We are so excited to share our favorite place with our favorite people. We hope you'll fall in love with Key West like we have. Let this weekend be a time of relaxation, celebration, and fun- You're on island time now!
Jessica & Lee
June 19, 2026 • Key West, FL
50 Days To Go!
Jessica & Lee
June 19, 2026 • Key West, FL
50 Days To Go!
Our fav Key West spots!
Our Favorite Key West spots!
The Best Food
Blue Heaven- THE Brunch Spot (Lobster and Steak Benedict- YES)
Cuban Coffee Queen- Quick Cafe Con Leche and Cuban Breakfast Items (Try the Guava and Cheese Bread)
Moon Dog- A fun brunch/lunch spot with the most incredible pastry/dessert counter (and to go window)
Angelina's Pizza- Voted best pizza on the island by 3 out of 4 in our family in a official taste test. (Home of the world famous Sit with Kit podcast)
Mr. Z's- Lee's vote for best pizza and also known for their Philly cheesesteaks
Garbo's Grille- Food Truck inside of Hank's- don't miss the Burger AND Korean Beef Tacos (get both!)
Frita's Cuban Burger Cafe- We've never had a bad bite here. It's a hole in the wall, but you can't go wrong. Add on the Sangria (trust us) and ask for Henry!
Pepe's Cafe- Oldest eatery in the Keys- the best happy hour deals you'll find. Key West Pink Shrimp/Oysters/Fresh Margaritas all under $7
El Siboney- Jessica's all time favorite restaurant. The best Cuban food you'll find- off the beaten path but worth it.
Kermit's- Our fav. key lime pie, but don't let this stop you from trying one everywhere you go!
Flamingo Crossing- Don't leave the island without trying one or more scoops. The kids favorite icecream place ever!
Drinks- Because it IS Key West
Captain Tony's- always our first stop. The original Sloppy Joe's packed full of history. Try a Pirate Punch (but just one) and hang your dollar here.
Mary Ellen's- The best late night spot for the night owls!
Tree Bar- Right in the middle of the action, great people watching, and perhaps the best drink on the island. You won't regret a fresh orange crush.
Chart Room- Free crockpot hotdogs, peanuts, and popcorn- but the history makes this spot worth the stop.
Green Parrot- Where the locals hang. Iconic Key West and fun late night music.
Sunset Pier- If you've never been to Key West, this is the photo opp.
Hank's Hair of the Dog- Lee and Penny's favorite Key West spot- the local music spot can't be topped.
Things you have to see:
Mallory Square- The iconic sunset view every night, live street performers, and Lee's buddy the Catman!
Hemingway House- Even if you aren't well versed in Hemingway, this tour is incredible. Classic Key West house and plenty of 6- toed cats (yes, really).
Key West Lighthouse- Classic and iconic. Tours offered.
Books and Books- the cutest local bookstore. Owned by Judy Blume- who you may get lucky enough to meet (she still runs the register some days).
Southernmost Point Buoy- the most iconic Key West stop. You can't leave without your picture here.
Old Town Trolley Tours- For the best lay of the land- hop on an off tour to visits all the best spots.
Fort Zachary Taylor State Park- if you want a beach day, this is the spot. Plus explore the historical fort on site, have a picnic, and soak up the views.
Robert the Doll- Visit him if you dare- but he is creepy!
Fury Water Adventures- If you want to experience the water down here, this is the best best. They offer sunset music cruises, snorkeling, and more.