Casey & Matt
Things To Do
The Southernmost Point Buoy
One of the most popular and touristy things to do in Key West is get a picture with the famous striped buoy. Located on the water at the corner of Whitehead Street and South Street, this point is just 90 north of Cuba. Go early in the morning to avoid the long line!
Ernest Hemingway Home and Museum
Tour the home and gardens of one of Key West's most famous residents, author Ernest Hemingway. While you're there make sure to look for the six-toed cats. There are more than 40 roaming around the property!
Truman Little White House
Harry Truman ran his winter operations from this former naval station command center, making 11 trips here during his presidency. The museum shows logs from Truman’s visits, giving visitors an idea of what crucial decisions were made here, as well as Key West historical documents and presidential artifacts.
Sunset at Mallory Square
Head to Mallory Square to experience the famous Sunset Celebration! Every evening about two hours before sunset, people gather to watch the beautiful sunset and to enjoy street performers, food vendors, and local artisans. A tradition that began in the 1960s, and is still celebrated every day!
Blue Heaven
Our favorite restaurant in Key West! It's a casual atmosphere with incredible food. There's always live music and breakfast is served until 2 p.m.! Just make sure you get there as early as possible. Lines can get painfully long as early as 8:30am, even on weekdays.
The Breakfast Club, too
Best spot for breakfast or lunch, with indoor and outdoor seating. They have 22 different bloody marys, including the Monster Mary garnished with picked veggies, bacon, jerky, shrimp and a chicken wing. Come hungry!
Sebago Watersports
Sebago Watersports offers amazing catamaran and schooner sailing tours. Choose from Key West sunset sails, water sports, kayak and snorkel tours, and parasailing. A great way to spend the day out on the water!
Fishing in Key West
Book a charter and go fishing! All three are highly recommended by the locals. Captain Chris Cahill of Knotty Game Charters https://www.knottygamecharters.com/ Captain Colin Barr of Fish Key West Charters http://fishkeywestflorida.com/ Captain Jamie Connell of Flying Fish Charters http://www.flyingfishkw.com/