29 days in East Coast of USA & Wisconsin Itinerary

29 days in East Coast of USA & Wisconsin Itinerary

Created using Inspirock United States itinerary planner

Make it your trip
Fly
1
Key West
— 3 nights
Fly
2
Orlando
— 4 nights
Drive
3
Savannah
— 3 nights
Taxi to Hilton Head, Fly to Washington DC
4
Washington DC
— 4 nights
Train
5
New York City
— 4 nights
Fly
6
Boston
— 4 nights
Fly
7
Milwaukee
— 2 nights
Drive
8
Wisconsin Dells
— 2 nights
Train to Milwaukee Intermodal Station, Fly to Sydney

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Key West

— 3 nights

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.
We've included these beaches for you: Fort Zachary Taylor and Bahia Honda State Park. Get some cultural insight at U.S. Coast Guard Cutter Ingham Maritime Museum and Key West Garden Club. Change things up with a short trip to Sombrero Beach in Marathon (about 1h 5 min away). Next up on the itinerary: admire all the interesting features of The Overseas Highway, browse the exhibits of Key West Lighthouse and Keeper's Quarters Museum, cast your line with a fishing tour, and get engrossed in the history at Truman Little White House.

For other places to visit, maps, traveler tips, and other tourist information, read Key West road trip app.

Sydney, Australia to Key West is an approximately 26.5-hour flight. Traveling from Sydney to Key West, you'll gain 15 hours due to the time zone difference. Traveling from Sydney in July, things will get much hotter in Key West: highs are around 37°C and lows about 32°C. Wrap up your sightseeing on the 18th (Mon) early enough to fly to Orlando.

Things to do in Key West

Outdoors · Parks · Beaches · Museums

Side Trips

Orlando

— 4 nights

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.
Get a sense of the local culture at St. Augustine Lighthouse & Maritime Museum, Inc. and The Dali Museum. We've included these beaches for you: St. Pete Beach and Beach at Daytona Beach. Explore Orlando's surroundings by going to Ormond Beach (in Ormond Beach), St. Augustine (Flagler College, St. Augustine Distillery, &more) and St. Augustine Beach (in Saint Augustine Beach). There's still lots to do: look for gifts at Angell & Phelps Chocolate Factory.

Find out how to plan Orlando trip without stress by asking Inspirock to help create an itinerary.

You can fly from Key West to Orlando in 3 hours. Other options are to drive; or take a bus. Plan for slightly colder nights when traveling from Key West in July since evenings lows in Orlando dip to 28°C. Finish up your sightseeing early on the 22nd (Fri) so you can go by car to Savannah.

Things to do in Orlando

Parks · Outdoors · Beaches · Museums

Side Trips

Savannah

— 3 nights

The Hostess City of the South

Georgia's oldest city, Savannah displays its colonial history proudly on every corner.
You'll explore the less-touristy side of things at Cathedral of St. John the Baptist and Tybee Island Beach. Your cultural itinerary includes sights like Bonaventure Cemetery and Tybee Island Light Station And Museum. You'll find plenty of places to visit near Savannah: Hilton Head (Speed Boats Tours, Coligny Beach, &more). There's much more to do: steep yourself in history at Olde Pink House, walk around Forsyth Park, don't miss a visit to Historic River Street, and get to know the fascinating history of Fort Pulaski National Monument.

To see photos, reviews, where to stay, and more tourist information, refer to the Savannah route planner.

Drive from Orlando to Savannah in 4.5 hours. Alternatively, you can fly; or take a train. In July, plan for daily highs up to 38°C, and evening lows to 27°C. Wrap up your sightseeing on the 25th (Mon) early enough to travel to Washington DC.

Things to do in Savannah

Historic Sites · Outdoors · Parks · Beaches

Side Trips

Washington DC

— 4 nights
The capital of the United States, the District of Columbia contains the lion's share of the country's most treasured monuments, memorials, and public museums.
Step off the beaten path and head to Smithsonian National Museum of Natural History and United States Holocaust Memorial Museum. Get a sense of the local culture at Arlington National Cemetery and National Gallery of Art. And it doesn't end there: appreciate the extensive heritage of National Mall, ponder the world of politics at United States Capitol, pause for some photo ops at Vietnam Veterans Memorial, and see the interesting displays at The National Archives Museum.

Planning Washington DC trip won't be overwhelming when you use Inspirock's itinerary maker.

Traveling by combination of taxi and flight from Savannah to Washington DC takes 4.5 hours. Alternatively, you can drive; or take a train. In July, daytime highs in Washington DC are 37°C, while nighttime lows are 26°C. Wrap up your sightseeing on the 29th (Fri) early enough to fly to New York City.

Things to do in Washington DC

Museums · Historic Sites · Parks

Side Trip

New York City

— 4 nights

Big Apple

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Eschew the tourist crowds and head to New York Public Library and St. Patrick's Cathedral. Get a sense of the local culture at The Metropolitan Museum of Art and 9/11 Memorial. And it doesn't end there: go for a walk through Central Park, take a stroll through Times Square, snap pictures at Brooklyn Bridge, and appreciate the history behind Statue of Liberty National Monument.

For more things to do, traveler tips, where to stay, and other tourist information, read our New York City online route planner.

You can fly from Washington DC to New York City in 3 hours. Other options are to take a train; or drive. Expect a daytime high around 35°C in July, and nighttime lows around 26°C. Wrap up your sightseeing on the 2nd (Tue) early enough to fly to Boston.

Things to do in New York City

Museums · Parks · Historic Sites · Neighborhoods

Boston

— 4 nights

Beantown

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.
We've included these beaches for you: Ogunquit Beach and Hampton Beach State Park. Do some cultural sightseeing at The Breakers and Cliff Walk. Explore Boston's surroundings by going to Ogunquit (Marginal Way Walkway & Perkins Cove). There's lots more to do: take a tour of Boston Tea Party Ships & Museum, buy something for everyone on your list at Faneuil Hall Marketplace, get engrossed in the history at USS Constitution Museum, and wander the streets of North End.

To see photos, where to stay, maps, and other tourist information, read our Boston trip itinerary planner.

You can fly from New York City to Boston in 2.5 hours. Alternatively, you can drive; or take a train. Plan for a bit cooler nights when traveling from New York City in August since evenings lows in Boston dip to 21°C. Wrap up your sightseeing on the 6th (Sat) to allow time to fly to Milwaukee.

Things to do in Boston

Parks · Outdoors · Museums · Historic Sites

Side Trips

Milwaukee

— 2 nights

Brew City

Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Start off your visit on the 7th (Sun): examine the collection at Harley-Davidson Museum, then explore the world behind art at Milwaukee Art Museum, and then make a trip to Historic Third Ward. Keep things going the next day: stroll through Bartel's Beach, tour the pleasant surroundings at Atwater Park & Beach, and then sample the tasty concoctions at Lakefront Brewery.

To see maps, more things to do, photos, and tourist information, read our Milwaukee trip itinerary builder website.

Traveling by flight from Boston to Milwaukee takes 5 hours. Alternatively, you can drive; or take a train. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. August in Milwaukee sees daily highs of 30°C and lows of 20°C at night. Wrap up your sightseeing on the 8th (Mon) early enough to drive to Wisconsin Dells.

Things to do in Milwaukee

Museums · Parks · Outdoors · Beaches

Side Trips

Wisconsin Dells

— 2 nights

Waterpark Capital of the World

Named after a nearby scenic gorge famous for its steep sandstone formations, Wisconsin Dells features more than 20 water parks, making it one of the most popular vacation areas in this region.
Start off your visit on the 9th (Tue): admire the striking features of The House on the Rock, admire the landmark architecture of Taliesin Preservation: Frank Lloyd Wright Visitor Center , and then admire the majestic nature at Devil's Lake State Park. Here are some ideas for day two: admire nature's wide array of creatures at Wisconsin Deer Park, then get interesting insight from Tours, and then get a new perspective on things with Boat Tours & Water Sports.

To see traveler tips, ratings, where to stay, and tourist information, you can read our Wisconsin Dells trip itinerary builder website.

You can drive from Milwaukee to Wisconsin Dells in 2.5 hours. Other options are to take a train; or do a combination of bus and train. Traveling from Milwaukee in August, plan for slightly colder nights in Wisconsin Dells, with lows around 17°C. Finish up your sightseeing early on the 10th (Wed) so you can catch the flight back home.

Things to do in Wisconsin Dells

Tours · Outdoors · Parks · Museums

Side Trips

Wisconsin travel guide

4.2
Specialty Museums · Water Parks · Zoos
The Badger State
Wisconsin is known as "America's Dairyland" because of its status as the nation's most famous producer of milk and cheese. A growing favorite with foreign tourists, the state is a perfect holiday destination for nature lovers, offering year-round outdoor activities like fishing, boating, kayaking, and hiking. Dotted with thousands of inland lakes and waterways alongside apple and cherry orchards, Wisconsin also offers numerous urban tourist attractions, its cities hosting renowned beer and art festivals each year.