Caitlyn & Brody
Things To Do
Duval Street
This corridor in Old Town is a go-to place for a night out on the town. Running from the Gulf of Mexico to the Atlantic Ocean, it is home to endless dining, shopping, and entertainment options.
Southernmost Point of the Continental U.S.A.
Get your picture taken at the southernmost point of the contiguous states of North America! It is marked by the "Southernmost Point Buoy," a concrete buoy that is permanently anchored in Key West. Cuba is about 90 miles south of this location!
Fort Zachary Taylor Historic State Park
Visit the historic Fort Zachary Taylor State Park and relax on the beach. Brody and Caitlyn can't recommend these tropical views enough!
Truman Waterfront Market
Hit Key West's local farmer's market on Thursday from 2-7 pm at the Truman Waterfront for fresh grown produce, gorgeous orchids & native plants, artisan selection of meats and cheeses, pickles, honey, nuts & dried fruits, natural soaps and so much more. You’ll find Key West crafts, gifts and the perfect souvenir to take home!
Mallory Square
As dusk approaches, head to Mallory Square for the nightly Sunset Celebration. Get there early to enjoy street performers and delicious food before watching the sun sink into the water.
Conch Train Tour
For an easy way to take in the sights, book your spot on a Conch Tour Train. The one-day tour includes three stops and a full loop through Old Town.
Key West Lighthouse
Climb 88 steps to the top of the Lighthouse Tower to get one of the best views of the island and its surrounding turquoise waters!
The Hemingway Home and Museum
The Ernest Hemingway Home operates as a museum providing guided tours every fifteen minutes from 9-5. Hemingway lived and wrote in this house for ten years. Visit this National Historic/Literary Landmark that is recognized by the Library of Congress for its importance in U.S. History, grand architecture, lush gardens, educational tours, book store, gift shop, and the world famous six-toed cats!
The Key West Butterfly and Nature Conservatory
A recommendation by Brody's mom, Jennifer! Take a walk among hundreds of free flying butterflies, exotic birds and glorious flamingos inside the soaring glass-domed tropical butterfly habitat.
Blue Heaven
The BEST Key Lime Pie in the Keys! Located in historic Bahama Village, Blue Heaven, one of the most casual of Key West restaurants features indoor & outdoor dining, live entertainment and american, caribbean and vegetarian cuisine.
Cuban Coffee Queen Downtown
"Drink more Cuban Coffee and Do Stupid Things Faster." On our last trip to Key West, we enjoyed Cuban Coffee Queen every morning!
Sandy's Café
A recommendation by Brody's grandpa, Papa! Home to the best and original Cuban sandwich! Stop by Sandy’s Café for fast friendly service with two convenient walk-up windows.
Tart Tales
Take a Key Lime Pie Walking Tour for $15. Coffee and pie included!
Moondog Cafe Key West
Enjoy the beautiful pastry case and dessert at Moondog Cafe!
Schooner Wharf Bar
Highly recommend morning happy hour at Schooner Wharf Bar. This funky open-air bar is located on the site of the old Singleton Shrimp factory and had delicious cuisine and great live music!
Two Friends Patio Restaurant
Craving a Bloody Mary? Head to Two Friends Patio for the best Bloody on the island. Also home to local seafood dishes including shrimp, fish, lobster, oysters, conch, and crab, and they proudly serve the Island’s best char-grilled steaks and burgers, and the now-Famous Basin Street Broiled Oysters. Don't forget live music everyday and karaoke every Friday and Saturday night!
El Siboney Restaurant (Stock Island)
A recommendation by Brody's grandpa, Papa! El Siboney has a reputation as Key West's top restaurant for authentic Cuban food, Paella, and local seafood.
Sloppy Joe's Bar
Sloppy Joe’s history began with the end of prohibition in 1933. Located at the corner of Duval and Greene since 1937, it is one of the most famous bars in America and is known worldwide. Sloppy Joe’s is full of Key West history and characters. The bar offers drinks, food, a retail store, and live music 365 days a year… and is still the best party in Key West.
Irish Kevin's Restaurant & Bar
Since July of 1998 Irish Kevin’s Bar has been inviting guests to “come on in”! Irish Kevin’s is located in the heart of Old Town Key West on the World-Famous Duval Street. They have a full bar with unique cocktails and an array of beers on tap. Live entertainment is served up seven days a week, and be sure to try their Guinness braised, slow cooked, piled high Reuben!
Green Parrot Bar
Grab a drink and listen to live music at the Green Parrot Bar, one of Key West’s most iconic watering holes. Found off Duval Street, this spot has been an island staple since 1890 and is known for its signature rum drinks and Monday night Bingo!
Sunset Watersports
Book Sunset Watersports for the island's best experiences, including Key West’s best sandbar charters, reef snorkeling, parasailing, sunset cruises, jetski tours, dinner cruises, boat rentals, eco kayak adventures in the Mangrove Sanctuary & more!
Key West Seaplane Adventures
Key West Seaplane Adventures provides transportation into Dry Tortugas National Park.
Cowboy Cowgirl SportFishing Charters
Dive into the depths of Key West’s waters with Deep Sea Fishing Adventures. Target a variety of big game species and feel the thrill of a challenging catch.
Tropic Cinema
Visit Tropic Cinema for a wide range of films, a great beer & wine selection, and the best popcorn in town!