36 days in Chicago & East Coast of USA Itinerary

36 days in Chicago & East Coast of USA Itinerary

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Route & dates

36 days in Chicago & East Coast of USA Itinerary

Start: Copenhagen
Fly:  12​h 45​min
1
Chicago
— 7 nights
Fly + bus:  4​h 45​min
2
New York City
— 4 nights
Fly:  3​h 15​min
3
Washington DC
— 5 nights
Fly:  4​h
4
Savannah
— 3 nights
Drive:  3​h 15​min
5
St. Augustine
— 4 nights
Drive:  2​h 45​min
6
Crystal River
— 2 nights
+2
bus + foot + Fly:  6​h 30​min
7
Key West
— 4 nights
Fly:  2​h 30​min
8
Miami
— 5 nights
Fly:  12​h 30​min
End: Copenhagen

7
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your inner history buff will appreciate Chicago Riverwalk and Millennium Park. Your cultural itinerary includes sights like The Art Institute of Chicago and Basilica of the Sacred Heart. Venture out of the city with trips to Grant Park (in South Milwaukee), Baha'i House of Worship (in Wilmette) and Starved Rock State Park (in Utica). There's still lots to do: explore the landscape on two wheels at Lakefront Trail, take in nature's colorful creations at Garfield Park Conservatory, identify plant and animal life at Jasper-Pulaski Fish and Wildlife Area, and explore the world behind art at Richard H. Driehaus Museum.

To find reviews, photos, where to stay, and tourist information, use the Chicago trip maker app .

Copenhagen, Denmark to Chicago is an approximately 13-hour flight. You can also do a combination of flight and bus; or do a combination of flight and train. The time zone changes from Central European Time to Central Standard Time, which is usually a -7 hour difference. In May, Chicago is a bit warmer than Copenhagen - with highs of 25°C and lows of 13°C. Finish your sightseeing early on the 10th (Sun) to allow enough time to travel to New York City.

Things to do in Chicago

Parks Outdoors Trails

Side Trips

Starved Rock State Park, Jasper-Pulaski Fish and Wildlife Area, Basilica of the Sacred Heart, Geneva Lake Shore Path, Baha'i House of Worship
Highlights from your plan
Basilica of the Sacred Heart ©
Basilica of the Sacred Heart
Starved Rock State Park ©
Starved Rock State Park
The Art Institute of Chicago ©
The Art Institute of Chicago

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 The Met Cloisters and Frick Collection. Your cultural itinerary includes sights like The Metropolitan Museum of Art and St. Patrick's Cathedral. Next up on the itinerary: explore the galleries of 9/11 Memorial, wander the streets of Times Square, see the interesting displays at New York Public Library, and take in the pleasant sights at Central Park.

To find where to stay, photos, ratings, and more tourist information, read New York City trip itinerary builder website .

Traveling by combination of flight and bus from Chicago to New York City takes 5 hours. Alternatively, you can fly; or drive. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. In May, plan for daily highs up to 24°C, and evening lows to 15°C. Finish your sightseeing early on the 14th (Thu) so you can travel to Washington DC.

Things to do in New York City

Museums Historic Sites Parks
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
The Met Cloisters ©
The Met Cloisters
9/11 Memorial ©
9/11 Memorial

5
nights
Washington DC

Washington DC ©
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.
You'll explore the less-touristy side of things at The Tomb of the Unknown Soldier and Fort McHenry National Monument. Get some historical perspective at Basilica of the National Shrine of the Immaculate Conception and Hillwood Estate, Museum & Gardens. There's still lots to do: admire the masterpieces at National Gallery of Art, take a stroll through Georgetown, get to know the fascinating history of Capitol Hill, and take an in-depth tour of National Portrait Gallery.

To find ratings, other places to visit, and other tourist information, read our Washington DC trip itinerary planner .

Getting from New York City to Washington DC by flight takes about 3.5 hours. Other options: take a train; or drive. Traveling from New York City in May, expect nights in Washington DC to be about the same, around 17°C, while days are a bit warmer, around 28°C. On the 19th (Tue), wrap the sightseeing up by early afternoon so you can travel to Savannah.

Things to do in Washington DC

Museums Historic Sites Neighborhoods

Side Trips

Fort McHenry National Monument, The Tomb of the Unknown Soldier
Highlights from your plan

3
nights
Savannah

Savannah ©
Georgia's oldest city, Savannah displays its colonial history proudly on every corner.
Your cultural itinerary includes sights like Mickve Israel Temple and Juliette Gordon Low's Birthplace. Escape the urban bustle at Wormsloe Historic Site and Savannah National Wildlife Refuge. Get out of town with these interesting Savannah side-trips: Old Sheldon Church Ruins (in Yemassee) and Pat Conroy Literary Center (in Beaufort). There's much more to do: contemplate the long history of Owens-Thomas House & Slave Quarters, wander the streets of Savannah Historic District, learn about all things military at Webb Military Museum, and explore the different monuments and memorials at Colonial Park Cemetery.

For more things to do, photos, other places to visit, and more tourist information, go to the Savannah trip itinerary maker .

Traveling by flight from Washington DC to Savannah takes 4 hours. Alternatively, you can do a combination of subway, bus, and flight; or drive. Traveling from Washington DC in May, things will get somewhat warmer in Savannah: highs are around 33°C and lows about 20°C. Wrap up your sightseeing on the 22nd (Fri) early enough to drive to St. Augustine.

Things to do in Savannah

Historic Sites Parks Wildlife

Side Trips

Old Sheldon Church Ruins, Dolphin & Whale Watching, Pat Conroy Literary Center, Savannah National Wildlife Refuge
Highlights from your plan
Wormsloe Historic Site ©
Wormsloe Historic Site
Mickve Israel Temple ©
Mickve Israel Temple
Dolphin & Whale Watching

4
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Eschew the tourist crowds and head to Mission of Nombre de Dios and Colonial Quarter. St. Augustine Lighthouse & Maritime Museum, Inc. and Villa Zorayda Museum will appeal to history buffs. Take a break from St. Augustine with a short trip to Ravine Gardens State Park in Palatka, about 46 minutes away. Spend the 26th (Tue) on the water with a fishing tour. Next up on the itinerary: take in the architecture and atmosphere at Memorial Presbyterian Church, see the interesting displays at St. Photios Greek Orthodox National Shrine, take an in-depth tour of Medieval Torture Collection, and enjoy the sand and surf at Vilano Beach.

For ratings, more things to do, other places to visit, and tourist information, read our St. Augustine online holiday planner .

You can drive from Savannah to St. Augustine in 3.5 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 33°C in May, and nighttime lows around 22°C. Cap off your sightseeing on the 26th (Tue) early enough to go by car to Crystal River.

Things to do in St. Augustine

Outdoors Wildlife Historic Sites

Side Trip

Ravine Gardens State Park
Highlights from your plan
Mission of Nombre de Dios ©
Mission of Nombre de Dios
Colonial Quarter ©
Colonial Quarter

2
nights
Crystal River

The jewel of Florida's Nature Coast, Crystal River spreads around spring-fed Kings Bay, known for maintaining a constant 22 C (72 F) temperature all year long.
Start off your visit on the 27th (Wed): glide peacefully along the water with some of the best stand-up paddleboarding in the area and then look for all kinds of wild species at Wildlife Areas. On your second day here, look for all kinds of wild species at Alpaca Magic USA, then admire the majestic nature at Crystal River Preserve State Park, then examine the collection at Coastal Heritage Museum, and finally contemplate the long history of Crystal River Archaeological State Park.

To see reviews, other places to visit, more things to do, and tourist information, read Crystal River online holiday planner .

Traveling by car from St. Augustine to Crystal River takes 3 hours. Alternatively, you can take a bus. Traveling from St. Augustine in May, you can expect nighttime temperatures to be a bit cooler in Crystal River, with lows of 19°C. Finish your sightseeing early on the 28th (Thu) to allow enough time to travel to Key West.

Things to do in Crystal River

Outdoors Tours Wildlife

Side Trip

Alpaca Magic USA
Highlights from your plan
Stand-Up Paddleboarding
Scuba & Snorkeling
Alpaca Magic USA ©
Alpaca Magic USA

4
nights
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.
Get some historical perspective at Saint Mary Star of the Sea and Key West Garden Club. Get in touch with nature at Stand-Up Paddleboarding and Key West Butterfly & Nature Conservatory. There's still lots to do: paddle through the water with a kayaking and canoeing tour, learn about all things military at U.S. Coast Guard Cutter Ingham Maritime Museum, take in the waterfront at Key West Historic Seaport, and visit a coastal fixture at Key West Lighthouse and Keeper's Quarters Museum.

To see maps, ratings, more things to do, and more tourist information, read our Key West trip builder app .

Traveling by combination of bus and flight from Crystal River to Key West takes 6.5 hours. Alternatively, you can do a combination of taxi, bus, and flight; or drive. Expect somewhat warmer evenings in Key West when traveling from Crystal River in May, with lows around 29°C. Finish your sightseeing early on the 1st (Mon) to allow enough time to travel to Miami.

Things to do in Key West

Tours Outdoors Adventure
Highlights from your plan
Kayaking & Canoeing
Stand-Up Paddleboarding
Saint Mary Star of the Sea ©
Saint Mary Star of the Sea

5
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.
Visiting Green Cay Nature Center and Wetlands and Waterskiing & Jetskiing will get you outdoors. Visit Plymouth Congregational Church and Deering Estate for their historical value. Explore the numerous day-trip ideas around Miami: Wakodahatchee Wetlands (in Delray Beach) and Gumbo Limbo Nature Center (in Boca Raton). Spend the 6th (Sat) on the water with a fishing tour. There's much more to do: explore the world behind art at Wynwood Walls, examine the collection at Lock & Load Museum, explore the different monuments and memorials at Charlotte Jane Memorial Park Cemetary, and get the adrenaline pumping with an extreme tour.

For reviews, other places to visit, ratings, and more tourist information, read our Miami online itinerary planner .

Traveling by flight from Key West to Miami takes 2.5 hours. Alternatively, you can do a combination of flight and bus; or drive. June in Miami sees daily highs of 37°C and lows of 29°C at night. Finish up your sightseeing early on the 6th (Sat) so you can travel back home.

Things to do in Miami

Wildlife Museums Parks

Side Trips

Gumbo Limbo Nature Center, Green Cay Nature Center and Wetlands, Wakodahatchee Wetlands
Highlights from your plan
Wakodahatchee Wetlands ©
Wakodahatchee Wetlands
Gumbo Limbo Nature Center ©
Gumbo Limbo Nature Center
Waterskiing & Jetskiing

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