Rough Draft: 5 Day Itinerary for the Florida Keys

June 2020

Rough Draft: Florida Keys

Due to the COVID quarantine, I am creating rough draft, “off the shelf” travel itineraries for when travel resumes normal operations so we do not waste any time getting out and exploring!

A popular request was an itinerary for the Florida Keys and I can’t say I blame you – this looks like a fabulous post-quarantine getaway, especially as international travel seems to be on hold. The time you have for this vacation will play a big role in how you structure an itinerary. While the Florida Keys can easily stand alone as its own vacation, if you have more time it can adjunct onto a Florida trip to extending to Miami or Everglades National Park. It is also easy to focus on one island in the Florida Keys exclusively. It really depends on what you want to do with the time you have!

From Miami, the southern most point of the Florida Keys is 3.5 hours and from Ft Lauderdale the drive is 4 hours. This gives some flexibility to flight routes and prices since it is really not that big of a difference in travel time. While it is a longer drive, it is certainly a scenic one and there are so many stops you can make along the way. I would get the drive out of the way at the beginning of the trip and then make my way island hopping on the way back.

Best time to visit seems to be in the winter months but it does depend on what you are going to the Keys for. If your focus is water activities, make sure it is seasonally warm enough to do so. Avoid hurricane season in the fall or buy some good travel insurance. And I read it can be extremely hot in the summer months.

Key West definitely has the most going on so you could spend your entire trip on this island. Key West is also great if you need a shorter trip or only have a weekend to spent in the Keys. Here are some things to consider when building your itinerary for Key West:

  • Take a sunset cruise or watch at the Mallory Square Sunset Celebration
  • Explore beaches and waters
    • Fort Zachary Taylor State Park
    • Take a day trip to Dry Tortugas National Park by ferry or seaplane
    • Water activities include snorkeling, scuba diving, parasailing, kayaking, water jets, paddleboarding, and more.
  • Visit some of these locations for lo-key sightseeing:
    • The Key West Butterfly and Nature Conservatory
    • Southernmost Point of the Continental US
    • The Ernest Hemingway Home
    • Truman Little White House  
    • Audubon House and Tropical Gardens
    • Key West Historic Memorial Sculpture Garden
  • Allocate relaxation time!

For us, I want to explore as much of the Keys as possible. Five islands in five days in an aggressive itinerary for some people, especially since one of the “keys” to visiting the Florida Keys is relaxation. That being said, it is not our speed to sit still and we like to fit as much as possible into our trips. So know this rough draft itinerary may not be best for everyone and because of that, I included how to make your own version at the end of the post.

Here is how I would structure 5 days in the Florida Keys:

Day 0 Afternoon Land in Miami
Evening Drive to Key West 
Day 1 Morning Water activities
Evening Mallory Square for sunset
Day 2 Morning Explore downtown

  • Ernest Hemingway House
  • Southernmost Point
  • Fort Zachary Taylor State Park
Day 3 Morning Drive to Big Pine Key

Kayak Keys Backcountry or explore Bahia Honda State Park

Afternoon Drive to Marathon

Turtle Hospital or Bahia Honda State Park

Evening Drive to Islamorada
Day 4 Morning Robbie’s Marina 

Florida Keys Brewing

Afternoon Florida Keys Wild Bird Rehabilitation Center 
Evening Drive to Key Largo
Day 5 Morning John Pennekamp Coral Reef State Park
Evening Depart Florida Keys

To make your own itinerary, here is a guide of what there is to do at each popular island spot as well as where to eat. Pick things from each category to mix and match to create your trip!

Key West

Things to Do Places to Eat 

  • The Key West Butterfly and Nature Conservatory
  • Southernmost Point of the Continental US
  • The Ernest Hemingway Home
  • Truman Little White House  
  • Audubon House and Tropical Gardens
  • First Flight Island Brewery
  • Key West Historic Memorial Sculpture Garden 
  • Books & Books 

Book sunset cruise or watch from Mallory Square (Sunset Celebration)

Day trip or camping overnight at Dry Tortugas National Park – take a seaplane or ferry

Water activities:

  • Plenty of companies offering half or full day snorkel, scuba, etc excursions
  • Fort Zachary Taylor State Park 
  • All the surrounding beaches
El Siboney 

Blue Heaven 

Firefly Key West


Garbo’s Grill

Bistro 245 

Hot Tin Roof


Fisherman’s Cafe 

Cuban Coffee Queen

Matt’s Stock Island Kitchen

El Mocho

Hogfish Bar and Grill

Green Parrot (Bar)

Big Pine Key 

Things to Do Places to Eat 
Bahia Honda State Park 

Kayaking Keys Backcountry 

No Name Pub


Things to Do Places to Eat 
Turtle Hospital

Curry Hammock State Park 

Sunset Grille 

Curly’s Coffee 

Key’s Fisheries

Butterfly Cafe


Things to Do Places to Eat 
Robbie’s Marina 

Blond Giraffe Key Lime Pie Factory 

Florida Keys Wild Bird Rehabilitation Center 

Florida Keys Brewing 

Bob’s Bunz

Bad Boy Burrito

Morado Bay

Chef Michael’s 

Pierre’s Restaurant

Ciao Hound

Marker 88

Cafe Moka

Key Largo

Things to Do Places to Eat 
The Botanic Gardens at Kona Kai Resort 

Coral Restoration Foundation Education Center 

John Pennekamp Coral Reef State Park (snorkel or Scuba)

Mrs Mac’s Kitchen

Key Largo Chocolates and Ice Cream 


The Fish House

Sol by the Sea


How would you spend a trip to the Florida Keys?

If you have been to the Florida Keys before, let me know what I missed and what your favorites are!

Don’t forget to check out all DESKRIB itineraries here!

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