Major city travel itineraries immerse visitors in the energy, culture, and character of America’s most iconic urban destinations, combining renowned attractions, diverse neighborhoods, local cuisine, museums, entertainment, and hidden gems into a memorable city experience. From historic landmarks and world-class arts to vibrant waterfronts and dynamic downtowns, each itinerary offers a unique perspective on the people and stories that define the city.
Places to See on Route 66
Los Angeles 5 Day Itinerary
Los Angeles
Five-day journey from the Hollywood Hills to Santa Monica's beaches, tracing Los Angeles' evolution from frontier settlement to entertainment capital.
Las Vegas Area 7 Day Itinerary
Las Vegas
Seven-day journey blending Las Vegas' themed casinos and entertainment with nearby natural wonders like the Grand Canyon.
San Francisco 5 Day Itinerary
San Francisco
Five-day itinerary through San Francisco's iconic bay views, historic neighborhoods, and the Golden Gate Bridge.
Honolulu Waikiki 3 Day Itinerary
Honolulu
Three-day tour tracing Honolulu and Waikiki from the historic palaces of Downtown to the famous shores of Waikiki Beach.
San Diego 3 Day Itinerary
San Diego
Three-day itinerary spanning Balboa Park's museums and gardens to the dramatic coastline of La Jolla and Torrey Pines.
Santa Fe 3 Day Itinerary
Santa Fe
Three-day tour of Santa Fe's historic Plaza, Canyon Road galleries, and centuries-old adobe architecture.
Phoenix 3 Day Itinerary
Phoenix
Three-day tour of the Sonoran Desert, from Phoenix's museums and botanical gardens to Frank Lloyd Wright's desert masterpiece.
Seattle 3 Day Itinerary
Seattle
Three-day tour from Pike Place Market to the Seattle Center, exploring the Emerald City's maritime heritage and coffee culture.
Portland 2 Day Itinerary
Portland
Two-day tour of Portland's Japanese gardens, historic neighborhoods, and bridges over the Willamette River.
Dallas Fort Worth 3 Day Itinerary
Dallas
Three-day tour pairing Dallas' modern skyline and history with Fort Worth's cowboy heritage and acclaimed museums.
New Orleans 5 Day Itinerary
New Orleans
Five-day journey through the French Quarter, Garden District mansions, and the live oaks of City Park.
Austin 3 Day Itinerary
Austin
Three-day tour of Austin's spring-fed swimming holes, scenic trails, and legendary live music scene.
Houston Galveston 3 Day Itinerary
Houston
Three-day itinerary from Houston's space exploration museums to Galveston's historic Gulf Coast beaches.
San Antonio 2 Day Itinerary
San Antonio
Two-day tour of the Alamo, the River Walk, and San Antonio's UNESCO-listed Spanish Missions.
Nashville 3 Day Itinerary
Nashville
Three-day journey from downtown honky-tonks to the studios and landmarks that built Music City.
Memphis 3 Day Itinerary
Memphis
Three-day tour of Beale Street, Graceland, and the studios and museums that shaped American music and civil rights history.
Orlando 5 Day Itinerary
Orlando
Five-day vacation through Orlando's most iconic theme parks and attractions, from storybook kingdoms to marine encounters and tropical lagoons.
Miami 3 Day Itinerary
Miami
Three-day tour of Miami's Art Deco architecture, colorful murals, tropical gardens, and world-famous beaches.
Atlanta 3 Day Itinerary
Atlanta
Three-day tour from the birthplace of Dr. Martin Luther King Jr. to Atlanta's world-renowned museums and green spaces.
Tampa Bay Sarasota 5 Day Itinerary
Tampa
Five-day route along Florida's Gulf Coast from Tampa's historic districts to the beaches and gardens of Sarasota.
Charleston 3 Day Itinerary
Charleston
Three-day tour of Charleston's cobblestone streets, historic churches, and Lowcountry plantations and coastline.
Savannah 3 Day Itinerary
Savannah
Three-day tour of Savannah's oak-lined historic squares, coastal forts, and Southern architecture.
New York City 5 Day Itinerary
New York City
Five-day route through Manhattan and Brooklyn combining iconic landmarks, world-famous museums, and unforgettable skyline views.
Washington DC 5 Day Itinerary
Washington, D.C.
Five-day tour of the National Mall, Capitol Hill, Georgetown, and Washington D.C.'s most celebrated monuments and museums.
Philadelphia 3 Day Itinerary
Philadelphia
Three-day tour of Independence Hall, colonial streets, and the museums where the American story began.
Boston 3 Day Itinerary
Boston
Three-day walk through Boston's Freedom Trail landmarks, Beacon Hill, Harvard University, and world-renowned museums.
Chicago 5 Day Itinerary
Chicago
Five-day exploration of Chicago's bold skyscraper architecture, world-class museums, and Lake Michigan waterfront.
Minneapolis St Paul 3 Day Itinerary
Minneapolis
Three-day tour of the Twin Cities' historic mills, sculpture gardens, cathedral domes, and lakes.
Overview
U.S. Route 66 or U.S. Highway 66 (US 66 or Route 66) was one of the original highways in the United States Numbered Highway System. It was established on November 11, 1926, with road signs erected the following year. The highway ran from Chicago, Illinois, through Missouri, Kansas, Oklahoma, Texas, New Mexico and Arizona before terminating in Santa Monica, California, covering a total of 2,448 miles (3,940 km).
US 66 was a primary route for those who migrated west, especially during the Dust Bowl of the 1930s, and it supported the economies of the communities through which it passed. People doing business along the route became prosperous and they later fought to keep it alive in the face of the growing threat of being bypassed by the more advanced freeways of the Interstate Highway System in the 1960s and 1970s.
US 66 underwent many improvements and realignments over its lifetime, but it was officially removed from the United States Highway System in 1985 after it was entirely replaced by segments of the Interstate Highway System. Portions of the road that passed through Illinois, Missouri, Oklahoma, New Mexico, Arizona and California have been communally designated a National Scenic Byway by the name Historic Route 66, returning the name to some maps.
In John Steinbeck's novel The Grapes of Wrath (1939), the highway symbolizes escape, loss, and the hope of a new beginning; Steinbeck dubbed it the Mother Road. Other designations and nicknames include the Will Rogers Highway and the Main Street of America, the latter nickname shared with U.S. Route 40. It is also featured in the Disney/Pixar animated feature film franchise Cars.
Much of the early highway, like all the other early highways, was gravel or graded dirt. Due to the efforts of the U.S. Highway 66 Association, in 1938 US 66 became the first highway to be completely paved.
In the 1950s, US 66 became the main highway for vacationers heading to Los Angeles. The road passed through the Painted Desert and near the Grand Canyon. Meteor Crater in Arizona was another popular stop. This sharp increase in tourism in turn gave rise to a burgeoning trade in all manner of roadside attractions, including teepee-shaped motels, frozen custard stands, Indian curio shops and reptile farms. Meramec Caverns near St. Louis, began advertising on barns, billing itself as the "Jesse James hideout". The Big Texan advertised a free 72-ounce (2.0 kg) steak dinner to anyone who could consume the entire meal in one hour. It also marked the birth of the fast-food industry: Red's Giant Hamburg in Springfield, Missouri, site of the first drive-through restaurant and the first McDonald's in San Bernardino, California. Changes like these to the landscape further cemented 66's reputation as a near-perfect microcosm of the culture of America, now linked by the automobile.
The beginning of the decline for US 66 came in 1956 with the signing of the Interstate Highway Act by President Dwight D. Eisenhower. During its nearly 60-year existence, US 66 was under constant change. As highway engineering became more sophisticated, engineers constantly sought more direct routes between cities and towns. Increased traffic led to a number of major and minor realignments of US 66 through the years, particularly in the years immediately following World War II when Illinois began widening US 66 to four lanes through virtually the entire state from Chicago to the Mississippi River just east of St. Louis and included bypasses around virtually all of the towns. By the early to mid-1950s, Missouri also upgraded its sections of US 66 to four lanes complete with bypasses. Most of the newer four-lane 66 paving in both states was upgraded to freeway status in later years.
Bobby Troup wrote "(Get Your Kicks on) Route 66", which was popularized by Nat King Cole with the King Cole Trio and later covered by artists ranging from Chuck Berry and Glenn Frey to The Manhattan Transfer, John Mayer and Brian Setzer, as well as the Rolling Stones.
This article uses material from the Wikipedia article "Route 66", which is released under the Creative Commons Attribution-Share-Alike License 3.0