7 days in Florida Keys Itinerary

7 days in Florida Keys Itinerary

Created using Inspirock Florida Keys trip planner

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Route & dates

7 days in Florida Keys Itinerary

Start: Boston
Fly + shuttle:  8​h
1
Islamorada
— 1 night
Drive:  1​h
2
Key Largo
— 1 night
Drive:  1​h 30​min
3
Marathon
— 1 night
bus:  1​h 30​min
4
Key West
— 3 nights
Fly:  6​h 30​min
End: Boston

1
night
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
On the 8th (Tue), shop like a local with Michelle Nicole Lowe Art Gallery.

To see ratings, where to stay, maps, and other tourist information, read our Islamorada trip builder .

Boston to Islamorada is an approximately 8-hour combination of flight and shuttle. You can also do a combination of flight, bus, and shuttle; or drive. Prepare for warmer weather when traveling from Boston in October: high temperatures in Islamorada hover around 87°F and lows are around 77°F. Finish up your sightseeing early on the 9th (Wed) so you can go by car to Key Largo.

Things to do in Islamorada

Tours Outdoors Wildlife
Highlights from your plan
Scuba & Snorkeling
History of Diving Museum ©
History of Diving Museum
Parasailing & Paragliding

1
night
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.
On the 10th (Thu), take a tour by water with Boat Tours & Water Sports, take a tour of African Queen Canal Cruise, then look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, and finally identify plant and animal life at Molasses Reef.

For other places to visit, photos, reviews, and other tourist information, you can read our Key Largo road trip site .

You can drive from Islamorada to Key Largo in an hour. Alternatively, you can do a combination of bus and taxi. In October, daily temperatures in Key Largo can reach 85°F, while at night they dip to 73°F. Wrap up your sightseeing on the 10th (Thu) early enough to drive to Marathon.

Things to do in Key Largo

Wildlife Parks Tours
Highlights from your plan
Molasses Reef ©
Molasses Reef
Parasailing & Paragliding

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.
Kick off your visit on the 11th (Fri): identify plant and animal life at Dolphin Research Center, identify plant and animal life at Crane Point Museum & Nature Center, then paddle through the water with a kayaking and canoeing tour, and finally snap pictures at Seven Mile Bridge.

For reviews, photos, other places to visit, and tourist information, read Marathon trip planner .

Getting from Key Largo to Marathon by car takes about 1.5 hours. Other options: take a bus. October in Marathon sees daily highs of 87°F and lows of 77°F at night. Cap off your sightseeing on the 11th (Fri) early enough to catcht the bus to Key West.

Things to do in Marathon

Wildlife Parks Tours
Highlights from your plan
Dolphin Research Center ©
Dolphin Research Center
Crane Point Museum & Nature Center ©
Crane Point Museum & Nature Center
Seven Mile Bridge ©
Seven Mile Bridge

3
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.
Saint Mary Star of the Sea and Key West Garden Club will appeal to history buffs. Step off the beaten path and head to Kayaking & Canoeing and U.S. Coast Guard Cutter Ingham Maritime Museum. The adventure continues: find your balance on the water with some of the best stand-up paddleboarding in the area, stroll the grounds of Key West Cemetery, see the interesting displays at Mel Fisher Maritime Heritage Museum, and visit a coastal fixture at Key West Lighthouse and Keeper's Quarters Museum.

To see photos, traveler tips, maps, and more tourist information, go to the Key West road trip website .

You can take a bus from Marathon to Key West in 1.5 hours. Alternatively, you can drive. In October, daytime highs in Key West are 86°F, while nighttime lows are 77°F. Cap off your sightseeing on the 14th (Mon) early enough to travel back home.

Things to do in Key West

Tours Outdoors Parks
Highlights from your plan
Saint Mary Star of the Sea ©
Saint Mary Star of the Sea
Vandenberg Wreck ©
Vandenberg Wreck
Kayaking & Canoeing

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