32 days in Midwest & East Coast of USA Itinerary

32 days in Midwest & East Coast of USA Itinerary

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Route & dates

32 days in Midwest & East Coast of USA Itinerary

Start: Springfield
+2
bus + taxi + Fly:  7​h 30​min
1
Rapid City
— 3 nights
Fly:  5​h 15​min
2
Traverse City
— 3 nights
Fly:  8​h 45​min
3
Bar Harbor, Mount Desert Island
— 3 nights
Fly + bus:  7​h 15​min
4
New York City
— 3 nights
bus + Fly:  4​h 45​min
5
Charleston
— 2 nights
Drive:  2​h 30​min
6
Hilton Head
— 3 nights
Drive:  4​h
7
St. Augustine
— 2 nights
+2
Drive + Fly + shuttle:  6​h 15​min
8
Marathon
— 2 nights
bus:  1​h 15​min
9
Key West
— 4 nights
ferry:  2​h 30​min
10
Marco Island
— 2 nights
+2
bus + taxi + Fly:  6​h 45​min
End: Springfield

3
nights
Rapid City

Rapid City ©
South Dakota's second-largest city, Rapid City has for many years served as a gateway to the West.
Step off the beaten path and head to Custer State Park and Wildlife Loop Road. Get outdoors at Bear Country USA and Panorama Point Overlook. Explore Rapid City's surroundings by going to Badlands National Park (Badlands Wall, Homestead Overlook, & more). There's lots more to do: wander the streets of Downtown Rapid City, explore the wealth of natural beauty at Badlands National Park, and tee off at The Golf Club at Red Rock.

To find photos, where to stay, maps, and tourist information, you can read our Rapid City online visit planner .

Springfield to Rapid City is an approximately 7.5-hour combination of bus and flight. You can also fly; or drive. Traveling from Springfield to Rapid City, you'll gain 1 hour due to the time zone difference. Prepare for little chillier weather when traveling from Springfield in May: high temperatures in Rapid City hover around 65°F and lows are around 45°F. Finish your sightseeing early on the 7th (Tue) to allow enough time to travel to Traverse City.

Things to do in Rapid City

Parks Outdoors Nature

Side Trips

Badlands National Park, Custer
Highlights from your plan
Custer State Park ©
Custer State Park
Badlands Wall ©
Badlands Wall
Wildlife Loop Road ©
Wildlife Loop Road

3
nights
Traverse City

Traverse City ©
Traverse City might be well known for its huge cherry industry, but its position along Grand Traverse Bay in Lake Michigan endows it with fine scenery and a wealth of outdoor attractions.
Escape the urban bustle at Sleeping Bear Dunes National Lakeshore and Platte Plains Trail. You'll explore the less-touristy side of things at Hidden River Golf and Casting Club and Dunes Trail. Explore Traverse City's surroundings by going to Old Indian Trail (in Empire), North Western State Trail (in Petoskey) and Crooked Vine Vineyard & Winery (in Alanson). Spend the 11th (Sat) exploring nature at D.H. Day Campground. There's still lots to do: sample the tasty concoctions at Lake Ann Brewing Company and learn about winemaking at Bel Lago Winery.

For other places to visit, maps, photos, and tourist information, use the Traverse City trip website .

You can fly from Rapid City to Traverse City in 5.5 hours. Alternatively, you can drive; or take a bus. The time zone difference when traveling from Rapid City to Traverse City is 2 hours. In May, daytime highs in Traverse City are 67°F, while nighttime lows are 43°F. Finish your sightseeing early on the 11th (Sat) to allow enough time to travel to Bar Harbor.

Things to do in Traverse City

Parks Outdoors Nature

Side Trips

Empire, North Western State Trail, Hidden River Golf and Casting Club, Crooked Vine Vineyard & Winery, Bel Lago Winery
Highlights from your plan
D.H. Day Campground ©
D.H. Day Campground
Dunes Trail ©
Dunes Trail

3
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Get in touch with nature at Cadillac Mountain and Schoodic Institute at Acadia National Park. You'll discover tucked-away gems like Mount Desert Island and Indian Point Blagden Preserve. Change things up with a short trip to Charlotte Rhoades Garden and Butterfly Park in Southwest Harbor (about 32 minutes away). Next up on the itinerary: look for all kinds of wild species at Shore Path, stroll through Jordan Cliffs Trail, explore the striking landscape of Eagle Lake Acadia National Park, and take an in-depth tour of Somesville Historical Museum and Gardens.

To see other places to visit, photos, ratings, and more tourist information, you can read our Bar Harbor day trip planning app .

Traveling by flight from Traverse City to Bar Harbor takes 9 hours. Alternatively, you can do a combination of flight, bus, and taxi; or drive. Traveling from Traverse City in May, expect nights in Bar Harbor to be about the same, around 43°F, while days are little chillier, around 60°F. Finish your sightseeing early on the 15th (Wed) so you can travel to New York City.

Things to do in Bar Harbor

Parks Wildlife Nature

Side Trips

Acadia National Park, Mount Desert Island, Charlotte Rhoades Garden and Butterfly Park, Schoodic Institute at Acadia National Park
Highlights from your plan
Cadillac Mountain ©
Cadillac Mountain
Shore Path ©
Shore Path
Indian Point Blagden Preserve ©
Indian Point Blagden Preserve

3
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.
Get some cultural insight at The Metropolitan Museum of Art and Times Square. The adventure continues: go for a walk through Central Park, admire the striking features of Empire State Building, appreciate the history behind Statue of Liberty National Monument, and see the interesting displays at 9/11 Memorial.

To find more things to do, maps, where to stay, and tourist information, read New York City online route planner .

Traveling by combination of flight and bus from Bar Harbor to New York City takes 7.5 hours. Alternatively, you can drive; or do a combination of bus and train. Traveling from Bar Harbor in May, expect New York City to be a bit warmer, temps between 69°F and 55°F. Finish your sightseeing early on the 19th (Sun) so you can travel to Charleston.

Things to do in New York City

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

2
nights
Charleston

Charleston ©
Many visitors describe their Charleston holiday as a warm embrace by an old, dear friend--who lived about 200 years ago.
Kick off your visit on the 20th (Mon): learn about all things military at Patriots Point, take in the views from Arthur Ravenel Jr. Bridge, and then get the lay of the land with Walking tours. Get ready for a full day of sightseeing on the next day: get a new perspective on things with Boat Tours & Water Sports, then explore the striking landscape at Angel Oak Tree, and then deepen your knowledge of military history at Fort Sumter National Monument.

To find photos, ratings, where to stay, and other tourist information, you can read our Charleston route planner.

Do a combination of bus and flight from New York City to Charleston in 5 hours. Alternatively, you can fly; or drive. Expect a bit warmer temperatures when traveling from New York City in May; daily highs in Charleston reach 81°F and lows reach 64°F. Wrap up your sightseeing on the 21st (Tue) early enough to drive to Hilton Head.

Things to do in Charleston

Museums Tours Historic Sites

Side Trips

Patriots Point, Angel Oak Tree
Highlights from your plan
Patriots Point ©
Patriots Point
Dolphin & Whale Watching
Angel Oak Tree ©
Angel Oak Tree

3
nights
Hilton Head

A Hilton Head vacation may be heaven for a golfer, but the area also offers all kinds of other options for sports fans.
Explore hidden gems such as Hilton Head Island Bike Trails and Waterskiing & Jetskiing. Get outdoors at Coligny Beach and Alder Lane Beach Access. The adventure continues: see majestic marine mammals with a dolphin and whale watching tour, get some thrills on the water with a speed boat tour, view the masterpieces at The Silver Garden Silversmiths and Art Gallery, and soothe aching muscles at some of the top local wellness centers.

For ratings, maps, traveler tips, and tourist information, refer to the Hilton Head day trip planner.

You can drive from Charleston to Hilton Head in 2.5 hours. Alternatively, you can take a bus. May in Hilton Head sees daily highs of 80°F and lows of 66°F at night. Finish your sightseeing early on the 24th (Fri) to allow enough time to drive to St. Augustine.

Things to do in Hilton Head

Outdoors Parks Tours
Highlights from your plan
Dolphin & Whale Watching
Hilton Head Island Bike Trails ©
Hilton Head Island Bike Trails
Waterskiing & Jetskiing

2
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Kick off your visit on the 25th (Sat): contemplate in the serene atmosphere at Cathedral Basilica of St. Augustine, then visit a coastal fixture at St. Augustine Lighthouse & Maritime Museum, Inc., then enjoy the sand and surf at St. Augustine Beach, and finally brush up on your knowledge of spirits at St. Augustine Distillery. Keep things going the next day: explore the striking landscape of Fort Matanzas National Monument.

To see where to stay, ratings, and tourist information, read our St. Augustine online route planner .

Traveling by car from Hilton Head to St. Augustine takes 4 hours. Alternatively, you can do a combination of taxi and train; or take a bus. Expect a daytime high around 83°F in May, and nighttime lows around 67°F. Wrap up your sightseeing on the 26th (Sun) to allow time to travel to Marathon.

Things to do in St. Augustine

Parks Historic Sites Nature
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
Fort Matanzas National Monument ©
Fort Matanzas National Monument

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.
Explore hidden gems such as Fishing Charters & Tours and The Turtle Hospital. Get in touch with nature at Bahia Honda State Park and Scuba & Snorkeling. Step out of Marathon with an excursion to Parasailing & Paragliding in Islamorada--about 34 minutes away. And it doesn't end there: look for all kinds of wild species at Dolphin Research Center, kick back and relax at Sombrero Beach, and snap pictures at Seven Mile Bridge.

To see photos, maps, ratings, and other tourist information, use the Marathon trip builder website .

Traveling by combination of car, flight, and shuttle from St. Augustine to Marathon takes 6.5 hours. Alternatively, you can drive; or do a combination of bus, flight, and shuttle. Traveling from St. Augustine in May, you can expect nighttime temperatures to be somewhat warmer in Marathon, with lows of 77°F. Wrap up your sightseeing on the 29th (Wed) to allow time to take a bus to Key West.

Things to do in Marathon

Outdoors Wildlife Parks

Side Trips

Islamorada, Bahia Honda State Park
Highlights from your plan
The Turtle Hospital ©
The Turtle Hospital
Fishing Charters & Tours
Scuba & Snorkeling

4
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 the less-touristy side of things at Dolphin & Whale Watching and Fishing Charters & Tours. Take a break from the city and head to Dry Tortugas National Park and The Overseas Highway. There's much more to do: steep yourself in history at Truman Little White House, immerse yourself in nature at Fort Zachary Taylor, learn about all things military at U.S. Coast Guard Cutter Ingham Maritime Museum, and find your balance on the water with some of the best stand-up paddleboarding in the area.

To see ratings, maps, other places to visit, and more tourist information, read our Key West trip planner .

Take a bus from Marathon to Key West in 1.5 hours. Alternatively, you can drive. In May, plan for daily highs up to 85°F, and evening lows to 77°F. Finish your sightseeing early on the 2nd (Sun) to allow enough time to ride a ferry to Marco Island.

Things to do in Key West

Outdoors Tours Wildlife
Highlights from your plan
Fort Zachary Taylor ©
Fort Zachary Taylor
Dry Tortugas National Park ©
Dry Tortugas National Park
Fishing Charters & Tours

2
nights
Marco Island

Marco Island is a city in Collier County, Florida, United States, located on an island by the same name in the Gulf of Mexico off the coast of Southwest Florida. Kick off your visit on the 3rd (Mon): get some thrills out on the water with a waterskiing or jet-skiing adventure, then see majestic marine mammals with a dolphin and whale watching tour, and then contemplate the waterfront views at Capri Paddlecraft Park. Get ready for a full day of sightseeing on the next day: glide through the air with a parasailing or paragliding tour and then get some thrills on the water with a speed boat tour.

To see maps, reviews, ratings, and tourist information, read Marco Island online itinerary planner .

You can ride a ferry from Key West to Marco Island in 2.5 hours. Another option is to drive. Traveling from Key West in June, Marco Island is slightly colder at night with lows of 74°F. Finish your sightseeing early on the 4th (Tue) so you can travel back home.

Things to do in Marco Island

Tours Outdoors Wildlife

Side Trip

Speed Boats Tours
Highlights from your plan
Waterskiing & Jetskiing
Dolphin & Whale Watching
Parasailing & Paragliding

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