20 days in United States Itinerary

20 days in United States Itinerary

Created using Inspirock United States trip planner

Make it your trip
Fly
1
Stowe
— 2 nights
Drive
2
Woodstock
— 1 night
Drive
3
Bar Harbor, Mount Desert Island
— 1 night
Fly
4
Salem
— 1 night
Drive
5
Plymouth
— 2 nights
Taxi to Hyannis, MA, Ferry to Nantucket
6
Nantucket
— 1 night
Drive
7
East Haddam
— 1 night
Drive
8
Rehoboth Beach
— 1 night
Drive
9
Yorktown
— 1 night
Drive
10
Charleston
— 1 night
Drive
11
Savannah
— 3 nights
Taxi to Hilton Head, Fly to San Diego

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Stowe

— 2 nights

The Ski Capital of the East

Stowe bustles in winter when skiers and snowboarders flock here to challenge themselves on the long, steep trails careening down Vermont's tallest peak, Mt.
On the 2nd (Sat), stop by Stowe Mercantile, then hike along Stowe Recreation Path, and then take a peaceful walk through Wiessner Woods. Get ready for a full day of sightseeing on the next day: pause for some serene contemplation at Blessed Sacrament Church, then take a peaceful walk through Cady Hill Forest, and then get outside with Peace Pups Dog Sledding.

To find more things to do, other places to visit, maps, and more tourist information, use the Stowe holiday maker site.

San Diego to Stowe is an approximately 9-hour flight. You can also drive; or do a combination of bus and car. You'll lose 3 hours traveling from San Diego to Stowe due to the time zone difference. Traveling from San Diego in October, you will find days in Stowe are little chillier (60°F), and nights are cooler (39°F). Finish your sightseeing early on the 3rd (Sun) so you can drive to Woodstock.

Things to do in Stowe

Parks · Nature · Outdoors · Shopping

Side Trip

Woodstock

— 1 night
Woodstock is the shire town of Windsor County, Vermont, United States. Start off your visit on the 4th (Mon): steep yourself in history at FH Gillingham & Sons General Store and then explore the activities along Ottaquechee River.

To see reviews, photos, and tourist information, read Woodstock trip planner.

You can drive from Stowe to Woodstock in 1.5 hours. Other options are to do a combination of train and taxi; or do a combination of train and bus. October in Woodstock sees daily highs of 62°F and lows of 40°F at night. Finish your sightseeing early on the 4th (Mon) so you can fly to Bar Harbor.

Things to do in Woodstock

Parks · Nature · Shopping · Historic Sites

Bar Harbor, Mount Desert Island

— 1 night
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Start off your visit on the 5th (Tue): see the interesting displays at Maine Granite Industry Museum, then take in the architecture and atmosphere at St. Saviour's Church :, and then stroll around Agamont Park. On your second day here, hike along Great Head Trail, enjoy the sand and surf at Sand Beach, and then visit a coastal fixture at Egg Rock Light.

For where to stay and tourist information, read our Bar Harbor road trip planning app.

You can fly from Woodstock to Bar Harbor in 5.5 hours. Alternatively, you can drive; or take a bus. October in Bar Harbor sees daily highs of 59°F and lows of 42°F at night. Wrap up your sightseeing on the 6th (Wed) early enough to fly to Salem.

Things to do in Bar Harbor

Parks · Historic Sites · Outdoors · Beaches

Side Trips

Salem

— 1 night

Witch City

Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
Start off your visit on the 7th (Thu): steep yourself in history at Ropes Mansion, then examine the collection at Salem Toy Museum, then see the interesting displays at Salem Witch Museum, and finally look for gifts at Magika - Chapel of Archangel Michael.

To see reviews, more things to do, other places to visit, and other tourist information, read Salem trip planner.

Fly from Bar Harbor to Salem in 3 hours. Alternatively, you can drive; or do a combination of bus and train. In October, plan for daily highs up to 64°F, and evening lows to 45°F. Wrap up your sightseeing on the 7th (Thu) to allow time to drive to Plymouth.

Things to do in Salem

Museums · Historic Sites · Shopping

Plymouth

— 2 nights

America's Hometown

Rightly calling itself "America's Hometown," Plymouth holds a prominent place in the nation's history and culture as the site of the first Puritan colony.
Kick off your visit on the 8th (Fri): explore the different monuments and memorials at Burial Hill, then take an in-depth tour of Mayflower II, then contemplate the long history of Plymouth Rock, and finally take an in-depth tour of Mayflower Society House and Library. Get ready for a full day of sightseeing on the next day: take an in-depth tour of Pilgrim Hall Museum, then steep yourself in history at Jabez Howland House, then learn about winemaking at Plymouth Bay Winery, and finally admire the natural beauty at Brewster Gardens.

For traveler tips, where to stay, and more tourist information, refer to the Plymouth road trip app.

Drive from Salem to Plymouth in 1.5 hours. Alternatively, you can take a bus; or take a train. In October, daily temperatures in Plymouth can reach 65°F, while at night they dip to 46°F. Finish your sightseeing early on the 9th (Sat) so you can fly to Nantucket.

Things to do in Plymouth

Historic Sites · Museums · Parks · Wineries

Nantucket

— 1 night
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Kick off your visit on the 10th (Sun): steep yourself in history at Old Gaol, then examine the collection at Nantucket Lightship Basket Museum, and then don't miss a visit to St Paul's Episcopal Church. On the 11th (Mon), you'll have a packed day of sightseeing: see the interesting displays at Whaling Museum, steep yourself in history at Hadwen House, and then contemplate the long history of Quaker Meeting House.

For traveler tips, ratings, and more tourist information, use the Nantucket attractions planner.

Traveling by flight from Plymouth to Nantucket takes 2 hours. Alternatively, you can do a combination of taxi and ferry; or do a combination of bus and ferry. In October in Nantucket, expect temperatures between 64°F during the day and 51°F at night. Wrap up your sightseeing on the 11th (Mon) to allow time to travel to East Haddam.

Things to do in Nantucket

Historic Sites · Museums

East Haddam

— 1 night
East Haddam is a town in Middlesex County, Connecticut, United States. On the 12th (Tue), get engrossed in the history at Slater Memorial Museum, then explore the different monuments and memorials at Norwichtown Historic Cemetary, and then immerse yourself in nature at Devil's Hopyard State Park. Get ready for a full day of sightseeing on the next day: do a tasting at Staehly Farm Winery and then see the interesting displays at Allegra Farm And The Horsedrawn Carriage And Sleigh Museum Of New England.

To see maps, traveler tips, ratings, and more tourist information, you can read our East Haddam vacation planner.

Drive from Nantucket to East Haddam in 5 hours. Alternatively, you can drive. Expect a daytime high around 64°F in October, and nighttime lows around 48°F. Wrap up your sightseeing on the 13th (Wed) to allow time to travel to Rehoboth Beach.

Things to do in East Haddam

Museums · Parks · Nature · Historic Sites

Side Trip

Rehoboth Beach

— 1 night

Nation's Summer Capital

The population of the city of Rehoboth Beach expands by 25,000 every summer.
Kick off your visit on the 14th (Thu): look for gifts at The Spice & Tea Exchange of Rehoboth and then learn insider's secrets on Delmarva Discovery Tours.

To find maps, photos, other places to visit, and more tourist information, go to the Rehoboth Beach road trip site.

Drive from East Haddam to Rehoboth Beach in 5.5 hours. Alternatively, you can do a combination of car and flight. Traveling from East Haddam in October, expect nights in Rehoboth Beach to be about the same, around 51°F, while days are a bit warmer, around 70°F. Wrap up your sightseeing on the 14th (Thu) to allow time to drive to Yorktown.

Things to do in Rehoboth Beach

Breweries & Distilleries · Tours · Wildlife · Wineries

Yorktown

— 1 night
Yorktown is a census-designated place (CDP) in York County, Virginia, United States. Start off your visit on the 15th (Fri): take an in-depth tour of American Revolution Museum at Yorktown, take an in-depth tour of Moore House, and then take a tour by water with Boat Tours & Water Sports.

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

Drive from Rehoboth Beach to Yorktown in 4.5 hours. Alternatively, you can do a combination of bus and flight; or do a combination of bus, subway, and flight. October in Yorktown sees daily highs of 73°F and lows of 54°F at night. Finish your sightseeing early on the 15th (Fri) so you can fly to Charleston.

Things to do in Yorktown

Historic Sites · Museums · Tours · Outdoors

Charleston

— 1 night
Many visitors describe their Charleston holiday as a warm embrace by an old, dear friend--who lived about 200 years ago.
Start off your visit on the 16th (Sat): pause for some serene contemplation at St. Michael's Church, capture your vacation like a pro with an inspiring photography tour, and then take an in-depth tour of Heyward-Washington House.

To see ratings, maps, where to stay, and other tourist information, use the Charleston online travel planner.

You can fly from Yorktown to Charleston in 5 hours. Alternatively, you can drive; or do a combination of taxi, train, and car. Plan for somewhat warmer nights when traveling from Yorktown in October since evenings lows in Charleston dip to 60°F. Wrap up your sightseeing on the 17th (Sun) early enough to drive to Savannah.

Things to do in Charleston

Historic Sites · Museums · Tours

Savannah

— 3 nights

The Hostess City of the South

Georgia's oldest city, Savannah displays its colonial history proudly on every corner.
Visiting May River Excursions and Horse-Drawn Carriage Tours will get you outdoors. Owens-Thomas House & Slave Quarters and American Prohibition Museum are good opportunities to explore the local culture. Change things up with a short trip to The Church of the Cross in Bluffton (about 34 minutes away). There's still lots to do: pause for some serene contemplation at Congregation Mickve Israel, brush up on your military savvy at Webb Military Museum, go on a hair-raising tour with a ghost and vampire tour, and contemplate the long history of Juliette Gordon Low's Birthplace.

To see ratings, where to stay, photos, and tourist information, go to the Savannah tour itinerary planning app.

You can drive from Charleston to Savannah in 2.5 hours. Another option is to take a bus. In October, plan for daily highs up to 79°F, and evening lows to 60°F. Finish your sightseeing early on the 20th (Wed) to allow enough time to travel back home.

Things to do in Savannah

Historic Sites · Museums · Tours · Outdoors

Side Trip

United States travel guide

4.5
Specialty Museums · Nightlife · Beaches
More than the country of car-packed streets seen in TV shows and movies, the United States of America is a complex and diverse home to over 300 million people living in a wide range of landscapes and climates. From its big-city skyscrapers to its sprawling natural parks, the country's ''melting pot'' combines many ethnic groups that share a strong sense of national identity despite their cultural differences. A country of road trips and big blue skies, the United States harbors orderly cities filled with restaurants, parks, museums, and innumerable sightseeing opportunities, as well as pristine natural areas perfect for a holiday in the great outdoors. To see as much as you can of this diverse land quickly, drive over some of the more than 6 million km (4 million mi) of highways leading through deserts, mountain peaks, fertile fields, and giant urban centers.

Maine travel guide

4.6
Beaches · Lighthouses · Mountains
The Pine Tree State
The easternmost state in New England, Maine features an indented coastline and forested interior, carved eons ago by receding glaciers. Maine includes more lighthouses and quaint resort villages than you could ever hope to explore in a single trip, but the state is also one of the country's most sparsely populated, the majority of its land pristine and uninhabited wilderness. The temperate coastal regions, historically supported by fishing and lobstering, contain most of the state's urban centers and are the most popular spots in the state for holidays. The sea is the focus here, so it shouldn't come as a surprise that water plays an important role in the distinct character of the state, shaping its economy, tourism, cuisine, politics, sports, and art.

Massachusetts travel guide

4.3
History Museums · Art Museums · Historic Walking Areas
The Bay State
Known as the "Bay State" because of the three bays dominating its coastline, Massachusetts has played a significant cultural and commercial role through most of the country's history. An increasingly popular vacation destination for foreign travelers, Massachusetts offers numerous places to visit, ranging from historical sites to modern urban centers famous for their culinary, art, and nightlife scenes. With the majority of its population living in and around the city of Boston, in the 20th century Massachusetts went from a state largely dependent on fishing and agriculture to the country's leader in higher education, healthcare, high technology, and financial services. Home to renowned universities and research centers, the state's cities attract a young crowd of students, scientists, artists, and business professionals.

Connecticut travel guide

4.3
Aquariums · Theaters · Observatories
The Constitution State
Perhaps best known for its renowned private and public universities, Connecticut was once home to the country's first law school and still boasts one of the oldest secondary schools in America. More than just a small state packed with students, Connecticut offers visitors a chance to explore some of New England's finest tourist attractions while on vacation, including lighthouses, beaches, theaters, museums, galleries, and restaurants. Despite its small size, the state also boasts two large casino complexes, both located on Native American reservations. Rich in history and natural beauty, Connecticut draws newcomers from around the world, with large Polish, Chinese, and Hispanic communities.

Delaware travel guide

4.2
Beaches · Theme Parks · History Museums
The First State
Nicknamed the "First State" for its role in ratifying the U.S. Constitution, Delaware is only 160 km (100 mi) long and about 80 km (49 mi) wide at its widest point. Despite its small size, the state is a patchwork of complex and diverse communities, with an industrialized north and rural south. More than just a tax-free shopping haven, the state features great sightseeing in its picturesque countryside interspersed with sleepy colonial villages and long sandy beaches. It also offers several organized trail systems that focus on things to do in the outdoors, including history, geocaching, culinary activities, and wine and spirits. Largely because of its size, Delaware remains one of the country's least-explored states.

Virginia travel guide

4.6
History Museums · Wineries & Vineyards · Historic Sites
Old Dominion
The home of the first permanent English colony in the New World, Virginia is a prime holiday destination for those looking to immerse themselves in American heritage. Proud of its colorful history, distinct culture, and southern drawl, Virginians see their state as the place where the imaginary line between the north and the south is drawn. With scenic beauties as diverse as its people, Virginia is a land of rolling hills, rugged mountains, lush valleys, dense forests, and secluded beaches along picturesque bays. Bordered on the east by the Atlantic and the west by the Appalachian Mountains, with rolling farmland in the middle, the state offers countless places to visit for history buffs, nature lovers, and passionate foodies.

Coastal South Carolina travel guide

4.3
Dolphin & Whale Watching · Gardens · Beaches