31 days in United States Itinerary

31 days in United States Itinerary

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Route & dates

31 days in United States Itinerary

Start: New York City
Drive:  1​h 45​min
1
New Haven
— 1 night
+3
train + bus + Fly + taxi:  6​h 30​min
2
Gatlinburg
— 4 nights
Drive:  4​h
3
Nashville
— 2 nights
Fly:  12​h 45​min
4
Honolulu, Oahu
— 4 nights
Fly:  3​h
5
Lahaina, Maui
— 4 nights
Fly:  3​h 30​min
6
Kailua-Kona, Island of Hawaii
— 6 nights
Fly:  13​h 15​min
7
Cincinnati
— Few hours
Fly:  2​h
8
Cleveland
— 2 nights
Drive:  5​h 45​min
9
Sharpsburg
— 1 day
Drive:  2​h
10
Baltimore
— 3 nights
train:  3​h
End: New York City

1
night
New Haven

New Haven ©
New Haven, in the U.S. On the 1st (Sat), kick back and relax at Hammonasset Beach State Park and then step into the grandiose world of Castle Craig. Here are some ideas for day two: stroll through Compo Beach, explore the world behind art at Yale University Art Gallery, and then admire all the interesting features of Yale University.

To see ratings, more things to do, traveler tips, and other tourist information, go to the New Haven tour website .

New York City to New Haven is an approximately 2-hour car ride. You can also take a bus; or take a train. Traveling from New York City in December, plan for slightly colder nights in New Haven, with lows around 31°F. Wrap up your sightseeing on the 2nd (Sun) early enough to travel to Gatlinburg.

Things to do in New Haven

Parks Outdoors Beaches

Side Trips

Compo Beach, Castle Craig, Hammonasset Beach State Park
Highlights from your plan
Hammonasset Beach State Park ©
Hammonasset Beach State Park
Yale University Art Gallery ©
Yale University Art Gallery
Castle Craig ©
Castle Craig

4
nights
Gatlinburg

Gatlinburg ©
Nestled in the lush, wooded forests of the Great Smoky Mountains National Park, Gatlinburg is Tennessee’s premier mountain resort destination.
Get some cultural insight at Walker Sisters' Cabin and Fowler's Clay Works. Take a break from the city and head to Mount LeConte and Cades Cove. Take a break from Gatlinburg with a short trip to Clingmans Dome in Great Smoky Mountains National Park, about 48 minutes away. And it doesn't end there: identify plant and animal life at Roaring Fork, hike along Charlies Bunion, stroll through Alum Cave Trail, and cruise along Newfound Gap Road.

To see more things to do, where to stay, reviews, and tourist information, read our Gatlinburg tour builder .

You can do a combination of train, flight, and taxi from New Haven to Gatlinburg in 6.5 hours. Alternatively, you can do a combination of train, bus, flight, and taxi; or drive. When traveling from New Haven in December, plan for somewhat warmer days in Gatlinburg, with highs around 53°F, while nights are about the same with lows around 36°F. Finish up your sightseeing early on the 7th (Fri) so you can go by car to Nashville.

Things to do in Gatlinburg

Parks Outdoors Nature

Side Trips

Great Smoky Mountains National Park, Pigeon Forge
Highlights from your plan
Mount LeConte ©
Mount LeConte
Roaring Fork ©
Roaring Fork
Chimney Tops Trail ©
Chimney Tops Trail

2
nights
Nashville

Nashville ©
Known as the capital of country music, the thriving city of Nashville combines old-world southern charm with a progressive urban flair.
Kick off your visit on the 8th (Sat): contemplate the long history of Lotz House Museum, then test your problem-solving skills at popular escape rooms, then see the interesting displays at Andrew Jackson's Hermitage, and finally catch a live performance at Grand Ole Opry. Get ready for a full day of sightseeing on the 9th (Sun): see the interesting displays at Country Music Hall of Fame and Museum, then get engrossed in the history at The Johnny Cash Museum & Cafe, and then wander the streets of Downtown Nashville.

To find more things to do, traveler tips, reviews, and other tourist information, refer to the Nashville driving holiday planning tool .

Drive from Gatlinburg to Nashville in 4 hours. Alternatively, you can do a combination of taxi and flight; or do a combination of car and flight. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. In December in Nashville, expect temperatures between 53°F during the day and 36°F at night. Finish your sightseeing early on the 9th (Sun) to allow enough time to travel to Honolulu.

Things to do in Nashville

Museums Neighborhoods Historic Sites

Side Trip

Lotz House Museum
Highlights from your plan
Lotz House Museum ©
Lotz House Museum
Country Music Hall of Fame and Museum ©
Andrew Jackson's Hermitage ©
Andrew Jackson's Hermitage

4
nights
Honolulu, Oahu

Honolulu ©
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Your inner history buff will appreciate USS Arizona Memorial and Iolani Palace. Visiting Waikiki Beach and Kailua Beach Park will get you outdoors. Change things up with these side-trips from Honolulu: Pu’u O Mahuka Heiau State Monument (in Pupukea), Lanikai Beach (in Kailua) and Sunset Beach Park (in Haleiwa). The adventure continues: take in the pleasant sights at Diamond Head State Monument, take a memorable drive along Makapu'u Point, explore the activities along Hanauma Bay Nature Preserve, and see some colorful creatures with a scuba or snorkeling tour.

To see where to stay, maps, reviews, and tourist information, read our Honolulu route planner.

You can fly from Nashville to Honolulu in 13 hours. Other options are to do a combination of bus, taxi, and flight; or do a combination of bus and flight. The time zone changes from Central Standard Time (CST) to Hawaii Standard Time (HST), which is usually a -4 hour difference. Plan for much warmer temperatures traveling from Nashville in December, with highs in Honolulu at 82°F and lows at 69°F. Cap off your sightseeing on the 14th (Fri) early enough to travel to Lahaina.

Things to do in Honolulu

Outdoors Parks Beaches

Side Trips

Kailua, Pu’u O Mahuka Heiau State Monument, Sunset Beach Park, Makapu'u Point
Highlights from your plan
Diamond Head State Monument ©
Diamond Head State Monument
USS Arizona Memorial ©
USS Arizona Memorial
Waikiki Beach ©
Waikiki Beach

4
nights
Lahaina, Maui

Lahaina ©
Once the booming capital of the Hawaiian Kingdom, the tropical paradise of Lahaina still remains one of Maui's top vacation attractions, providing both culture and recreation.
Visiting Haleakala Crater and Dolphin & Whale Watching will get you outdoors. Visit Ka'anapali Beach and Black Rock for some beach relaxation. Step out of Lahaina with an excursion to Wailea Beach in Wailea--about 46 minutes away. Spend the 18th (Tue) exploring the striking scenery along Hana Highway - Road to Hana. The adventure continues: make a trip to Lahaina Banyan Court and look for gifts at Glass Mango Designs.

For reviews, where to stay, photos, and other tourist information, go to the Lahaina trip itinerary maker .

Getting from Honolulu to Lahaina by combination of flight and bus takes about 3 hours. Other options: do a combination of flight, taxi, and ferry. In December, plan for daily highs up to 78°F, and evening lows to 68°F. Cap off your sightseeing on the 18th (Tue) early enough to travel to Kailua-Kona.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

Maui, Wailea Beach, Haleakala Crater
Highlights from your plan
Ka'anapali Beach ©
Ka'anapali Beach
Haleakala Crater ©
Haleakala Crater
Hana Highway - Road to Hana ©
Hana Highway - Road to Hana

6
nights
Kailua-Kona, Island of Hawaii

Thanks to its favorable location near a mountain range blocking the northeasterly trade winds, Kailua-Kona gets little rainfall, allowing adventure seekers and nature lovers a chance to enjoy over 300 days of sunshine each year.
Pu'uhonua O Honaunau National Historical Park and St. Michael the Archangel Church are good opportunities to explore the local culture. Deepen your sense of the past at sights like Puukohola National Historic Park and Kealakekua Bay. Change things up with these side-trips from Kailua-Kona: Hawaii Volcanoes National Park (Devastation Trail & Kilauea Iki Trailhead), Honaunau Bay (in Honaunau) and Hapuna Beach State Recreation Area (in Puako). There's much more to do: get close to the beloved marine mammals with a swim-with-the-dolphins experience, see majestic marine mammals with a dolphin and whale watching tour, explore the striking landscape of Kaloko-Honokohau National Historical Park, and get outside with Keauhou Bay Adventures.

To see photos, more things to do, where to stay, and tourist information, you can read our Kailua-Kona day trip planning tool .

Getting from Lahaina to Kailua-Kona by combination of bus and flight takes about 3.5 hours. Other options: do a combination of bus, flight, and taxi. In December, plan for daily highs up to 82°F, and evening lows to 70°F. Finish your sightseeing early on the 24th (Mon) so you can travel to Cincinnati.

Things to do in Kailua-Kona

Parks Outdoors Nature

Side Trips

Hawaii Volcanoes National Park, Honaunau, Kealakekua Bay, Kona Joe Coffee, Hapuna Beach State Recreation Area
Highlights from your plan
Swim with Dolphins
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Hapuna Beach State Recreation Area ©

few
hours
Cincinnati

Cincinnati ©
Situated on the north bank of the Ohio River, Cincinnati distinguished itself as the only U.S.
Start off your visit on the 25th (Tue): explore the different monuments and memorials at Spring Grove Cemetery & Arboretum and then appreciate the extensive heritage of Mount Adams.

To see more things to do, photos, and tourist information, read our Cincinnati trip planner .

Traveling by combination of flight and bus from Kailua-Kona to Cincinnati takes 13.5 hours. Alternatively, you can do a combination of flight, taxi, and bus. The time zone difference moving from Hawaii Standard Time to Eastern Standard Time is 5 hours. Plan for much colder temperatures traveling from Kailua-Kona in December, with highs in Cincinnati at 45°F and lows at 29°F. Wrap up your sightseeing on the 25th (Tue) early enough to travel to Cleveland.

Things to do in Cincinnati

Historic Sites Parks Neighborhoods
Highlights from your plan
Spring Grove Cemetery & Arboretum ©
Spring Grove Cemetery & Arboretum
Mount Adams ©
Mount Adams

2
nights
Cleveland

Cleveland ©
A culturally diverse city situated on the shores of Lake Erie, Cleveland boasts many places to visit, such as world-class museums, popular amusement parks, and sprawling recreational areas.
Start off your visit on the 26th (Wed): browse the eclectic array of goods at West Side Market, then don't miss a visit to Wade Memorial Chapel, then admire the masterpieces at The Cleveland Museum of Art, and finally see the interesting displays at Rock & Roll Hall of Fame. On your second day here, identify plant and animal life at F.A. Seiberling Nature Realm, take in nature's colorful creations at Stan Hywet Hall & Gardens, and then pause for some serene contemplation at St John's Cathedral.

For traveler tips, reviews, maps, and other tourist information, go to the Cleveland trip builder app .

Traveling by flight from Cincinnati to Cleveland takes 2 hours. Alternatively, you can drive; or take a bus. In December, plan for daily highs up to 42°F, and evening lows to 31°F. Wrap up your sightseeing on the 27th (Thu) early enough to travel to Sharpsburg.

Things to do in Cleveland

Parks Historic Sites Museums

Side Trip

Akron
Highlights from your plan
The Cleveland Museum of Art ©
The Cleveland Museum of Art
F.A. Seiberling Nature Realm ©
F.A. Seiberling Nature Realm
Rock & Roll Hall of Fame ©
Rock & Roll Hall of Fame

1
day
Sharpsburg

Sharpsburg ©
Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Start off your visit on the 28th (Fri): take in the history at Antietam National Battlefield.

For reviews, other places to visit, traveler tips, and tourist information, read our Sharpsburg tour itinerary builder website .

You can drive from Cleveland to Sharpsburg in 5 hours. Alternatively, you can fly. In December, daily temperatures in Sharpsburg can reach 47°F, while at night they dip to 30°F. Cap off your sightseeing on the 28th (Fri) early enough to travel to Baltimore.

Things to do in Sharpsburg

Parks Historic Sites Nature
Highlights from your plan
Antietam National Battlefield ©
Antietam National Battlefield

3
nights
Baltimore

Baltimore ©
A major center for tourism and travel, Baltimore is famous as the city where amateur poet Francis Scott Key wrote the lyrics for the United States' national anthem.
Step out of the city life by going to Audubon Naturalist Society Woodend Sanctuary and Fort McHenry National Monument. Get a sense of the local culture at Hammond-Harwood House and The Walters Art Museum. Change things up with a short trip to Quiet Waters Park in Annapolis (about 46 minutes away). There's much more to do: try to win big at Horseshoe Casino, admire all the interesting features of Oriole Park at Camden Yards, don't miss a visit to National Katyn Memorial, and sample the fine beverages at Sagamore Spirit Distillery.

For photos and more tourist information, read our Baltimore online tour itinerary planner .

You can drive from Sharpsburg to Baltimore in 1.5 hours. Plan for somewhat warmer nights when traveling from Sharpsburg in December since evenings lows in Baltimore dip to 37°F. Finish up your sightseeing early on the 31st (Mon) so you can catch the train back home.

Things to do in Baltimore

Parks Historic Sites Fun & Games

Side Trips

Annapolis, Audubon Naturalist Society Woodend Sanctuary
Highlights from your plan
The Walters Art Museum ©
The Walters Art Museum
Hammond-Harwood House ©
Hammond-Harwood House

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