Looking for Presidents Day Weekend Vacation Ideas in the US this year?

Whether you’re seeking a cozy winter retreat, a cultural adventure, or an outdoor escape, the long weekend offers plenty of opportunities to explore new places.

From vibrant cities with rich history to stunning mountain resorts, there’s a destination to suit every traveler.

Many locations feature special events, winter sales, and fewer crowds, making it an ideal time to experience something new.

This list of 8 ideas will help you with inspiration on where to go for this long weekend. 

Presidents Day Weekend Vacation ideas include Chicago, Boston, Milwaukee, Sedona, DC, New York, Miami, and Nashville. 

Chicago

Best for: City life

Following Christmas in Chicago, the rest of winter in the windy city tends to be low season.  This could make Presidents Day Weekend an ideal time to visit Chicago due to fewer crowds!

I recommend bundling up and checking on a Chicago winter packing list to make sure you stay warm for the sometimes freezing temperatures.

There will be plenty of indoor activities to stay warm from famous museums and Broadway shows to famous views from the 360 Skydeck or other rooftop attractions. 

Finish your day with a deep-dish pizza to warm up and enjoy a true Chicago culinary experience!

Stay: River Hotel

Boston

Best for: Classic

Boston is an excellent destination for Presidents Day Weekend, blending rich history, winter charm, and vibrant culture.

Explore the historic Freedom Trail, visit the iconic Paul Revere House, or warm up with a hot drink in the cozy cafes of Beacon Hill (or on a hot coca cruise!)

The Museum of Fine Arts and the New England Aquarium are perfect indoor spots to escape the cold, while the ice skating rink at Frog Pond in Boston Common is a classic winter activity.

Or take a classic Fenway Park Tour– one of the most popular tours in the city.

Presidents Day Weekend often brings special events and winter sales, making it an ideal time to shop along Newbury Street or check out the Boston Pops Orchestra.

Dress in layers, as temperatures can be chilly.

Stay: The Revolution Hotel

Milwaukee

Best for: Off the beaten path

Milwaukee is a hidden gem for a Presidents Day Weekend getaway, offering a perfect blend of cozy winter vibes and cultural attractions.

Visit the Milwaukee Art Museum, with its impressive architecture and collection. Interested in something different? Explore the Harley-Davidson Museum or the Grohmann Museum.

Winter events like the Milwaukee Winter Market and ice skating at Red Arrow Park add to the city’s charm. My favorite place to grab a bite to eat while exploring is at the Milwaukee Public Market! I love sampling cuisine from local restaurants.

Presidents Day Weekend is great for avoiding summer crowds and enjoying the city’s laid-back atmosphere.

Stay: Cambria Hotel Downtown Milwaukee

Sedona

Best for: Red Rock Formations

Winter in Sedona is low season so Presidents Day Weekend could be the perfect time to explore this beautiful Southwest escape without the crowds. I visit Sedona often, and Winter is one of my favorite seasons to visit!

Known for its breathtaking red rock formations, Sedona is ideal for hiking and other outdoor activities, with trails like Cathedral Rock and Bell Rock.

Sedona also has a thriving arts scene, with numerous galleries showcasing local artists.

Pack layers, as temperatures vary throughout the winter.  Don’t miss the opportunity for stargazing in this clear, dark sky region.

Stay: Sedona Village Lodge

DC

Best for: Historic Exploring

Visiting D.C. over Presidents Day Weekend combines history and culture.

Visit iconic landmarks like the Lincoln Memorial and the Washington Monument. Most museums are also free!

The National Mall is particularly scenic in winter, with fewer crowds, allowing for a more reflective experience at the Smithsonian museums. You can also explore local neighborhoods like Alexandria or find outdoor activities like Great Falls National Park.

Presidents Day Weekend often features special events and reenactments that honor the nation’s history, including ceremonies at the George Washington Masonic National Memorial.

Tip: Dress warmly, as temperatures can dip, but the brisk air makes the monuments even more striking.

Also, consider taking a winter monuments night tour to see the landmarks beautifully illuminated. (I personally walk around at my own pace and enjoy the glowing monuments at night for free!)

Stay: Generator Washington DC

New York City

Best for: City Dwellers

New York City is a fantastic destination for Presidents Day Weekend, especially if you’re looking for a mix of culture, history, and winter charm.

While temperatures can be chilly, the city is magical in winter with its iconic landmarks like Times Square, Central Park (perfect for a snow-covered stroll), and the Statue of Liberty.

Warm up at world-class museums like the Metropolitan Museum of Art or the Museum of Modern Art, or catch a Broadway show for a true NYC experience.

Presidents Day Weekend is ideal for taking advantage of sales at some of the city’s best shopping spots. 

Stay: The Chelsesan Hotel

Miami

Best for: Beach Lovers

Miami could be the destination for you if you are looking for warm weather, beaches, and plenty of city activities!

You can relax on the sun-drenched beaches of South Beach, explore the colorful Art Deco District, or visit the Wynwood Walls for a dose of street art.

Check out Little Havana for Cuban food and music or take a boat tour through Biscayne Bay.

Presidents Day Weekend is great in Miami since the weather is comfortably warm but not too hot, and the city’s lively atmosphere is at its peak with outdoor festivals and events.

Stay: Tower Hotel Little Havana

Nashville

Best for: Music Enthusiasts

Nashville is a fantastic choice for Presidents Day Weekend, offering a lively mix of music, food, and Southern hospitality.

Spend your days exploring the famous honky-tonk bars along Broadway, where live music fills the air, or visit the Country Music Hall of Fame to dive into Nashville’s rich musical history.

Winter temperatures are mild, making it a great time to enjoy outdoor attractions like Centennial Park or stroll through the vibrant 12 South neighborhood.

Presidents Day Weekend also brings unique events like the Nashville Home Show, as well as seasonal deals at local boutiques.

Stay: SoBro Guest House

Conclusion

No matter where you choose to go, Presidents Day Weekend is the perfect opportunity to break away and explore something new.

Whether you’re chasing warm weather, winter adventures, or cultural experiences, there’s a destination to match every interest.

These cities offer unique attractions, seasonal events, and the chance to make lasting memories—all in just a few days.

Whatever your plans, a Presidents Day escape is the ideal way to recharge before the year ahead!