Start a day of sightseeing in Key West off with a cafe con leche or a cortadito at Cuban Coffee Queen (284 Margaret St., Key West. 305-292-4747, cubancoffeequeen.com), where you order at a pickup window and take your food to go. Explore the sidewalk cafes, open-air bars and museums on foot or catch a ride on the Conch Tour Train that highlights the island's history and various attractions. The Ernest Hemingway Home and Museum (907 Whitehead St., Key West. 305-294-1136, hemingwayhome.com) makes for an interesting stop for literary buffs; plus, 50-some six-toed infamous Hemingway cats call the property home.
Visit the Ernest Hemingway Home and Museum in Key West, where the author lived from 1931 to 1939. LAURENCE NORAH / FLORIDA KEYS NEWS BUREAU
At sunset, meander over to Mallory Square to experience the nightly “sunset celebration” — expect musicians, jugglers, acrobats and other performers. If you’re feeling extra-touristy, head to the giant Southernmost Point marker and pose for a pic at the southernmost point in the continental United States — just 90 miles from Cuba.
In Key West, water activities are plentiful. Fury Water Adventures (furycat.com) offers a popular Ultimate Adventure option — an action-packed day that includes parasailing, jet skiing, kayaking and snorkeling. They also offer more low-key options, like sunset cruises and a Dolphin Watch & Snorkel tour.
Will Soto performs a juggling and high-wire act at the Sunset Celebration at Mallory Square in Key West. ROB O’NEAL / FLORIDA KEYS NEWS BUREAU
Next, enjoy a leisurely drive up through the Lower Keys, heading into Marathon for the day. While you're there, a great family-friendly activity is a visit to the Florida Keys Aquarium Encounters (11710 Overseas Highway, Marathon. 305-407-3262, floridakeysaquariumencounters.com). If you're staying the night in Marathon, treat yourself to a decadent meal at the Butterfly Café (2600 Overseas Highway, Marathon. 305-289-7177, tranquilitybay.com/dining/butterflycafe); otherwise, keep on driving toward Grassy Key for a stop at the Dolphin Research Center (58901 Overseas Highway, Grassy Key. 305-289-1121, dolphins.org), which is home to a family of dolphins and California sea lions.
Then you might want to consider a stop at Duck Key, home to the 60-acre Hawks Cay Resort (61 Hawks Cay Blvd., Duck Key. 1-888-395-5539, hawkscay.com), which partially reopened in March with 100 villas and its Calm Waters Spa, Sunset Pool, Coral Cay kids' activities center, and Angler and Ale restaurant. The main hotel, with 177 guestrooms, is set to reopen this summer.
In the Keys, Henry Flagler’s original Seven Mile Bridge bisects Pigeon Key on the right, while today’s modern-day bridge is on the left. ANDY NEWMAN / FLORIDA KEYS NEWS BUREAU
Moving north, you can settle into Islamorada for a few days. While you're in the "sport-fishing capital of the world," grab lunch and dine with your toes in the sand and the brilliant aqua waters in the background at Lazy Days Restaurant (79867 Overseas Highway, MM 80, Islamorada. 305-664-5256, lazydaysrestaurant.com) or the Morada Bay Beach Café (81600 Overseas Highway, Islamorada. 305-664-3225, moradabay.com). In the late afternoon, belly up to the taproom bar at the Florida Keys Brewing Co. (81611 Old Highway, Islamorada. 305-916-5206, floridakeysbrewingco.com) for a tasting. Cap off the day with sunset drinks at Marker 88 (88000 Overseas Highway, Islamorada. 305-852-9315, marker88.info) or revel in some fine dining at Pierre's (81600 Overseas Highway, Islamorada. 305-664-3225, moradabay.com/pierres).
The Moorings is an idyllic, beachfront property in laid-back Islamorada, featuring freestanding cottages and a palm-fringed beach. CONTRIBUTED BY THE MOORINGS
For the ultimate indulgence, check in to one of the freestanding, picturesque cottages at the Moorings (123 Beach Road, Islamorada. 305-664-4708, themooringsvillage.com) — a striking beachfront resort where the Netflix series "Bloodline" filmed. The cottages (ranging from one to three bedrooms) offer full kitchens and furnished porches. While the Moorings' structures suffered little damage from Hurricane Irma, its lush landscaping is a different story — but replanting efforts are already underway. The iconic dock was rebuilt, and the swimming pool was completely replaced, restoring the resort's beauty.
After leaving the peaceful community of Islamorada, consider a stop in Key Largo, where the Ocean Pointe Suites (500 Burton Drive, MM 92.5, Key Largo. 305-853-3000, providentresorts.com) reopened at the end of March with a restored private beach.
When you’re done vacationing, drive up to Miami to fly out — and ponder when you can return to the Keys.
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