Key West Travel Guide

The final stop of our Florida vacation was Key West! This was another city my sister and I had never been to and were so excited to spend a few days there as a family before heading back to the chilly weather at home. Our drive in our Toyota Highlander Hybrid was about three and a half hours, but we stopped along the way for a lunch break and some sun. We stopped at Cheeca Lodge on Islamorada and was blown away how gorgeous the water was driving in. We had an amazing lunch full of seafood (I think I had some type of fish almost at every meal this trip!) and it was the perfect break in our drive. Now on to Key West!

WHERE TO STAY
The Perry Hotel: I LOVED our hotel in Key West. The Perry Hotel just opened within the last year and this boutique hotel is located right off the Stock Island Marina. About a fifteen minute drive from downtown Key West, we loved that it was a little separated from the busy downtown. With only 100 rooms too, the hotel didn’t feel over crowded and we were able to easily grab pool chairs or the hammocks to lay out in during the day and a great meal at one of their two restaurants. Another favorite thing was the hotel smelled INCREDIBLE! My mom ended up asking the staff what it was and buying the air diffusers for our home too. We also loved walking through the marina with a cocktail in hand during happy hour. Highly recommend!

WHERE TO EAT AND DRINK
Sloppy Joe’s: Definitely a dive bar, but this is a classic Key West establishment you have to stop in. Known for their extra strong Hemmingway Mojitos, it’s a fun spot to kick off the night, or have a night cap at while visiting.

Santiago’s Bodega: We escaped the rain here one afternoon and had an amazing lunch of tapas and sangria. Everything was amazing, including the prices and portions, and highly recommend this spot for a filling lunch or dinner.

Southernmost Beach Café: One of the coolest things about Key West is that you are at the southernmost point of the country! We had an amazing beach seafood dinner and drinks right on the edge of the point and was so peaceful to hear the waves while we ate. 

Matt’s Stock Island Kitchen & Bar: A great perk of our hotel was the amazing food they had. We had a delicious poolside lunch one day of fish tacos, shrimp salad and a fish sandwich and was blown away by how delicious everything was (and the huge portions!)

Blue Heaven: This outdoor restaurant was the number one spot that came recommended to me and after three attempts to finally get a table, it was definitely worth the wait! We came for dinner and shared a few appetizers but the true winner was their famous Meringue Key Lime Pie. A must to try while in town!

VIV Wine Bistro: If you end up waiting for a table at Blue Heaven like we did, we loved grabbing a glass of wine and a cheese board at this adorable wine bistro. Live music and a great selection of wines and cheeses, it was the ideal happy hour spot to cool down in as well.

WHAT TO DO
Take a boat ride: One of our favorite parts of our trip was the sunset sailboat cruise we took during happy hour one night. The sail was about two hours long and they provided cheese and wine and it was a gorgeous way to see the sunset out on the water. It was a little bumpy warning if you’re someone you gets seasick. There are also so many options of different boat rides to do while in Key West from scuba diving to dolphin watching! 

Watch the sunset at Mallory Square: Mallory Square is the main area downtown where you can shop from local street vendors, grab a cocktail and catch the sunset. The area gets packed come sunset time so head there early to grab a seat and drink and soak up the picturesque scene. 

Visit Hemmingway’s Home: While we unfortunately ran out of time to make a visit here, this historical spot is open to the public almost everyday for 30 minute tours. One of the main reasons I was sad we missed this was because the property is filled with cats! I did see a few (and a lot of roosters too!) walking around town though during our stay.

Explore downtown: From the colorful houses to beach side shops, there’s a ton of great shopping and spots to see right in downtown Key West. I loved walking around and seeing all the gorgeous historic homes and fun tourist shops before cocktail hour every night.

WHAT I WORE IN FLORIDA
Thanks to some amazing sales during Christmas, I stocked up on some new bikinis from J. Crew (always my go to) and brought a lot of my summer favorites too in my suitcase. I also love wearing white when on vacation and was so excited to wear this gorgeous dress that Persifor sent me for vacation! Their pieces are always my favorite to bring because they can easily be dressed up or down which is key on vacation!

For all my Florida travel guides (and other cities too!) remember to head to my travel guide page