The Ultimate Weekend In Key West
Looking for the ultimate tropical escape? A weekend in Key West is the perfect mix of laid-back island vibes, beautiful beaches, delicious dining, and can't-miss experiences. Whether you're planning a romantic trip, a girls’ getaway, or a spontaneous weekend escape, this Key West itinerary covers all the must-dos.
Let’s dive into the perfect 2-day Key West itinerary - sunsets, seafood, and sipping cocktails included.
Weekend In Key West, Florida
Stay:
Ocean Key Resort & Spa
Ocean Key Resort & Spa is a dreamy waterfront property that sits right at the edge of Duval Street, offering the perfect mix of relaxation and walkability. Think: spacious rooms with private balconies, beautiful ocean views, an award-winning spa, and a stunning infinity pool overlooking the water. You’re also steps from Mallory Square, which means front-row seats to the famous Key West sunsets.
Casa Marina Key West, A Waldorf Astoria Resort (Splurge)
If you’re looking to splurge for an iconic, ultra luxe property, Casa Marina Key West is for you. This property blends historic charm with elevated luxury - think grand architecture, gorgeous tropical grounds, and the largest private beach on the island. As a guest, you can soak up the sun in a cabana by the oceanfront pool, indulge in a spa treatment, or enjoy sunset cocktails with toes in the sand. It’s peaceful, romantic, and just far enough from Duval Street to feel like a true retreat.
Allure Travel Co. Tip: At Allure Travel Co., we have partnerships with thousands of hotels around the world. Booking a stay through us is a complimentary service-meaning no extra cost to you! Not only will you save valuable time, but you’ll also unlock exclusive perks (like hotel credits and complimentary room upgrades, if available) and experience VIP treatment throughout your stay.
Day 1
Start with Breakfast at Sarabeth's
A charming local favorite, Sarabeth’s is the ideal place to kick off your Key West weekend. Grab a seat on the garden patio and order the eggs Benedict, lobster sliders, or their avocado toast with a tropical twist.
Tour the Hemingway Home & Museum
A must for literature lovers, the Hemingway Home offers a peek into the life of one of America’s most iconic writers. Explore beautiful gardens, Spanish Colonial architecture, and the famous six-toed cats that still roam the property.
Climb the Key West Lighthouse
Right across from the Hemingway Home, this historic lighthouse offers full views of the island from the top. The on-site museum shares stories from lighthouse keepers past.
Snap a Photo at the Southernmost Point
You can’t visit Key West without stopping by the iconic Southernmost Point Buoy. Located just a short walk from Duval Street, it’s the perfect photo op to prove you made it to the southern tip of the continental U.S.
Lunch at Garbo’s Grill
Garbo’s Grill is a food truck gem, serving up some of the best fish tacos, burgers, and Korean BBQ in town. Pro tip: order the Umami burger and enjoy it under the shade of palm trees.
Stroll Along Duval Street
Spend the afternoon exploring vibrant Duval Street. From colorful shops and historic bars to local art galleries and lively cafes, it’s the heart of Key West.
Watch the Sunset at Mallory Square
Join locals and travelers for the nightly Sunset Celebration at Mallory Square. Expect street performers, live music, and one of the most stunning sunsets you’ll ever see.
Dinner at Louie’s Backyard
Tucked away from the buzz of Duval, Louie’s Backyard is a romantic oceanfront restaurant with unforgettable views and even better seafood. Make a reservation in advance - it’s popular for a reason!
Dessert at Better Than Sex Dessert Bar
End the night at one of the most unique dessert spots in the country - Better Than Sex Dessert Bar. Expect a moody, sultry atmosphere and rich treats like the Cookie Nookie Pie.
Day 2
Breakfast at Blue Heaven
Blue Heaven is a Key West classic and perfect for a slow, tropical morning. Don’t miss the lobster BLT Benny or banana pancakes. No reservations are accepted, so plan for a little wait (it's worth it!).
Relax at Smathers Beach
Smathers Beach is the largest public beach in Key West - great for sunbathing, paddleboarding, or relaxing with your toes in the sand.
Lunch at Sloppy Joe’s Bar
A true Key West institution, Sloppy Joe’s has been around since the 1930s. Grab a sandwich, sip on a cold beer, and soak up the laid-back vibes.
Sunset Catamaran Cruise
One of the best ways to experience Key West is by water. Book a sunset catamaran cruise and enjoy island views, ocean breezes, and sparkling cocktails as the sun dips below the horizon.
Dinner at Santiago’s Bodega
Santiago’s Bodega is a cozy tapas spot, perfect for dinner with friends or a romantic date. Menu musts: bacon-wrapped dates, lamb patties, and shrimp and grits. Save room for the housemade key lime pie.
Bar Hop on Duval Street
End your weekend in Key West with a night out on lively Duval Street. Whether you want live music at The Green Parrot, frozen drinks at Fat Tuesday, or a rooftop cocktail at The Bull, every spot has its own vibe - and they’re all walkable.
Interested in booking a trip to Key West?
At Allure Travel Co., we don’t just plan trips-we curate experiences. We offer bespoke travel planning, luxury hotel bookings, and travel concierge services. If you’re looking for full-service planning or to simply elevate your experience, we’d love to work with you!
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