24 days in Florida Keys Itinerary

24 days in Florida Keys Itinerary

Created using Inspirock Florida Keys travel route planner

This plan was created by another user. Make it your plan

Route & dates

24 days in Florida Keys Itinerary

Start: San Francisco
Fly + Shuttle:  9​h 45​min
1
Islamorada
— 3 nights
Drive:  45​min
2
Key Largo
— 3 nights
Drive:  1​h 30​min
3
Marathon
— 4 nights
Drive:  30​min
4
Big Pine Key
— 2 nights
Drive:  4​h 30​min
5
Dry Tortugas National Park
— 1 night
Travel:  3​h 45​min
6
Key West
— 9 nights
Fly:  10​h
End: San Francisco

3
nights
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Your itinerary includes some good beach time at Anne's Beach and Library Beach Park. Visiting Scuba & Snorkeling and Alligator Reef Light House will get you outdoors. There's still lots to do: view the masterpieces at Old Road Gallery, fly like a bird with a parasailing or paragliding tour, stop by Bella Sol Fragrance Bar and Gifts, and tour the water at your own pace with AquaBlue Adventures.

For more things to do, ratings, other places to visit, and other tourist information, use the Islamorada road trip planning app .

San Francisco to Islamorada is an approximately 10-hour combination of flight and shuttle. You can also do a combination of flight and bus; or drive. The time zone changes from Pacific Standard Time (PST) to Eastern Standard Time (EST), which is usually a 3 hour difference. Traveling from San Francisco in September, expect nights in Islamorada to be much warmer, around 79°F, while days are somewhat warmer, around 90°F. Cap off your sightseeing on the 8th (Sat) early enough to go by car to Key Largo.

Things to do in Islamorada

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

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 Molasses Reef. Step out of the city life by going to Spiegel Grove and Parasailing & Paragliding. There's lots more to do: tour the water at your own pace with Key Largo Watersports, stop by Shell World Florida Keys, see the vivid underwater world at Key Largo Dry Rocks, and look for all kinds of wild species at Grecian Rocks.

To find more things to do, where to stay, reviews, and tourist information, read Key Largo online vacation planner .

You can drive from Islamorada to Key Largo in an hour. Alternatively, you can do a combination of bus and taxi. In September, daytime highs in Key Largo are 88°F, while nighttime lows are 76°F. Wrap up your sightseeing on the 11th (Tue) to allow time to drive to Marathon.

Things to do in Key Largo

Wildlife Parks Tours
Highlights from your plan
Molasses Reef ©
Molasses Reef
Spiegel Grove ©
Spiegel Grove

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.
You'll explore the less-touristy side of things at Dolphin Research Center and Sunset Park Beach. Get outdoors at Captain Hook's Marina & Dive Center and Sombrero Beach. There's still lots to do: look for all kinds of wild species at Crane Point Museum & Nature Center, take a tour by water with Coco's Boat Rentals, take in the views from Seven Mile Bridge, and take a memorable tour with All Aboard Boat Rentals.

To find ratings, more things to do, where to stay, and other tourist information, read our Marathon trip website .

You can drive from Key Largo to Marathon in 1.5 hours. Other options are to take a bus; or do a combination of taxi and bus. In September in Marathon, expect temperatures between 90°F during the day and 79°F at night. Finish your sightseeing early on the 15th (Sat) to allow enough time to drive to Big Pine Key.

Things to do in Marathon

Outdoors Tours Transportation

Side Trip

Sunset Park Beach
Highlights from your plan
Dolphin Research Center ©
Dolphin Research Center
Crane Point Museum & Nature Center ©
Crane Point Museum & Nature Center
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 16th (Sun): stroll through Calusa Beach and then admire the majestic nature at Bahia Honda State Park. Keep things going the next day: get a taste of the local shopping with Artists in Paradise Gallery, then stop by Out of the Blue Gallery, and then identify plant and animal life at National Key Deer Refuge.

To see maps, ratings, other places to visit, and other tourist information, refer to the Big Pine Key trip planner .

Big Pine Key is just a stone's throw from Marathon. In September, daily temperatures in Big Pine Key can reach 90°F, while at night they dip to 79°F. Wrap up your sightseeing on the 17th (Mon) to allow time to travel to Dry Tortugas National Park.

Things to do in Big Pine Key

Parks Outdoors Beaches
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Artists in Paradise Gallery ©
Artists in Paradise Gallery

1
night
Dry Tortugas National Park

Dry Tortugas National Park ©
What Dry Tortugas National Park lacks in size, it makes up for in abundance of marine life.
Kick off your visit on the 18th (Tue): take in the dramatic natural features at Little Africa, then step off the mainland to explore Garden Key, and then contemplate the long history of Fort Jefferson.

Quickly create a custom-made itinerary for Dry Tortugas National Park using our trip planner.

The Route module can help you plan travel from Big Pine Key to Dry Tortugas National Park. In September, daily temperatures in Dry Tortugas National Park can reach 88°F, while at night they dip to 80°F. Finish up your sightseeing early on the 18th (Tue) so you can travel to Key West.

Things to do in Dry Tortugas National Park

Parks Nature Wildlife
Highlights from your plan
Fort Jefferson ©
Fort Jefferson
Garden Key ©
Garden Key

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.
Visit Smathers Beach and South Beach for some beach relaxation. Head to Peppers of Key West and Alan S. Maltz Galleryfor some retail therapy. Spend the 25th (Tue) airborne with a parasailing or paragliding tour. And it doesn't end there: find your balance on the water with some of the best stand-up paddleboarding in the area, see the interesting displays at Mel Fisher Maritime Heritage Museum, paddle through the water with a kayaking and canoeing tour, and relax and rejuvenate at some of the top local wellness centers.

To find ratings, traveler tips, photos, and other tourist information, you can read our Key West trip planner .

Explore your travel options from Dry Tortugas National Park to Key West with the Route module. In September, daily temperatures in Key West can reach 88°F, while at night they dip to 80°F. Wrap up your sightseeing on the 27th (Thu) early enough to travel back home.

Things to do in Key West

Outdoors Parks Tours
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Vandenberg Wreck ©
Vandenberg Wreck
Saint Mary Star of the Sea ©
Saint Mary Star of the Sea

Similar Plans

3 days in Florida Keys BY A USER FROM UNITED STATES August, teens, kids, relaxing, beaches, wildlife, hidden gems PREFERENCES: August, teens, kids, relaxing, beaches, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium 6 days in Florida Keys BY A USER FROM UNITED STATES November, kids, popular sights PREFERENCES: November, kids ATTRACTION STYLE: Popular sights PACE: Medium 7 days in Florida Keys & Miami BY A USER FROM UNITED STATES December, teens, kids, popular sights PREFERENCES: December, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 5 days in Florida Keys BY A USER FROM UNITED STATES September, beaches, museums, shopping, popular sights PREFERENCES: September, beaches, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 3 days in Florida Keys BY A USER FROM UNITED STATES August, popular sights PREFERENCES: August ATTRACTION STYLE: Popular sights PACE: Medium 6 days in Florida Keys BY A USER FROM UNITED KINGDOM October, popular sights PREFERENCES: October ATTRACTION STYLE: Popular sights PACE: Medium 7 days in Florida Keys BY A USER FROM UNITED STATES October, relaxing, beaches, historic sites, slow & easy, popular sights PREFERENCES: October, relaxing, beaches, historic sites ATTRACTION STYLE: Popular sights PACE: Slow & easy 5 days in Florida Keys BY A USER FROM UNITED STATES May, popular sights PREFERENCES: May ATTRACTION STYLE: Popular sights PACE: Medium 3 days in Florida Keys BY A USER FROM UNITED STATES September, popular sights PREFERENCES: September ATTRACTION STYLE: Popular sights PACE: Medium 5 days in Florida Keys BY A USER FROM UNITED STATES February, popular & hidden gems PREFERENCES: February ATTRACTION STYLE: Popular & hidden gems PACE: Medium 6 days in Florida Keys BY A USER FROM AUSTRIA March, popular & hidden gems PREFERENCES: March ATTRACTION STYLE: Popular & hidden gems PACE: Medium 4 days in Florida Keys BY A USER FROM UNITED STATES October, kids, culture, outdoors, beaches, historic sites, museums, wildlife, hidden gems PREFERENCES: October, kids, culture, outdoors, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium
View more plans