28 days in United States Itinerary

28 days in United States Itinerary

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Route & dates

28 days in United States Itinerary

Start: Ocean City
Shuttle + Fly:  7​h 30​min
1
Chicago
— 5 nights
Fly:  3​h 45​min
2
Huntsville
— 4 nights
Drive:  1​h 45​min
3
Jasper
— 1 night
Drive:  2​h
4
Montgomery
— 3 nights
Drive:  3​h 30​min
5
Gulf Shores
— 3 nights
Drive:  4​h 30​min
6
Baton Rouge
— 4 nights
Fly:  6​h
7
Boynton Beach
— 6 nights
Fly + Bus:  8​h 15​min
End: Ocean City

5
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, parks, nightlife, zoos & aquariums, and childrens museums. Your plan includes some of its best attractions: engage your brain at Museum of Science and Industry, take a leisurely stroll along Navy Pier, admire the masterpieces at The Art Institute of Chicago, and enjoy breathtaking views from Skydeck Chicago - Willis Tower.

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

Ocean City to Chicago is an approximately 7.5-hour combination of shuttle and flight. You can also do a combination of shuttle, train, and flight; or drive. Due to the time zone difference, you'll gain 1 hour traveling from Ocean City to Chicago. Traveling from Ocean City in December, expect Chicago to be little chillier, temps between 38°F and 26°F. Finish your sightseeing early on the 28th (Sat) to allow enough time to travel to Huntsville.

Things to do in Chicago

Museums Childrens Museums Fun & Games

Side Trip

Horseshoe Hammond
Highlights from your plan
Museum of Science and Industry ©
Museum of Science and Industry
Navy Pier ©
Navy Pier
Shedd Aquarium ©
Shedd Aquarium

4
nights
Huntsville

Huntsville ©
The three historical districts of Huntsville are tucked amid the lush greenery of nearly 60 parks within the city limits.
Venture out of the city with trips to Barber Vintage Motorsports Museum (in Birmingham), Cathedral Caverns State Park (in Woodville) and Horse Pens 40 (in Steele). The adventure continues: engage your brain at U.S. Space and Rocket Center, identify plant and animal life at Monte Sano Nature Preserve, have some family-friendly fun at Bad Axe Throwing, and walk around Little River Canyon National Preserve.

To find other places to visit, reviews, where to stay, and tourist information, use the Huntsville online trip itinerary planner .

Traveling by flight from Chicago to Huntsville takes 4 hours. Alternatively, you can drive; or do a combination of train and bus. Expect a bit warmer temperatures when traveling from Chicago in December; daily highs in Huntsville reach 55°F and lows reach 38°F. Finish your sightseeing early on the 1st (Wed) to allow enough time to travel to Jasper.

Things to do in Huntsville

Parks Nature Fun & Games

Side Trips

Beehive Bathhouse, Little River Canyon National Preserve, Horse Pens 40, Barber Vintage Motorsports Museum, Cathedral Caverns State Park
Highlights from your plan
Horse Pens 40 ©
Horse Pens 40
U.S. Space and Rocket Center ©
U.S. Space and Rocket Center

1
night
Jasper

Jasper ©
Jasper is a city in Walker County, Alabama, United States. Start off your visit on the 2nd (Thu): contemplate the waterfront views at Walker County Public Fishing Lake, explore the landscape on two wheels at Clear Creek, and then explore the activities along Lewis Smith Lake Dam.

To find ratings, more things to do, traveler tips, and other tourist information, refer to the Jasper trip itinerary planning site .

Traveling by car from Huntsville to Jasper takes 2 hours. Traveling from Huntsville in January, you will find days in Jasper are somewhat warmer (55°F), and nights are about the same (31°F). Finish your sightseeing early on the 2nd (Thu) so you can travel to Montgomery.

Things to do in Jasper

Nature Parks Outdoors
Highlights from your plan
Lewis Smith Lake Dam ©
Lewis Smith Lake Dam

3
nights
Montgomery

Montgomery ©
Montgomery is the capital of the U.S. Change things up with these side-trips from Montgomery: Cherokee Ridge Alpine Trail (in Dadeville) and Kreher Preserve & Nature Center (in Auburn). Next up on the itinerary: hit the bull's-eye at Montgomery Indoor Shooting Complex, take an in-depth tour of Equal Justice Initiative, make a trip to Jackson Lake Island, and admire the masterpieces at Legacy Museum.

To find other places to visit, maps, photos, and more tourist information, go to the Montgomery journey planning app .

Traveling by car from Jasper to Montgomery takes 2 hours. Expect a daytime high around 57°F in January, and nighttime lows around 36°F. Wrap up your sightseeing on the 5th (Sun) to allow time to drive to Gulf Shores.

Things to do in Montgomery

Historic Sites Parks Fun & Games

Side Trips

Kreher Preserve & Nature Center, Jackson Lake Island, Cherokee Ridge Alpine Trail
Highlights from your plan
Montgomery Indoor Shooting Complex ©
Cherokee Ridge Alpine Trail ©
Cherokee Ridge Alpine Trail
Kreher Preserve & Nature Center ©
Kreher Preserve & Nature Center

3
nights
Gulf Shores

Gulf Shores is a resort city in Baldwin County, Alabama, United States. Venture out of the city with trips to Mobile (Cathedral of the Immaculate Conception & Battleship USS ALABAMA) and Fairhope Avenue (in Fairhope). And it doesn't end there: see majestic marine mammals with a dolphin and whale watching tour, stop by Pepper Palace, get a new perspective on things with Boat Tours & Water Sports, and push the limits with an extreme tour.

To find traveler tips, other places to visit, photos, and tourist information, read our Gulf Shores road trip planner .

Drive from Montgomery to Gulf Shores in 3.5 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of flight and taxi. Traveling from Montgomery in January, plan for a bit warmer nights in Gulf Shores, with lows around 42°F. Cap off your sightseeing on the 8th (Wed) early enough to go by car to Baton Rouge.

Things to do in Gulf Shores

Outdoors Parks Tours

Side Trips

Orange Beach, Mobile, Fairhope Avenue
Highlights from your plan
Dolphin & Whale Watching
Parasailing & Paragliding
Gulf State Park ©
Gulf State Park

4
nights
Baton Rouge

Baton Rouge ©
Baton Rouge is the capital of the U.S. Venture out of the city with trips to Lafayette (Louisiana Airborne Memorial Bridge and Monument, Acadian Village, & more), Lake Martin (in Breaux Bridge) and Nottoway Plantation (in White Castle). And it doesn't end there: contemplate the long history of Oak Alley Plantation, identify plant and animal life at Mike the Tiger Habitat, take an in-depth tour of Abita Springs Trailhead Museum, and hike along Mandeville Trailhead Cultural Interpretive Center.

For traveler tips, reviews, where to stay, and tourist information, read Baton Rouge itinerary planner .

You can drive from Gulf Shores to Baton Rouge in 4.5 hours. Alternatively, you can do a combination of taxi and flight; or do a combination of car and flight. In January, plan for daily highs up to 61°F, and evening lows to 40°F. Wrap up your sightseeing on the 12th (Sun) to allow time to travel to Boynton Beach.

Things to do in Baton Rouge

Historic Sites Parks Outdoors

Side Trips

Lafayette, Houmas House Plantation and Gardens, Abita Springs Trailhead Museum, Oak Alley Plantation, Nottoway Plantation
Highlights from your plan
Oak Alley Plantation ©
Oak Alley Plantation
Tammany Trace ©
Tammany Trace
Vermilionville ©
Vermilionville

6
nights
Boynton Beach

Boynton Beach ©
Boynton Beach is a city in Palm Beach County, Florida, United States. Get out of town with these interesting Boynton Beach side-trips: Panther Ridge Conservation Center (in Wellington), Jupiter (Joey D Golf Sports Training Center, Scuba & Snorkeling, & more) and Loggerhead Marinelife Center (in Juno Beach). There's still lots to do: identify plant and animal life at Hobe Sound National Wildlife Refuge, get outside with Osceola Outdoors, get to know the resident critters at Palm Beach Zoo & Conservation Society, and walk around Sugar Sand Park.

To see ratings, where to stay, traveler tips, and tourist information, refer to the Boynton Beach trip planner .

Getting from Baton Rouge to Boynton Beach by flight takes about 6 hours. Other options: do a combination of flight and train; or drive. You'll lose 1 hour traveling from Baton Rouge to Boynton Beach due to the time zone difference. While traveling from Baton Rouge, expect a bit warmer days and warmer nights in Boynton Beach, ranging from highs of 74°F to lows of 62°F. Wrap up your sightseeing by early afternoon on the 19th (Sun) to allow enough time to travel back home.

Things to do in Boynton Beach

Parks Wildlife Outdoors

Side Trips

Boca Raton, Jupiter, West Palm Beach, Okeechobee, Panther Ridge Conservation Center
Highlights from your plan
Panther Ridge Conservation Center ©
Panther Ridge Conservation Center
Loggerhead Marinelife Center ©
Loggerhead Marinelife Center
Wakodahatchee Wetlands ©
Wakodahatchee Wetlands

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