4-Day Key West, Florida Itinerary

Key West, Florida Idea Board

How will I be able to access?

Already signed up? Once you requested, you will see this idea board added to your account in the next 12 hours.

Haven't signed up yet? Once you requested, you'll receive an invitation to a journey. You can then follow the link to sign up and access this board on your account.

4 Days in Key West, Florida

The island's boisterous history, free-spirited outlook and unique “Floribbean” vibe are powerful draws for all kinds of visitors, whether you're into water-sports, night-life, nature, or art.

Day 1 Highlights


DoubleTree Resort by Hilton Grand Key

DoubleTree Resort by Hilton Grand Key

A 4-star hotel with outdoor pool that's close to the infamous Smathers Beach.

Extreme Adventures Shark Tours

Extreme Adventures Shark Tours

See wild sharks, dolphins, stingrays and other marine life in action on this Key West boat tour that lets you get up close while staying dry. Slip on provided polarized sunglasses for prime viewing of these amazing creatures, and keep your camera handy as the captain drops bait to lure a variety of sharks right to the side of the boat for a safe yet thrilling swarm.

Nancy Forrester's Secret Garden

Nancy Forrester's Secret Garden

An educational parrot sanctuary that has been open to the public for 35 years. They rescue, rehome, train parrots.

Sunset Sail with Full Bar, Live Music & Hors D'oeuvres

Sunset Sail with Full Bar, Live Music & Hors D'oeuvres

Watch the sun set and the moon rise off the coast of Key West on this sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 70-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset as the sun glistens and gently settles into the water.

Smather’s Beach

Smather’s Beach

Go to Smather’s Beach (or Higgs) at night, the stars are incredible. It is Key West's largest beach that runs along the southern shore of the island for almost 2 miles. Beach activity ranges from tanning, volleyball, and watersport/beachsport rentals.

Day 2 Highlights


Ernest Hemingway  Home & Museum

Ernest Hemingway Home & Museum

Set up much as it was when Hemingway himself lived in Key West, the Hemingway house sits on a large plot along Whitehead Street, boarded by a red brick wall. The square, whitewashed, Spanish-Colonial style house is set back amid lush green palms which hide the building’s façade from the road making it feel more secluded on entry. Inside is airy and spacious, with minimal décor.

Key West Lighthouse

Key West Lighthouse

The current lighthouse opened in 1848 with a woman as its Keeper; nearly unheard of during the 19th century. In the years following, the Key West Lighthouse underwent a number of upgrades including the installation of a Third Order Fresnel Lens, an extension to the tower which allowed the light to be seen from a greater distance, the addition of Keeper’s Quarters, and finally the electrification of the light.

Bight Marina

Bight Marina

Rows upon rows of boats moored to wooden docks surround the edge of Key West. Bight Marina in Downtown Key West is one such area and is a refreshing place to explore.

Santiago's Bodega

Santiago's Bodega

Santiago’s Bodega embodies the heart and soul of its original island home in Key West, FL. Where characters, stories, cultures and food combine to create the perfect union. Relaxed, eclectic, perhaps even a little odd elsewhere, but one human family at The Bodega. Petite, charming tapas bar pairs global small plates with house-specialty sangria in a warm room.

Butterfly and Nature Conservatory

Butterfly and Nature Conservatory

Feel your stress fade away as you enter our magical world of butterflies. Relax and be amazed as you stroll through their tropical paradise. Walk through a magical and inviting environment filled with hundreds of the most beautiful winged creatures in nature. Witness a variety of some 50 to 60 butterfly species from around the world, along with over 20 exotic bird species, all under a climate- controlled, glass enclosed habitat.

Robert The Doll

Robert The Doll

We’ve all experienced it: That eerie feeling that something or someone was watching us; that an inanimate object had, in actuality, come alive. In Key West, many have not only experienced that feeling, but have also witnessed it when viewing the famous toy – Robert The Doll.

Day 3 Highlights


Half-Day Snorkeling Excursion

Half-Day Snorkeling Excursion

Enjoy an afternoon of swimming and snorkeling on this cruise off the coast of Key West. Spend a relaxing afternoon on a 69-foot catamaran headed to North America's only living coral barrier reef for the adventure of a lifetime. Pass some of Key West’s top attractions on the way, then dive right in to see more than 600 species of colorful fish, coral, and other sea life.

Mangrove Kayak Eco Tour

Mangrove Kayak Eco Tour

Paddle a kayak through mangrove creeks and shallow water on a Key West kayaking tour that offers an up-close look that this unique coastal environment. This guided tour is the perfect way to spot Florida wildlife in a natural habitat.

Jet Ski Tour

Jet Ski Tour

Discover 28 miles (45 kms) of the Floridian coast on a 1.5-hour jet ski tour. With four daily tours, you can easily find a time that fits with your schedule.

A&B Lobster House

A&B Lobster House

A fine dining institution that’s been serving up some of the area’s most decadent dishes since 1947. While the dining room is charming and has an upscale steakhouse feel, the wraparound balcony with perfect marina views is where you want to be.

Day 4 Highlights


Watersports Adventure (Do It All)

Watersports Adventure (Do It All)


Cool off in Key West on a 6-hour water sports tour that features 12 different water activities for you to try, from snorkeling to windsurfing to Wave Runners.