25 days in Florida Itinerary

25 days in Florida Itinerary

Created using Inspirock Florida holiday planner

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Route & dates

25 days in Florida Itinerary

Start: Montreal
Fly + taxi:  9​h
1
Pensacola
— 3 nights
Fly:  4​h 15​min
2
Miami
— 4 nights
Drive:  1​h 45​min
3
Islamorada
— 4 nights
bus:  2​h
4
Key West
— 5 nights
Fly:  4​h 15​min
5
Orlando
— 5 nights
Drive:  2​h
6
St. Petersburg
— 3 nights
+2
bus + foot + Fly:  7​h
End: Montreal

3
nights
Pensacola

Pensacola ©
Surrounded on three sides by water, Pensacola offers access to white-sand beaches and emerald-green ocean unspoiled by large resorts.
Let the collections at National Naval Aviation Museum and Pensacola Lighthouse and Museum capture your imagination. Visit Navarre Beach and Gulf Islands National Seashore for some beach relaxation. When in Pensacola, make a side trip to see Fort Pickens Area in Pensacola Beach, approximately 42 minutes away. And it doesn't end there: take a tour by water with Boat Tours & Water Sports, get a taste of the local shopping with Quayside, and stop by Innerlight Surf Shop.

To find maps, reviews, other places to visit, and more tourist information, go to the Pensacola road trip website .

Montreal, Canada to Pensacola is an approximately 9-hour combination of flight and taxi. You can also do a combination of flight and car; or drive. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. Expect somewhat warmer temperatures when traveling from Montreal in June; daily highs in Pensacola reach 36°C and lows reach 27°C. Wrap up your sightseeing on the 27th (Sat) early enough to travel to Miami.

Things to do in Pensacola

Outdoors Beaches Parks

Side Trips

Pensacola Beach, Navarre Beach
Highlights from your plan
National Naval Aviation Museum ©
National Naval Aviation Museum
Navarre Beach ©
Navarre Beach
Dolphin & Whale Watching

4
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.
Give yourself a bit of retail therapy at Lincoln Road and Aventura Mall. You'll explore and learn at Vizcaya Museum and Gardens and Lock & Load Museum. Step out of Miami with an excursion to Wiener Museum of Decorative Arts (WMODA) in Dania Beach--about 40 minutes away. Next up on the itinerary: get to know the fascinating history of Art Deco Historic District, buy something for everyone on your list at Bayside Marketplace, go for a walk through Espanola Way, and steep yourself in history at Barnacle State Historic Site.

To find traveler tips, photos, more things to do, and tourist information, go to the Miami trip maker app .

You can fly from Pensacola to Miami in 4.5 hours. Alternatively, you can do a combination of taxi and flight; or drive. Traveling from Pensacola to Miami, you'll lose 1 hour due to the time zone difference. Expect a daytime high around 37°C in June, and nighttime lows around 29°C. Wrap up your sightseeing on the 1st (Wed) to allow time to drive to Islamorada.

Things to do in Miami

Shopping Neighborhoods Historic Sites

Side Trips

Miami Beach, Aventura Mall, Wiener Museum of Decorative Arts (WMODA)
Highlights from your plan
Lincoln Road ©
Lincoln Road
South Beach ©
South Beach
Vizcaya Museum and Gardens ©
Vizcaya Museum and Gardens

4
nights
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Shop till you drop at Pasta Pantaleo Signature Gallery and Shell World Florida Keys. Get some historical perspective at San Pablo Catholic Church and Indian Key State Historic Site. Take a break from Islamorada with a short trip to John Pennekamp Coral Reef State Park in Key Largo, about 32 minutes away. And it doesn't end there: take a tour by water with Boat Tours & Water Sports, sample the tasty concoctions at Islamorada Beer Company, take an in-depth tour of History of Diving Museum, and get a taste of the local shopping with Lobster Trap Art Gallery.

For photos, maps, other places to visit, and other tourist information, read Islamorada travel itinerary planner .

Drive from Miami to Islamorada in 2 hours. Alternatively, you can take a bus. Expect a daytime high around 39°C in July, and nighttime lows around 32°C. Cap off your sightseeing on the 5th (Sun) early enough to catcht the bus to Key West.

Things to do in Islamorada

Wildlife Parks Tours

Side Trips

Key Largo, San Pablo Catholic Church
Highlights from your plan
Island Dolphin Care ©
Island Dolphin Care
Scuba & Snorkeling

5
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.
The Ernest Hemingway Home and Museum and Truman Little White House will appeal to museum buffs. Give yourself a bit of retail therapy at Alan S. Maltz Gallery and Collections Key West. The adventure continues: stroll through Fort Zachary Taylor, contemplate the long history of Audubon House & Tropical Gardens, identify plant and animal life at Key West Butterfly & Nature Conservatory, and visit a coastal fixture at Key West Lighthouse and Keeper's Quarters Museum.

To find other places to visit, where to stay, traveler tips, and tourist information, go to the Key West trip itinerary planning tool .

You can take a bus from Islamorada to Key West in 2 hours. Another option is to drive. Expect a daytime high around 37°C in July, and nighttime lows around 32°C. Wrap up your sightseeing on the 10th (Fri) to allow time to travel to Orlando.

Things to do in Key West

Museums Outdoors Historic Sites
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Dolphin & Whale Watching

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.
Pack the 13th (Mon) with family-friendly diversions at Discovery Cove. Pack the 11th (Sat) with family-friendly diversions at Universal Orlando Resort. There's much more to do: discover the magic at Walt Disney World Resort, find something for the whole family at SeaWorld Orlando, take in a show at Happily Ever After Fireworks, and stop by MacroBaby.

For more things to do, traveler tips, reviews, and more tourist information, read our Orlando journey builder website .

Fly from Key West to Orlando in 4.5 hours. Alternatively, you can drive; or take a bus. Expect a bit cooler evenings in Orlando when traveling from Key West in July, with lows around 28°C. Wrap up your sightseeing on the 15th (Wed) to allow time to drive to St. Petersburg.

Things to do in Orlando

Theme Parks Beaches Parks
Highlights from your plan
Universal Orlando Resort ©
Universal Orlando Resort
Walt Disney World Resort ©
Walt Disney World Resort
Discovery Cove ©
Discovery Cove

3
nights
St. Petersburg

St. Petersburg ©
Located on a peninsula between Tampa Bay and the Gulf of Mexico, St.
You'll explore and learn at Duncan McClellan Gallery and James Museum of Western & Wildlife Art. Visit Sarasota National Cemetery and St. Nicholas Greek Orthodox Cathedral for their historical value. Get out of town with these interesting St. Petersburg side-trips: Philippe Park (in Safety Harbor), Siesta Key Rum (in Sarasota) and Siesta Beach (in Siesta Key). And it doesn't end there: enjoy the sand and surf at Clearwater Beach, have some family-friendly fun at Outerlife Studios - Escape Room St. Pete, and glide through the air with a parasailing or paragliding tour.

To see ratings, reviews, other places to visit, and more tourist information, go to the St. Petersburg trip planner.

You can drive from Orlando to St. Petersburg in 2 hours. Alternatively, you can take a bus; or take a train. In July, plan for daily highs up to 38°C, and evening lows to 30°C. Wrap up your sightseeing on the 18th (Sat) early enough to travel back home.

Things to do in St. Petersburg

Parks Outdoors Beaches

Side Trips

Sarasota, Philippe Park, Siesta Beach, Parasailing & Paragliding, St. Nicholas Greek Orthodox Cathedral
Highlights from your plan
Duncan McClellan Gallery ©
Duncan McClellan Gallery
Clearwater Beach ©
Clearwater Beach
Siesta Beach ©
Siesta Beach

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