29 days in Chesapeake City & Florida Itinerary

29 days in Chesapeake City & Florida Itinerary

Created using Inspirock United States trip planner

Plan created by another user. Make it yours
1
Chesapeake City
— 5 nights
2
Key West
— 4 nights
3
Big Pine Key
— 3 nights
4
Key Largo
— 4 nights
5
Everglades National Park
— 3 nights
6
Fort Lauderdale
— 2 nights
7
Merritt Island
— 1 night
8
Orlando
— 5 nights
9
Amelia Island
— 1 night

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5
nights
Chesapeake City

Chesapeake City ©
Chesapeake City is a town in Cecil County, Maryland, USA. Appreciate the collections at C&D Canal Museum and Upper Bay Museum. Get some cultural insight at M/V Bay Breeze of Chesapeake City and Historical Society of Kent County. Get out of town with these interesting Chesapeake City side-trips: Chestertown (MassoniArt Gallery & Schooner Sultana), Blue Earl Brewing Company (in Smyrna) and Crow Farm and Vineyard and Winery (in Kennedyville). There's lots more to do: contemplate the long history of Historic Odessa Foundation, snap pictures at Gilpin's Falls Covered Bridge, explore the activities along Bohemia RIver, and relax in the rural setting at Filasky's Produce.

To see traveler tips, reviews, where to stay, and tourist information, refer to the Chesapeake City road trip tool.

Newport News to Chesapeake City is an approximately 4.5-hour car ride. In August, plan for daily highs up to 84°F, and evening lows to 66°F. Finish up your sightseeing early on the 21st (Fri) so you can travel to Key West.

Things to do in Chesapeake City

Parks · Museums · Wineries · Outdoors

Side Trips

Highlights from your trip
©
State Park
Elk Neck State Park
4.3
©
Wine Tour / Tasting
M/V Bay Breeze of Chesapeake City
4.6

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.
Your cultural itinerary includes sights like The Ernest Hemingway Home and Museum and Fort Zachary Taylor. Get in touch with nature at Scuba & Snorkeling and Key West Butterfly & Nature Conservatory. And it doesn't end there: steep yourself in history at Truman Little White House, visit a coastal fixture at Key West Lighthouse and Keeper's Quarters Museum, examine the collection at Mel Fisher Maritime Heritage Museum, and browse the exhibits of Key West Shipwreck Treasure Museum.

To see traveler tips, where to stay, reviews, and other tourist information, use the Key West travel website.

The Route module can help you plan travel from Chesapeake City to Key West. In August, Key West is a bit warmer than Chesapeake City - with highs of 90°F and lows of 81°F. Finish up your sightseeing early on the 25th (Tue) so you can go by car to Big Pine Key.

Things to do in Key West

Highlights from your trip

3
nights
Big Pine Key

Big Pine Key ©
Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. Take a break from the city and head to Bahia Honda State Park and Long Beach. Your cultural itinerary includes sights like American Shoal Lighthouse and Artists in Paradise Gallery. There's lots more to do: discover the deep blue sea with Looe Key Dive Center, look for all kinds of wild species at National Key Deer Refuge, enjoy breathtaking views from Sugarloaf Key Bat Tower, and cross one thing off your bucket list with Skydive Key West.

For more things to do, photos, traveler tips, and other tourist information, read our Big Pine Key online visit planner.

Drive from Key West to Big Pine Key in an hour. Alternatively, you can take a shuttle; or take a bus. In August, daily temperatures in Big Pine Key can reach 92°F, while at night they dip to 80°F. Cap off your sightseeing on the 28th (Fri) early enough to go by car to Key Largo.

Things to do in Big Pine Key

Parks · Outdoors · Wildlife · Beaches

Side Trips

Highlights from your trip
©
Wildlife Area
National Key Deer Refuge
4.0
©
Skydiving
Skydive Key West
4.9

4
nights
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.
Visiting Scuba & Snorkeling and John Pennekamp Coral Reef State Park will get you outdoors. Popular historic sites such as Indian Key State Historic Site and Pasta Pantaleo Signature Gallery are in your itinerary. Take a break from Key Largo with a short trip to Anne's Beach in Islamorada, about 34 minutes away. There's still lots to do: identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, shop like a local with Rain Barrel Village, view the masterpieces at Old Road Gallery, and get interesting insight from Capt. Sterling's Everglades Eco-Tours.

To see photos, more things to do, reviews, and other tourist information, go to the Key Largo road trip planning site.

Drive from Big Pine Key to Key Largo in 2 hours. Alternatively, you can take a bus. In August, plan for daily highs up to 90°F, and evening lows to 77°F. Finish your sightseeing early on the 1st (Tue) so you can take a bus to Everglades National Park.

Things to do in Key Largo

Outdoors · Parks · Wildlife · Museums

Side Trip

Highlights from your trip
©
Scuba / Snorkeling
Scuba & Snorkeling
4.5
©
Nature / Wildlife Tour
Capt. Sterling's Everglades Eco-Tours
4.7

3
nights
Everglades National Park

Everglades National Park ©

Largest Subtropical Wilderness in the United States

A vast expanse of pristine wetlands, Everglades National Park holds the distinction of being the largest tropical wilderness in the U.S.
Escape the urban bustle at Gumbo Limbo Trail and Anhinga Trail. Satisfy your inner culture vulture at Flamingo and Miccosukee Indian Village. There's more to do: appreciate the views at Shark Valley Visitor Center and trek along Pineland Trail.

To find reviews, where to stay, more things to do, and more tourist information, use the Everglades National Park journey planning site.

Take a bus from Key Largo to Everglades National Park in 2.5 hours. In September in Everglades National Park, expect temperatures between 90°F during the day and 79°F at night. Finish your sightseeing early on the 4th (Fri) so you can take a train to Fort Lauderdale.

Things to do in Everglades National Park

Parks · Trails · Outdoors · Wildlife

Side Trip

Highlights from your trip
©
Wildlife Area
Anhinga Trail
4.6
©
Hiking Trail
Gumbo Limbo Trail
3.2

2
nights
Fort Lauderdale

Fort Lauderdale ©

Venice of America

Known as the "Venice of America" because of its extensive network of navigable waterways, Fort Lauderdale welcomes over 10 million annual visitors, most of them attracted by the city's popular beaches and marinas.
On the 5th (Sat), examine the collection at International Swimming Hall of Fame, then enjoy the sand and surf at South Beach, and then walk around Lincoln Road. Here are some ideas for day two: examine the collection at Vizcaya Museum and Gardens, then get engrossed in the history at Stranahan House, and then fly like a bird with Fort Lauderdale Watersports.

To see reviews, photos, maps, and other tourist information, read our Fort Lauderdale online travel route planner.

Getting from Everglades National Park to Fort Lauderdale by train takes about 2.5 hours. Other options: do a combination of bus and train; or take a bus. In September, plan for daily highs up to 89°F, and evening lows to 77°F. Finish up your sightseeing early on the 6th (Sun) so you can go by car to Merritt Island.

Things to do in Fort Lauderdale

Museums · Parks · Outdoors · Shopping

Side Trips

Highlights from your trip
©
Must see
Lincoln Road
4.2
©
Beach
South Beach
4.2
©
Specialty Museum
Vizcaya Museum and Gardens
4.7

1
night
Merritt Island

Merritt Island ©
Kick off your visit on the 7th (Mon): tour the pleasant surroundings at Jetty Park and then get a new perspective on things with Time and Tide Tours.

To see photos, where to stay, ratings, and other tourist information, read Merritt Island trip itinerary maker app.

Traveling by car from Fort Lauderdale to Merritt Island takes 3.5 hours. Alternatively, you can fly; or do a combination of bus and taxi. In September, plan for daily highs up to 87°F, and evening lows to 77°F. Wrap up your sightseeing on the 7th (Mon) to allow time to drive to Orlando.

Things to do in Merritt Island

Outdoors · Parks · Beaches · Tours

Side Trips

Highlights from your trip
©
Beach
Jetty Park
4.0

5
nights
Orlando

Orlando ©

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.
Satisfy your inner culture vulture at Charles Hosmer Morse Museum of American Art and Cape Canavarel National Cemetery. Go for a jaunt from Orlando to Ponce Inlet to see Ponce de Leon Inlet Lighthouse & Museum about 1h 15 min away. Pack the 11th (Fri) with family-friendly diversions at Discovery Cove. Have a day of magic on the 10th (Thu) at Walt Disney World Resort. It doesn't end there: get in on the family fun at Universal Orlando Resort.

To see traveler tips, more things to do, ratings, and more tourist information, refer to the Orlando online vacation planner.

You can drive from Merritt Island to Orlando in 1.5 hours. Expect a daytime high around 89°F in September, and nighttime lows around 74°F. Cap off your sightseeing on the 12th (Sat) early enough to go by car to Amelia Island.

Things to do in Orlando

Theme Parks · Outdoors · Parks · Beaches

Side Trips

Highlights from your trip

1
night
Amelia Island

Amelia Island ©
The southernmost Sea Island off the coast of Florida, Amelia Island takes its name from Princess Amelia of England.
Kick off your visit on the 13th (Sun): contemplate the long history of Amelia Island Historic District, then sample the fine beverages at Marlin & Barrel Distillery, then immerse yourself in nature at Fort Clinch State Park, and finally trot along with Amelia Island Horseback Riding.

To see reviews, photos, maps, and other tourist information, go to the Amelia Island day trip app.

Getting from Orlando to Amelia Island by car takes about 3 hours. Other options: do a combination of train and taxi; or do a combination of bus and taxi. September in Amelia Island sees daily highs of 86°F and lows of 74°F at night. Cap off your sightseeing on the 13th (Sun) early enough to travel back home.

Things to do in Amelia Island

Historic Sites · Nature · Parks · Outdoors
Highlights from your trip
©
Horseback Riding Tour
Amelia Island Horseback Riding
5.0

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