21 days in United States Itinerary

21 days in United States Itinerary

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Route & dates

21 days in United States Itinerary

Start: San Juan, Puerto Rico
Fly:  5​h 30​min
1
Miami
— 3 nights
Drive:  1​h
2
Fort Lauderdale
— 2 nights
Drive:  4​h 15​min
3
Key West
— 5 nights
Drive:  45​min
4
Big Pine Key
— 1 night
Drive:  30​min
5
Marathon
— 2 nights
Drive:  45​min
6
Islamorada
— 1 night
Drive:  25​h
7
Chicago
— 4 nights
Fly:  7​h 45​min
End: San Juan, Puerto Rico

3
nights
Miami

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Your day-by-day itinerary now includes Charlotte Jane Memorial Park Cemetary, Everglades National Park and Zoo Miami. You'll explore the less-touristy side of things at Anhinga Trail and Wynwood.

To see reviews, maps, more things to do, and other tourist information, read our Miami trip itinerary builder site .

San Juan, Puerto Rico to Miami is an approximately 5.5-hour combination of flight and tram. You can also do a combination of flight and train. The time zone difference moving from Atlantic Standard Time to Eastern Standard Time is minus 1 hour. Plan for a bit cooler nights when traveling from San Juan in March since evenings lows in Miami dip to 65°F. You will leave for Fort Lauderdale on the 30th (Sat).

Things to do in Miami

Parks Zoos & Aquariums Nature

Side Trips

Everglades National Park, Anhinga Trail
Highlights from your plan
Anhinga Trail ©
Anhinga Trail
Everglades National Park ©
Everglades National Park
Wynwood ©
Wynwood

2
nights
Fort Lauderdale

Fort Lauderdale ©
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 30th (Sat), learn more about the world around you at Secret Woods Nature Center and then enjoy the sand and surf at Hollywood North Beach Park. Keep things going the next day: look for all kinds of wild species at Panther Ridge Conservation Center, discover the deep blue sea with a scuba or snorkeling tour, and then experience rural life at Bedner's Farm Fresh Market.

To find traveler tips, photos, other places to visit, and other tourist information, read Fort Lauderdale visit website .

Traveling by car from Miami to Fort Lauderdale takes an hour. Alternatively, you can take a bus; or take a train. Expect a daytime high around 80°F in March, and nighttime lows around 65°F. Cap off your sightseeing on the 1st (Mon) early enough to travel to Key West.

Things to do in Fort Lauderdale

Wildlife Outdoors Parks

Side Trips

Panther Ridge Conservation Center, Scuba & Snorkeling, Bedner's Farm Fresh Market, Secret Woods Nature Center, Hollywood North Beach Park
Highlights from your plan
Panther Ridge Conservation Center ©
Panther Ridge Conservation Center
Scuba & Snorkeling
Secret Woods Nature Center ©
Secret Woods Nature Center

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.
You'll explore and learn at Mel Fisher Maritime Heritage Museum and Key West Lighthouse and Keeper's Quarters Museum. Explore hidden gems such as Stand-Up Paddleboarding and Spas & Wellness. The adventure continues: add some adventure to your tour with a kayaking and canoeing tour, indulge in some culinary diversions at a local gastronomic tour, steep yourself in history at West Martello Tower, and engage your brain at Florida Keys Eco-Discovery Center.

For traveler tips, ratings, maps, and other tourist information, refer to the Key West trip itinerary planner.

You can fly from Fort Lauderdale to Key West in 3.5 hours. Other options are to do a combination of train, tram, and flight; or drive. April in Key West sees daily highs of 83°F and lows of 74°F at night. Wrap up your sightseeing on the 6th (Sat) early enough to take a bus to Big Pine Key.

Things to do in Key West

Outdoors Tours Historic Sites
Highlights from your plan
Saint Mary Star of the Sea ©
Saint Mary Star of the Sea
Vandenberg Wreck ©
Vandenberg Wreck

1
night
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. Kick off your visit on the 6th (Sat): shop like a local with Artists in Paradise Gallery, cast your line with a fishing tour, and then relax in the rural setting at Grimal Grove.

To find photos, more things to do, traveler tips, and tourist information, use the Big Pine Key online holiday planner .

Traveling by bus from Key West to Big Pine Key takes an hour. Alternatively, you can drive. In April, daytime highs in Big Pine Key are 86°F, while nighttime lows are 75°F. Finish your sightseeing early on the 7th (Sun) to allow enough time to take a bus to Marathon.

Things to do in Big Pine Key

Outdoors Wildlife Tours
Highlights from your plan
Fishing Charters & Tours
Artists in Paradise Gallery ©
Artists in Paradise Gallery

2
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.
Start off your visit on the 7th (Sun): see the vivid underwater world at Sombrero Reef, identify plant and animal life at Crane Point Museum & Nature Center, and then paddle through the water with a kayaking and canoeing tour. Get ready for a full day of sightseeing on the 8th (Mon): pause for some serene contemplation at San Pablo Catholic Church, enjoy the sand and surf at Sunset Park Beach, and then get a new perspective on things with Boat Tours & Water Sports.

Before you visit Marathon, use our trip planner to discover what you can do and see there.

Marathon is just a stone's throw from Big Pine Key. In April in Marathon, expect temperatures between 86°F during the day and 75°F at night. Wrap up your sightseeing on the 9th (Tue) early enough to drive to Islamorada.

Things to do in Marathon

Outdoors Wildlife Parks

Side Trip

Key Colony Beach
Highlights from your plan
Crane Point Museum & Nature Center ©
Sunset Park Beach ©
Sunset Park Beach
Fishing Charters & Tours

1
night
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Start off your visit on the 9th (Tue): choose your vessel at Spray Watersports, then indulge your thirst for a good beer at Islamorada Beer Company Brewery and Tasting Room, then view the masterpieces at Lobster Trap Art Gallery, and finally indulge your thirst for a good beer at Florida Keys Brewing Company. Get ready for a full day of sightseeing on the 10th (Wed): get a new perspective on things with Boat Tours & Water Sports.

To find more things to do, where to stay, and other tourist information, use the Islamorada travel route planning tool .

Getting from Marathon to Islamorada by car takes about an hour. Other options: take a bus. In April, plan for daily highs up to 86°F, and evening lows to 75°F. Finish your sightseeing early on the 10th (Wed) so you can travel to Chicago.

Things to do in Islamorada

Outdoors Tours Wildlife

Side Trip

Fishing Charters & Tours
Highlights from your plan
Fishing Charters & Tours
Florida Keys Brewing Company ©
Florida Keys Brewing Company

4
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You'll discover tucked-away gems like John Deere Historic Site and Museum of the Gilding Arts. Escape the urban bustle at Weko Park and Lowden State Park. Get out of town with these interesting Chicago side-trips: Pontiac (Livingston County Courthouse, Pontiac-Oakland Automobile Museum, & more), Standard Oil Gas Station (in Odell) and August Hill Winery & Illinois Sparkling Co. Tasting Room (in Utica). Next up on the itinerary: admire the natural beauty at Fernwood Botanical Garden and Nature Preserve.

To see other places to visit, maps, more things to do, and other tourist information, use the Chicago trip itinerary planning website .

Do a combination of shuttle and flight from Islamorada to Chicago in 7.5 hours. Alternatively, you can do a combination of shuttle, bus, and flight; or drive. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. Traveling from Islamorada in April, things will get much colder in Chicago: highs are around 59°F and lows about 40°F. Cap off your sightseeing on the 15th (Mon) early enough to travel back home.

Things to do in Chicago

Parks Museums Outdoors

Side Trips

Pontiac, Fernwood Botanical Garden and Nature Preserve, Lowden State Park, Weko Park, John Deere Historic Site
Highlights from your plan