21 days in Florida Itinerary

21 days in Florida Itinerary

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Route & dates

21 days in Florida Itinerary

Start: Sydney
Fly:  9​h 30​min
1
Key West
— 2 nights
bus:  1​h 15​min
2
Marathon
— 3 nights
Drive:  4​h 15​min
3
Naples
— 4 nights
Drive:  4​h 30​min
4
Cocoa Beach
— 3 nights
Drive:  1​h 30​min
5
Daytona Beach
— 3 nights
bus:  1​h
6
St. Augustine
— 3 nights
bus + Fly:  26​h
End: Sydney

2
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 South Beach and Fort Zachary Taylor for some beach relaxation. Step out of the city life by going to Higgs Beach and Simonton Street Beach. There's much more to do: admire the masterpieces at Fort East Martello Museum, kick back and relax at Smathers Beach, fly like a bird with Sebago Key West, and take in the waterfront at Edward B. Knight Pier.

For more things to do, where to stay, reviews, and tourist information, read Key West trip itinerary planner.

Sydney, Australia to Key West is an approximately 26-hour flight. You can also do a combination of flight and shuttle; or do a combination of flight and ferry. The time zone difference moving from Australian Eastern Standard Time (New South Wales) (AEST) to Eastern Standard Time (EST) is minus 15 hours. Expect a bit warmer weather when traveling from Sydney in September: highs in Key West hover around 36°C, while lows dip to 31°C. Wrap up your sightseeing on the 23rd (Wed) early enough to take a bus to Marathon.

Things to do in Key West

Outdoors Beaches Parks
Highlights from your plan
Fort Zachary Taylor ©
Fort Zachary Taylor
Fort East Martello Museum ©
Fort East Martello Museum
Smathers Beach ©
Smathers Beach

3
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.
Explore hidden gems such as Sunset Park Beach and Anne's Beach. Step out of the city life by going to Captain Hook's and Coco Plum Beach. And it doesn't end there: pause for some serene contemplation at San Pablo Catholic Church, snap pictures at Seven Mile Bridge, enjoy the sand and surf at Sombrero Beach, and admire the majestic nature at Bahia Honda State Park.

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

Traveling by bus from Key West to Marathon takes 1.5 hours. Alternatively, you can drive. In September, plan for daily highs up to 38°C, and evening lows to 30°C. Finish your sightseeing early on the 26th (Sat) to allow enough time to drive to Naples.

Things to do in Marathon

Outdoors Beaches Parks

Side Trips

Anne's Beach, Bahia Honda State Park, Sunset Park Beach
Highlights from your plan
Sunset Park Beach ©
Sunset Park Beach
San Pablo Catholic Church ©
San Pablo Catholic Church
Anne's Beach ©
Anne's Beach

4
nights
Naples

Naples ©
Naples is a city in Collier County, Florida, United States. Get some cultural insight at Collier Museum at Government Center and Celebration Community Beach Church. Get in touch with nature at Capt. Ron's Awesome Everglades Adventures and Tigertail Beach. You'll find plenty of places to visit near Naples: Fort Myers Beach (Fort Myers Beach & Fort Myers Beach Public Library). The adventure continues: kick back and relax at Lowdermilk Beach, look for gifts at Toucan's World, get active on the water at Captain CJ's JetPack Adventures, and take in the waterfront at Naples Pier.

To find traveler tips, where to stay, ratings, and more tourist information, go to the Naples road trip tool .

You can drive from Marathon to Naples in 4.5 hours. Other options are to do a combination of bus and flight; or do a combination of bus and train. September in Naples sees daily highs of 37°C and lows of 28°C at night. Wrap up your sightseeing on the 30th (Wed) to allow time to drive to Cocoa Beach.

Things to do in Naples

Outdoors Beaches Parks

Side Trips

Marco Island, Fort Myers Beach
Highlights from your plan
Fort Myers Beach ©
Fort Myers Beach
Collier Museum at Government Center ©

3
nights
Cocoa Beach

Cocoa Beach ©
Situated in one of Florida's busiest vacation areas, Cocoa Beach burst onto the world scene in the 1960s, when it became a popular setting for parades honoring the nation's "Apollo" astronauts.
You'll enjoy a bit of beach vacationing at Canova Beach Dog Park and Sea Turtle Preservation Society Melbourne Beach. Step off the beaten path and head to Nex Generation Surfing School and Secrets of Cocoa Beach. There's lots more to do: take a leisurely stroll along Rikki Tiki Tavern at Cocoa Beach Pier, stroll through Cocoa Beach, relax and rejuvenate at Beach Pole Fitness, and head outdoors with A1A Beach Rentals.

To find maps and more tourist information, refer to the Cocoa Beach day trip site .

You can drive from Naples to Cocoa Beach in 4.5 hours. Alternatively, you can take a bus; or do a combination of bus and flight. In September, daily temperatures in Cocoa Beach can reach 36°C, while at night they dip to 29°C. Wrap up your sightseeing on the 3rd (Sat) to allow time to drive to Daytona Beach.

Things to do in Cocoa Beach

Outdoors Beaches Parks

Side Trips

Cape Canaveral, Canova Beach Dog Park, Sea Turtle Preservation Society Melbourne Beach
Highlights from your plan
Cocoa Beach ©
Cocoa Beach
Beach Pole Fitness ©
Beach Pole Fitness
Secrets of Cocoa Beach ©
Secrets of Cocoa Beach

3
nights
Daytona Beach

Daytona Beach ©
The iconic seaside destination of Daytona Beach once supported sugar mill plantations, but now entertains up to 8 million visitors a year.
Get outdoors at Lighthouse Point Park and Ormond Beach. MOAS - Museum of Arts and Sciences and Ponce de Leon Inlet Lighthouse & Museum will appeal to museum buffs. There's much more to do: enjoy the sand and surf at Andy Romano Beachfront Park, tour the pleasant surroundings at Beach at Daytona Beach, take in the waterfront at Daytona Beach Boardwalk and Pier, and take an in-depth tour of Halifax Historical Museum.

To see where to stay, photos, and more tourist information, go to the Daytona Beach road trip website .

Traveling by car from Cocoa Beach to Daytona Beach takes 1.5 hours. Alternatively, you can take a bus. Plan for little chillier nights when traveling from Cocoa Beach in October since evenings lows in Daytona Beach dip to 22°C. Cap off your sightseeing on the 6th (Tue) early enough to catcht the bus to St. Augustine.

Things to do in Daytona Beach

Beaches Parks Outdoors

Side Trips

Ponce Inlet, Ormond Beach
Highlights from your plan
Beach at Daytona Beach ©
Beach at Daytona Beach
MOAS - Museum of Arts and Sciences ©
Ormond Beach ©
Ormond Beach

3
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. You'll explore and learn at Lightner Museum and St. Augustine Lighthouse & Maritime Museum, Inc.. Get in touch with nature at Jacksonville Beach and Atlantic Beach. Change things up with a short trip to Kathryn Abbey Hanna Park in Jacksonville (about 58 minutes away). The adventure continues: get interesting insight from Tours by the Sea and tour the pleasant surroundings at St. Augustine Beach.

For ratings, other places to visit, photos, and more tourist information, read our St. Augustine vacation planner.

Traveling by bus from Daytona Beach to St. Augustine takes an hour. Alternatively, you can drive. In October in St. Augustine, expect temperatures between 31°C during the day and 22°C at night. Cap off your sightseeing on the 9th (Fri) early enough to travel back home.

Things to do in St. Augustine

Parks Outdoors Beaches

Side Trips

Jacksonville, Jacksonville Beach
Highlights from your plan
Jacksonville Beach ©
Jacksonville Beach
Lightner Museum ©
Lightner Museum
St. Augustine Beach ©
St. Augustine Beach

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