37 days in Florida Keys Itinerary

37 days in Florida Keys Itinerary

Created using Inspirock Florida Keys trip itinerary maker

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Route & dates

37 days in Florida Keys Itinerary

Start: Halifax
Fly:  10​h 45​min
1
Key West
— 9 nights
Drive:  45​min
2
Sugarloaf Key
— 1 night
Drive:  30​min
3
Big Pine Key
— 3 nights
Drive:  30​min
4
Marathon
— 6 nights
Drive:  45​min
5
Islamorada
— 10 nights
Drive:  45​min
6
Key Largo
— 7 nights
shuttle + Fly:  10​h 45​min
End: Halifax

9
nights
Key West

Key West ©
Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Spend the 30th (Mon) exploring nature at Dry Tortugas National Park. There's still lots to do: see the interesting displays at The Ernest Hemingway Home and Museum, identify plant and animal life at Key West Butterfly & Nature Conservatory, take a memorable tour with Tours, and take a leisurely stroll along Mallory Square.

To find other places to visit, reviews, and tourist information, you can read our Key West day trip app .

Halifax, Canada to Key West is an approximately 11-hour flight. The time zone difference moving from Atlantic Standard Time to Eastern Standard Time is minus 1 hour. Expect much hotter temperatures when traveling from Halifax in December; daily highs in Key West reach 30°C and lows reach 25°C. Cap off your sightseeing on the 5th (Sun) early enough to go by car to Sugarloaf Key.

Things to do in Key West

Outdoors Parks Wildlife
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Mallory Square ©
Mallory Square

1
night
Sugarloaf Key

Sugarloaf Key ©
Sugarloaf Key is a single island in the lower Florida Keys that forms a loop on the Atlantic Ocean side giving the illusion of separate islands. Kick off your visit on the 6th (Mon): enjoy the sea views from American Shoal Lighthouse and then get outside with Key West Angling.

For traveler tips, where to stay, reviews, and more tourist information, use the Sugarloaf Key trip itinerary planner.

Getting from Key West to Sugarloaf Key by car takes about an hour. In January, daily temperatures in Sugarloaf Key can reach 28°C, while at night they dip to 22°C. Finish your sightseeing early on the 6th (Mon) so you can drive to Big Pine Key.

Things to do in Sugarloaf Key

Outdoors Historic Sites
Highlights from your plan
American Shoal Lighthouse ©
American Shoal Lighthouse

3
nights
Big Pine Key

Big Pine Key ©
Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. Big Pine Key is known for nature, wildlife, adventure, nightlife, and shopping. Your plan includes some of its best attractions: immerse yourself in nature at Bahia Honda State Park, experience rural life at Grimal Grove, view the masterpieces at Artists in Paradise Gallery, and identify plant and animal life at Blue Hole.

To find traveler tips, where to stay, reviews, and other tourist information, you can read our Big Pine Key trip tool .

Big Pine Key is just a short distance from Sugarloaf Key. January in Big Pine Key sees daily highs of 29°C and lows of 22°C at night. Wrap up your sightseeing on the 9th (Thu) early enough to drive to Marathon.

Things to do in Big Pine Key

Outdoors Wildlife Parks
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Stand-Up Paddleboarding

6
nights
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Go for a jaunt from Marathon to Cudjoe Key to see Fishing Charters & Tours about 42 minutes away. And it doesn't end there: look for all kinds of wild species at The Turtle Hospital, take in the views from Seven Mile Bridge, get all the information you need at Pigeon Key Foundation, and enjoy the sand and surf at Sombrero Beach.

To see reviews, where to stay, photos, and other tourist information, use the Marathon trip itinerary maker website .

Marathon is very close to Big Pine Key. In January, daytime highs in Marathon are 29°C, while nighttime lows are 22°C. Finish up your sightseeing early on the 15th (Wed) so you can go by car to Islamorada.

Things to do in Marathon

Parks Outdoors Wildlife

Side Trips

Sunset Park Beach, Fishing Charters & Tours, Veterans Memorial Park
Highlights from your plan
Crane Point Museum & Nature Center ©
The Turtle Hospital ©
The Turtle Hospital
Sombrero Beach ©
Sombrero Beach

10
nights
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Islamorada is known for wildlife, adventure, museums, beaches, and breweries & distilleries. Your plan includes some of its best attractions: see what you can catch with a fishing tour, get outside with Dee Cee Charters, sample the tasty concoctions at Florida Keys Brewing Company, and take an in-depth tour of History of Diving Museum.

To find photos, traveler tips, more things to do, and tourist information, refer to the Islamorada trip itinerary maker tool .

You can drive from Marathon to Islamorada in an hour. Alternatively, you can take a bus. In January, plan for daily highs up to 29°C, and evening lows to 22°C. Cap off your sightseeing on the 25th (Sat) early enough to go by car to Key Largo.

Things to do in Islamorada

Outdoors Parks Tours
Highlights from your plan
A  Lil' Tail Charters ©
A Lil' Tail Charters
Fishing Charters & Tours
Lignumvitae Key Botanical State Park ©

7
nights
Key Largo

Key Largo ©
The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
Key Largo is known for wildlife, nature, adventure, zoos & aquariums, and shopping. Your plan includes some of its best attractions: identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, observe the fascinating underwater world at Dolphins Plus Marine Mammal Responder, step aboard Spiegel Grove, and admire the majestic nature at John Pennekamp Coral Reef State Park.

To find where to stay, traveler tips, more things to do, and more tourist information, refer to the Key Largo online vacation builder .

Traveling by car from Islamorada to Key Largo takes an hour. Alternatively, you can do a combination of bus and taxi. Traveling from Islamorada in January, expect slightly colder with lows of 19°C in Key Largo. On the 1st (Sat), you'll have the morning to explore before heading back home.

Things to do in Key Largo

Parks Outdoors Tours
Highlights from your plan
Island Dolphin Care ©
Island Dolphin Care
Scuba & Snorkeling

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