59 days in Southeast Florida Itinerary

59 days in Southeast Florida Itinerary

Created using Inspirock Southeast Florida journey maker

Plan created by another user. Make it yours
1
Key West
— 12 nights
2
Marathon
— 11 nights
3
Key Largo
— 12 nights
4
Miami Beach
— 12 nights
5
Delray Beach
— 11 nights

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12
nights
Key West

Key West ©

Conch Republic

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.
Take a break from Key West with a short trip to Fort Jefferson in Dry Tortugas National Park, about 3h 45 min away. Spend the 18th (Sun) exploring nature at Dry Tortugas National Park. There's much more to do: examine the collection at The Ernest Hemingway Home and Museum, take in nature's colorful creations at Audubon House & Tropical Gardens, get interesting insight from Tours, and fly like a bird with a parasailing or paragliding tour.

Plan my trip to Key West with suggested itineraries provided by Inspirock.

Chicago to Key West is an approximately 6.5-hour flight. You can also drive; or take a bus. Traveling from Chicago to Key West, you'll lose 1 hour due to the time zone difference. Traveling from Chicago in November, things will get much hotter in Key West: highs are around 81°F and lows about 73°F. Cap off your sightseeing on the 27th (Tue) early enough to go by car to Marathon.

Things to do in Key West

Outdoors · Tours · Parks · Wildlife

Side Trip

Highlights from your plan
The Ernest Hemingway Home and Museum ©
The Ernest Hemingway Home and Museum
Key West Butterfly & Nature Conservatory ©
Key West Butterfly & Nature Conservatory
Parasailing & Paragliding

11
nights
Marathon

Marathon ©

Heart of the Florida Keys

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Venture out of the city with trips to Big Pine Key (Out of the Blue Gallery, Blue Hole, &more) and Sea Bird Marina (in Long Key). There's much more to do: enjoy the sand and surf at Bahia Honda State Park, stroll through Sunset Park Beach, snap pictures at Seven Mile Bridge, and add some adventure to your tour with Captain Hook's.

Plan a Marathon trip in moments using our itinerary builder.

You can drive from Key West to Marathon in 1.5 hours. Alternatively, you can take a bus. In November, daytime highs in Marathon are 82°F, while nighttime lows are 72°F. Finish your sightseeing early on the 8th (Sat) to allow enough time to drive to Key Largo.

Things to do in Marathon

Parks · Outdoors · Wildlife · Transportation

Side Trips

Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
The Turtle Hospital ©
The Turtle Hospital
Crane Point Museum & Nature Center ©
Crane Point Museum & Nature Center

12
nights
Key Largo

Diving Capital of the World

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.
Venture out of the city with trips to Islamorada (Anne's Beach, Indian Key State Historic Site, &more) and Homestead (Homestead Miami Speedway, Coral Castle, &more). And it doesn't end there: discover the deep blue sea with Key Largo Adventures - an Islamorada Boat Charter, observe the fascinating underwater world at Island Dolphin Care, immerse yourself in nature at John Pennekamp Coral Reef State Park, and sample the tasty concoctions at Florida Keys Brewing Company.

For where to stay, reviews, and tourist information, refer to the Key Largo trip itinerary planner.

Drive from Marathon to Key Largo in 1.5 hours. Alternatively, you can take a bus. Traveling from Marathon in December, you can expect nighttime temperatures to be a bit cooler in Key Largo, with lows of 66°F. Cap off your sightseeing on the 20th (Thu) early enough to go by car to Miami Beach.

Things to do in Key Largo

Outdoors · Tours · Parks · Wildlife

Side Trips

Highlights from your plan
Fishing Charters & Tours
Homestead Miami Speedway ©
Homestead Miami Speedway

12
nights
Miami Beach

Miami Beach ©

The World's Playground

Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
Venture out of the city with trips to Miami (Dolphin Mall & Zoo Miami), Fairchild Tropical Botanic Garden (in Coral Gables) and Aventura Mall (in Aventura). The adventure continues: kick back and relax at South Beach, have fun at Lock & Load Miami, browse the different shops at Bayside Marketplace, and catch a live event at American Airlines Arena.

For where to stay, ratings, more things to do, and more tourist information, use the Miami Beach road trip planning app.

You can drive from Key Largo to Miami Beach in 1.5 hours. Other options are to take a bus; or take a bus. In December, daily temperatures in Miami Beach can reach 81°F, while at night they dip to 68°F. Finish your sightseeing early on the 1st (Tue) so you can drive to Delray Beach.

Things to do in Miami Beach

Parks · Shopping · Zoos & Aquariums · Museums

Side Trips

Highlights from your plan
Lock & Load Miami ©
Lock & Load Miami
South Beach ©
South Beach
Lincoln Road ©
Lincoln Road

11
nights
Delray Beach

Delray Beach ©
Explore Delray Beach's surroundings by going to Fort Lauderdale (E Las Olas Blvd, Fort Lauderdale Beach, &more), Jupiter (Busch Wildlife Sanctuary, Jupiter Inlet Lighthouse & Museum, &more) and West Palm Beach (Norton Museum of Art, Grassy Waters Nature Preserve, &more).

To see traveler tips, where to stay, and more tourist information, read our Delray Beach trip planner.

Traveling by car from Miami Beach to Delray Beach takes 1.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. In January, daytime highs in Delray Beach are 74°F, while nighttime lows are 62°F. On the 12th (Sat), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Delray Beach

Parks · Wildlife · Outdoors · Beaches

Side Trips

Highlights from your plan
Fort Lauderdale Beach ©
Fort Lauderdale Beach
Stranahan House ©
Stranahan House
Worth Avenue ©
Worth Avenue

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