5 days in Florida Itinerary

5 days in Florida Itinerary

Created using Inspirock Florida trip planner
Make it your trip
Fly
1
Key West
— 1 day
Drive
2
Marathon
— 2 nights
Shuttle to Miami, Fly to St. Augustine
3
St. Augustine
— 2 nights
Fly

S M T W T F S
4
5
6
7
8
9
10
11
12
13
14
15
16
17

Key West — 1 day

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.
On the 9th (Fri), stop by We Cycle, visit a coastal fixture at Key West Lighthouse and Keeper's Quarters Museum, and then see majestic marine mammals with a dolphin and whale watching tour.

For other places to visit, more things to do, and more tourist information, read our Key West online vacation builder.

New York City to Key West is an approximately 5-hour flight. You can also drive; or take a bus. Traveling from New York City in September, expect Key West to be a bit warmer, temps between 88°F and 80°F. Finish up your sightseeing early on the 9th (Fri) so you can go by car to Marathon.
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Marathon — 2 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.
On the 10th (Sat), identify plant and animal life at Dolphin Research Center, cast your line with a fishing tour, and then sample the tasty concoctions at Florida Keys Brewing Company. On your second day here, look for all kinds of wild species at The Turtle Hospital, snap pictures at Seven Mile Bridge, and then enjoy the sand and surf at Sombrero Beach.

To find reviews, ratings, where to stay, and more tourist information, read Marathon day trip planner.

You can drive from Key West to Marathon in 1.5 hours. Another option is to take a bus. Expect a daytime high around 90°F in September, and nighttime lows around 79°F. Finish your sightseeing early on the 11th (Sun) to allow enough time to travel to St. Augustine.
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Wildlife · Parks · Outdoors · Breweries & Distilleries
Side Trip
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St. Augustine — 2 nights

St. Kick off your visit on the 12th (Mon): brush up on your military savvy at Spanish Military Hospital Museum, take in the architecture and atmosphere at Cathedral Basilica of St. Augustine, then deepen your understanding at Flagler College, and finally take a stroll through Old City. On the 13th (Tue), you'll have a packed day of sightseeing: contemplate the long history of Old Jail Museum, then enjoy the sand and surf at St. Augustine Beach, and then identify plant and animal life at St. Augustine Alligator Farm Zoological Park.

To see other places to visit, reviews, and more tourist information, read our St. Augustine holiday website.

Getting from Marathon to St. Augustine by combination of shuttle and flight takes about 6.5 hours. Other options: drive; or take a bus. Expect slightly colder temperatures when traveling from Marathon in September; daily highs in St. Augustine reach 85°F and lows reach 73°F. Wrap up your sightseeing on the 13th (Tue) to allow time to fly back home.
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Historic Sites · Parks · Wildlife · Neighborhoods
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Florida travel guide

4.3
Disney Parks & Activities · Beaches · Theme Parks
The Sunshine State
The “Sunshine State,” Florida became a favorite winter destination for the affluent crowd over a century ago. Today, the state attracts visitors from around the world with its golden beaches and modern theme parks. You can spend your entire vacation enjoying the state's highly developed seaside areas, but remember that some of Florida's best-kept secrets are in secluded locations. Visit the big cities and their comfortable resorts offering top-notch dining and nightlife, but leave some time to see the peninsula's swampy landscape, filled with wild creatures and native plants. Farther away from the tourist-packed urban areas, the untamed wetlands of Florida offer a selection of things to do, such as kayaking, boat rides, and numerous other outdoor activities.
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