10 Presidents Day Weekend Vacation Ideas [2026]

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

Whether you’re seeking a cozy winter retreat, a cultural adventure, or beach days, the long weekend offers plenty of travel opportunities.

As a teacher, maximizing my time off for travel opportunities is very important to me. If you begin flight tracking for deals in advance, you can plan for some budget-friendly opportunities.

Here are some ideas to get you started for the 2026 holiday weekend!

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

10 Presidents’ Day Weekend Vacation Ideas

1. 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

2. Savannah

If you’re looking for a Presidents Day weekend trip with charm and character, Savannah should be at the top of your list. 

Picture oak trees draped in Spanish moss and historic squares that feel like movie sets!

Some of the best things to do in Savannah include exploring Forsyth Park, hopping on a trolley tour, or checking out the city’s famous historic homes. 

When the sun starts to set, head to the riverfront for dinner with a view and a little shopping along the cobblestones.

Over Presidents’ Day weekend in Savannah, you can expect comfortable, cool weather. Daytime highs usually sit in the low to mid-60s °F, while nights drop into the 40s °F. It’s one of the best times to explore because the humidity is low and the crowds are lighter than in spring.

3. 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

4. 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

5. 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

6. 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

7. 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

8. 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!

This is a lively city that totally took me by surprise.

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.

My favorite thing to do in Miami is explore Little Havana for Cuban food and music.

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

9. 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, or visit the Country Music Hall of Fame.

You can also sign up for amazing tours, like a Nashville food tour or dinner cruise.

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

10. Austin

Austin, Texas is a lively spot for a Presidents’ Day weekend trip. The city’s music scene is unbeatable—catch live shows on Sixth Street or at smaller local venues. 

Food is another highlight, with barbecue joints and taco trucks on nearly every corner. 

By day, explore Lady Bird Lake, stroll South Congress for boutique shopping, or tour the Texas State Capitol. 

The mix of culture, outdoor spaces, and incredible food makes Austin an easy choice for a long weekend getaway.

In Austin over Presidents Day weekend, the weather is generally mild and a little warmer than many other U.S. destinations that time of year. 

Daytime highs typically range from the mid-60s to the low 70s °F, while nighttime temperatures can dip into the 40s °F.  Rain is possible.

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!