Big Cheezees Pub.
On Friday we had a free day, so we decided to try a few Cubanos. Right down the street from our condo was Cuban’s Corner. This was our favorite Cubano of the trip! If you are looking for authentic Cuban food, I couldn’t recommend this place more. We also had to have the Cubano at Cuban Coffee Queen. We’ve had this one many times and it’s excellent. We bar hopped the rest of the afternoon and stopped at a few of our wedding spots to take pictures. We had happy hour at Old Town Mexican Café (get the chorizo nachos) and grabbed mojitos to watch the sunset in Mallory Square.
Saturday was our “try something new” day, so I worked with Kelly Hopkins, the concierge girl, to book a private sandbar charter for Saturday. I could not recommend this trip more. You can book a half-day or a full day trip and Kelly’s husband Keith takes you out on the water to show you all the sandbars. You can bring your own snacks and beverages and it’s just a nice way to get on the water without being on a huge charter with hundreds of strangers. We ended our night with a fun anniversary dinner at Hot Tin Roof. Make a reservation and watch the sunset from the balcony.
Last Three Days – Marathon
Our last three days of vacation were very relaxing. We spent a lot of time at the beach reading and hanging out. We had dinner at one of our favorite spots in Islamorada, Lorelei. We also have a hidden gem favorite The Lagoon on Grassy Key. They have a little bar and restaurant, Bongos that serves yummy food and has an excellent craft cocktail menu. They also have a great craft beer menu. Our last day of the trip was our wedding anniversary, so we started our day fishing with Tarpon Time. We do a half-day charter and this is an activity we’ve come to love doing every year. I also made reservations at Chef Michael’s in Islamorada. We’d never eaten here before, but thought it was so good and great for a special occasion.
I have our whole trip saved on a highlight on Instagram called FL Keys ’24. 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!