26 days in Florida Itinerary

26 days in Florida Itinerary

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Route & dates

26 days in Florida Itinerary

Start: Toronto
Fly + bus:  10​h 30​min
1
St. Augustine
— 4 nights
Drive:  1​h 30​min
2
Amelia Island
— 1 night
+4
taxi + Fly + foot + bus + taxi:  5​h
3
Marco Island
— 3 nights
Drive:  1​h 15​min
4
Fort Myers Beach
— 2 nights
Drive:  30​min
5
Sanibel Island
— 3 nights
taxi + Fly:  2​h 45​min
6
Key West
— 5 nights
bus:  1​h 15​min
7
Marathon
— 4 nights
Drive:  45​min
8
Islamorada
— 3 nights
shuttle + Fly:  8​h 15​min
End: Toronto

4
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. You'll discover tucked-away gems like Fort Matanzas National Monument and Market To Market. Relax by the water at St. Augustine Beach and Beach at Daytona Beach. Explore the numerous day-trip ideas around St. Augustine: Ponce Inlet (Ponce de Leon Inlet Lighthouse & Museum & Ponce Preserve) and Santa Maria del Mar Catholic Church (in Flagler Beach). There's still lots to do: sample the fine beverages at St. Augustine Distillery.

For ratings, other places to visit, and other tourist information, you can read our St. Augustine travel itinerary planner.

Toronto, Canada to St. Augustine is an approximately 10.5-hour flight. You can also drive. Traveling from Toronto in November, expect St. Augustine to be much warmer, temps between 26°C and 17°C. Finish up your sightseeing early on the 17th (Fri) so you can go by car to Amelia Island.

Things to do in St. Augustine

Parks Historic Sites Beaches

Side Trips

Ponce Inlet, Beach at Daytona Beach, Santa Maria del Mar Catholic Church
Find places to stay Nov 13 — 17:
Highlights from your plan
Fort Matanzas National Monument ©
Fort Matanzas National Monument
St. Augustine Beach ©
St. Augustine Beach
Beach at Daytona Beach ©
Beach at Daytona Beach

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.
To find maps, other places to visit, ratings, and tourist information, read our Amelia Island travel itinerary planner.

Traveling by car from St. Augustine to Amelia Island takes 1.5 hours. Alternatively, you can do a combination of bus and taxi. In November in Amelia Island, expect temperatures between 25°C during the day and 15°C at night. Wrap up your sightseeing by early afternoon on the 18th (Sat) to allow time for travel to Marco Island.

Things to do in Amelia Island

Nature Parks Historic Sites
Find places to stay Nov 17 — 18:
Highlights from your plan
Fort Clinch State Park ©
Fort Clinch State Park

3
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. Do some cultural sightseeing at Marco Island Historical Museum and Fifth Avenue South. Get outdoors at Parasailing & Paragliding and Lowdermilk Beach. Next up on the itinerary: enjoy the sand and surf at Tigertail Beach and get some thrills out on the water with a waterskiing or jet-skiing adventure.

To see traveler tips, where to stay, maps, and other tourist information, you can read our Marco Island itinerary planner.

Do a combination of taxi, flight, and bus from Amelia Island to Marco Island in 5 hours. Alternatively, you can drive; or do a combination of taxi and bus. Expect a bit warmer weather when traveling from Amelia Island in November: highs in Marco Island hover around 30°C, while lows dip to 18°C. Finish up your sightseeing early on the 21st (Tue) so you can go by car to Fort Myers Beach.

Things to do in Marco Island

Outdoors Beaches Parks

Side Trip

Naples
Find places to stay Nov 18 — 21:
Highlights from your plan
Parasailing & Paragliding
Waterskiing & Jetskiing
Tigertail Beach ©
Tigertail Beach

2
nights
Fort Myers Beach

Fort Myers Beach ©
Fort Myers Beach is a town located on Estero Island in Lee County, Florida, United States. On the 22nd (Wed), take in nature's colorful creations at Edison and Ford Winter Estates and then tour the pleasant surroundings at Fort Myers Beach. Get ready for a full day of sightseeing on the next day: immerse yourself in nature at Lovers Key State Park and then make a trip to Times Square.

For traveler tips, photos, maps, and other tourist information, use the Fort Myers Beach vacation planner.

Drive from Marco Island to Fort Myers Beach in 1.5 hours. Alternatively, you can ride a ferry. Expect a daytime high around 31°C in November, and nighttime lows around 19°C. Wrap up your sightseeing on the 23rd (Thu) to allow time to drive to Sanibel Island.

Things to do in Fort Myers Beach

Parks Wildlife Nature

Side Trip

Edison & Ford Winter Estates
Find places to stay Nov 21 — 23:
Highlights from your plan
Fort Myers Beach ©
Fort Myers Beach
Lovers Key State Park ©
Lovers Key State Park
Edison & Ford Winter Estates ©
Edison & Ford Winter Estates

3
nights
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Get outdoors at Captiva Beach and Bowman's Beach. You'll discover tucked-away gems like Blind Pass Beach Park and The Bailey-Matthews National Shell Museum.

For where to stay, traveler tips, reviews, and tourist information, use the Sanibel Island vacation planner.

Sanibel Island is just a stone's throw from Fort Myers Beach. In November, plan for daily highs up to 32°C, and evening lows to 19°C. Wrap up your sightseeing by early afternoon on the 26th (Sun) to allow time for travel to Key West.

Things to do in Sanibel Island

Beaches Outdoors Parks

Side Trip

Captiva Beach
Find places to stay Nov 23 — 26:
Highlights from your plan
Captiva Beach ©
Captiva Beach
Blind Pass Beach Park ©
Blind Pass Beach Park

5
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.
Discover out-of-the-way places like Dolphin & Whale Watching and Key West Lighthouse and Keeper's Quarters Museum. Visiting Scuba & Snorkeling and The Schooner Wolf - Private Charters will get you outdoors. Spend the 27th (Mon) exploring nature at Dry Tortugas National Park. There's lots more to do: get a new perspective on things with Boat Tours & Water Sports, explore the different monuments and memorials at Key West Cemetery, steep yourself in history at Fort Zachary Taylor, and see the interesting displays at Mel Fisher Maritime Museum.

To see more things to do, where to stay, ratings, and tourist information, read our Key West trip itinerary builder.

Do a combination of taxi and flight from Sanibel Island to Key West in 3 hours. Alternatively, you can do a combination of taxi and ferry; or drive. Expect somewhat warmer evenings in Key West when traveling from Sanibel Island in November, with lows around 25°C. Cap off your sightseeing on the 1st (Fri) early enough to go by car to Marathon.

Things to do in Key West

Outdoors Tours Adventure
Find places to stay Nov 26 — Dec 1:
Highlights from your plan
Stand-Up Paddleboarding
Mel Fisher Maritime Heritage Museum ©

4
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 Dolphin Research Center and Crane Point Museum & Nature Center. Take a break from the city and head to Scuba & Snorkeling and The Turtle Hospital. And it doesn't end there: snap pictures at Seven Mile Bridge, have fun at The Art Studio, stroll through Sombrero Beach, and see what you can catch with a fishing tour.

To find where to stay, other places to visit, photos, and other tourist information, use the Marathon vacation trip planner.

You can drive from Key West to Marathon in 1.5 hours. Alternatively, you can take a bus. In December, daytime highs in Marathon are 31°C, while nighttime lows are 24°C. Wrap up your sightseeing on the 5th (Tue) to allow time to drive to Islamorada.

Things to do in Marathon

Outdoors Parks Wildlife

Side Trip

Bahia Honda State Park
Find places to stay Dec 1 — 5:
Highlights from your plan
Dolphin Research Center ©
Dolphin Research Center
Bahia Honda State Park ©
Bahia Honda State Park
Sombrero Beach ©
Sombrero Beach

3
nights
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Escape the urban bustle at Florida Keys Wild Bird Rehabilitation Center and A Lil' Tail Charters. Satisfy your inner culture vulture at History of Diving Museum and Michelle Nicole Lowe Art Gallery. There's still lots to do: head outdoors with Takedown Charters, sample the tasty concoctions at Islamorada Beer Company Brewery and Tasting Room, take in the exciting artwork at Old Road Gallery, and see what you can catch with Robbie's of Islamorada.

To find reviews, more things to do, maps, and more tourist information, refer to the Islamorada online itinerary creator.

You can drive from Marathon to Islamorada in an hour. Alternatively, you can take a shuttle; or take a bus. In December in Islamorada, expect temperatures between 29°C during the day and 22°C at night. Wrap up your sightseeing on the 8th (Fri) to allow time to travel back home.

Things to do in Islamorada

Outdoors Wildlife Adventure

Side Trip

Florida Keys Wild Bird Rehabilitation Center
Find places to stay Dec 5 — 8:
Highlights from your plan
Robbie's of Islamorada ©
Robbie's of Islamorada
A Lil' Tail Charters ©
A Lil' Tail Charters

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