26 days in United States Itinerary

26 days in United States Itinerary

Created using Inspirock United States tour builder

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Route & dates

26 days in United States Itinerary

Start: Johannesburg
Fly:  20​h 45​min
1
Boston
— 4 nights
Fly:  4​h
2
Chicago
— 2 nights
Fly:  5​h
3
Sanibel Island
— 3 nights
Drive:  3​h
4
Miami
— 2 nights
Drive:  15​min
5
Miami Beach
— 2 nights
Drive:  2​h
6
Islamorada
— 2 nights
bus:  2​h
7
Key West
— 5 nights
Fly:  2​h 45​min
8
Tampa
— Few hours
Fly + bus:  5​h
9
New York City
— 4 nights
Fly:  19​h 15​min
End: Johannesburg


Learn more about your trip

4
nights
Boston

Boston ©
Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Your day-by-day itinerary now includes Quincy Market. Head to Franklin Pierce Homestead and Newbury Streetfor some retail therapy. Popular historic sites such as The Elms and Strawbery Banke Museum are in your itinerary. You'll find plenty of places to visit near Boston: Plimoth Plantation (in Plymouth) and Ogunquit Beach (in Ogunquit). There's still lots to do: browse the different shops at Faneuil Hall Marketplace.

For maps, where to stay, reviews, and tourist information, read Boston online trip maker .

Johannesburg, South Africa to Boston is an approximately 21-hour combination of flight and bus. You can also do a combination of flight and train; or do a combination of flight and bus. The time zone difference when traveling from Johannesburg to Boston is minus 7 hours. Plan for colder temperatures traveling from Johannesburg in December, with highs in Boston at 7°C and lows at 0°C. Finish your sightseeing early on the 18th (Tue) so you can travel to Chicago.

Things to do in Boston

Shopping Historic Sites Museums

Side Trips

Ogunquit Beach, Strawbery Banke Museum, Plimoth Plantation, The Elms, Franklin Pierce Homestead State Historic Site
Highlights from your plan
Newbury Street ©
Newbury Street
Ogunquit Beach ©
Ogunquit Beach
The Elms
The Elms

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Start off your visit on the 19th (Wed): stroll through Millennium Park, enjoy the sand and surf at Oak Street Beach, and then enjoy the sand and surf at North Avenue Beach.

For traveler tips, more things to do, where to stay, and more tourist information, refer to the Chicago day trip planner.

Traveling by combination of bus and flight from Boston to Chicago takes 4 hours. Alternatively, you can do a combination of bus and flight; or drive. Due to the time zone difference, you'll gain 1 hour traveling from Boston to Chicago. Expect little chillier temperatures when traveling from Boston in December; daily highs in Chicago reach 3°C and lows reach -3°C. Wrap up your sightseeing on the 20th (Thu) to allow time to travel to Sanibel Island.

Things to do in Chicago

Parks Beaches Outdoors
Highlights from your plan
Oak Street Beach ©
Oak Street Beach
North Avenue Beach ©
North Avenue Beach
Millennium Park ©
Millennium Park

3
nights
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
You'll get in some beach time at Bowman's Beach and Gulfside Beach. Explore hidden gems such as Fort Myers Beach and Bailey's General Store. Go for a jaunt from Sanibel Island to Bonita Springs to see Barefoot Beach Preserve about 1h 05 min away.

To see ratings, where to stay, other places to visit, and other tourist information, refer to the Sanibel Island vacation planner .

You can do a combination of flight and taxi from Chicago to Sanibel Island in 5 hours. Alternatively, you can drive; or do a combination of bus and taxi. The time zone difference when traveling from Chicago to Sanibel Island is 1 hour. Plan for much warmer temperatures traveling from Chicago in December, with highs in Sanibel Island at 31°C and lows at 19°C. Finish your sightseeing early on the 23rd (Sun) to allow enough time to drive to Miami.

Things to do in Sanibel Island

Beaches Parks Outdoors

Side Trips

Fort Myers Beach, Barefoot Beach Preserve
Highlights from your plan
Bowman's Beach ©
Bowman's Beach
Barefoot Beach Preserve ©
Barefoot Beach Preserve
Fort Myers Beach ©
Fort Myers Beach

2
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.
Start off your visit on the 23rd (Sun): admire the striking features of Freedom Tower, browse the different shops at Bayside Marketplace, and then buy something for everyone on your list at Sawgrass Mills. Get ready for a full day of sightseeing on the 24th (Mon): see the interesting displays at Vizcaya Museum and Gardens, make a trip to Coral Castle, and then shop like a local with Aventura Mall.

To see traveler tips, other places to visit, maps, and tourist information, read Miami trip planner .

Traveling by car from Sanibel Island to Miami takes 3 hours. Alternatively, you can do a combination of taxi and bus. Plan for somewhat warmer nights when traveling from Sanibel Island in December since evenings lows in Miami dip to 23°C. Finish your sightseeing early on the 25th (Tue) to allow enough time to drive to Miami Beach.

Things to do in Miami

Shopping Museums Historic Sites

Side Trips

Coral Castle, Sawgrass Mills, Aventura Mall
Highlights from your plan
Sawgrass Mills ©
Sawgrass Mills
Aventura Mall ©
Aventura Mall
Vizcaya Museum and Gardens ©
Vizcaya Museum and Gardens

2
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.
Kick off your visit on the 25th (Tue): stroll through Haulover Beach Park, then get a taste of the local shopping with Britto Central, then wander the streets of Lincoln Road, and finally admire the masterpieces at The Wolfsonian - Florida International University. Here are some ideas for day two: kick back and relax at South Beach, then appreciate the extensive heritage of Art Deco Historic District, then take a stroll through Ocean Drive, and finally don't miss a visit to Collins Avenue.

To find where to stay, more things to do, other places to visit, and more tourist information, go to the Miami Beach holiday maker tool .

Miami Beach is very close to Miami. Expect a daytime high around 31°C in December, and nighttime lows around 22°C. Wrap up your sightseeing on the 27th (Thu) to allow time to drive to Islamorada.

Things to do in Miami Beach

Neighborhoods Shopping Parks

Side Trip

Haulover Beach Park
Highlights from your plan
Lincoln Road ©
Lincoln Road
Art Deco Historic District ©
Art Deco Historic District
Haulover Beach Park ©
Haulover Beach Park

2
nights
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
On the 27th (Thu), look for gifts at Ocean Gardens, sample the tasty concoctions at Islamorada Beer Company Brewery and Tasting Room, get a taste of the local shopping with Michelle Nicole Lowe Art Gallery, then contemplate the long history of Indian Key State Historic Site, and finally enjoy the sand and surf at Anne's Beach. Here are some ideas for day two: view the masterpieces at Lobster Trap Art Gallery, get engrossed in the history at History of Diving Museum, look for gifts at Petals With Pizzazz, then view the masterpieces at The Rain Barrel Artisan Village, and finally explore and take pictures at African Queen Canal Cruise.

To see ratings, traveler tips, reviews, and tourist information, go to the Islamorada trip planning site .

Drive from Miami Beach to Islamorada in 2 hours. Alternatively, you can take a bus. In December, daytime highs in Islamorada are 29°C, while nighttime lows are 22°C. Finish up your sightseeing early on the 29th (Sat) so you can go by car to Key West.

Things to do in Islamorada

Shopping Museums Historic Sites

Side Trip

African Queen Canal Cruise
Highlights from your plan
Rain Barrel Village ©
Rain Barrel Village
History of Diving Museum ©
History of Diving Museum

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.
Popular historic sites such as Fort Zachary Taylor and Key West Garden Club are in your itinerary. Key West Pottery and Mel Fisher Maritime Heritage Museum will appeal to museum buffs. Next up on the itinerary: look for gifts at Peppers of Key West, explore the galleries of Key West Lighthouse and Keeper's Quarters Museum, relax and rejuvenate at some of the top local wellness centers, and see the interesting displays at The Ernest Hemingway Home and Museum.

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

Drive from Islamorada to Key West in 2 hours. Alternatively, you can take a bus. Expect a daytime high around 30°C in December, and nighttime lows around 25°C. Cap off your sightseeing on the 3rd (Thu) early enough to travel to Tampa.

Things to do in Key West

Parks Outdoors Museums
Highlights from your plan
Fort Zachary Taylor ©
Fort Zachary Taylor
Saint Mary Star of the Sea ©
Saint Mary Star of the Sea

few
hours
Tampa

Tampa ©
Tampa ranks among the country's most livable cities, attracting newcomers with its growing economy and status as a major port on the Gulf of Mexico.
To find more things to do, reviews, where to stay, and tourist information, use the Tampa trip itinerary builder app .

Traveling by flight from Key West to Tampa takes 3 hours. Alternatively, you can do a combination of ferry, taxi, and bus; or drive. Traveling from Key West in January, expect Tampa to be little chillier, temps between 25°C and 13°C. Wrap up your sightseeing by early afternoon on the 3rd (Thu) to allow time for travel to New York City.

Things to do in Tampa

Breweries & Distilleries
Highlights from your plan
Cigar City Brewing ©
Cigar City Brewing

4
nights
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Step off the beaten path and head to Chelsea Market and Cupsogue Beach County Park. Let the collections at The Metropolitan Museum of Art and Frick Collection capture your imagination. Explore New York City's surroundings by going to Ponquogue Beach (in Hampton Bays) and Gateway National Recreation (in Sandy Hook). And it doesn't end there: take a stroll through Fifth Avenue, take in the architecture and atmosphere at St. Patrick's Cathedral, pause for some photo ops at 9/11 Memorial, and don't miss a visit to Times Square.

For more things to do, other places to visit, photos, and more tourist information, go to the New York City trip itinerary tool .

Traveling by combination of flight and bus from Tampa to New York City takes 5 hours. Alternatively, you can do a combination of flight and train; or drive. Prepare for much colder weather when traveling from Tampa in January: high temperatures in New York City hover around 5°C and lows are around -5°C. Finish your sightseeing early on the 7th (Mon) to allow enough time to travel back home.

Things to do in New York City

Parks Museums Beaches

Side Trips

Cupsogue Beach County Park, Ponquogue Beach, Gateway National Recreation
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial
Frick Collection ©
Frick Collection

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