60 days in Florida Itinerary

60 days in Florida Itinerary

Created using Inspirock Florida trip planner

Make it your trip
Fly
1
Key West
— 8 nights
Fly
2
Miami
— 7 nights
Drive
3
Naples
— 5 nights
Drive
4
Sarasota
— 6 nights
Drive
5
Orlando
— 8 nights
Drive
6
St. Augustine
— 6 nights
Drive
7
Tallahassee
— 6 nights
Drive
8
Panama City Beach
— 7 nights
Drive
9
Pensacola Beach
— 6 nights
Fly

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Key West

— 8 nights

Conch Republic

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.
Escape the urban bustle at Scuba & Snorkeling and Vandenberg Wreck. Venture out of the city with trips to Dolphin Research Center (in Grassy Key), Marathon (Crane Point Museum & Nature Center, Sombrero Beach, &more) and Sunset Park Beach (in Key Colony Beach). Spend the 4th (Thu) exploring nature at Dry Tortugas National Park. Next up on the itinerary: identify plant and animal life at Key West Butterfly & Nature Conservatory, examine the collection at The Ernest Hemingway Home and Museum, kick back and relax at Bahia Honda State Park, and admire the majestic nature at Fort Zachary Taylor.

For reviews, photos, maps, and more tourist information, use the Key West trip itinerary planning website.

Portland to Key West is an approximately 7.5-hour flight. You can also drive; or do a combination of bus and train. Plan for much warmer temperatures traveling from Portland in November, with highs in Key West at 81°F and lows at 73°F. Cap off your sightseeing on the 9th (Tue) early enough to catch the flight to Miami.

Things to do in Key West

Parks · Wildlife · Outdoors · Museums

Side Trips

Miami

— 7 nights

Magic City

Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Get outdoors at Shark Valley Visitor Center and South Beach. Explore the numerous day-trip ideas around Miami: Everglades National Park (in Florida City), Homestead Miami Speedway (in Homestead) and Key Largo (Scuba & Snorkeling & Capt. Sterling's Everglades Eco-Tours). Next up on the itinerary: tour the pleasant surroundings at Anhinga Trail, trek along Pineland Trail, admire the masterpieces at The Wolfsonian - Florida International University, and identify plant and animal life at Nine Mile Pond Canoe Trail.

For other places to visit, reviews, where to stay, and tourist information, read our Miami trip planner.

You can fly from Key West to Miami in 2.5 hours. Alternatively, you can drive; or take a bus. In November, daytime highs in Miami are 82°F, while nighttime lows are 70°F. Finish your sightseeing early on the 16th (Tue) to allow enough time to drive to Naples.

Things to do in Miami

Parks · Outdoors · Wildlife · Nature

Side Trips

Naples

— 5 nights
Step out of the city life by going to Island Time Dolphin & Shelling Cruises and Everglades Day Safari. Explore Naples' surroundings by going to Fort Myers Beach (in Fort Myers Beach), Redfish Pass (in Captiva Island) and Happehatchee Center (in Estero).

For other places to visit, reviews, where to stay, and tourist information, read our Naples vacation planner.

You can drive from Miami to Naples in 2 hours. Alternatively, you can take a bus. Plan for a bit cooler nights when traveling from Miami in November since evenings lows in Naples dip to 65°F. Finish your sightseeing early on the 21st (Sun) so you can drive to Sarasota.

Things to do in Naples

Outdoors · Wildlife · Parks · Nature

Side Trips

Sarasota

— 6 nights
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. state of Florida. Step out of the city life by going to Anna Maria Island Dolphin Tours and Clearwater Beach. Change things up with these side-trips from Sarasota: Venice (T. Mabry Carlton Reserve & Black Duck Charters), Busch Gardens Tampa Bay (in Tampa) and Duncan McClellan Gallery (in St. Petersburg). There's much more to do: explore the different monuments and memorials at Sarasota National Cemetery, immerse yourself in nature at Ted Sperling Park, identify plant and animal life at Tampa Electric's Manatee Viewing Center, and walk around Siesta Beach.

To find photos, traveler tips, more things to do, and tourist information, go to the Sarasota day trip site.

Drive from Naples to Sarasota in 2 hours. Alternatively, you can take a bus; or do a combination of bus and taxi. In November, daytime highs in Sarasota are 80°F, while nighttime lows are 62°F. Wrap up your sightseeing on the 27th (Sat) to allow time to drive to Orlando.

Things to do in Sarasota

Outdoors · Parks · Historic Sites · Trails

Side Trips

Orlando

— 8 nights

Theme Park Capital of the World

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.
Step out of the city life by going to Scuba & Snorkeling and Crystal River Preserve State Park. Have a day of magic on the 28th (Sun) at Walt Disney World Resort. Pack the 1st (Wed) with family-friendly diversions at Universal's Islands of Adventure. The adventure continues: find something for the whole family at Universal Orlando Resort, make an unforgettable trip to Epcot, and explore the world behind art at Charles Hosmer Morse Museum of American Art.

To find reviews, traveler tips, where to stay, and tourist information, go to the Orlando trip itinerary maker website.

Traveling by car from Sarasota to Orlando takes 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In November, daytime highs in Orlando are 78°F, while nighttime lows are 62°F. Wrap up your sightseeing on the 5th (Sun) early enough to drive to St. Augustine.

Things to do in Orlando

Theme Parks · Wildlife · Tours · Outdoors

Side Trips

St. Augustine

— 6 nights
St. Step out of the city life by going to St. Augustine Wild Reserve and SemperFi Charters. Explore St. Augustine's surroundings by going to Catty Shack Ranch Wildlife Sanctuary (in Jacksonville), Welaka State Forest (in Welaka) and Atlantic Beach (Tide Views Preserve & Sunset Pier Park). There's lots more to do: sample the fine beverages at St. Augustine Distillery, enjoy the sea views from St. Augustine Lighthouse & Maritime Museum, Inc., explore the landscape on two wheels at Mala Compra Mountain Bike Trail, and get engrossed in the history at St. Augustine Pirate & Treasure Museum.

To find photos and more tourist information, use the St. Augustine holiday builder site.

Traveling by car from Orlando to St. Augustine takes 2 hours. Alternatively, you can take a bus. Traveling from Orlando in December, expect nights in St. Augustine to be about the same, around 55°F, while days are little chillier, around 70°F. Cap off your sightseeing on the 11th (Sat) early enough to go by car to Tallahassee.

Things to do in St. Augustine

Parks · Wildlife · Outdoors · Tours

Side Trips

Tallahassee

— 6 nights
Take a break from the city and head to St. Marks National Wildlife Refuge and JR Alford Greenway. Change things up with these side-trips from Tallahassee: Apalachicola Bluffs and Ravines Preserve (in Bristol), Fishing Charters & Tours (in Steinhatchee) and Hinson Conservation and Recreation Area (in Marianna).

For photos, other places to visit, maps, and tourist information, you can read our Tallahassee day trip planning tool.

You can drive from St. Augustine to Tallahassee in 3.5 hours. Other options are to take a bus; or fly. Traveling from St. Augustine in December, Tallahassee is a bit cooler at night with lows of 48°F. Cap off your sightseeing on the 17th (Fri) early enough to go by car to Panama City Beach.

Things to do in Tallahassee

Parks · Outdoors · Wildlife · Nature

Side Trips

Panama City Beach

— 7 nights

World's Most Beautiful Beaches

Boasting 43 km (27 mi) of white sandy beaches and plenty of sunshine, Panama City Beach is an ideal choice for a relaxing holiday.
Get in touch with nature at IntraCoastal Experience and Apalachicola National Estuarine Research Reserve. Change things up with these side-trips from Panama City Beach: Miramar Beach (YOLO Board Adventures Sandestin, Waterfront Gifts and Art, &more), Turkey Creek Nature Trail (in Niceville) and St. Joseph Peninsula State Park (in Port Saint Joe). Next up on the itinerary: enjoy the sand and surf at Panama City Beach, learn about winemaking at Panama City Beach Winery, head outdoors with Blue Water Connection, and ride a horse along Sunshine Riding Trails - Day Tours.

To see other places to visit, photos, maps, and tourist information, read Panama City Beach online trip maker.

Getting from Tallahassee to Panama City Beach by car takes about 2.5 hours. In December, daily temperatures in Panama City Beach can reach 69°F, while at night they dip to 49°F. Finish your sightseeing early on the 24th (Fri) so you can drive to Pensacola Beach.

Things to do in Panama City Beach

Outdoors · Parks · Beaches · Wildlife

Side Trips

Pensacola Beach

— 6 nights
Pensacola Beach is an unincorporated community located on Santa Rosa Island, a barrier island, in Escambia County, Florida, United States. Get in touch with nature at Jolly Sailing and Dolphin Cruises and Pensacola Beach. Explore the numerous day-trip ideas around Pensacola Beach: Blackwater River State Park (in Holt) and Navarre (Navarre Beach Marine Science Station, Navarre Beach, &more). There's still lots to do: tour the pleasant surroundings at Gulf Islands National Seashore, take a leisurely stroll along Pensacola Beach Gulf Pier, contemplate the long history of Fort Pickens Area, and get outside with LTD WaterSports.

For ratings, other places to visit, photos, and other tourist information, you can read our Pensacola Beach trip itinerary planning site.

Traveling by car from Panama City Beach to Pensacola Beach takes 2.5 hours. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. Expect a daytime high around 67°F in December, and nighttime lows around 50°F. Wrap up your sightseeing by early afternoon on the 30th (Thu) to allow time for the flight back home.

Things to do in Pensacola Beach

Outdoors · Parks · Beaches · Wildlife

Side Trips

Florida travel guide

4.4
Disney Parks & Activities · Beaches · Theme Parks
The Sunshine State
The “Sunshine State,” Florida became a favorite winter destination for the affluent crowd over a century ago. Today, the state attracts visitors from around the world with its golden beaches and modern theme parks. You can spend your entire vacation enjoying the state's highly developed seaside areas, but remember that some of Florida's best-kept secrets are in secluded locations. Visit the big cities and their comfortable resorts offering top-notch dining and nightlife, but leave some time to see the peninsula's swampy landscape, filled with wild creatures and native plants. Farther away from the tourist-packed urban areas, the untamed wetlands of Florida offer a selection of things to do, such as kayaking, boat rides, and numerous other outdoor activities.

Florida Panhandle travel guide

4.4
Beaches · Water Sports · Military Museums
The Emerald Coast
Stretching over 322 km (200 mi) of beautiful coastline along the Gulf of Mexico, the Florida Panhandle encompasses an area of pristine white-sand beaches and turquoise waters, earning it the nickname the Emerald Coast. Distinguished from the rest of the Sunshine State by its laid-back southern influence, the region remains a popular tropical holiday destination for those looking to avoid the larger vacation hubs of Miami and Orlando. Explore the beachfront shops and fresh-caught seafood cafes of the region's fishing villages, or head to the bigger seaside communities of Pensacola and Panama City for a wide selection of retail and entertainment options, including some of the coast's most active nightlife.