5 days in Florida Keys Itinerary

5 days in Florida Keys Itinerary

Created using Inspirock Florida Keys trip planner

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Route & dates

5 days in Florida Keys Itinerary

Start: Portland
Fly:  10 h 30 min
1
Key West
— 1 night
Bus:  45 min
2
Big Pine Key
— 1 night
Drive:  30 min
3
Marathon
— 1 night
Bus + Fly:  12 h
End: Portland

1
night
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.
On the 12th (Wed), stop by Peppers of Key West, look for gifts at De La Gallery, then stop by Uva Wine Shop & Bar, then immerse yourself in nature at Fort Zachary Taylor, and finally hunt for treasures at Sunset Celebration. On your second day here, look for all kinds of wild species at Key West Butterfly & Nature Conservatory, see the interesting displays at The Ernest Hemingway Home and Museum, then take an in-depth tour of Truman Little White House, then stop by Tucker's Provisions, and finally stop by Kermit's Key West Key Lime Shoppe.

For photos, other places to visit, traveler tips, and tourist information, refer to the Key West road trip website .

Portland to Key West is an approximately 10.5-hour flight. You can also drive; or do a combination of train and bus. Traveling from Portland to Key West, you'll lose 3 hours due to the time zone difference. Traveling from Portland in September, expect nights in Key West to be much warmer, around 80°F, while days are somewhat warmer, around 88°F. Wrap up your sightseeing on the 13th (Thu) to allow time to drive to Big Pine Key.

Things to do in Key West

Shopping Historic Sites Museums
Highlights from your plan
The Ernest Hemingway Home and Museum ©
The Ernest Hemingway Home and Museum
Fort Zachary Taylor ©
Fort Zachary Taylor
Truman Little White House ©
Truman Little White House

1
night
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. Kick off your visit on the 14th (Fri): take in the exciting artwork at Artists in Paradise Gallery, then stop by Out of the Blue Gallery, and then admire the majestic nature at Bahia Honda State Park.

For photos, maps, and other tourist information, read our Big Pine Key tour planner.

Getting from Key West to Big Pine Key by car takes about an hour. Other options: take a bus. In September, daytime highs in Big Pine Key are 90°F, while nighttime lows are 79°F. Cap off your sightseeing on the 14th (Fri) early enough to go by car to Marathon.

Things to do in Big Pine Key

Beaches Outdoors Parks
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
Artists in Paradise Gallery ©
Artists in Paradise Gallery
Out of the Blue Gallery ©
Out of the Blue Gallery

1
night
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Start off your visit on the 15th (Sat): tour the pleasant surroundings at Sombrero Beach and then look for gifts at Bayshore Clothing.

For other places to visit, where to stay, and tourist information, go to the Marathon trip planner .

Marathon is just a stone's throw from Big Pine Key. September in Marathon sees daily highs of 90°F and lows of 79°F at night. On the 15th (Sat), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Marathon

Beaches Outdoors Parks
Highlights from your plan
Sombrero Beach ©
Sombrero Beach
Bayshore Clothing ©
Bayshore Clothing

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