27 days in Florida Itinerary

27 days in Florida Itinerary

Created using Inspirock Florida visit planner

Plan created by another user. Make it yours
1
Key West
— 1 night
2
Marathon
— 2 nights
3
Marco Island
— 2 nights
4
Sanibel Island
— 2 nights
5
Sarasota
— 2 nights
6
Tampa
— 2 nights
7
St. Augustine
— 2 nights
8
Orlando
— 4 nights
9
Saint Cloud
— 3 nights
10
Pensacola Beach
— 3 nights
11
Daytona Beach
— 3 nights

S M T W T F S
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21

1
night
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.
On the 22nd (Fri), examine the collection at The Ernest Hemingway Home and Museum, identify plant and animal life at Key West Butterfly & Nature Conservatory, then observe the fascinating underwater world at Florida Keys Eco-Discovery Center, then brush up on your military savvy at U.S. Coast Guard Cutter Ingham Maritime Museum, and finally go for a walk through Key West Garden Club. Get ready for a full day of sightseeing on the next day: examine the collection at Mel Fisher Maritime Heritage Museum, then get engrossed in the history at Key West Firehouse Museum, and then take in the architecture and atmosphere at Saint Mary Star of the Sea.

For ratings, photos, more things to do, and more tourist information, use the Key West driving holiday planner.

Boston to Key West is an approximately 7-hour flight. You can also drive; or do a combination of train and bus. Expect warmer temperatures when traveling from Boston in November; daily highs in Key West reach 81°F and lows reach 73°F. Cap off your sightseeing on the 23rd (Sat) early enough to go by car to Marathon.

Things to do in Key West

Museums · Parks · Historic Sites · Zoos & Aquariums
Highlights from your plan
Florida Keys Eco-Discovery Center ©
Florida Keys Eco-Discovery Center
Mel Fisher Maritime Heritage Museum ©
Mel Fisher Maritime Heritage Museum
Saint Mary Star of the Sea ©
Saint Mary Star of the Sea

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.
On the 24th (Sun), see the vivid underwater world at Sombrero Reef, stroll through Sombrero Beach, then examine the collection at Crane Point Museum & Nature Center, and finally take in the views from Old Seven Mile Bridge. Here are some ideas for day two: enjoy the sand and surf at Bahia Honda State Park, look for all kinds of wild species at Dolphin Research Center, and then get a taste of the local shopping with Shady Palm Art Gallery & Photography.

For ratings, reviews, and more tourist information, refer to the Marathon sightseeing planning site.

Getting from Key West to Marathon by car takes about 1.5 hours. Other options: take a bus. Expect a daytime high around 82°F in November, and nighttime lows around 72°F. Finish your sightseeing early on the 25th (Mon) to allow enough time to drive to Marco Island.

Things to do in Marathon

Parks · Wildlife · Beaches · Outdoors

Side Trip

Highlights from your plan
Crane Point Museum & Nature Center ©
Crane Point Museum & Nature Center
Dolphin Research Center ©
Dolphin Research Center
Bahia Honda State Park ©
Bahia Honda State Park

2
nights
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. Start off your visit on the 26th (Tue): get a dose of the wild on a nature and wildlife tour, then tour the pleasant surroundings at Cape Romano, and then kick back and relax at Keewaydin Island. Get ready for a full day of sightseeing on the 27th (Wed): get up close to creatures of the deep with a dolphin and whale watching tour, walk around Frank E. Mackle Park, and then have some family-friendly fun at Marco Golf and Garden.

To see where to stay, ratings, and tourist information, read Marco Island trip builder site.

Traveling by car from Marathon to Marco Island takes 4 hours. Alternatively, you can do a combination of bus and ferry; or take a bus. Traveling from Marathon in November, you can expect nighttime temperatures to be little chillier in Marco Island, with lows of 64°F. Finish your sightseeing early on the 27th (Wed) so you can drive to Sanibel Island.

Things to do in Marco Island

Outdoors · Parks · Tours · Wildlife
Highlights from your plan
Dolphin & Whale Watching
Keewaydin Island ©
Keewaydin Island
Frank E. Mackle Park ©
Frank E. Mackle Park

2
nights
Sanibel Island

Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Start off your visit on the 28th (Thu): contemplate in the serene atmosphere at Captiva Chapel By-The-Sea, then see what you can catch with a fishing tour, then get outside with Whitney's Bait and Tackle, and finally let the kids burn off some steam at Sanibel Community Playground. On the 29th (Fri), you'll have a packed day of sightseeing: enjoy the sand and surf at Captiva Beach, stroll through Bowman's Beach, and then kick back and relax at Little Hickory Beach Park.

For where to stay, maps, photos, and tourist information, use the Sanibel Island trip website.

You can drive from Marco Island to Sanibel Island in 2 hours. Alternatively, you can do a combination of bus and taxi. In November, daytime highs in Sanibel Island are 82°F, while nighttime lows are 63°F. Wrap up your sightseeing on the 29th (Fri) early enough to drive to Sarasota.

Things to do in Sanibel Island

Outdoors · Parks · Beaches · Fun & Games

Side Trips

Highlights from your plan
Fishing Charters & Tours
Captiva Beach ©
Captiva Beach
Bowman's Beach ©
Bowman's Beach

2
nights
Sarasota

Sarasota ©
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. On the 30th (Sat), enjoy the sand and surf at North Jetty Beach, tour the pleasant surroundings at Coquina Beach, and then get up close and personal with brilliant marine life at Mote Marine Laboratory & Aquarium. Get ready for a full day of sightseeing on the next day: get up close to creatures of the deep with a dolphin and whale watching tour, admire the majestic nature at Ted Sperling Park, then kick back and relax at South Lido Park, and finally stroll around Payne Park.

Use Inspirock's suggestions to plan your Sarasota trip and find the best activities and attractions for your vacation.

Getting from Sanibel Island to Sarasota by car takes about 2 hours. Other options: do a combination of taxi and bus. In November in Sarasota, expect temperatures between 80°F during the day and 62°F at night. Finish your sightseeing early on the 1st (Sun) so you can drive to Tampa.

Things to do in Sarasota

Parks · Outdoors · Beaches · Wildlife

Side Trips

Highlights from your plan
North Jetty Beach ©
North Jetty Beach
Mote Marine Laboratory & Aquarium ©
Mote Marine Laboratory & Aquarium
Payne Park ©
Payne Park

2
nights
Tampa

Tampa ©

Big Guava

Tampa ranks among the country's most livable cities, attracting newcomers with its growing economy and status as a major port on the Gulf of Mexico.
Kick off your visit on the 2nd (Mon): find something for the whole family at Busch Gardens Tampa Bay and then walk around Lettuce Lake Regional Park. Get ready for a full day of sightseeing on the next day: explore the engaging exhibits at Glazer Children's Museum, then learn about wildlife with up-close encounters at Big Cat Rescue, and then enjoy the sand and surf at Treasure Island Beach.

To see reviews, other places to visit, photos, and tourist information, use the Tampa holiday app.

You can drive from Sarasota to Tampa in 1.5 hours. Alternatively, you can do a combination of taxi and bus; or take a bus. In December, plan for daily highs up to 78°F, and evening lows to 61°F. Finish up your sightseeing early on the 3rd (Tue) so you can go by car to St. Augustine.

Things to do in Tampa

Parks · Theme Parks · Beaches · Outdoors

Side Trip

Highlights from your plan
Big Cat Rescue ©
Big Cat Rescue
Lettuce Lake Regional Park ©
Lettuce Lake Regional Park
Busch Gardens Tampa Bay ©
Busch Gardens Tampa Bay

2
nights
St. Augustine

St. Augustine ©
St. On the 4th (Wed), kick back and relax at Crescent Beach Public Beach, have some family-friendly fun at Fiesta Falls Miniature Golf, take an in-depth tour of Medieval Torture Museum, then brush up on your knowledge of spirits at St. Augustine Distillery, and finally get engrossed in the history at Old Florida Museum. Get ready for a full day of sightseeing on the next day: tour the pleasant surroundings at Atlantic Beach, then tour the pleasant surroundings at Jacksonville Beach, and then kick back and relax at Vilano Beach.

For reviews, ratings, traveler tips, and more tourist information, read St. Augustine trip planner.

Traveling by car from Tampa to St. Augustine takes 3.5 hours. Alternatively, you can take a bus; or fly. Traveling from Tampa in December, things will get a bit cooler in St. Augustine: highs are around 70°F and lows about 55°F. Finish your sightseeing early on the 5th (Thu) so you can drive to Orlando.

Things to do in St. Augustine

Beaches · Parks · Outdoors · Fun & Games

Side Trips

Highlights from your plan
Vilano Beach ©
Vilano Beach
Jacksonville Beach ©
Jacksonville Beach
Fiesta Falls Miniature Golf ©
Fiesta Falls Miniature Golf

4
nights
Orlando

Orlando ©

Theme Park Capital of the World

For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
You'll explore the less-touristy side of things at Tree of Life and Avatar Flight of Passage. Next up on the itinerary: discover the magic at Pandora – The World of Avatar.

To see where to stay, other places to visit, photos, and more tourist information, refer to the Orlando online sightseeing planner.

Getting from St. Augustine to Orlando by car takes about 2 hours. Other options: take a bus. Expect a bit warmer weather when traveling from St. Augustine in December: highs in Orlando hover around 77°F, while lows dip to 59°F. On the 9th (Mon), wrap the sightseeing up by early afternoon so you can drive to Saint Cloud.

Things to do in Orlando

Highlights from your plan
Avatar Flight of Passage ©
Avatar Flight of Passage
Tree of Life ©
Tree of Life
Pandora – The World of Avatar ©
Pandora – The World of Avatar

3
nights
Saint Cloud

Saint Cloud ©
You've now added Wild Willy's Airboat Tours to your itinerary. On the 10th (Tue), kick back and relax at Dan Tarrell Memorial Point, get a new perspective on things with Wild Willy's Airboat Tours, and then tee off at Royal St Cloud Golf Links. On your second day here, experience rural life at LaPorte Farms and then see what you can catch with a fishing tour.

To see more things to do, traveler tips, maps, and tourist information, go to the Saint Cloud driving holiday site.

Getting from Orlando to Saint Cloud by car takes about an hour. Other options: do a combination of train and taxi; or do a combination of bus and taxi. December in Saint Cloud sees daily highs of 78°F and lows of 57°F at night. On the 12th (Thu), wrap the sightseeing up by early afternoon so you can travel to Pensacola Beach.

Things to do in Saint Cloud

Outdoors · Tours · Wildlife · Parks

Side Trip

Highlights from your plan
Wild Willy's Airboat Tours ©
Wild Willy's Airboat Tours
Reptile World Serpentarium ©
Reptile World Serpentarium
LaPorte Farms ©
LaPorte Farms

3
nights
Pensacola Beach

Pensacola Beach ©
Pensacola Beach is an unincorporated community located on Santa Rosa Island, a barrier island, in Escambia County, Florida, United States. Your day by day itinerary now includes Pensacola Beach. You'll visit kid-friendly attractions like Gulf Islands National Seashore and Fort Pickens Area. You'll explore the less-touristy side of things at Emerald Coast Zoo and Destin Dog Park. Explore Pensacola Beach's surroundings by going to Fort Walton Beach (Garnier Post Office & Fishing Charters & Tours). It doesn't end there: stop by Innerlight Surf Shop and sample the fine beverages at Rollins Distillery.

For maps, reviews, ratings, and other tourist information, you can read our Pensacola Beach trip builder.

You can fly from Saint Cloud to Pensacola Beach in 5.5 hours. Other options are to drive; or do a combination of taxi and bus. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. Expect slightly colder temperatures when traveling from Saint Cloud in December; daily highs in Pensacola Beach reach 67°F and lows reach 50°F. Cap off your sightseeing on the 15th (Sun) early enough to travel to Daytona Beach.

Things to do in Pensacola Beach

Outdoors · Parks · Beaches · Tours

Side Trips

Highlights from your plan
Pensacola Beach ©
Pensacola Beach
Gulf Islands National Seashore ©
Gulf Islands National Seashore
Fort Pickens Area ©
Fort Pickens Area

3
nights
Daytona Beach

Daytona Beach ©

The World's Most Famous Beach

The iconic seaside destination of Daytona Beach once supported sugar mill plantations, but now entertains up to 8 million visitors a year.
You've now added Beach at Daytona Beach to your itinerary. On the 16th (Mon), don't miss a visit to Ritchey Plaza, enjoy the sand and surf at Beach at Daytona Beach, then take in the architecture and atmosphere at Our Lady of Lourdes Catholic Church, and finally contemplate the long history of Mary Bethune Home. Get ready for a full day of sightseeing on the 17th (Tue): join the crowd at Daytona International Speedway, see the interesting displays at MOAS - Museum of Arts and Sciences, then learn about all things military at Veterans Museum & Education Center, and finally join the crowd at Richard Petty Driving Experience.

For reviews, other places to visit, traveler tips, and more tourist information, read our Daytona Beach trip itinerary planning site.

Traveling by flight from Pensacola Beach to Daytona Beach takes 6 hours. Alternatively, you can drive; or do a combination of taxi and bus. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. In December, Daytona Beach is somewhat warmer than Pensacola Beach - with highs of 75°F and lows of 57°F. Wrap up your sightseeing by early afternoon on the 18th (Wed) to allow time for travel back home.

Things to do in Daytona Beach

Parks · Historic Sites · Beaches · Outdoors

Side Trips

Highlights from your plan
Beach at Daytona Beach ©
Beach at Daytona Beach
Daytona International Speedway ©
Daytona International Speedway
Mary Bethune Home
Mary Bethune Home

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