25 days in Florida Itinerary

25 days in Florida Itinerary

Created using Inspirock Florida holiday planner

Plan created by another user. Make it yours

Route & dates

1
Pensacola
— 3 nights
2
Miami
— 4 nights
3
Islamorada
— 4 nights
4
Key West
— 5 nights
5
Orlando
— 5 nights
6
St. Petersburg
— 3 nights

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.
Appreciate the collections at National Naval Aviation Museum and Quayside. You'll get in some beach time at Navarre Beach and Gulf Islands National Seashore. Go for a jaunt from Pensacola to Pensacola Beach to see Fort Pickens Area about 42 minutes away. There's more to do: stop by Innerlight Surf Shop and visit a coastal fixture at Pensacola Lighthouse & Maritime Museum.

For where to stay, more things to do, photos, and tourist information, use the Pensacola day trip website.

Montreal, Canada to Pensacola is an approximately 9-hour flight. You can also drive; or take a bus. You'll gain 1 hour traveling from Montreal to Pensacola due to the time zone difference. Traveling from Montreal in June, things will get somewhat warmer in Pensacola: highs are around 36°C and lows about 27°C. Cap off your sightseeing on the 27th (Sat) early enough to travel to Miami.

Things to do in Pensacola

Museums · Outdoors · Beaches

Side Trips

Pensacola Beach, Navarre Beach
Highlights from your plan
National Naval Aviation Museum ©
National Naval Aviation Museum
Navarre Beach ©
Navarre Beach
Gulf Islands National Seashore ©
Gulf Islands National Seashore

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.
Let the collections at Vizcaya Museum and Gardens and Wiener Museum of Decorative Arts (WMODA) capture your imagination. For shopping fun, head to Lincoln Road or Dolphin Mall. There's lots more to do: get to know the fascinating history of Art Deco Historic District, don't miss a visit to Bayside Marketplace, explore the different monuments and memorials at Charlotte Jane Memorial Park Cemetary, and wander the streets of Collins Avenue.

To find out how to plan a trip to Miami, use our trip itinerary maker.

You can fly from Pensacola to Miami in 4.5 hours. Other options are to drive; or take a bus. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. In June, daytime highs in Miami are 37°C, while nighttime lows are 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, Wiener Museum of Decorative Arts (WMODA), Aventura Mall
Highlights from your plan
Lincoln Road ©
Lincoln Road
South Beach ©
South Beach
Art Deco Historic District ©
Art Deco Historic District

4
nights
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Head to Lobster Trap Art Gift Shop and Gallery and Old Road Galleryfor plenty of shopping. You'll explore and learn at Pasta Pantaleo Signature Gallery and History of Diving Museum. Get out of town with these interesting Islamorada side-trips: John Pennekamp Coral Reef State Park (in Key Largo) and San Pablo Catholic Church (in Marathon). Next up on the itinerary: get to know the fascinating history of Indian Key State Historic Site, indulge your thirst for a good beer at Islamorada Brewery & Distillery, take in the exciting artwork at Gallery Morada, and look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center.

For where to stay, reviews, and other tourist information, use the Islamorada trip itinerary planning website.

You can drive from Miami to Islamorada in 2 hours. Another option is to take a bus. In July, daytime highs in Islamorada are 39°C, while nighttime lows are 32°C. Cap off your sightseeing on the 5th (Sun) early enough to go by car to Key West.

Things to do in Islamorada

Wildlife · Outdoors · Tours

Side Trips

Key Largo, San Pablo Catholic Church
Highlights from your plan
Fishing Charters & Tours
Scuba & Snorkeling
Dolphins Plus Marine Mammal Responder ©
Dolphins Plus Marine Mammal Responder

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.
Get some historical perspective at Fort Zachary Taylor and Key West Lighthouse and Keeper's Quarters Museum. Give yourself a bit of retail therapy at Alan S. Maltz Gallery and Art On Duval Key West. Next up on the itinerary: see the interesting displays at The Ernest Hemingway Home and Museum, shop like a local with Collections Key West, browse the exhibits of Truman Little White House, and get interesting insight from Tours.

To see where to stay, more things to do, other places to visit, and other tourist information, you can read our Key West trip itinerary maker website.

Drive from Islamorada to Key West in 2 hours. Alternatively, you can take a bus. In July, plan for daily highs up to 37°C, and evening lows to 32°C. Wrap up your sightseeing on the 10th (Fri) early enough to travel to Orlando.

Things to do in Key West

Museums · Outdoors · Historic Sites
Highlights from your plan
The Ernest Hemingway Home and Museum ©
The Ernest Hemingway Home and Museum
Key West Butterfly & Nature Conservatory ©
Truman Little White House ©
Truman Little White House

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 11th (Sat) with family-friendly diversions at Universal Orlando Resort. Pack the 13th (Mon) with family-friendly diversions at Discovery Cove. Next up on the itinerary: get in on the family fun at Walt Disney World Resort, discover the magic at Happily Ever After Fireworks, and look for gifts at MacroBaby.

For other places to visit, photos, maps, and more tourist information, you can read our Orlando online sightseeing planner.

Getting from Key West to Orlando by flight takes about 4.5 hours. Other options: drive; or take a bus. Expect slightly colder evenings in Orlando when traveling from Key West in July, with lows around 28°C. Finish up your sightseeing early on the 15th (Wed) so you can go by car to St. Petersburg.

Things to do in Orlando

Theme Parks · Outdoors · Beaches
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.
Let the collections at Duncan McClellan Gallery and James Museum of Western & Wildlife Art capture your imagination. Get some historical perspective at Sarasota National Cemetery and St. Nicholas Greek Orthodox Cathedral. Explore the numerous day-trip ideas around St. Petersburg: Siesta Beach (in Siesta Key), Philippe Park (in Safety Harbor) and Siesta Key Rum (in Sarasota). And it doesn't end there: stroll through Clearwater Beach, fly like a bird with a parasailing or paragliding tour, and get your game on at Outerlife Studios - Escape Room St. Pete.

To see where to stay, other places to visit, ratings, and more tourist information, use the St. Petersburg sightseeing tool.

Getting from Orlando to St. Petersburg by car takes about 2 hours. Other options: take a bus; or do a combination of train and bus. In July in St. Petersburg, expect temperatures between 38°C during the day and 30°C at night. Wrap up your sightseeing on the 18th (Sat) early enough to travel back home.

Things to do in St. Petersburg

Outdoors · Parks · Beaches

Side Trips

Sarasota, Siesta Beach, Clearwater Beach, St. Nicholas Greek Orthodox Cathedral, Parasailing & Paragliding
Highlights from your plan
Sarasota National Cemetery ©
Sarasota National Cemetery
Clearwater Beach ©
Clearwater Beach
Siesta Beach ©
Siesta Beach

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