31 days in Florida Itinerary

31 days in Florida Itinerary

Created using Inspirock Florida visit planner

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Route & dates

31 days in Florida Itinerary

Start: Portland
Fly:  8 h 45 min
1
Amelia Island
— 1 night
Drive:  1 h 30 min
2
St. Augustine
— 1 night
Drive:  2 h 30 min
3
Cocoa Beach
— 1 night
Drive:  3 h
4
Fort Lauderdale
— 1 night
Drive:  45 min
5
Miami Beach
— 2 nights
Drive:  30 min
6
Miami
— 2 nights
Train:  1 h 45 min
7
Everglades National Park
— 2 nights
Bus:  2 h
8
Key Largo
— 2 nights
Drive:  45 min
9
Islamorada
— 2 nights
Drive:  45 min
10
Marathon, Florida Keys
— 2 nights
Bus:  1 h 15 min
11
Key West
— 4 nights
Ferry:  2 h 30 min
12
Marco Island
— 1 night
Drive:  45 min
13
Naples
— 1 night
Drive:  2 h
14
Sarasota
— 1 night
Drive:  1 h
15
Anna Maria, Anna Maria Island
— 1 night
Drive:  1 h
16
St. Petersburg
— 1 night
Drive:  2 h
17
Orlando
— 5 nights
Fly:  8 h 30 min
End: Portland

1
night
Amelia Island

Amelia Island ©
The southernmost Sea Island off the coast of Florida, Amelia Island takes its name from Princess Amelia of England.
On the 13th (Tue), explore the different monuments and memorials at Bosque Bello Cemetery, explore the activities along Egan's Creek Park, kick back and relax at Main Beach, then kick back and relax at Seaside Park, and finally examine the collection at Fernandina Beach Pinball Museum.

To find traveler tips, other places to visit, photos, and more tourist information, read our Amelia Island trip builder site.

Portland to Amelia Island is an approximately 9- hour flight. You can also do a combination of flight and car; or drive. Due to the time zone difference, you'll lose 3 hours traveling from Portland to Amelia Island. Prepare for somewhat warmer weather when traveling from Portland in October: high temperatures in Amelia Island hover around 81°F and lows are around 67°F. Wrap up your sightseeing on the 13th (Tue) early enough to drive to St. Augustine.

Things to do in Amelia Island

Parks Outdoors Beaches
Find places to stay Oct 12 — 13:
Highlights from your plan
Egan's Creek Park ©
Egan's Creek Park
Bosque Bello Cemetery ©
Bosque Bello Cemetery
Fernandina Beach Pinball Museum ©
Fernandina Beach Pinball Museum

1
night
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. On the 14th (Wed), view the masterpieces at High Tide Gallery Art & Gifts, steep yourself in history at Pena-Peck House and Woman's Exchange of St Augustine, see the interesting displays at Father Miguel O'Reilly House Museum, then contemplate the long history of The Oldest House Museum Complex, and finally snap pictures at Bridge of Lions.

For maps, reviews, where to stay, and other tourist information, use the St. Augustine trip itinerary planner.

You can drive from Amelia Island to St. Augustine in 1.5 hours. Alternatively, you can do a combination of taxi and bus. Expect a daytime high around 80°F in October, and nighttime lows around 67°F. Wrap up your sightseeing on the 14th (Wed) early enough to drive to Cocoa Beach.

Things to do in St. Augustine

Museums Historic Sites Shopping
Find places to stay Oct 13 — 14:
Highlights from your plan
The Oldest House Museum Complex ©
The Oldest House Museum Complex
Bridge of Lions ©
Bridge of Lions

1
night
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.
Kick off your visit on the 15th (Thu): get lost in a book at Cocoa Beach Public Library, indulge in some personalized pampering at some of the best spas, then putt your heart out at Lighthouse Cove Adventure Golf, and finally walk around Cocoa Beach Skate Park.

To see traveler tips, ratings, other places to visit, and other tourist information, you can read our Cocoa Beach trip planner.

You can drive from St. Augustine to Cocoa Beach in 2.5 hours. Another option is to do a combination of car and bus. Traveling from St. Augustine in October, Cocoa Beach is a bit warmer at night with lows of 73°F. Finish your sightseeing early on the 15th (Thu) to allow enough time to drive to Fort Lauderdale.

Things to do in Cocoa Beach

Fun & Games Parks Spas
Find places to stay Oct 14 — 15:
Highlights from your plan
Lighthouse Cove Adventure Golf ©
Lighthouse Cove Adventure Golf
Spas
Cocoa Beach Public Library ©
Cocoa Beach Public Library

1
night
Fort Lauderdale

Fort Lauderdale ©
Known as the "Venice of America" because of its extensive network of navigable waterways, Fort Lauderdale welcomes over 10 million annual visitors, most of them attracted by the city's popular beaches and marinas.
Kick off your visit on the 16th (Fri): explore the world behind art at Wiener Museum of Decorative Arts (WMODA), get outside with JP Outfitters Inc., get engrossed in the history at History Fort Lauderdale, then look for gifts at To the Moon, and finally take in the spiritual surroundings of Saint Demetrios Greek Orthodox Church.

For other places to visit, maps, traveler tips, and tourist information, use the Fort Lauderdale online trip builder.

Getting from Cocoa Beach to Fort Lauderdale by car takes about 3 hours. Other options: take a bus; or fly. In October in Fort Lauderdale, expect temperatures between 86°F during the day and 75°F at night. Finish up your sightseeing early on the 16th (Fri) so you can go by car to Miami Beach.

Things to do in Fort Lauderdale

Museums Historic Sites Outdoors

Side Trips

Wiener Museum of Decorative Arts (WMODA), JP Outfitters Inc.
Find places to stay Oct 15 — 16:
Highlights from your plan
Wiener Museum of Decorative Arts (WMODA) ©
History Fort Lauderdale ©
History Fort Lauderdale
Saint Demetrios Greek Orthodox Church ©

2
nights
Miami Beach

Miami Beach ©
Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
On the 17th (Sat), take in the exciting artwork at Britto Central, then kick back and relax at North Shore Open Space Park, then stroll through Bal Harbor Beach, and finally enjoy the sand and surf at Haulover Beach Park. On the 18th (Sun), you'll have a packed day of sightseeing: examine the collection at Miami Auto Museum, contemplate the long history of The Ancient Spanish Monastery, then identify plant and animal life at Enchanted Forest Elaine Gordon Park, and finally admire the masterpieces at The Wolfsonian - Florida International University.

Plan my day in Miami Beach using traveler tips and tourist information provided by Inspirock.

Traveling by car from Fort Lauderdale to Miami Beach takes an hour. Alternatively, you can take a bus; or do a combination of train and bus. In October in Miami Beach, expect temperatures between 87°F during the day and 74°F at night. Wrap up your sightseeing on the 18th (Sun) to allow time to drive to Miami.

Things to do in Miami Beach

Parks Outdoors Beaches

Side Trips

North Miami, The Ancient Spanish Monastery, Haulover Beach Park
Find places to stay Oct 16 — 18:
Highlights from your plan
Haulover Beach Park ©
Haulover Beach Park
Britto Central ©
Britto Central

2
nights
Miami

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Start off your visit on the 19th (Mon): enjoy the sand and surf at Bill Baggs Cape Florida State Park, enjoy the sea views from Cape Florida Lighthouse, then enjoy some diversion at Lock & Load Miami, then see the interesting displays at Lock & Load Museum, and finally take in the views from Venetian Causeway. Get ready for a full day of sightseeing on the 20th (Tue): stroll around Deering Point, then contemplate the long history of Deering Estate, then take in nature's colorful creations at Pinecrest Gardens, and finally get interesting insight from Tours.

For other places to visit, reviews, traveler tips, and other tourist information, go to the Miami day trip planner.

Miami is very close to Miami Beach. In October in Miami, expect temperatures between 87°F during the day and 74°F at night. Cap off your sightseeing on the 20th (Tue) early enough to catch the train to Everglades National Park.

Things to do in Miami

Outdoors Wildlife Parks

Side Trips

Key Biscayne, Pinecrest Gardens, Deering Point
Find places to stay Oct 18 — 20:
Highlights from your plan
Bill Baggs Cape Florida State Park ©
Bill Baggs Cape Florida State Park
Cape Florida Lighthouse ©
Cape Florida Lighthouse
Deering Estate ©
Deering Estate

2
nights
Everglades National Park

Everglades National Park ©
A vast expanse of pristine wetlands, Everglades National Park holds the distinction of being the largest tropical wilderness in the U.S.
On the 21st (Wed), identify plant and animal life at Mahogany Hammock, then visit Flamingo, and then take a leisurely stroll along West Lake Trail. On your second day here, trek along Pa-hay-okee Trail, stroll through Pineland Trail, then step off the mainland to explore Long Pine Key, and finally look for all kinds of wild species at Nine Mile Pond Canoe Trail.

To find maps, other places to visit, ratings, and other tourist information, use the Everglades National Park online itinerary planner.

Traveling by train from Miami to Everglades National Park takes 2 hours. Alternatively, you can take a bus. Expect a daytime high around 87°F in October, and nighttime lows around 77°F. Wrap up your sightseeing on the 22nd (Thu) early enough to travel to Key Largo.

Things to do in Everglades National Park

Parks Wildlife Trails
Find places to stay Oct 20 — 22:
Highlights from your plan
Mahogany Hammock ©
Mahogany Hammock
Nine Mile Pond Canoe Trail ©
Nine Mile Pond Canoe Trail
Flamingo ©
Flamingo

2
nights
Key Largo

Key Largo ©
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.
Kick off your visit on the 23rd (Fri): get some thrills out on the water with a waterskiing or jet-skiing adventure, kick back and relax at Harry Harris Park, then revel in the low prices at Sandal Factory Outlet, and finally get answers to all your questions at Florida Keys Visitor Center. Get ready for a full day of sightseeing on the next day: look for gifts at florida keys key lime products, explore the gorgeous colors at Grecian Rocks, then see the vivid underwater world at North Dry Rocks, and finally take in the architecture and atmosphere at Key Largo Baptist Church.

For photos, other places to visit, ratings, and other tourist information, read Key Largo online road trip planner.

Take a bus from Everglades National Park to Key Largo in 2 hours. In October, daily temperatures in Key Largo can reach 85°F, while at night they dip to 73°F. Cap off your sightseeing on the 24th (Sat) early enough to go by car to Islamorada.

Things to do in Key Largo

Parks Outdoors Wildlife
Find places to stay Oct 22 — 24:
Highlights from your plan
Grecian Rocks ©
Grecian Rocks
Waterskiing & Jetskiing
florida keys key lime products ©
florida keys key lime products

2
nights
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
On the 25th (Sun), see the interesting displays at Florida Keys History & Discovery Center, enjoy the sand and surf at Library Beach Park, then look for gifts at Ocean Gardens, and finally identify plant and animal life at Alligator Reef Light House. On the 26th (Mon), you'll have a packed day of sightseeing: take in the dramatic natural features at Windley Key Fossil Reef Geological State Park, take in the exciting artwork at Old Road Gallery, then take in the exciting artwork at Pasta Pantaleo Signature Gallery, and finally get outside with Takedown Charters.

To find ratings, where to stay, photos, and more tourist information, go to the Islamorada attractions planner.

You can drive from Key Largo to Islamorada in an hour. Another option is to do a combination of taxi and bus. October in Islamorada sees daily highs of 87°F and lows of 77°F at night. Finish your sightseeing early on the 26th (Mon) to allow enough time to drive to Marathon.

Things to do in Islamorada

Parks Shopping Museums
Find places to stay Oct 24 — 26:
Highlights from your plan
Alligator Reef Light House ©
Alligator Reef Light House
Takedown Charters ©
Takedown Charters

2
nights
Marathon, Florida Keys

Marathon ©
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 27th (Tue): shop like a local with Shady Palm Art Gallery & Photography, then see the vivid underwater world at Sombrero Reef, then browse the exhibits of Crane Point Museum & Nature Center, and finally enjoy the sand and surf at Sunset Park Beach. On the 28th (Wed), you'll have a packed day of sightseeing: take in the architecture and atmosphere at San Pablo Catholic Church and then get interesting insight from Tours.

To find where to stay, other places to visit, traveler tips, and tourist information, you can read our Marathon online sightseeing planner.

Traveling by car from Islamorada to Marathon takes an hour. Alternatively, you can take a bus. In October, plan for daily highs up to 87°F, and evening lows to 77°F. Finish your sightseeing early on the 28th (Wed) to allow enough time to take a bus to Key West.

Things to do in Marathon

Wildlife Outdoors Parks

Side Trips

Fishing Charters & Tours, Sunset Park Beach
Find places to stay Oct 26 — 28:
Highlights from your plan
Crane Point Museum & Nature Center ©
Crane Point Museum & Nature Center
Sunset Park Beach ©
Sunset Park Beach
Fishing Charters & Tours

4
nights
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.
Your cultural itinerary includes sights like Saint Mary Star of the Sea and West Martello Tower. You'll get in some beach time at Simonton Street Beach and South Beach. The adventure continues: get interesting insight from Tours, see the vivid underwater world at Vandenberg Wreck, take in the waterfront at Key West Historic Seaport, and stroll through Smathers Beach.

To find photos, traveler tips, other places to visit, and other tourist information, read Key West trip planner.

Getting from Marathon to Key West by bus takes about 1.5 hours. Other options: drive. In October, plan for daily highs up to 86°F, and evening lows to 77°F. Finish up your sightseeing early on the 1st (Sun) so you can catch the ferry to Marco Island.

Things to do in Key West

Parks Outdoors Historic Sites
Find places to stay Oct 28 — Nov 1:
Highlights from your plan
Dolphin & Whale Watching
Saint Mary Star of the Sea ©
Saint Mary Star of the Sea
Key West Historic Seaport ©
Key West Historic Seaport

1
night
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. Start off your visit on the 2nd (Mon): identify plant and animal life at Otter Mound Preserve, head off the coast to Cape Romano, then get a new perspective on things with Boat Tours & Water Sports, and finally indulge in some personalized pampering at some of the best spas.

To find other places to visit, more things to do, traveler tips, and tourist information, read our Marco Island tour site.

Ride a ferry from Key West to Marco Island in 2.5 hours. Alternatively, you can drive. Traveling from Key West in November, expect a bit cooler with lows of 64°F in Marco Island. Finish your sightseeing early on the 2nd (Mon) to allow enough time to drive to Naples.

Things to do in Marco Island

Outdoors Parks Wildlife
Find places to stay Nov 1 — 2:
Highlights from your plan
Cape Romano ©
Cape Romano
Nature & Wildlife Tours
Otter Mound Preserve ©
Otter Mound Preserve

1
night
Naples

Naples ©
Naples is a city in Collier County, Florida, United States. Start off your visit on the 3rd (Tue): look for all kinds of wild species at Conservancy of Southwest Florida, steep yourself in history at Naples Historical Society, and then hike along Tamiami Trail.

Plan my Naples trip by asking Inpirock to come up with tips and suggestions.

Traveling by car from Marco Island to Naples takes an hour. In November in Naples, expect temperatures between 82°F during the day and 65°F at night. Wrap up your sightseeing on the 3rd (Tue) early enough to drive to Sarasota.

Things to do in Naples

Parks Wildlife Historic Sites

Side Trip

Tamiami Trail
Find places to stay Nov 2 — 3:
Highlights from your plan
Conservancy of Southwest Florida ©
Conservancy of Southwest Florida
Naples Historical Society ©
Naples Historical Society

1
night
Sarasota

Sarasota ©
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. On the 4th (Wed), immerse yourself in nature at Red Bug Slough Preserve, relax and rejuvenate at some of the best spas, immerse yourself in nature at Ted Sperling Park, look for gifts at Pepper Palace, then explore the activities along Ken Thompson Park, and finally contemplate the long history of The Powel Crosley Estate.

For other places to visit, where to stay, maps, and tourist information, read our Sarasota travel planner.

Traveling by car from Naples to Sarasota takes 2 hours. Alternatively, you can take a bus. In November, plan for daily highs up to 80°F, and evening lows to 62°F. Cap off your sightseeing on the 4th (Wed) early enough to go by car to Anna Maria.

Things to do in Sarasota

Parks Wildlife Nature
Find places to stay Nov 3 — 4:
Highlights from your plan
Red Bug Slough Preserve ©
Red Bug Slough Preserve
The Powel Crosley Estate ©
The Powel Crosley Estate
Spas

1
night
Anna Maria, Anna Maria Island

Anna Maria ©
Anna Maria, is a city in Manatee County, Florida, United States. On the 5th (Thu), look for gifts at Anna Maria Rocks, take an in-depth tour of Anna Maria Island Historical Museum, then get to know the fascinating history of Coquina Baywalk, and finally make a trip to Anna Maria Historic Green Village.

To find maps, photos, traveler tips, and other tourist information, read Anna Maria trip builder app.

You can drive from Sarasota to Anna Maria in an hour. Another option is to take a bus. In November, daily temperatures in Anna Maria can reach 80°F, while at night they dip to 62°F. Wrap up your sightseeing on the 5th (Thu) early enough to drive to St. Petersburg.

Things to do in Anna Maria

Parks Wildlife Historic Sites
Find places to stay Nov 4 — 5:
Highlights from your plan
Anna Maria Island Historical Museum ©
Anna Maria Rocks ©
Anna Maria Rocks

1
night
St. Petersburg

St. Petersburg ©
Located on a peninsula between Tampa Bay and the Gulf of Mexico, St.
On the 6th (Fri), relax and rejuvenate at some of the top local wellness centers, pause for some serene contemplation at St. Jude the Apostle Cathedral Church, then see the interesting displays at Imagine Museum, then take in the exciting artwork at St. Petersburg Clay Company, and finally have some family-friendly fun at Outerlife Studios - Escape Room St. Pete.

For where to stay, photos, and tourist information, go to the St. Petersburg trip itinerary planner.

Traveling by car from Anna Maria to St. Petersburg takes an hour. Alternatively, you can do a combination of taxi and bus. In November, daytime highs in St. Petersburg are 77°F, while nighttime lows are 65°F. Finish up your sightseeing early on the 6th (Fri) so you can go by car to Orlando.

Things to do in St. Petersburg

Museums Fun & Games Spas
Find places to stay Nov 5 — 6:
Highlights from your plan
Imagine Museum ©
Imagine Museum
St. Jude the Apostle Cathedral Church ©
Spas & Wellness

5
nights
Orlando

Orlando ©
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.
Get a sense of the local culture at SKELETONS: Museum of Osteology and White Sands Buddhist Center. Deepen your sense of the past at sights like The Howey Mansion and Dunlawton Sugar Mill Gardens. Get out of town with these interesting Orlando side-trips: Apopka (West Orange Trail & Lake Apopka Wildlife Trail), New Smyrna Beach (New Smyrna Town Beach & Apollo Beach) and Trout Lake Nature Center (in Eustis). And it doesn't end there: explore the activities along Lake Dora, look for all kinds of wild species at Audubon Center for Birds of Prey, catch some excitement at Expedition Everest - Legend of the Forbidden Mountain, and discover the deep blue sea with a scuba or snorkeling tour.

To find where to stay, more things to do, ratings, and more tourist information, read our Orlando trip itinerary site.

Drive from St. Petersburg to Orlando in 2 hours. Alternatively, you can take a bus; or take a train. In November in Orlando, expect temperatures between 78°F during the day and 62°F at night. Finish up your sightseeing early on the 11th (Wed) so you can travel back home.

Things to do in Orlando

Parks Wildlife Outdoors

Side Trips

Apopka, New Smyrna Beach, Audubon Center for Birds of Prey, The Howey Mansion, Dunlawton Sugar Mill Gardens
Find places to stay Nov 6 — 11:
Highlights from your plan
Audubon Center for Birds of Prey ©
Audubon Center for Birds of Prey
New Smyrna Town Beach ©
New Smyrna Town Beach
Lake Dora ©
Lake Dora

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