Key West Fun!
3 Nights is the perfect long weekend in Key West!!
Day 1
Welcome to Florida! If you’ve landed in Miami for your Key West getaway, pick up your rental car and head south. On your way through Homestead, take a quick five-minute detour to visit the Robert Is Here Fruit Stand. This iconic stop on the journey to Key West is the perfect place to recharge with fresh smoothies, including those made with tropical fruits for a true taste of Florida.
Part of the joy of driving from Miami to Key West is discovering the roadside attractions along the route. Be sure to pause in Islamorada to explore the History of Diving Museum, home to an impressive collection of vintage underwater gear, and wander through Rain Barrel Village, a tropical garden brimming with shops, souvenirs, and local art. Don’t miss Robbie’s of Islamorada, where you can enjoy a delicious lunch and the unique thrill of hand-feeding giant tarpon fish.
Once you arrive in Key West, the final stop in the stunning Florida Keys, check into Casa Marina Key West, Curio Collection by Hilton—your retreat for the week. After the nearly four-hour drive, take some time to unwind by appreciating the hotel’s historic architecture, indulging in a spa treatment, or relaxing in the oceanfront pools. For your first meal in Key West, reserve the Toes in the Sand dining experience and savor dinner on the hotel’s private beach.
Part of the joy of driving from Miami to Key West is discovering the roadside attractions along the route. Be sure to pause in Islamorada to explore the History of Diving Museum, home to an impressive collection of vintage underwater gear, and wander through Rain Barrel Village, a tropical garden brimming with shops, souvenirs, and local art. Don’t miss Robbie’s of Islamorada, where you can enjoy a delicious lunch and the unique thrill of hand-feeding giant tarpon fish.
Once you arrive in Key West, the final stop in the stunning Florida Keys, check into Casa Marina Key West, Curio Collection by Hilton—your retreat for the week. After the nearly four-hour drive, take some time to unwind by appreciating the hotel’s historic architecture, indulging in a spa treatment, or relaxing in the oceanfront pools. For your first meal in Key West, reserve the Toes in the Sand dining experience and savor dinner on the hotel’s private beach.
Day 2
Kick off your first full day in Key West with a short stroll to the Southernmost Point buoy, marking the furthest tip of the continental U.S. This historic landmark, just 90 miles (145 kilometers) from Cuba, is one of the island's most iconic photo opportunities. After capturing some memories, head up the lively Duval Street and enjoy breakfast at Banana Cafe, a beloved French-style bistro known for its sweet and savory crêpes.
With Key West spanning only 4 miles (6.4 kilometers) long and 2 miles (3.2 kilometers) wide, it's perfect for exploring on foot, by bike, or on an insightful trolley tour. Don’t miss out on visiting key attractions like the Key West Lighthouse and Mile Marker 0, where U.S.1 begins its journey from Key West to Maine. Literature enthusiasts will want to visit the Ernest Hemingway House & Museum, followed by lunch at Sloppy Joe’s, a favorite haunt of the famous author.
As the day winds down, make sure to witness Key West's famous sunsets, a daily celebration where visitors and locals gather at Mallory Square to watch the sun sink into the Gulf of Mexico. The square comes alive with local artists, food vendors, and street performers. Afterward, head over to Pepe’s Cafe & Steakhouse, the oldest restaurant in Key West, for a delicious surf and turf dinner.
With Key West spanning only 4 miles (6.4 kilometers) long and 2 miles (3.2 kilometers) wide, it's perfect for exploring on foot, by bike, or on an insightful trolley tour. Don’t miss out on visiting key attractions like the Key West Lighthouse and Mile Marker 0, where U.S.1 begins its journey from Key West to Maine. Literature enthusiasts will want to visit the Ernest Hemingway House & Museum, followed by lunch at Sloppy Joe’s, a favorite haunt of the famous author.
As the day winds down, make sure to witness Key West's famous sunsets, a daily celebration where visitors and locals gather at Mallory Square to watch the sun sink into the Gulf of Mexico. The square comes alive with local artists, food vendors, and street performers. Afterward, head over to Pepe’s Cafe & Steakhouse, the oldest restaurant in Key West, for a delicious surf and turf dinner.
Day 3
Start your day early with a quick breakfast at Cuban Coffee Queen, where you can enjoy hearty sandwiches and strong coffee. Don’t miss the chance to snap a photo in front of their iconic “Greetings from Key West” mural. From there, it’s just a short walk to board the Yankee Freedom III ferry, which will take you to the stunning Dry Tortugas National Park. For an extra thrill, consider a seaplane flight to the park. Whichever way you choose to travel, make sure to book in advance, as these options often sell out.
Once you arrive at Dry Tortugas—whether by the two-hour ferry or 40-minute seaplane—you’ll find yourself in one of the most secluded national parks. Spend your afternoon snorkeling among vibrant coral reefs, exploring Fort Jefferson, the country’s largest 19th-century fort, relaxing on the beach, and watching for local wildlife, including nearly 300 bird species. Ferry passengers will receive a boxed lunch, while seaplane travelers should bring their own food.
After a full day at the park, you might want to freshen up and relax before dinner. Though Key West is famous for its laid-back atmosphere, you can treat yourself to an upscale dining experience at Little Pearl in Old Town. This restaurant offers three dinner seatings (5 p.m., 7 p.m., and 9 p.m.), featuring a carefully curated four-course menu that highlights local seafood. Expect creative dishes like crispy lobster with spicy peanut sauce and a decadent miso tres leches for dessert.
Once you arrive at Dry Tortugas—whether by the two-hour ferry or 40-minute seaplane—you’ll find yourself in one of the most secluded national parks. Spend your afternoon snorkeling among vibrant coral reefs, exploring Fort Jefferson, the country’s largest 19th-century fort, relaxing on the beach, and watching for local wildlife, including nearly 300 bird species. Ferry passengers will receive a boxed lunch, while seaplane travelers should bring their own food.
After a full day at the park, you might want to freshen up and relax before dinner. Though Key West is famous for its laid-back atmosphere, you can treat yourself to an upscale dining experience at Little Pearl in Old Town. This restaurant offers three dinner seatings (5 p.m., 7 p.m., and 9 p.m.), featuring a carefully curated four-course menu that highlights local seafood. Expect creative dishes like crispy lobster with spicy peanut sauce and a decadent miso tres leches for dessert.
Day 4
Time to pack your bags and hit the road back to Miami! But before you say goodbye to Key West, treat yourself to breakfast at the local favorite, Glazed Donuts. This spot is so popular that they usually sell out by noon. But this isn’t just any donut shop—everything here is made from scratch, featuring creative flavors like mango habanero, brown butter hazelnut, and the Florida Keys-inspired Key lime pie donut. Pair your donut with a cup of freshly roasted coffee, and you’re all set for the journey ahead.
As you head north, make a pit stop in Marathon at the Turtle Hospital. Here, you can tour the facility and learn about the incredible work being done to rescue and rehabilitate sea turtles. Marathon is also home to the recently restored Old Seven Mile Bridge. Once open to vehicles and then closed for several years, it’s now a park perfect for jogging, fishing, and capturing stunning photos.
On your way back to Miami, your final stop should be in Key Largo. Don’t miss out on the award-winning conch chowder and homemade Key lime pie at Mrs. Mac’s Kitchen.
Whether you’re traveling solo, with friends, family, or that special someone, exploring the natural beauty and history of Key West is always a great idea. You’ll leave feeling sun-kissed, refreshed, and relaxed, thanks to the soothing white-sand beaches, fresh seafood, and good vibes that make this destination so special. And don’t forget to check out Key West’s vibrant calendar of festivals and events for your next visit!
As you head north, make a pit stop in Marathon at the Turtle Hospital. Here, you can tour the facility and learn about the incredible work being done to rescue and rehabilitate sea turtles. Marathon is also home to the recently restored Old Seven Mile Bridge. Once open to vehicles and then closed for several years, it’s now a park perfect for jogging, fishing, and capturing stunning photos.
On your way back to Miami, your final stop should be in Key Largo. Don’t miss out on the award-winning conch chowder and homemade Key lime pie at Mrs. Mac’s Kitchen.
Whether you’re traveling solo, with friends, family, or that special someone, exploring the natural beauty and history of Key West is always a great idea. You’ll leave feeling sun-kissed, refreshed, and relaxed, thanks to the soothing white-sand beaches, fresh seafood, and good vibes that make this destination so special. And don’t forget to check out Key West’s vibrant calendar of festivals and events for your next visit!
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