5 Exciting Urban Getaways for Labor Day Weekend

urban getaways

City escapes you’ll absolutely love

Are you looking for something different after months of fun in the sun? Urban getaways are the perfect chance to explore someplace new, indulge in a bit of culture, and treat your taste buds. And with Labor Day right around the corner, it’s the perfect way to end your summer. With so much to see and do, you’ll come home bursting with energy!

Not sure where to go? Check out the unique vibes of these spectacular cities.

  • Boston

    If you prefer urban getaways with an eclectic flair, look no further than Boston’s vibrant blend of historic sites and modern amenities.

    Start your visit on the Freedom Trail, a 2.5-mile walk that takes you through some of the most significant sites of the American Revolution. You’ll see museums, churches, burying grounds—even a warship!

    If you’d rather go more modern, head over to Boston’s waterfront for shops, art galleries, and some seriously delicious food. Whether you’re indulging in a lobster roll or crab legs, your taste buds will be in for a treat!

  • Chicago

    Culture meets cuisine in the Windy City!

    Enjoy the still-warm weather along the Chicago Riverwalk, with boat tours offering close-up views of Chicago’s iconic architecture. Continue your sightseeing with a stroll to Millenium Park, home of the famous “bean” sculpture. Then finish your art-filled wanderings at the Art Institute of Chicago, home to works by artists ranging from the Impressionists to exciting local creators.

    And because all that walking surely worked up your appetite, treat yourself to highlights from the city’s diverse foodie scene. Gourmet hot dogs, deep-dish pizza, or a Michelin-starred meal, whatever you’re in the mood for!

  • Miami

    Having a tough time choosing between beach trips and urban getaways? Then don’t! Get the best of both worlds with a trip to Miami.

    Begin your day with a South Beach vibe: relaxing in the sun, swimming in the crystal-clear waters, or people-watching at an oceanfront cafe. Enjoy a Cuban cafecito for the flavor and the caffeine—just what you need before you shop along Lincoln Road or explore the local Art Deco architecture.

    Speaking of energy…Miami’s nightlife is legendary! Enjoy live music and salsa dancing in Little Havana. Or head back to SoBe for packed clubs, swanky cocktail bars, or a classic Cuban mojito at a rooftop bar.

  • Nashville

    Pack your boots, you guys! Nashville is a prime Labor Day destination, with live music and delicious eats.

    Nashville is known as Music City, and with good reason. From local artists tucked into cozy country bars to shows at the famed Grand Ole Opry, the music spills into the streets everywhere you go.

    After a late night listening to music, you’ll be glad to know that the city is also known for its brunch culture. Feeling brave? Wake up your taste buds with Nashville’s famous hot chicken! Or indulge in some Southern comfort food, where biscuits and barbecue reign supreme.

  • Portland

    When it comes to mixing urban getaways and outdoor adventures, few cities do it as well as Portland.

    Pick up your lunch from one of Portland’s famous food carts, which sell everything from gourmet donuts to fusion street food. Then take your picnic to Washington Park, a 400-acre outdoor oasis that includes a zoo, a tranquil Japanese garden, and several walking trails. The park offers spectacular views of downtown Portland and—if the weather’s clear enough—you can even see Mt. Hood!

    Need more reasons to visit? Portland also has an amazing craft beer scene. If you’re a beer enthusiast, brewery tours and tastings at the local brew pubs are a definite must!

A quick Labor Day trip to explore a new city is the perfect way to end your summer. Which of these urban getaways is calling your name?

Wherever you head for Labor Day weekend, squeeze every last minute of fun into your trip by shipping your stuff to your final destination with LugLess. Forget suitcase hassles; you’ll be able to breeze by the crowds at baggage claim, hands-free and ready to enjoy your weekend!