20 days in Florida Keys Itinerary

20 days in Florida Keys Itinerary

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Route & dates

20 days in Florida Keys Itinerary

Start: Dallas
Fly:  5​h 45​min
1
Key West
— 5 nights
Drive:  2​h 30​min
2
Key Largo
— 3 nights
Drive:  45​min
3
Islamorada
— 5 nights
Drive:  45​min
4
Marathon
— 4 nights
Drive:  30​min
5
Big Pine Key
— 2 nights
Fly:  7​h 15​min
End: Dallas

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.
Explore hidden gems such as Spas & Wellness and Kayaking & Canoeing. You'll enjoy a bit of beach vacationing at Smathers Beach and Fort Zachary Taylor. There's lots more to do: get a new perspective on things with Boat Tours & Water Sports, examine the collection at Florida Keys Eco-Discovery Center, pause for some serene contemplation at Saint Mary Star of the Sea, and tour the water at your own pace with Far Out Fishing Charters.

To find traveler tips, ratings, more things to do, and tourist information, you can read our Key West route builder tool .

Dallas to Key West is an approximately 6-hour flight. You can also do a combination of flight, taxi, and ferry; or drive. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Traveling from Dallas in September, you can expect nighttime temperatures to be somewhat warmer in Key West, with lows of 80°F. Finish up your sightseeing early on the 13th (Thu) so you can go by car to Key Largo.

Things to do in Key West

Outdoors Parks Beaches
Highlights from your plan
Vandenberg Wreck ©
Vandenberg Wreck
Stand-Up Paddleboarding
Kayaking & Canoeing

3
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.
Eschew the tourist crowds and head to Florida Keys Wild Bird Rehabilitation Center and Spiegel Grove. Visiting Parasailing & Paragliding and Waterskiing & Jetskiing will get you outdoors. Next up on the itinerary: identify plant and animal life at Molasses Reef, look for gifts at Sandal Kingdom, get a new perspective on things with Boat Tours & Water Sports, and choose your vessel at Key Largo Watersports.

For photos, other places to visit, traveler tips, and more tourist information, refer to the Key Largo trip itinerary app .

Traveling by car from Key West to Key Largo takes 2.5 hours. Alternatively, you can take a bus; or take a bus. In September in Key Largo, expect temperatures between 88°F during the day and 76°F at night. Finish up your sightseeing early on the 16th (Sun) so you can go by car to Islamorada.

Things to do in Key Largo

Outdoors Tours Wildlife
Highlights from your plan
Spiegel Grove ©
Spiegel Grove
Waterskiing & Jetskiing
Parasailing & Paragliding

5
nights
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Get outdoors at Anne's Beach and Bayside Boat Rentals. Explore hidden gems such as Scuba & Snorkeling and Parasailing & Paragliding. The adventure continues: sample the tasty concoctions at Florida Keys Brewing Company, stroll through Library Beach Park, get outside with A Lil' Tail Charters, and explore the gorgeous colors at Alligator Reef Light House.

To find traveler tips, more things to do, reviews, and tourist information, read Islamorada holiday maker tool .

You can drive from Key Largo to Islamorada in an hour. Another option is to do a combination of taxi and bus. September in Islamorada sees daily highs of 90°F and lows of 79°F at night. Finish your sightseeing early on the 21st (Fri) so you can drive to Marathon.

Things to do in Islamorada

Outdoors Tours Transportation
Highlights from your plan
Florida Keys Brewing Company ©
Florida Keys Brewing Company
Parasailing & Paragliding
AquaBlue Adventures ©
AquaBlue Adventures

4
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.
Step out of the city life by going to Dolphin Research Center and Sunset Park Beach. Step off the beaten path and head to Seven Mile Bridge and Captain Hook's Marina & Dive Center. There's lots more to do: tour the pleasant surroundings at Sombrero Beach, soothe aching muscles at some of the top local wellness centers, look for all kinds of wild species at Crane Point Museum & Nature Center, and take in the views from Old Seven Mile Bridge.

To find ratings, more things to do, maps, and more tourist information, you can read our Marathon holiday builder tool .

You can drive from Islamorada to Marathon in an hour. Another option is to take a bus. In September, plan for daily highs up to 90°F, and evening lows to 79°F. Wrap up your sightseeing on the 25th (Tue) to allow time to drive to Big Pine Key.

Things to do in Marathon

Outdoors Transportation Tours

Side Trip

Sunset Park Beach
Highlights from your plan
Dolphin Research Center ©
Dolphin Research Center
Curry Hammock State Park ©
Curry Hammock State Park
Sunset Park Beach ©
Sunset Park Beach

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 26th (Wed): stop by Out of the Blue Gallery, immerse yourself in nature at Bahia Honda State Park, and then glide peacefully along the water with some of the best stand-up paddleboarding in the area. On the 27th (Thu), you'll have a packed day of sightseeing: tour the pleasant surroundings at Calusa Beach and then look for all kinds of wild species at National Key Deer Refuge.

For traveler tips, ratings, photos, and other tourist information, use the Big Pine Key tour builder tool .

Big Pine Key is just a short distance from Marathon. Expect a daytime high around 90°F in September, and nighttime lows around 79°F. Wrap up your sightseeing on the 27th (Thu) early enough to travel back home.

Things to do in Big Pine Key

Parks Beaches Outdoors
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

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