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Travel Inspiration
The Top U.S. Cities For Converting A Layover Into A Day Trip


Stopovers are a well-known part of international travel made even more popular with budget airlines WOW and Icelandair dropping passengers in Reykjavik en route to Europe. Because of airline ticketing rules, the practice is less widespread domestically, but it is still possible. Whether you choose a long connection or purposely book a multi-city itinerary, several airport and city pairs make convenient options for your layover-turned-day-trip.

Plane flying over Boston
Plane flying over Boston, Massachusetts

Logan International Airport provides visitors with free train transportation from the airport to Boston’s South Station, but if you want to start your sightseeing early, use the water taxi. First-timers will enjoy Old Town Trolley’s hop-on-hop-off tour. The narration is excellent, and it serves as a fine mode of transport. Catch the trolley at South Station and ride far west into Back Bay or far north to the USS Constitution Museum and Bunker Hill Monument, the northernmost point on the Freedom Trail. Even though the charming streets of Boston twist and turn, getting lost is hard as a real red brick road called The Freedom Trail leads the way many of the must-see attractions. 

Cleveland, Ohio
Cleveland, Ohio

Taking a direct train link can get you quickly from Cleveland Hopkins International Airport to Tower City at the heart of downtown and only steps away from Public Square, the city’s newly renovated 6.5-acre urban oasis. Buy a transit day pass for $5.50 and continue to use the train service to visit the 1912-era restored West Side Market and expanding Ohio City neighborhood. You’ll have your choice of delectable dining options, including southern, vegan, Mexican and more. Visit local boutiques, breweries and coffee shops, or explore Cleveland’s famous art museum’s west-side outpost. If you have more time, rent a bike and ride to the shores of Lake Erie and Edgewater Beach or return downtown, where a free trolley service will take you to the Rock & Roll Hall of Fame. Located just next door is a restored bulk freighter that both kids and adults love to tour. Make one last use of your transit day pass and take a direct bus line to the front door of the Cleveland Museum of Art, botanical gardens, and other art and history museums.

George Washington Masonic National Memorial, Arlington, Virginia
George Washington Masonic National Memorial

If the weather is nice, your tour of D.C. begins as you fly over the monuments surrounding Reagan National Airport. Reagan is served by two transit lines that can get you quickly to attractions in northern Virginia or D.C. If you’re a first-time visitor to D.C., you might take the blue line north to the Smithsonian stop in the heart of the National Mall. From there you can walk to the excellent free guided tours of the Lincoln Memorial, Library of Congress, U.S. Capitol and Supreme Court. If the weather is lousy, duck into one of the countless free museums or take Old Town Trolley’s hop-on-hop-off city tour that will drive you between 25 different stops with narration the entire way.

If you’ve been to D.C. before, you might head instead south from the airport to visit Old Town Alexandria, Virginia, just two stops from the airport. Next to the train station is the George Washington Masonic National Memorial. In the other direction is King Street, where a free trolley will take you past local restaurants, galleries, boutiques and gift shops selling unique local wares. Your reward at the end of the street is the seaport with restaurant patios, boat cruises, and other water activities, depending on the season. There is also the Torpedo Factory Art Center, where you can meet more than  80 working artists in their studios.

Denver, Colorado
Denver, Colorado

Denver is perfectly crafted for stopovers. Just take a ride on the airport’s A-Line train and in just 40 minutes you’ll reach the city's beautifully restored 19th-century Union Station. When exiting Union Station, stow your luggage with LUGDEN, a van parked across the street from the station. Without your bags, you can walk, scoot or take a free bus down the length of 16th Street, which is free of vehicle traffic. Take your time, stopping at independent booksellers, restaurants and boutiques, or just relax in the median parks. If you make it all the way to North Broadway where the pedestrian zone ends, head to the State Capitol for a free tour. The history lesson is interesting, and access to the exterior of the Capitol’s dome is an exciting end to the tour. There is no shortage of food or brewery tours in Denver, but for something unique, visit the U.S. Mint and see how the nation’s coins are produced. If you’ve been to the city before or have more time on your hands, consider taking a half- or a full-day trip to the mountains with Aspire Tours. With four hours to spare, you can explore Red Rock Canyon and catch a view of the Rocky Mountain foothills. With a full day at your disposal, you can see big horn sheep and elk up close as you drive above 11,000 feet into the Rockies.

Chicago River Walk, Chicago
Chicago Riverwalk, Chicago, Illinois

Whether flying into Chicago via O’Hare International (ORD) in the northwest or Midway International (MDW) in the southwest, you can quickly get to the city center via train. The orange line from Midway and the blue line from O’Hare both run through The Loop at the heart of the city. From here, your options are endless. You might walk to the newly developed Chicago Riverwalk, descend to river level and rent a boat or kayak or have a riverside meal. If you head north of the river, you can walk to the Navy Pier and catch a sightseeing or dinner cruise. South of the river you can explore The Art Institute of Chicago or rent a bike and enjoy the miles of coastline bike trails. Bike out to the peninsula where the Shedd Aquarium is located for a refreshing view of the city. Chicago is unique because of its neighborhoods, so if you’ve already explored downtown, head north. The red line can take you to explore the streets of Andersonville, known for its high concentration of local shops and restaurants. Or tour the tree-lined streets of Lincoln Park, just steps from the city’s free zoo. If you’d rather sit down and let the scenery pass you by, check out the Riverwalk onboard Chicago’s First Lady cruises for a river architecture tour.