33 days in Florida City & Florida Keys Itinerary

33 days in Florida City & Florida Keys Itinerary

Created using Inspirock Florida sightseeing planner
Make it your trip
Drive
1
Florida City
— 3 nights
Drive
2
Key Largo
— 4 nights
Drive
3
Islamorada
— 4 nights
Unknown
4
Layton
— 1 day
Drive
5
Marathon
— 4 nights
Drive
6
Big Pine Key
— 3 nights
Drive
7
Key West
— 10 nights
Drive
8
Stock Island
— 1 night
Drive
9
Dry Tortugas National Park
— 2 nights
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Florida City — 3 nights

Florida City is a city in Miami-Dade County, Florida, United States and is the southernmost municipality in the South Florida metropolitan area. Step out of Florida City with an excursion to Pineland Trail in Everglades National Park--about 30 minutes away. Spend the 30th (Tue) exploring nature at Everglades National Park. There's still lots to do: trek along Gumbo Limbo Trail, get some fabulous bargains at Florida Keys Outlet Marketplace, contemplate the long history of Coral Castle, and look for all kinds of wild species at Everglades Alligator Farm.

For ratings, where to stay, other places to visit, and other tourist information, you can read our Florida City trip site.

Richmond to Florida City is an approximately 14-hour car ride. Expect a bit warmer evenings in Florida City when traveling from Richmond in August, with lows around 77°F. Wrap up your sightseeing on the 1st (Thu) to allow time to drive to Key Largo.
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Parks · Nature · Outdoors · Trails
Side Trips

Key Largo — 4 nights

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.
Key Largo is known for wildlife, nature, and adventure. Your trip includes some of its best attractions: discover the deep blue sea with a scuba or snorkeling tour, do a tasting at Keys' Meads, walk around Harry Harris Park, and meet the residents at Island Dolphin Care.

To find other places to visit, traveler tips, maps, and more tourist information, read Key Largo trip itinerary maker.

Drive from Florida City to Key Largo in an hour. Expect a daytime high around 88°F in September, and nighttime lows around 76°F. Wrap up your sightseeing by early afternoon on the 5th (Mon) to allow enough time to drive to Islamorada.
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Parks · Wildlife · Outdoors · Spas

Islamorada — 4 nights

The Village of Islands

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Islamorada is known for wildlife, adventure, and museums. Your trip includes some of its best attractions: take a tour by water with Boat Tours & Water Sports, head off the coast to Windley Key, explore the gorgeous colors at Alligator Reef Light House, and take an in-depth tour of History of Diving Museum.

To find where to stay, maps, ratings, and other tourist information, refer to the Islamorada trip itinerary builder tool.

Islamorada is very close to Key Largo. In September, plan for daily highs up to 90°F, and evening lows to 79°F. Wrap up your sightseeing on the 9th (Fri) to allow time to travel to Layton.
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Historic Sites · Museums · Outdoors · Wildlife

Layton — 1 day

Start off your visit on the 9th (Fri): get outside with Dooda Charters and then admire the majestic nature at Long Key State Park.

To plan Layton vacation without wasting time, ask Inspirock to design an itinerary.

Layton is just a short distance from Islamorada. Finish your sightseeing early on the 9th (Fri) to allow enough time to drive to Marathon.
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Outdoors · Parks · Nature
Side Trip
Highlights from your trip

Marathon — 4 nights

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.
Marathon is known for wildlife, beaches, and sightseeing. Your trip includes some of its best attractions: look for all kinds of wild species at The Turtle Hospital, discover the deep blue sea with a scuba or snorkeling tour, see the vivid underwater world at Sombrero Reef, and examine the collection at EAA Air Museum.

To find photos, where to stay, more things to do, and other tourist information, you can read our Marathon trip planner.

Marathon is very close to Layton. In September, plan for daily highs up to 90°F, and evening lows to 79°F. Wrap up your sightseeing on the 13th (Tue) to allow time to drive to Big Pine Key.
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Parks · Wildlife · Outdoors · Beaches
Side Trip

Big Pine Key — 3 nights

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. Big Pine Key is known for beaches, wildlife, and adventure. Your trip includes some of its best attractions: tour the pleasant surroundings at Bahia Honda State Park, walk around Veterans Memorial Park, relax and rejuvenate at SpaTerre at Little Palm Island Resort, and shop like a local with Artists in Paradise Gallery.

For traveler tips, where to stay, and other tourist information, go to the Big Pine Key route site.

Big Pine Key is just a stone's throw from Marathon. September in Big Pine Key sees daily highs of 90°F and lows of 79°F at night. Finish your sightseeing early on the 16th (Fri) so you can drive to Key West.
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Parks · Outdoors · Wildlife · Beaches
Side Trip

Key West — 10 nights

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.
Key West is known for sightseeing, wildlife, and adventure. Your trip includes some of its best attractions: see the interesting displays at The Ernest Hemingway Home and Museum, enjoy the sand and surf at Fort Zachary Taylor, observe the fascinating underwater world at Key West Aquarium, and look for all kinds of wild species at Key West Butterfly & Nature Conservatory.

To see where to stay, photos, reviews, and more tourist information, you can read our Key West trip maker app.

Traveling by car from Big Pine Key to Key West takes an hour. Alternatively, you can take a shuttle; or take a bus. In September, daily temperatures in Key West can reach 88°F, while at night they dip to 80°F. Cap off your sightseeing on the 26th (Mon) early enough to go by car to Stock Island.
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Museums · Parks · Shopping · Historic Sites

Stock Island — 1 night

Stock Island is a census-designated place (CDP) & Unincorporated community on an island of the same name in Monroe County, Florida, United States. Kick off your visit on the 27th (Tue): get close to the beloved marine mammals with Sea Monkey Ocean Adventures and then take in panoramic vistas at Sugarloaf Key Bat Tower.

To see photos, ratings, traveler tips, and other tourist information, refer to the Stock Island road trip planner.

Stock Island is just a stone's throw from Key West. In September, daily temperatures in Stock Island can reach 89°F, while at night they dip to 80°F. Cap off your sightseeing on the 27th (Tue) early enough to travel to Dry Tortugas National Park.
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Outdoors · Wildlife · Tours
Side Trip

Dry Tortugas National Park — 2 nights

What Dry Tortugas National Park lacks in size, it makes up for in abundance of marine life.
Kick off your visit on the 28th (Wed): take in the dramatic natural features at Little Africa, explore the striking landscape at Tortugas Banks, then head off the coast to Garden Key, and finally tour the pleasant surroundings at Fort Jefferson. Here are some ideas for day two: see some colorful creatures with Florida Keys National Marine Sanctuary and then identify plant and animal life at Looe Key (Florida Keys National Marine Sanctuary).

To find ratings, other places to visit, where to stay, and tourist information, go to the Dry Tortugas National Park trip itinerary website.

Use the Route module to find suitable travel options from Stock Island to Dry Tortugas National Park. In September, daytime highs in Dry Tortugas National Park are 88°F, while nighttime lows are 80°F. Finish your sightseeing early on the 29th (Thu) to allow enough time to travel back home.
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Parks · Wildlife · Nature · Outdoors
Side Trip

Florida Keys travel guide

4.3
Scuba & Snorkeling · Parasailing & Paragliding · Landmarks
An archipelago of about 1,700 islands extending in a gentle arc south and southwest of Florida's mainland, the Florida Keys divide the Atlantic from the Gulf of Mexico. Many visitors on vacation come to scuba dive in the coral reefs, fossilized and exposed as sea levels declined over thousands of years. In addition to being one of the world's top diving and fishing spots, the Keys feature hundreds of shops, restaurants, bars, and various tourist attractions, most of them crowded all year long with visitors on vacation. To soak up the Keys' atmosphere and discover writer Ernest Hemingway's former haunts, drive from one island to the other all the way to Key West, located just 140 km (90 mi) from Cuba.
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Long Key travel guide

3.7
State Parks · Outdoor Activities
Long Key is an island in the middle Florida Keys. Long Key was called Cayo Víbora (Rattlesnake Key) by early Spanish explorers, a reference to the shape of the island, which resembles a snake with its jaws open, rather than to its denizens. The city of Layton is located on Long Key. The 965acre state park (3.9 km²) was dedicated October 1, 1969.U.S. 1 (or the Overseas Highway) crosses the key at approximately mile markers 65.5--71, between Fiesta Key and Conch Key. It is the home of Long Key State Park, a favorite of campers and nature lovers, the camp sites are on the beach but the proximity of US1 makes it noisy. It is smaller and less developed than the neighboring incorporated village of Islamorada to the northeast and city of Marathon to the southwest.It was visited by C.W. Pierce in his boat, Bonton (1885). He stopped at the lower end of the key where there was a house with a cistern and replenished his water supply.The key was a depot site during the railroad years, and was also the site of the well known Long Key Fishing Camp.

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