3 days you’ll remember in Key West, Florida.
Key West invites you to leave your shoes, worries, and schedules at the shore. This southernmost point of the continental U.S. is more than sunshine and snorkeling—it’s a quirky, colorful playground where sunsets are celebrated daily and roosters roam freely. Hemingway once called it home, and you just might call it paradise by the end of day three.
This Foresyte itinerary will guide you through island time in its purest form—where rum meets rhythm, and every sunset feels like a standing ovation.
Let’s take it from the top.
Itinerary inspired by the Foresyte community.
📍 Sippin’ and Sailin’
Day 1: Sunset Sail
“Set your watch to golden hour. Drift along the turquoise horizon as the sky lights up in flamingo pinks and tangerine hues.”
Day 1: Dinner @ Prime Steakhouse
“Old-school elegance meets island indulgence. Perfectly charred steaks and crisp martinis await behind cool marble and dim lights.”
Day 2: Snorkel Adventure
“Swim with schools of neon fish and maybe a turtle or two, the coral reefs are teeming with life just offshore.”
Day 2: Lunch @ Kaya Island Eats
“Tropical fusion plates with a kick. Think Caribbean-Japanese vibes with a view that matches the flavor.”
Day 2: Jet Ski Tour
“Throttle through mangrove mazes and wave-chop your way around the island, adrenaline with a side of sea spray.”
Day 2: Dinner @ Red Shoe Island Bar
“A Key West legend with tiki vibes, live music, and rum-fueled dance breaks. No judgment if you leave with new friends.”
Day 3: Brunch @ Nine One Five
“Refined dining on a wraparound porch. Truffle fries, seared scallops, and an ever-so-slight breeze of sophistication.”
Day 3: Shark Sightings
“Hop aboard a guided tour and spot nurse sharks gliding below, an exhilarating reminder that you’re in their playground.”
Day 3: Bites @ Santiago’s Bodega
“Tapas done right. Graze through plates of chorizo, lamb lollipops, and blue cheese-stuffed dates while the wine keeps flowing.”
Day 3: Mangrove Kayaking
“Paddle through quiet, tangled tunnels of green. Keep an eye out for herons, iguanas, and secrets hiding in the stillness.”
Day 3: Dinner @ Atlas Izakaya
“A sultry izakaya tucked off the beaten path. Order the omakase and let the chefs take you on a midnight sushi ride.”
Key West Itinerary FAQ.
What are the best things to do in Key West for a weekend trip?
Tour the Ernest Hemingway Home, visit the Southernmost Point Buoy, enjoy a sunset sail, explore Duval Street, and snorkel at Dry Tortugas National Park.
When is the best time to visit Key West for a weekend getaway?
December through May offers sunny skies, mild temps, and vibrant energy without the hurricane-season humidity. Winter and early spring are peak travel windows.
Where should I stay in Key West for a weekend trip?
Opt for Old Town to stay close to the action—Duval Street, Mallory Square, and local dining. Boutique guesthouses and charming inns are especially popular here.
What are the best restaurants to try in Key West on a weekend trip?
Don’t miss Blue Heaven for brunch, Eaton Street Seafood for lobster rolls, El Siboney for Cuban flavors, and Latitudes for waterfront dining with sunset views.
Is Key West safe for weekend travelers?
Yes, Key West is generally safe, walkable, and welcoming. Most visitors find the vibe relaxed and friendly, with plenty of well-lit areas for evening adventures.
How should I spend a Sunday in Key West?
Start with a waterfront breakfast, then rent a bike to explore the island. Wrap it up with live music, a sunset toast at Mallory Square, and one last conch fritter.
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