Islamorada isn’t just one of the Upper Keys, it’s six: Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key, and the offshore islands of Indian Key and Lignumvitae Key. Known for its fishing and watersports, Islamorada is a great place to play.
Day 1: Sportfishing Capital of the World
7:00 a.m.
Islamorada is known as the “Sportfishing Capital of the World,” so start the day by heading over to Robbie’s of Islamorada marina for a private charter or spot on the Capt. Michael fishing party boat. Be sure to feed the tarpon at the end of Robbie’s dock. www.robbies.com
2:00 p.m.
It’s time to eat your catch, so bring it to one of Islamorada’s better restaurants, like the Hungry Tarpon (right at Robbie’s), Chef Michaels, or Pierre’s Restaurant & Lounge at Morada Bay. www.islamoradachamber.com
Day 2: Above and Below
8:00 a.m.
Spend the morning underwater with a snorkeling or scuba diving tour, taking in some of the Keys’ best underwater attractions like Davis Reef, Conch Wall, Alligator Reef, or Pickles Reef. www.fla-keys.com/islamorada
Spend the afternoon learning about another active Islamorada sport with a kiteboarding lesson at oTHErside Board Sports. www.othersideboardsports.com
4:00 p.m.
Relax before dinner with a signature Hot Lava Shell Massage treatment at Cheeca Lodge & Spa’s Cheeca Spa. www.cheecaspa.com
Day 3: A Walk on the Mild Side
9:00 a.m.
Spend a relaxing morning wandering through the burgeoning Morada Way Art & Cultural District, looking for locally produced artworks. Consider taking one of the classes offered by more than a dozen artisans on topics ranging from pottery and painting to writing and woodwork. http://moradaway.org
1:00 p.m.
After lunch, head over to the Rain Barrel Artisan Village, a small artists’ enclave with art galleries, jewelry, glass, and stained-glass studios. www.keysdirectory.com/rainbarrel
7:00 p.m.
End the day at the restaurant named for the famed Western novelist and keen Keys catch-andrelease fisherman Zane Grey. The Zane Grey Long Key Lounge is located on the second floor of World Wide Sportsman, a Bass Pro Shops store with a marina that hosts dozens of charter captains. http://restaurants.basspro.com/ZaneGreyLounge