Maddy & Tommy
Things To Do
The Hemingway Home and Museum
For our literary history (and 11-toed cat!) fans, this historic home is a neat spot to checkout!
Fort Zachary Taylor Historic State Park
Our favorite beach on the island. Don’t skip out on a free tour of Fort Zachary by one of the park guides! If you feel comfortable swimming, there is a small snorkel spot off the beach.
West Martello Tower and Key West Garden Club
Maddy’s favorite spot on the island :)
Fury Water Adventures Key West
The go-to water sports tours. Some of our favorites are the Reef & Ritas Snorkel Trip or a sunset cruise!
General Horseplay
One of our favorite bars on the island! Roll a dice for the price of your drink on happy hour (M-F, 3-6 pm). Also where we had our engagement photos done!
Grand Cafe Key West
Can’t miss Happy Hour in the back bar! (4-7 pm) Half off all appetizers and drinks including martinis, wines, and specialty cocktails! Maddy's favorite happy hour item is their Beef Tenderloin Carpaccio!
Latitudes
Our favorite restaurant to catch a sunset in the world! Be sure to schedule a reservation far in advance and be ready to splurge. Your reservation includes a ferry to the island of Sunset Key.
Schooner Wharf Bar
The bar Kenny Chesney is singing about in his song, "Bar at the End of the World" Needless to say, it is one of Tommy's favorite bars! Enjoy affordable cocktails waterfront with live music playing nearly every hour of the day. They also have two happy hours daily from 7am-noon and 5pm-7pm. See happy hour in the attached link
Hogfish Bar & Grill
Some of the freshest fish if you are in the mood for seafood! We recommend the hogfish sandwich. Located on Stock Island (near hotel).
Martin's
One our of favorite happy hours in Key West! They have half off tapas and $6 Martini's during their daily happy hour from 4-6pm
Blue Heaven
A fantastic breakfast spot. Dine with the locals (roosters)! Get the Lobster Eggs Benedict if you come here!
Better Than Sex - A Dessert Restaurant
It sounds crazy, but this is a delightful dessert restaurant! Make a reservation in advance.
Bagatelle
Daily happy hour from 4-6pm! Must try their happy hour lobster mac n' cheese or their expresso martini!
Lazy Dog Adventures
Cheap kayak & paddle board rentals on Stock Island. Take a guided tour or just schedule a rental for a few hours. Paddle through mangrove tunnels straight from the Caribbean to the Atlantic!
Robbie's of Islamorada
Hand-Feed Tarpon here! A Florida Keys must!
Wahoo's Seafood Bar and Grill Restaurant
Great happy hour overlooking the water in Islamorada on the way down. See link for their happy hour menu
Islamorada Brewery & Distillery (Islamorada)
Tommy's favorite beer is located at this distillery named: No Wake Zone! It is a Coconut Key Lime ale. Stop by for a pint on your way down or for a "Pre-flight Brewski"
Lazy Days
Waterfront seafood restaurant that serves on of our favorite dishes, Hogfish served Lazy Days Style. It is Tommy's death row meal choice. It is Hogfish Encrusted with Japanese bread crumbs, sautéed, topped with tomatoes, scallions, parmesan cheese and a homemade Key Lime Butter Sauce. See photo of Hogfish Lazy Day's Style in the photo
Keys Fisheries
All day $20 for 5 Stone Crab claws with a great waterfront view! A must try if you have never had Stone Crab! Also, don't pass up their lobster reuben!
Square Grouper Bar and Grill
Come here for a grouper sandwich
Baby’s Coffee
Maddy's favorite coffee shop in the keys. Great place for breakfast or a coffee stop on your way to the airport
Alabama Jacks
If you are looking for a great dive bar, look no further! Think bayou meets Florida Everglades. Might not be for everyone...