18 days in Florida Keys Itinerary

18 days in Florida Keys Itinerary

Created using Inspirock Florida Keys itinerary planner

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Route & dates

18 days in Florida Keys Itinerary

Start: Huntsville
Fly:  5​h 30​min
1
Key West
— 5 nights
Drive:  45​min
2
Sugarloaf Key
— 1 night
Drive:  30​min
3
Little Torch Key
— 1 night
Drive:  15​min
4
Big Pine Key
— 2 nights
Drive:  30​min
5
Marathon
— 2 nights
Drive:  30​min
6
Long Key
— 1 night
Drive:  30​min
7
Islamorada
— 2 nights
Drive:  45​min
8
Key Largo
— 2 nights
shuttle + Fly:  6​h 45​min
End: Huntsville

5
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 14th (Sat) exploring nature at Dry Tortugas National Park. There's much more to do: see the interesting displays at The Ernest Hemingway Home and Museum, explore the galleries of Truman Little White House, don't miss a visit to Duval Street, and see what you can catch with a fishing tour.

For traveler tips, ratings, and tourist information, read Key West trip itinerary site .

Huntsville to Key West is an approximately 5.5-hour flight. You can also do a combination of bus and flight; or drive. Due to the time zone difference, you'll lose 1 hour traveling from Huntsville to Key West. Traveling from Huntsville in September, plan for a bit warmer nights in Key West, with lows around 80°F. Cap off your sightseeing on the 16th (Mon) early enough to go by car to Sugarloaf Key.

Things to do in Key West

Outdoors Tours Parks
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Parasailing & Paragliding

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 17th (Tue): head outdoors with Key West Angling and then enjoy the sea views from American Shoal Lighthouse.

For where to stay, maps, traveler tips, and more tourist information, go to the Sugarloaf Key online trip itinerary planner .

You can drive from Key West to Sugarloaf Key in an hour. In September in Sugarloaf Key, expect temperatures between 90°F during the day and 79°F at night. Finish your sightseeing early on the 17th (Tue) to allow enough time to drive to Little Torch Key.

Things to do in Sugarloaf Key

Outdoors Historic Sites
Highlights from your plan
Key West Angling ©
Key West Angling
American Shoal Lighthouse ©
American Shoal Lighthouse

1
night
Little Torch Key

Little Torch Key ©
On the 18th (Wed), stroll around Veterans Memorial Park.

For maps, other places to visit, and other tourist information, use the Little Torch Key attractions planner.

Little Torch Key is very close to Sugarloaf Key. September in Little Torch Key sees daily highs of 90°F and lows of 79°F at night. On the 18th (Wed), wrap the sightseeing up by early afternoon so you can drive to Big Pine Key.

Things to do in Little Torch Key

Parks
Highlights from your plan
Veterans Memorial Park ©
Veterans Memorial Park

2
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. Kick off your visit on the 19th (Thu): look for all kinds of wild species at National Key Deer Refuge, then stop by Out of the Blue Gallery, and then admire the majestic nature at Bahia Honda State Park. Keep things going the next day: glide peacefully along the water with some of the best stand-up paddleboarding in the area, then take in the exciting artwork at Artists in Paradise Gallery, and then look for all kinds of wild species at Blue Hole.

To find other places to visit, maps, traveler tips, and tourist information, read our Big Pine Key trip planning site .

Big Pine Key is very close to Little Torch Key. In September, daily temperatures in Big Pine Key can reach 90°F, while at night they dip to 79°F. Finish your sightseeing early on the 20th (Fri) to allow enough time to drive to Marathon.

Things to do in Big Pine Key

Parks Wildlife Nature
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Out of the Blue Gallery ©
Out of the Blue Gallery

2
nights
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 21st (Sat): get a taste of the local shopping with Shady Palm Art Gallery & Photography, identify plant and animal life at The Turtle Hospital, then see some colorful creatures with a scuba or snorkeling tour, and finally stroll through Sombrero Beach. Keep things going the next day: look for all kinds of wild species at Dolphin Research Center, then see what you can catch with a fishing tour, and then take in the views from Seven Mile Bridge.

To find ratings, photos, maps, and other tourist information, go to the Marathon road trip planning app .

Marathon is just a short distance from Big Pine Key. In September in Marathon, expect temperatures between 90°F during the day and 79°F at night. Cap off your sightseeing on the 22nd (Sun) early enough to travel to Long Key.

Things to do in Marathon

Wildlife Outdoors Tours
Highlights from your plan
Scuba & Snorkeling
The Turtle Hospital ©
The Turtle Hospital
Sombrero Beach ©
Sombrero Beach

1
night
Long Key

Long Key
Long Key is an island in the middle Florida Keys. Start off your visit on the 23rd (Mon): head outdoors with Dooda Charters.

To find where to stay and tourist information, you can read our Long Key road trip planning website .

Long Key is just a short distance from Marathon. In September, plan for daily highs up to 90°F, and evening lows to 79°F. Wrap up your sightseeing by early afternoon on the 23rd (Mon) to allow enough time to travel to Islamorada.

Things to do in Long Key

Outdoors

2
nights
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Start off your visit on the 24th (Tue): get a new perspective on things with Boat Tours & Water Sports, cast your line with a fishing tour, and then sample the tasty concoctions at Islamorada Brewery & Distillery. Get ready for a full day of sightseeing on the next day: get engrossed in the history at History of Diving Museum, then see some colorful creatures with a scuba or snorkeling tour, and then stroll through Anne's Beach.

To find where to stay, traveler tips, maps, and more tourist information, read our Islamorada online travel planner .

Islamorada is very close to Long Key. In September in Islamorada, expect temperatures between 90°F during the day and 79°F at night. Wrap up your sightseeing on the 25th (Wed) early enough to drive to Key Largo.

Things to do in Islamorada

Outdoors Tours Wildlife
Highlights from your plan
Fishing Charters & Tours
Scuba & Snorkeling
History of Diving Museum ©
History of Diving Museum

2
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.
On the 26th (Thu), see some colorful creatures with a scuba or snorkeling tour, identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, then fulfill a lifelong dream with a swim-with-the-dolphins experience, and finally grab your bike and head to Florida Keys Visitor Center. Get ready for a full day of sightseeing on the 27th (Fri): look for gifts at Robert Is Here, then identify plant and animal life at Everglades Alligator Farm, and then admire the majestic nature at John Pennekamp Coral Reef State Park.

For traveler tips, where to stay, other places to visit, and tourist information, read our Key Largo tour itinerary maker website .

Drive from Islamorada to Key Largo in an hour. Alternatively, you can do a combination of bus and taxi. In September in Key Largo, expect temperatures between 88°F during the day and 76°F at night. Finish your sightseeing early on the 27th (Fri) to allow enough time to travel back home.

Things to do in Key Largo

Wildlife Parks Tours

Side Trip

Homestead
Highlights from your plan
Scuba & Snorkeling
John Pennekamp Coral Reef State Park ©

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