28 days in Florida Itinerary

28 days in Florida Itinerary

Created using Inspirock Florida itinerary planner

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Route & dates

28 days in Florida Itinerary

Start: Tampa
Drive:  2​h 45​min
1
Naples
— 2 nights
Drive:  45​min
2
Marco Island
— 2 nights
ferry:  2​h 30​min
3
Key West
— 5 nights
bus:  1​h 15​min
4
Marathon
— 3 nights
Drive:  45​min
5
Islamorada
— 4 nights
Drive:  45​min
6
Key Largo
— 3 nights
Drive:  1​h 30​min
7
Miami Beach
— 3 nights
Fly:  3​h 30​min
8
Orlando
— 5 nights
Drive:  1​h 30​min
End: Tampa

2
nights
Naples

Naples is a city in Collier County, Florida, United States. Change things up with these side-trips from Naples: Captain Jack Boat Tours (in Matlacha) and Sanibel Public Library (in Sanibel Island). And it doesn't end there: get interesting insight from Tours, take in the waterfront at Naples Pier, identify plant and animal life at Shy Wolf Sanctuary Education & Experience Center, and see the interesting displays at Revs Institute.

For maps, more things to do, ratings, and tourist information, read Naples trip itinerary planning site .

Tampa to Naples is an approximately 3-hour car ride. You can also take a bus. In January, daytime highs in Naples are 75°F, while nighttime lows are 58°F. Wrap up your sightseeing on the 8th (Wed) early enough to drive to Marco Island.

Things to do in Naples

Wildlife Outdoors Tours

Side Trips

Shy Wolf Sanctuary Education & Experience Center, Sanibel Public Library, Captain Jack Boat Tours
Find places to stay Jan 6 — 8:
Highlights from your plan
Dolphin & Whale Watching
Revs Institute ©
Revs Institute
Captain Jack Boat Tours ©
Captain Jack Boat Tours

2
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. Start off your visit on the 9th (Thu): get some thrills out on the water with a waterskiing or jet-skiing adventure, glide through the air with a parasailing or paragliding tour, and then get some thrills on the water with a speed boat tour. Keep things going the next day: find your balance on the water with some of the best stand-up paddleboarding in the area, get up close to creatures of the deep with a dolphin and whale watching tour, and then walk around Canine Cove.

To see traveler tips, other places to visit, more things to do, and more tourist information, go to the Marco Island trip itinerary maker site .

Drive from Naples to Marco Island in an hour. Traveling from Naples in January, plan for slightly colder nights in Marco Island, with lows around 53°F. Cap off your sightseeing on the 10th (Fri) early enough to catch the ferry to Key West.

Things to do in Marco Island

Outdoors Tours Adventure

Side Trip

Speed Boats Tours
Find places to stay Jan 8 — 10:
Highlights from your plan
Dolphin & Whale Watching
Waterskiing & Jetskiing
Stand-Up Paddleboarding

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 13th (Mon) exploring nature at Dry Tortugas National Park. There's lots more to do: see the interesting displays at The Ernest Hemingway Home and Museum, make a trip to Duval Street, discover the deep blue sea with a scuba or snorkeling tour, and take in the waterfront at Mallory Square.

Ask Inspirock to suggest an itinerary and make planning a trip to Key West fast, fun, and easy.

Traveling by ferry from Marco Island to Key West takes 2.5 hours. Alternatively, you can drive. Traveling from Marco Island in January, plan for somewhat warmer nights in Key West, with lows around 66°F. Wrap up your sightseeing on the 15th (Wed) early enough to take a bus to Marathon.

Things to do in Key West

Parks Outdoors Wildlife
Find places to stay Jan 10 — 15:
Highlights from your plan
Alan S. Maltz Gallery ©
Alan S. Maltz Gallery
The Ernest Hemingway Home and Museum ©

3
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.
Take a break from Marathon with a short trip to National Key Deer Refuge in Big Pine Key, about 34 minutes away. And it doesn't end there: kick back and relax at Bahia Honda State Park, browse the collection at Monroe County Public Library, look for all kinds of wild species at The Turtle Hospital, and soothe aching muscles at some of the top local wellness centers.

For reviews, other places to visit, and tourist information, you can read our Marathon online trip itinerary planner .

Traveling by bus from Key West to Marathon takes 1.5 hours. Alternatively, you can drive. January in Marathon sees daily highs of 77°F and lows of 66°F at night. Cap off your sightseeing on the 18th (Sat) early enough to go by car to Islamorada.

Things to do in Marathon

Parks Outdoors Wildlife

Side Trip

Big Pine Key
Find places to stay Jan 15 — 18:
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Crane Point Museum & Nature Center ©

4
nights
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
You'll find plenty of places to visit near Islamorada: Everglades National Park (99 Mile Wilderness Waterway & Nine Mile Pond Canoe Trail). Next up on the itinerary: get interesting insight from Tours, head outdoors with A Lil' Tail Charters, immerse yourself in nature at Lignumvitae Key Botanical State Park, and look for gifts at Bella Sol Fragrance Bar and Gifts.

For reviews, where to stay, photos, and tourist information, refer to the Islamorada route planning tool .

Traveling by car from Marathon to Islamorada takes an hour. Alternatively, you can take a bus. Expect a daytime high around 77°F in January, and nighttime lows around 66°F. Finish your sightseeing early on the 22nd (Wed) so you can drive to Key Largo.

Things to do in Islamorada

Outdoors Wildlife Parks

Side Trip

Everglades National Park
Find places to stay Jan 18 — 22:
Highlights from your plan
Fishing Charters & Tours
99 Mile Wilderness Waterway ©
99 Mile Wilderness Waterway
Nine Mile Pond Canoe Trail ©
Nine Mile Pond Canoe Trail

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.
When in Key Largo, make a side trip to see Anhinga Trail in Everglades National Park, approximately 48 minutes away. The adventure continues: identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, fulfill a lifelong dream with a swim-with-the-dolphins experience, get up close and personal with brilliant marine life at Island Dolphin Care, and explore the landscape on two wheels at Florida Keys Visitor Center.

Ask Inspirock to suggest an itinerary and make planning a trip to Key Largo fast, fun, and easy.

Drive from Islamorada to Key Largo in an hour. Alternatively, you can do a combination of bus and taxi. Traveling from Islamorada in January, expect slightly colder with lows of 61°F in Key Largo. Cap off your sightseeing on the 25th (Sat) early enough to go by car to Miami Beach.

Things to do in Key Largo

Parks Wildlife Outdoors

Side Trip

Anhinga Trail
Find places to stay Jan 22 — 25:
Highlights from your plan
Island Dolphin Care ©
Island Dolphin Care
Anhinga Trail ©
Anhinga Trail

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.
Explore Miami Beach's surroundings by going to Fairchild Tropical Botanic Garden (in Coral Gables) and Everglades National Park (Shark Valley Visitor Center, Gumbo Limbo Trail, & more). There's still lots to do: stroll through South Beach, appreciate the extensive heritage of Art Deco Historic District, wander the streets of Lincoln Road, and explore the world behind art at The Wolfsonian - Florida International University.

For where to stay, other places to visit, ratings, and tourist information, read Miami Beach online vacation planner .

Getting from Key Largo to Miami Beach by car takes about 1.5 hours. Other options: take a bus. In January, plan for daily highs up to 77°F, and evening lows to 63°F. Wrap up your sightseeing on the 28th (Tue) to allow time to travel to Orlando.

Things to do in Miami Beach

Parks Outdoors Trails

Side Trips

Everglades National Park, Miami, Fairchild Tropical Botanic Garden
Find places to stay Jan 25 — 28:
Highlights from your plan
Lock & Load Museum ©
Lock & Load Museum
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Fairchild Tropical Botanic Garden ©
Fairchild Tropical Botanic Garden

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.
Orlando is known for theme parks, nightlife, fun & games, shopping, and museums. Your plan includes some of its best attractions: get in on the family fun at Walt Disney World Resort, discover the magic at Disney's Hollywood Studios, have some family-friendly fun at The Escape Game Orlando, and admire the natural beauty at Harry P. Leu Gardens.

For traveler tips, photos, and other tourist information, go to the Orlando trip planner .

Traveling by flight from Miami Beach to Orlando takes 3.5 hours. Alternatively, you can drive; or do a combination of bus and flight. Expect slightly colder temperatures when traveling from Miami Beach in January; daily highs in Orlando reach 71°F and lows reach 52°F. Finish your sightseeing early on the 2nd (Sun) so you can drive back home.

Things to do in Orlando

Theme Parks Parks Fun & Games

Side Trip

Charles Hosmer Morse Museum of American Art
Find places to stay Jan 28 — Feb 2:
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

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