Key West Itinerary

Jacob and I enjoyed our time in Key West. We went in spring and the flowers were in full bloom, the water was crystal clear, and the slight breeze helped us endure the heat. Many of the activities in Key West are outdoors. You can always catch a break by visiting the beach(s), or going in and out of the local shops scattered around the island. Our trip was not pre-planned, so each day was a “play by ear”. Here is a look at some of the activities we did, where we stayed and even some of the food stops we loved!

Where we stayed:

The Gates Hotel -We really enjoyed our stay here. It was quiet, clean, and offered a free shuttle to the downtown area.


Smathers Beach-We went here early one morning to see the sunrise and it was beautiful!

Old Town Trolley– We really enjoyed our historical tour of the island. It’s 90 minutes from start to end but you can get off and on at any time.

American 2.0 Sunset Sail-You can also sail during the day, but I highly advise going out for the sunset-it’s absolutely gorgeous.

Bike Rentals-There were too many on the island to count-you could even rent bikes from the hotel. Riding around the island was so fun and it gave us the freedom to sightsee how we wanted too! This ranged from $10-$15 for the day.

Sunset Celebration at Mallory Square: Every night on the island there is a sunset celebration. Everyone joins at Mallory Square (downtown) for street performances, food, and of course to watch the sun set over the water.

Shopping: There are honestly shops all over the place. We founded a hidden gem on the marina side, but there are also great stops near the port. Head to Duval Street for some of your favorite places like Express, Gap, Banana Republic.

Food Stops:

Kermit’s-Must try the key lime pie on a stick

The Conch Shack

The Waterfront Brewery

Hog’s Breath Saloon

The Blind Pig Food Truck

Hard Rock Cafe

If you go to the Sunset Celebration get the guacamole that two ladies serve on their cart-it’s so amazing!

(There were other little “shack” type places we stopped at around the island)


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