29 days in Florida Itinerary

29 days in Florida Itinerary

Created using Inspirock Florida trip itinerary planner

Plan created by another user. Make it yours
1
Key West
— 4 nights
2
Marathon
— 3 nights
3
Key Largo
— 3 nights
4
Naples
— 6 nights
5
Sarasota
— 5 nights
6
St. Augustine
— 7 nights

S M T W T F S
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4
nights
Key West

Key West ©

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.
Step out of the city life by going to Key West Wildlife Center and Dry Tortugas National Park. Discover out-of-the-way places like Key West Garden Club and Key West Historic Seaport. And it doesn't end there: pause for some serene contemplation at St. Paul's Episcopal Church, don't miss a visit to US 1 Mile Marker 0, explore the different monuments and memorials at Key West Cemetery, and sample the fine beverages at Key West First Legal Rum Distillery.

To find traveler tips, photos, and tourist information, read Key West trip itinerary website.

Atlanta to Key West is an approximately 4-hour flight. You can also drive; or take a bus. In January, Key West is much hotter than Atlanta - with highs of 76°F and lows of 66°F. Finish your sightseeing early on the 7th (Thu) to allow enough time to drive to Marathon.

Things to do in Key West

Historic Sites · Parks · Nature · Museums
Find places to stay Jan 3 — 7:
Highlights from your plan
Key West Garden Club ©
Key West Garden Club
Saint Mary Star of the Sea ©
Saint Mary Star of the Sea
Key West Wildlife Center ©
Key West Wildlife Center

3
nights
Marathon

Marathon ©

Heart of the Florida Keys

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Take a break from the city and head to Crane Point Museum & Nature Center and Dolphin Research Center. There's much more to do: soothe aching muscles at some of the top local wellness centers, tour the pleasant surroundings at Bahia Honda State Park, take in the views from Seven Mile Bridge, and see the top attractions with Ultimate HeliTours.

For where to stay, maps, reviews, and other tourist information, you can read our Marathon online road trip planner.

Traveling by car from Key West to Marathon takes 1.5 hours. Alternatively, you can take a bus. January in Marathon sees daily highs of 77°F and lows of 66°F at night. Finish up your sightseeing early on the 10th (Sun) so you can go by car to Key Largo.

Things to do in Marathon

Parks · Wildlife · Outdoors · Tours

Side Trip

Find places to stay Jan 7 — 10:
Highlights from your plan
Crane Point Museum & Nature Center ©
Crane Point Museum & Nature Center
Ultimate HeliTours ©
Ultimate HeliTours
Dolphin Research Center ©
Dolphin Research Center

3
nights
Key Largo

Key Largo ©

Diving Capital of the World

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.
Take a break from the city and head to Anhinga Trail and Florida Keys Wild Bird Rehabilitation Center. Explore hidden gems such as Capt. Sterling's Everglades Eco-Tours and Molasses Reef. You'll find plenty of places to visit near Key Largo: Homestead (Losner Park, Everglades Alligator Farm, &more). There's lots more to do: take an in-depth tour of History of Diving Museum, fulfill a lifelong dream with Theater of the Sea, and take a tour of African Queen Canal Cruise.

To see ratings, other places to visit, where to stay, and other tourist information, read our Key Largo trip itinerary planner.

Drive from Marathon to Key Largo in 1.5 hours. Alternatively, you can take a bus. Traveling from Marathon in January, Key Largo is a bit cooler at night with lows of 61°F. Wrap up your sightseeing on the 13th (Wed) to allow time to drive to Naples.

Things to do in Key Largo

Wildlife · Parks · Outdoors · Tours

Side Trips

Find places to stay Jan 10 — 13:
Highlights from your plan
Capt. Sterling's Everglades Eco-Tours ©
Capt. Sterling's Everglades Eco-Tours
Molasses Reef ©
Molasses Reef
Anhinga Trail ©
Anhinga Trail

6
nights
Naples

Naples ©
Eschew the tourist crowds and head to Captiva Beach and Winterberry Park. Visiting Barefoot Beach Preserve and Lowdermilk Beach will get you outdoors. Venture out of the city with trips to Speed Boats Tours (in Everglades City), Lovers Key State Park (in Fort Myers Beach) and Cullum’s Bonita Trail (in Bonita Springs).

For other places to visit, reviews, traveler tips, and tourist information, you can read our Naples online day trip planner.

Getting from Key Largo to Naples by car takes about 3 hours. Other options: take a bus. In January in Naples, expect temperatures between 75°F during the day and 58°F at night. Wrap up your sightseeing on the 19th (Tue) to allow time to drive to Sarasota.

Things to do in Naples

Parks · Outdoors · Wildlife · Beaches

Side Trips

Find places to stay Jan 13 — 19:
Highlights from your plan
Corkscrew Swamp ©
Corkscrew Swamp
Barefoot Beach Preserve ©
Barefoot Beach Preserve
Six Mile Cypress Slough Preserve ©
Six Mile Cypress Slough Preserve

5
nights
Sarasota

Sarasota ©
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. Step out of the city life by going to Robinson Nature Preserve and Tampa Electric's Manatee Viewing Center. You'll explore the less-touristy side of things at Venice Beach and Siesta Key Rum. Get out of town with these interesting Sarasota side-trips: Punta Gorda (Peace River Wildlife Center & Fishing Charters & Tours), Fort De Soto Park (in Tierra Verde) and Jungle Prada de Navarez Park (in St. Petersburg). And it doesn't end there: steep yourself in history at Ca d'Zan, enjoy the sand and surf at Saint Pete Beach, tour the pleasant surroundings at Treasure Island Beach, and get to know the fascinating history of Marie Selby Botanical Gardens.

To find other places to visit, reviews, more things to do, and other tourist information, you can read our Sarasota trip itinerary maker website.

Traveling by car from Naples to Sarasota takes 2 hours. Alternatively, you can take a bus; or do a combination of bus and taxi. Traveling from Naples in January, plan for slightly colder nights in Sarasota, with lows around 53°F. Wrap up your sightseeing on the 24th (Sun) to allow time to drive to St. Augustine.

Things to do in Sarasota

Parks · Wildlife · Outdoors · Beaches

Side Trips

Find places to stay Jan 19 — 24:
Highlights from your plan
Robinson Nature Preserve ©
Robinson Nature Preserve
Venice Beach ©
Venice Beach
Ca d'Zan ©
Ca d'Zan

7
nights
St. Augustine

St. Augustine ©
St. Your inner history buff will appreciate Mission of Nombre de Dios and Cathedral Basilica of St. Augustine. Explore hidden gems such as Lighthouse Point Park and The Old Senator Tree. Venture out of the city with trips to Ponce de Leon Inlet Lighthouse & Museum (in Ponce Inlet), Daytona Beach (Angell & Phelps Chocolate Factory, Daytona International Speedway, &more) and Fernandina Beach (Shrimping Museum, Fort Clinch State Park, &more). There's still lots to do: look for all kinds of wild species at St. Augustine Wild Reserve, examine the collection at First Colony, meet the residents at St. Augustine Aquarium, and make a trip to St. George Street.

To find ratings, where to stay, other places to visit, and tourist information, go to the St. Augustine trip itinerary builder app.

Drive from Sarasota to St. Augustine in 4.5 hours. Alternatively, you can fly; or take a bus. While traveling from Sarasota, expect little chillier days and about the same nights in St. Augustine, ranging from highs of 65°F to lows of 49°F. Finish your sightseeing early on the 31st (Sun) to allow enough time to travel back home.

Things to do in St. Augustine

Parks · Historic Sites · Outdoors · Beaches

Side Trips

Find places to stay Jan 24 — 31:
Highlights from your plan
Mission of Nombre de Dios ©
Mission of Nombre de Dios
St. Augustine Wild Reserve ©
St. Augustine Wild Reserve
Amelia Island Horseback Riding ©
Amelia Island Horseback Riding

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