27 days in Florida Itinerary

27 days in Florida Itinerary

Created using Inspirock Florida trip planner

Plan created by another user. Make it yours
1
Cocoa Beach
— 2 nights
2
St. Augustine
— 4 nights
3
Panama City Beach
— 1 night
4
Fort Walton Beach
— 4 nights
5
Islamorada
— 2 nights
6
Marathon
— 2 nights
7
Key West
— 3 nights
8
Marco Island
— 2 nights
9
Naples
— 3 nights
10
Sanibel Island
— 2 nights
11
Bradenton Beach, Anna Maria Island
— 1 night

S M T W T F S
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2
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.
Start off your visit on the 2nd (Fri): engage your brain at Space Shuttle Atlantis, take a leisurely stroll along Rikki Tiki Tavern at Cocoa Beach Pier, kick back and relax at Alan Shepard Beachfront Park, then examine the collection at The Dinosaur Store, and finally indulge in some personalized pampering at some of the best spas. Get ready for a full day of sightseeing on the 3rd (Sat): experience rural life at LaPorte Farms, wander the streets of Main Street Melbourne - Downtown Melbourne, enjoy the sand and surf at Sea Turtle Preservation Society Melbourne Beach, then kick back and relax at Paradise Beach & Park, and finally stroll around Wickham Park.

Quickly create a custom-made itinerary for Cocoa Beach using our trip planner.

Orlando to Cocoa Beach is an approximately 1.5-hour car ride. You can also do a combination of shuttle and bus; or take a bus. In October, daily temperatures in Cocoa Beach can reach 83°F, while at night they dip to 73°F. Wrap up your sightseeing on the 3rd (Sat) to allow time to drive to St. Augustine.

Things to do in Cocoa Beach

Parks · Outdoors · Beaches · Museums

Side Trips

Highlights from your plan
Space Shuttle Atlantis ©
Space Shuttle Atlantis
Wickham Park ©
Wickham Park
Spas

4
nights
St. Augustine

St. Augustine ©
St. You'll enjoy a bit of beach vacationing at Crescent Beach Public Beach and Ponte Vedra Beach. Bring the kids along to Santa Fe College Teaching Zoo and Carson Springs Wildlife Conservation Foundation. Change things up with these side-trips from St. Augustine: Sweetwater Wetlands Park (in Gainesville) and Princess Place Preserve (in Palm Coast). There's lots more to do: steep yourself in history at The Oldest House Museum Complex, cast your line with Reel Dream Fishing Charters, take an in-depth tour of Government House Museum, and see the interesting displays at Father Miguel O'Reilly House Museum.

For reviews, maps, where to stay, and more tourist information, go to the St. Augustine vacation maker.

Drive from Cocoa Beach to St. Augustine in 2.5 hours. Alternatively, you can drive; or do a combination of car and bus. Traveling from Cocoa Beach in October, St. Augustine is a bit cooler at night with lows of 67°F. Finish your sightseeing early on the 7th (Wed) to allow enough time to drive to Panama City Beach.

Things to do in St. Augustine

Parks · Outdoors · Wildlife · Museums

Side Trips

Highlights from your plan
Santa Fe College Teaching Zoo ©
Santa Fe College Teaching Zoo
Sweetwater Wetlands Park ©
Sweetwater Wetlands Park

1
night
Panama City Beach

Panama City Beach ©

World's Most Beautiful Beaches

Boasting 43 km (27 mi) of white sandy beaches and plenty of sunshine, Panama City Beach is an ideal choice for a relaxing holiday.
Start off your visit on the 8th (Thu): enjoy the sand and surf at Rosemary Beach Public Beach, then stroll around Conservation Park, then stroll around Rick Seltzer Park, and finally find something for the whole family at Coconut Creek Family Fun Park.

To see reviews, maps, where to stay, and more tourist information, refer to the Panama City Beach trip planner.

Drive from St. Augustine to Panama City Beach in 5.5 hours. Alternatively, you can drive; or fly. Traveling from St. Augustine in October, plan for slightly colder nights in Panama City Beach, with lows around 59°F. Finish your sightseeing early on the 8th (Thu) to allow enough time to drive to Fort Walton Beach.

Things to do in Panama City Beach

Parks · Outdoors · Beaches · Theme Parks

Side Trip

Highlights from your plan
Rosemary Beach Public Beach ©
Rosemary Beach Public Beach
Coconut Creek Family Fun Park ©
Coconut Creek Family Fun Park
Conservation Park ©
Conservation Park

4
nights
Fort Walton Beach

Fort Walton Beach ©
Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. Eschew the tourist crowds and head to Hummingbird Zipline Course and Adventure Island. Kids will enjoy Goofy Golf and Gulf Shores Public Beach. Explore the numerous day-trip ideas around Fort Walton Beach: Veterans Memorial Park (in Pensacola), Topsail Beach State Preserve (in Santa Rosa Beach) and Orange Beach (Orange Beach Waterfront Park, Hugh S. Branyon Backcountry Trail - Rosemary Dunes Trailhead, &more). And it doesn't end there: tour the water at your own pace with Luther's Pontoon, Waverunner, & Kayak Rentals, buy something for everyone on your list at Destin Commons, examine the collection at Indian Temple Mound and Museum, and walk around John C Beasley Park.

For where to stay, photos, and other tourist information, use the Fort Walton Beach trip builder site.

You can drive from Panama City Beach to Fort Walton Beach in 1.5 hours. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. In October, plan for daily highs up to 80°F, and evening lows to 60°F. Wrap up your sightseeing on the 12th (Mon) to allow time to travel to Islamorada.

Things to do in Fort Walton Beach

Outdoors · Parks · Tours · Theme Parks

Side Trips

Highlights from your plan
Luther's Pontoon, Waverunner, & Kayak Rentals ©
Gulf Shores Public Beach
Gulf Shores Public Beach
Wild Willy's Adventure Zone ©
Wild Willy's Adventure Zone

2
nights
Islamorada

Islamorada ©

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.
Kick off your visit on the 13th (Tue): get the adrenaline pumping with Florida Keys Jetpacks, shop like a local with Old Road Gallery, sample the tasty concoctions at Islamorada Brewery & Distillery, then take in the exciting artwork at Lobster Trap Art Gift Shop and Gallery, then relax and rejuvenate at Island Flow Yoga, and finally enjoy the sand and surf at Library Beach Park. Get ready for a full day of sightseeing on the next day: look for gifts at Bella Sol Fragrance Bar and Gifts, take in the exciting artwork at Rain Barrel Village, stroll around Founders Park, then get engrossed in the history at History of Diving Museum, then add some adventure to your tour with The Kayak Shack, and finally explore the gorgeous colors at Alligator Reef Light House.

To see photos, traveler tips, other places to visit, and tourist information, read Islamorada road trip planner.

Traveling by flight from Fort Walton Beach to Islamorada takes 6 hours. Alternatively, you can fly; or drive; or do a combination of bus and shuttle. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. Plan for a bit warmer temperatures traveling from Fort Walton Beach in October, with highs in Islamorada at 87°F and lows at 77°F. Wrap up your sightseeing on the 14th (Wed) early enough to drive to Marathon.

Things to do in Islamorada

Outdoors · Museums · Parks · Tours
Highlights from your plan
The Kayak Shack ©
The Kayak Shack
History of Diving Museum ©
History of Diving Museum
Alligator Reef Light House ©
Alligator Reef Light House

2
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.
Start off your visit on the 15th (Thu): see the interesting displays at Crane Point Museum & Nature Center, identify plant and animal life at Sombrero Reef, then glide through the air with Z Flight Watersports, then kick back and relax at Sunset Park Beach, and finally pause for some serene contemplation at San Pablo Catholic Church. On your second day here, take the plunge with Skydive Key West, look for all kinds of wild species at Looe Key (Florida Keys National Marine Sanctuary), kick back and relax at Calusa Beach, then examine the collection at EAA Air Museum, and finally immerse yourself in nature at Curry Hammock State Park.

To see other places to visit, photos, where to stay, and tourist information, go to the Marathon holiday planner.

You can drive from Islamorada to Marathon in an hour. Another option is to take a bus. In October, daily temperatures in Marathon can reach 87°F, while at night they dip to 77°F. Finish up your sightseeing early on the 16th (Fri) so you can go by car to Key West.

Things to do in Marathon

Parks · Outdoors · Wildlife · Beaches

Side Trips

Highlights from your plan
Z Flight Watersports ©
Z Flight Watersports
Sunset Park Beach ©
Sunset Park Beach
San Pablo Catholic Church ©
San Pablo Catholic Church

3
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.
You'll get in some beach time at Simonton Street Beach and Higgs Beach. Bring the kids along to Peppers of Key West and West Martello Tower. There's still lots to do: find your balance on the water with some of the best stand-up paddleboarding in the area, take an unforgettable tour with Air Adventures Helicopter Tours, take in nature's colorful creations at Audubon House & Tropical Gardens, and take in the pleasant sights at Key West Garden Club.

To find ratings, reviews, photos, and other tourist information, refer to the Key West driving holiday site.

Traveling by car from Marathon to Key West takes 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 86°F in October, and nighttime lows around 77°F. Wrap up your sightseeing on the 19th (Mon) early enough to ride a ferry to Marco Island.

Things to do in Key West

Parks · Outdoors · Beaches · Museums
Highlights from your plan
Air Adventures Helicopter Tours ©
Air Adventures Helicopter Tours
Florida Keys Eco-Discovery Center ©
Florida Keys Eco-Discovery Center
Smathers Beach ©
Smathers Beach

2
nights
Marco Island

Marco Island ©
Marco Island is a city in Collier County, Florida, United States, located on an island by the same name in the Gulf of Mexico off the coast of Southwest Florida. Kick off your visit on the 20th (Tue): take a memorable tour with Native Guided Fishing Charters, then enjoy the sand and surf at Keewaydin Island, and then indulge in some personalized pampering at some of the best spas. On the 21st (Wed), you'll have a packed day of sightseeing: get engrossed in the history at Marco Island Historical Museum, then go for a stroll along the water at Isles of Capri Marina, then view the masterpieces at Clyde Butcher's Big Cypress Gallery, and finally get a dose of the wild on a nature and wildlife tour.

To find traveler tips, other places to visit, photos, and more tourist information, use the Marco Island vacation builder app.

Ride a ferry from Key West to Marco Island in 3.5 hours. Alternatively, you can ride a ferry; or drive. Plan for little chillier nights when traveling from Key West in October since evenings lows in Marco Island dip to 68°F. Finish your sightseeing early on the 21st (Wed) so you can drive to Naples.

Things to do in Marco Island

Outdoors · Wildlife · Tours · Museums

Side Trip

Highlights from your plan
Native Guided Fishing Charters ©
Native Guided Fishing Charters
Keewaydin Island ©
Keewaydin Island
Marco Island Historical Museum ©
Marco Island Historical Museum

3
nights
Naples

Naples ©
You'll discover tucked-away gems like Vanderbilt Beach and Koreshan State Park. You'll visit kid-friendly attractions like All Water Excursions and Little Hickory Beach Park.

For ratings, reviews, and more tourist information, you can read our Naples trip planner.

Getting from Marco Island to Naples by car takes about an hour. Other options: take a bus. October in Naples sees daily highs of 87°F and lows of 71°F at night. Finish your sightseeing early on the 24th (Sat) so you can drive to Sanibel Island.

Things to do in Naples

Parks · Outdoors · Museums · Wildlife

Side Trips

Highlights from your plan
All Water Excursions ©
All Water Excursions
Vanderbilt Beach ©
Vanderbilt Beach
Naples Historical Society ©
Naples Historical Society

2
nights
Sanibel Island

Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
On the 25th (Sun), see what you can catch with a fishing tour, then enjoy the sand and surf at Gulfside Beach, and then enjoy the sand and surf at Tarpon Bay Beach. Get ready for a full day of sightseeing on the next day: visit Captiva Pass, soothe aching muscles at Ambu Yoga, then stop by Redfish Pass, then let little ones run wild at Sanibel Community Playground, and finally make a trip to St. Isabel Catholic Church.

For reviews and other tourist information, go to the Sanibel Island attractions site.

Drive from Naples to Sanibel Island in 1.5 hours. Expect a daytime high around 86°F in October, and nighttime lows around 70°F. Cap off your sightseeing on the 26th (Mon) early enough to go by car to Bradenton Beach.

Things to do in Sanibel Island

Outdoors · Parks · Wildlife · Tours

Side Trip

Highlights from your plan
Fishing Charters & Tours
Gulfside Beach ©
Gulfside Beach
Sanibel Community Playground ©
Sanibel Community Playground

1
night

Bradenton Beach ©
Bradenton Beach is a city on Anna Maria Island in Manatee County, Florida, United States. Start off your visit on the 27th (Tue): look for gifts at Bridge Street Bazaar, then take a leisurely stroll along Bridge Street Pier, then get some thrills out on the water with Gulf Islands Adventures, and finally stroll around Leffis Key Preserve.

For traveler tips, other places to visit, photos, and other tourist information, read Bradenton Beach journey builder website.

You can drive from Sanibel Island to Bradenton Beach in 2.5 hours. Other options are to drive; or do a combination of taxi and bus. Expect a daytime high around 86°F in October, and nighttime lows around 68°F. Wrap up your sightseeing on the 27th (Tue) early enough to drive back home.

Things to do in Bradenton Beach

Outdoors · Adventure · Wildlife · Tours

Side Trip

Highlights from your plan
Leffis Key Preserve ©
Leffis Key Preserve
Bridge Street Pier ©
Bridge Street Pier
Bridge Street Bazaar ©
Bridge Street Bazaar

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