The Ultimate 3 Day Key West ItineraryThe Perfect Weekend Guide to America's Southernmost City
- Cari
- 1 hour ago
- 6 min read
If you're dreaming of turquoise water, colorful streets, incredible seafood, unforgettable sunsets, and a little island charm without needing a passport, Key West, Florida should be at the top of your travel list. Located at the very end of the Florida Keys, Key West feels like a world all its own. From historic homes and lively Duval Street to snorkeling adventures and waterfront dining, it's one of the most unique destinations in the United States. Here's exactly how we'd spend three unforgettable days in Key West.
Why Visit Key West?
There's simply nowhere else quite like it. Key West combines Caribbean vibes, rich history, fresh seafood, live music, breathtaking sunsets, and some of the friendliest people you'll meet. Whether you're celebrating a special occasion or simply looking for an easy weekend getaway, Key West offers the perfect mix of relaxation and adventure.
Before You Go
How to Get to Key West
You have two great options when visiting Key West.
Fly Directly into Key West International Airport (EYW)
The easiest option is flying directly into Key West, located just minutes from Old Town.
Fly into Miami and Drive the Overseas Highway
If you have extra time, this is our favorite option. Fly into Miami International Airport (MIA) and drive the famous 127 mile Overseas Highway (U.S. Route 1) to Key West. The drive takes approximately 3.5 to 4 hours and is considered one of the most scenic road trips in America, with countless bridges connecting the Florida Keys and spectacular ocean views along the way.
Day 1
One of our favorite first stops in Key West is the Visitor Information Center. It's a great place to pick up free maps, brochures, and local coupons that can save you money on attractions, restaurants, trolley tours, museums, and water activities. The friendly staff can also answer questions, recommend hidden gems, help you plan your itinerary, and point you toward current events happening during your visit. Spending just a few minutes here can help you save money and make the most of your time in Key West. https://keywest123.com/
Arrive and Experience a Key West Sunset
After checking into your hotel, spend a little time exploring Old Town Key West before your first unforgettable island sunset. Walk Duval Street, browse the local shops, grab a frozen drink, and soak up the laid back atmosphere that makes Key West so special.
Golden Hour with Fury Catamaran
One of our favorite experiences in Key West is the Fury Sunset Catamaran Sail.
This relaxing evening cruise includes:
Live music
Unlimited drinks
Hors d'oeuvres
Incredible sunset views from the water
Watching the sun disappear into the Gulf of Mexico from a sailboat is something every visitor should experience at least once.
Dinner at Sunset Pier
After your cruise, head to Sunset Pier. Located right on the waterfront, it's one of the best places in Key West for fresh seafood, tropical drinks, and live music. Order fresh fish, watch the boats come in, and enjoy your first evening on island time.
Day 2
History, Dolphins, and Key Lime Pie
Breakfast at Sunny Eggs
Start your morning with breakfast at Sunny Eggs Key West, a local favorite known for hearty breakfast plates and excellent coffee.
Visit the Ernest Hemingway Home and Museum
Arrive early before the crowds. The Ernest Hemingway Home and Museum is one of Key West's most famous attractions. Walk through the beautifully preserved home where Hemingway lived and wrote, then meet the famous six toed cats that still roam the property today.
Lunch at Dorada
After exploring Old Town, stop by Dorada for lunch. It's a great place to enjoy fresh seafood and lighter fare before heading out on the water.
Dolphin Safari Charters
If we had to recommend one excursion in Key West, this would be it.
Spend the afternoon with Dolphin Safari Charters exploring crystal clear waters, snorkeling, sandbars, and hopefully spotting wild dolphins. If you can, ask for Captain Dan. He made our trip unforgettable and knows these waters incredibly well.
Dinner at Blue Heaven
No trip to Key West is complete without dinner at Blue Heaven. Known for its quirky outdoor courtyard, roaming chickens, Caribbean inspired cuisine, and live music, it's one of the most iconic restaurants on the island. And whatever you do...
Don't leave without ordering the Key Lime Pie. Trust us.
Day 3
Slow Down and Enjoy Island Time
One of our favorite things about Key West is that Sunday mornings feel different.
Nobody seems to be in a hurry.
Breakfast at Cuban Coffee Queen
Start your day with a classic café con leche and one of their famous breakfast sandwiches.
It's the perfect way to experience authentic Key West flavors before the day gets busy.
Explore Mallory Square
Before the crowds arrive, take a peaceful walk through Mallory Square.
Later in the day this area becomes famous for its nightly Sunset Celebration, but mornings offer a much quieter atmosphere that's perfect for photos. Take a picture at Mile Marker Zero and the Southern Most Point.
Visit the Key West Butterfly & Nature Conservatory
If you're looking for a relaxing activity, spend an hour wandering through one of the most beautiful attractions in Key West. Thousands of colorful butterflies fly freely throughout the tropical gardens, creating one of the most peaceful experiences on the island.
Lunch at The Lobster Shack
Before heading home, enjoy one last seafood meal at The Lobster Shack Key West.
Fresh lobster rolls are the star of the menu and the perfect way to end your weekend.
Head Home
Book an evening flight if possible so you can squeeze every last minute out of your Key West getaway before heading back to the airport.
Where to Stay in Key West
Whether you're planning a budget friendly getaway or celebrating something special, these hotels are excellent choices with consistently high guest ratings and are available through Booking.com.
Budget Pick
Ibis Bay Beach Resort
Best for:Â Travelers looking for affordable waterfront accommodations close to Old Town.
Why we recommend it:
Waterfront location
Tropical island atmosphere
Free parking
Great value for Key West
Excellent guest reviews
Mid Range Pick
Havana Cabana at Key West
This colorful resort captures the fun spirit of Key West while offering resort style amenities at a reasonable price.
Highlights:
One of the largest pools in Key West
Complimentary shuttle to Duval Street
Tropical décor
Excellent guest ratings
Luxury Pick
Ocean Key Resort & Spa
If you're celebrating an anniversary, honeymoon, or milestone birthday, this is one of the finest places to stay in Key West.
Why guests love it:
Prime location overlooking Mallory Square
Oceanfront rooms
Luxury spa
Sunset views
Walk to Duval Street
Outstanding guest reviews
Tips for Visiting Key West
Rent bikes or golf carts instead of driving.
Visit between November and May for the best weather.
Make dinner reservations well in advance.
Book sunset cruises early because they often sell out.
Wear comfortable shoes. Old Town is very walkable.
Don't rush your schedule. Some of the best moments in Key West happen when you simply slow down.
Frequently Asked Questions
Is three days enough for Key West?
Yes. Three days gives you enough time to experience the island's top attractions, enjoy the water, explore Duval Street, and relax without feeling rushed.
Should you fly or drive?
If you're short on time, fly directly into Key West. If you have an extra day, driving the Overseas Highway from Miami is one of the most scenic road trips in the country.
Is Key West walkable?
Absolutely. Old Town Key West is easy to explore on foot, by bicycle, or by golf cart.
What is the best time to visit Key West?
November through May offers warm temperatures, lower humidity, and plenty of sunshine.
Final Thoughts
Key West is one of those destinations that somehow feels both exciting and relaxing at the same time. Between sunset sails, fresh seafood, historic streets, crystal clear water, and unforgettable island sunsets, it's easy to understand why so many travelers return again and again.
If you're planning your first visit, this three day itinerary covers the perfect mix of sightseeing, adventure, and downtime so you can experience the very best of Key West.
Planning your trip? Book your hotel through our Booking.com links to support The Saltlife Family at no additional cost to you, and save this itinerary for your next Florida Keys adventure.