29 days in Florida Itinerary

29 days in Florida Itinerary

Created using Inspirock Florida holiday builder

This plan was created by another user.  Make it your plan

Route & dates

29 days in Florida Itinerary

Start: Toronto
Fly:  6​h 30​min
1
Miami Beach
— 3 nights
Drive:  1​h 30​min
2
Key Largo
— 3 nights
Drive:  45​min
3
Islamorada
— 4 nights
Drive:  45​min
4
Marathon
— 4 nights
bus:  1​h 15​min
5
Key West
— 5 nights
ferry:  2​h 30​min
6
Marco Island
— 3 nights
Drive:  4​h 15​min
7
Orlando
— 6 nights
Fly:  7​h
End: Toronto

3
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.
Venture out of the city with trips to Fairchild Tropical Botanic Garden (in Coral Gables) and Everglades National Park (Shark Valley Visitor Center & Slough Slog). There's still lots to do: kick back and relax at South Beach, enjoy some diversion at Lock & Load Miami, see the interesting displays at Vizcaya Museum and Gardens, and wander the streets of Lincoln Road.

For maps, more things to do, where to stay, and more tourist information, read our Miami Beach road trip site .

Toronto, Canada to Miami Beach is an approximately 6.5-hour flight. You can also do a combination of flight and train; or drive. Traveling from Toronto in September, things will get a bit warmer in Miami Beach: highs are around 38°C and lows about 29°C. Finish up your sightseeing early on the 20th (Fri) so you can go by car to Key Largo.

Things to do in Miami Beach

Parks Nature Outdoors

Side Trips

Miami, Everglades National Park, Fairchild Tropical Botanic Garden
Highlights from your plan
Lock & Load Museum ©
Lock & Load Museum
South Beach ©
South Beach
Lincoln Road ©
Lincoln Road

3
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.
Step out of Key Largo with an excursion to Anhinga Trail in Everglades National Park--about 48 minutes away. And it doesn't end there: look for all kinds of wild species at Wildlife Areas, zoom along the surf with a waterskiing or jet-skiing adventure, immerse yourself in nature at John Pennekamp Coral Reef State Park, and see the vivid underwater world at Spiegel Grove.

For other places to visit, more things to do, where to stay, and tourist information, go to the Key Largo online travel route builder .

Drive from Miami Beach to Key Largo in 1.5 hours. Alternatively, you can take a bus. In September, plan for daily highs up to 36°C, and evening lows to 28°C. Wrap up your sightseeing on the 23rd (Mon) early enough to drive to Islamorada.

Things to do in Key Largo

Parks Wildlife Outdoors

Side Trip

Anhinga Trail
Highlights from your plan
Island Dolphin Care ©
Island Dolphin Care
Scuba & Snorkeling
Spiegel Grove ©
Spiegel Grove

4
nights
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Get out of town with these interesting Islamorada side-trips: Everglades National Park (West Lake Trail & Mrazek Pond). There's still lots to do: cast your line with a fishing tour, view the masterpieces at Pasta Pantaleo Signature Gallery, look for gifts at Bella Sol Fragrance Bar and Gifts, and find your balance on the water with some of the best stand-up paddleboarding in the area.

For other places to visit, traveler tips, where to stay, and more tourist information, read our Islamorada itinerary planner.

Traveling by car from Key Largo to Islamorada takes an hour. Alternatively, you can do a combination of taxi and bus. In September, plan for daily highs up to 38°C, and evening lows to 30°C. Cap off your sightseeing on the 27th (Fri) early enough to go by car to Marathon.

Things to do in Islamorada

Wildlife Tours Outdoors

Side Trip

Everglades National Park
Highlights from your plan
Fishing Charters & Tours
Scuba & Snorkeling
Florida Keys Brewing Company ©
Florida Keys Brewing Company

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.
Step out of Marathon to go to Big Pine Key and see National Key Deer Refuge, which is approximately 34 minutes away. The adventure continues: immerse yourself in nature at Bahia Honda State Park, take in the architecture and atmosphere at San Pablo Catholic Church, add some adventure to your tour with a kayaking and canoeing tour, and soothe aching muscles at some of the top local wellness centers.

To find other places to visit, photos, maps, and other tourist information, read Marathon sightseeing planner .

You can drive from Islamorada to Marathon in an hour. Alternatively, you can take a bus. In September, daytime highs in Marathon are 38°C, while nighttime lows are 30°C. Finish your sightseeing early on the 1st (Tue) to allow enough time to take a bus to Key West.

Things to do in Marathon

Outdoors Wildlife Parks

Side Trip

Big Pine Key
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
The Turtle Hospital ©
The Turtle Hospital

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.
Spend the 4th (Fri) exploring nature at Dry Tortugas National Park. There's much more to do: see the interesting displays at The Ernest Hemingway Home and Museum, cast your line with a fishing tour, look for all kinds of wild species at Key West Butterfly & Nature Conservatory, and find your balance on the water with some of the best stand-up paddleboarding in the area.

To see photos, traveler tips, reviews, and other tourist information, go to the Key West trip itinerary planning website .

Take a bus from Marathon to Key West in 1.5 hours. Alternatively, you can drive. In October, plan for daily highs up to 35°C, and evening lows to 29°C. Finish your sightseeing early on the 6th (Sun) so you can ride a ferry to Marco Island.

Things to do in Key West

Parks Wildlife Tours
Highlights from your plan
Alan S. Maltz Gallery ©
Alan S. Maltz Gallery
The Ernest Hemingway Home and Museum ©

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. Step out of Marco Island with an excursion to Speed Boats Tours in Everglades City--about 38 minutes away. The adventure continues: see majestic marine mammals with a dolphin and whale watching tour, put a fun spin on your tour with Xtreme Escape Game, cast your line with a fishing tour, and zoom along the surf with a waterskiing or jet-skiing adventure.

To find photos, maps, ratings, and more tourist information, refer to the Marco Island trip planner .

Ride a ferry from Key West to Marco Island in 2.5 hours. Alternatively, you can drive. Traveling from Key West in October, plan for slightly colder nights in Marco Island, with lows around 23°C. Wrap up your sightseeing on the 9th (Wed) early enough to drive to Orlando.

Things to do in Marco Island

Tours Outdoors Wildlife

Side Trip

Speed Boats Tours
Highlights from your plan
Dolphin & Whale Watching
Waterskiing & Jetskiing
Parasailing & Paragliding

6
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.
Orlando is known for theme parks, nightlife, fun & games, shopping, and museums. Your plan includes some of its best attractions: discover the magic at Walt Disney World Resort, get in on the family fun at Discovery Cove, try out the rides at Happily Ever After Fireworks, and take in nature's colorful creations at Harry P. Leu Gardens.

Quickly create a custom-made itinerary for Orlando using our trip planner.

Traveling by car from Marco Island to Orlando takes 4.5 hours. Alternatively, you can do a combination of bus and flight; or take a bus. Expect a daytime high around 34°C in October, and nighttime lows around 24°C. Finish your sightseeing early on the 15th (Tue) to allow enough time to travel back home.

Things to do in Orlando

Theme Parks Parks Beaches

Side Trip

Charles Hosmer Morse Museum of American Art
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Universal Orlando Resort ©
Universal Orlando Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure

Similar Plans

30 days in United States BY A USER FROM UNITED KINGDOM July, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: July, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 31 days in United States BY A USER FROM AUSTRALIA January, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, popular & hidden gems PREFERENCES: January, culture, outdoors, relaxing, romantic, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 43 days in United States & St. Thomas BY A USER FROM BRAZIL December, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, slow & easy, popular & hidden gems PREFERENCES: December, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 16 days in Florida BY A USER FROM CROATIA February, teens, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: February, teens, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 30 days in United States BY A USER FROM NEW ZEALAND January, culture, relaxing, historic sites, museums, shopping, popular sights PREFERENCES: January, culture, relaxing, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 4 days in Florida BY A USER FROM UNITED STATES October, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife, hidden gems PREFERENCES: October, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium 9 days in Florida BY A USER FROM UNITED STATES November, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: November, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 21 days in Florida & New York City BY A USER FROM COSTA RICA December, teens, culture, outdoors, relaxing, historic sites, museums, shopping, wildlife, slow & easy, popular sights PREFERENCES: December, teens, culture, outdoors, relaxing, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 31 days in Florida BY A USER FROM UNITED STATES September, kids, popular & hidden gems PREFERENCES: September, kids ATTRACTION STYLE: Popular & hidden gems PACE: Medium 32 days in Florida BY A USER FROM AUSTRALIA January, kids, slow & easy, popular sights PREFERENCES: January, kids ATTRACTION STYLE: Popular sights PACE: Slow & easy 7 days in Florida BY A USER FROM UNITED STATES October, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, hidden gems PREFERENCES: October, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium 12 days in Florida BY A USER FROM UNITED STATES December, kids, outdoors, relaxing, beaches, historic sites, museums, wildlife, popular & hidden gems PREFERENCES: December, kids, outdoors, relaxing, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium
View more plans