Summer Weekend Getaways and Day Trips

Location:

Aspen, Colorado

Highlights:

Famous for world-class skiing and breathtaking alpine scenery, Aspen is a Rocky Mountain gem that offers more than just snow. With a walkable, high-end downtown and a lineup of year-round outdoor experiences, this elegant mountain town is a dream for adventurers, food lovers, and culture seekers alike.

We Recommend This For:

Skiers, hikers, luxury travelers, couples, and festival-goers looking for an all-seasons escape wrapped in natural beauty and boutique indulgence.

What we Love:

The snow-covered slopes in winter, scenic trails and whitewater thrills in summer, plus a downtown full of art galleries, gourmet dining, and designer shops—all with a mountain view.

• Play in the powder—Aspen’s world-renowned ski resorts offer excellent terrain for all skill levels with unforgettable mountain vistas.
• Explore beyond the snow—Aspen is a year-round destination for outdoor lovers, with hiking, kayaking, horseback riding, fly fishing, and rafting during the warmer months.
• Stroll through the charming downtown district, where luxury boutiques, renowned restaurants, and art galleries create a chic alpine village feel.
• Celebrate Aspen’s creative culture with iconic annual events like the Food and Wine Classic and the acclaimed Aspen Film Festival.
• Escape the city—Aspen is just a three-hour scenic drive from Denver, making it perfect for a weekend mountain retreat.

Location:

Louisville, Kentucky

Highlights:

Known for its southern charm, historic racetrack, and legendary sandwich, Louisville is a cultural gem that blends tradition, flavor, and excitement. From springtime Derby festivities to year-round foodie experiences, this city offers more than just a day at the races.

We Recommend This For:

Derby enthusiasts, food lovers, cultural travelers, and those craving a city with character and charm.

What we Love:

The electric atmosphere during Derby season, the timeless taste of a Hot Brown at its original home, and a city that knows how to celebrate with style.

• Experience the thrill of the Kentucky Derby at Churchill Downs—one of the most iconic sporting events in the U.S., steeped in tradition and flair.
• Join the fun each spring when tourists flood the city in extravagant Derby hats, enjoying parades, events, and all things equestrian.
• Taste Louisville’s most famous dish, the Hot Brown—a decadent open-faced sandwich with roasted turkey, bacon, and bubbling Mornay sauce.
• Dine where it all began at The Brown Hotel, the birthplace of the Hot Brown in 1926 and a must-stop for culinary history buffs.

Location:

Beaufort, North Carolina

Highlights:

Nestled along the scenic Beaufort Inlet, this historic coastal town offers a blend of 18th-century charm, family-friendly attractions, and access to some of North Carolina’s most stunning natural landscapes. Whether you’re day-tripping from Charlotte or staying for a relaxing weekend, Beaufort is a small-town gem that delivers big on beauty and charm.

We Recommend This For:

History lovers, families, nature explorers, and foodies looking for a peaceful yet enriching coastal escape.

What we Love:

The walkable historic district, nearby barrier island adventures, fascinating maritime history, and lively festivals that celebrate Beaufort’s pirate past and culinary scene.

• Explore the historic heart of town with a visit to the Beaufort Historic District and the Carteret County Home, both listed on the National Register of Historic Places.
• Learn something new at the North Carolina Maritime Museum, a favorite for families and maritime buffs alike.
• Discover nearby natural wonders like the Cape Lookout National Seashore and Cedar Island National Wildlife Refuge, both offering stunning views, trails, and wildlife.
• Join the fun at annual festivals like the swashbuckling Beaufort Pirate Invasion and the flavorful Beaufort Food and Wine Festival.
• Get away without going far—Beaufort is an easy day trip from Charlotte, Charleston, and Virginia Beach, making it an ideal weekend escape.

Location:

Burlington, Vermont

Highlights:

Set along the shimmering shores of Lake Champlain, Burlington is Vermont’s largest city and a vibrant blend of natural beauty, historic charm, and indie culture. With walkable downtown streets, breathtaking lake views, and a thriving arts and food scene, it’s an ideal getaway for outdoor adventurers and urban explorers alike.

We Recommend This For:

Couples, families, beer lovers, bookworms, and nature seekers looking for a relaxed, creative city with a small-town feel.

What we Love:

Sunsets over the lake, a stroll down Church Street, and the perfect pairing of mountain trails and local craft beer—Burlington delivers it all in a compact, cozy package.

• Visit Lake Champlain for scenic waterfront activities like paddleboarding, sailing, or just watching the sunset from the shore.
• Explore Church Street Marketplace, Burlington’s pedestrian-friendly heart, packed with indie shops, cozy cafés, art galleries, and live street performers.
• Discover local culture at the Flying Pig Bookstore, Echo Lake Aquarium and Science Center, or the Ethan Allen Homestead Museum, a tribute to Vermont’s Revolutionary past.
• Play outside with easy access to skiing trails, bike paths, and hiking routes just minutes from downtown.
• Stay in charming bed & breakfasts nestled in the area’s rustic landscapes for a peaceful, homey retreat.
• Drink local at standout breweries like Burlington Beer Company and Four Quarters Brewing—a must for any craft beer aficionado.

Location:

Carmel-by-the-Sea, California

Highlights:

Nestled on the iconic Monterey Peninsula, Carmel-by-the-Sea is a coastal village that feels like a fairytale. With enchanting architecture, ocean views, and an unmistakable artistic spirit, it’s the kind of place where every winding lane and cottage tells a story. Whether you're here for romance, culture, or coastal hikes, Carmel delivers magic at every turn.

We Recommend This For:

Couples, art enthusiasts, wine lovers, and anyone craving a whimsical, walkable retreat by the sea.

What we Love:

Charming storybook cottages, a century of creative history, serene beaches, and world-class wine tasting—all set against a backdrop of rugged California coastline.

• Step back in time in this 1916 artist colony, once frequented by literary greats like Mary Austin and Jack London.
• Wander through a storybook setting of Hugh Comstock's whimsical 1920s-era cottages and over 100 art galleries scattered around the village.
• Explore the Carmel Mission, one of California’s most historic and picturesque missions, nestled among gardens and Spanish-style architecture.
• Adventure outdoors at Point Lobos State Natural Reserve—a stunning coastal preserve known for scenic trails and wildlife viewing—or snorkel and birdwatch at nearby Carmel River State Beach.
• Sip and savor in the Central Coast Wine Country, where Carmel’s tasting rooms offer premium pours from regional vineyards.

Location:

Charlottesville, Virginia

Highlights:

With roots deep in American history and landscapes that open into the Blue Ridge Mountains, Charlottesville offers a rich blend of heritage, culture, and nature. From presidential homes to award-winning wineries, this charming Virginia city invites exploration at every turn.

We Recommend This For:

History lovers, wine and beer enthusiasts, college town wanderers, and Blue Ridge adventurers looking for an easygoing yet enriching getaway.

What we Love:

Jeffersonian architecture, the peaceful Monticello countryside, scenic drives along Skyline Drive, and cozy sips along the Brew and Wine Trails.

• Tour the University of Virginia, one of the country’s most beautiful campuses, designed by Thomas Jefferson himself.
• Step back into the past at Monticello, Jefferson’s historic estate, featuring preserved grounds, a guided house tour, and an unflinching look at plantation life, including reconstructed slave quarters.
• Visit Highland, the refined and personal home of President James Monroe, showcasing original furnishings and peaceful gardens.
• Drink local along the Brew Ridge Trail, where award-winning craft breweries pour bold IPAs, smooth stouts, and seasonal small-batch favorites.
• Unwind with a glass of Virginia wine—there are nearly three dozen wineries on the Monticello Wine Trail, many with stunning vineyard views.
• Explore nearby Shenandoah National Park, a haven for hiking, scenic drives, and wildlife viewing in the majestic Blue Ridge Mountains.

Location:

Door County, Wisconsin

Highlights:

Nestled between Lake Michigan and Green Bay, Door County is a picture-perfect peninsula dotted with lighthouses, parks, orchards, and quaint towns. With outdoor adventures, historic maritime culture, and a thriving arts scene, it’s one of the Midwest’s best-kept secrets for a relaxing yet enriching escape.

We Recommend This For:

Nature lovers, art enthusiasts, lighthouse seekers, and couples or families looking for a charming lakeside getaway.

What we Love:

The serene state parks, coastal views, scenic wineries, and storybook towns—plus the iconic lighthouses and creative events that give Door County its distinct personality.

• Explore breathtaking nature at Peninsula State Park and Newport State Park, known for hiking trails, lake vistas, and stargazing.
• Wander through 11 charming towns like Ephraim, Fish Creek, and Sister Bay, each offering its own coastal flavor and local charm.
• Visit the Door County Maritime Museum to dive into the region’s tugboat, shipwreck, and lighthouse history—great for all ages.
• Tour scenic wineries, orchards, and art galleries, or hop aboard a Door County Trolley Tour for a fun and informative way to explore.
• Climb the 97-step Cana Island Lighthouse for panoramic lake views, or visit the 1836 Pottawatomie Lighthouse, the oldest on Lake Michigan.
• Celebrate creativity at the Door County Plein Air Festival, the Midwest’s largest outdoor painting event.

Location:

Friday Harbor, San Juan Island, Washington

Highlights:

Accessible only by ferry and packed with island charm, Friday Harbor is the heart of Washington’s San Juan Islands. With its walkable downtown, world-class marine research, and front-row views of orcas and lavender fields, this peaceful port town offers a refreshing blend of science, scenery, and small-town allure.

We Recommend This For:

Nature lovers, marine biology fans, romantic weekenders, and those seeking a ferry-accessible island escape.

What we Love:

Ferry rides with views, spotting whales from shore, hands-on marine education, and strolling through lavender fields with the Olympic Mountains in the distance.

• Arrive by scenic Washington State Ferry—a relaxing and picturesque way to reach San Juan Island.
• Stroll through downtown’s art galleries, boutique shops, antique stores, and the Friday Harbor Whale Museum, a family-friendly spot dedicated to marine conservation and orca research.
• Visit the Friday Harbor Laboratories, a world-renowned marine biology station affiliated with the University of Washington.
• Watch whales from land at Lime Kiln State Park, one of the best onshore whale-watching spots in the world, complete with trails and a historic lighthouse.
• Wander through Pelindaba Lavender Farm, a 25-acre sensory haven with stunning purple fields and views of the Olympic Mountains.

Location:

Galena, Illinois

Highlights:

Step into the past with a visit to Galena, one of Illinois’ most beloved tourist towns. With its cobblestone streets, Victorian architecture, and presidential legacy, Galena offers a nostalgic journey through 19th-century Americana—paired with breathtaking views and small-town charm that feels straight out of a postcard.

We Recommend This For:

History buffs, architecture lovers, couples on a cozy weekend getaway, and anyone looking for a classic small-town escape.

What we Love:

The perfectly preserved buildings, Main Street’s timeless feel, and scenic spots like Horseshoe Mound where you can see three states at once—it’s Midwest magic at its finest.

• Stroll through the Galena Historic District, a National Register-listed treasure with Victorian-era homes, churches, and storefronts around every bend.
• Explore the stately Ulysses S. Grant Home, a beautifully maintained Italianate-style house turned living history museum honoring Galena’s most famous resident.
• Admire one of America’s best Main Streets (as ranked by *Travel and Leisure*), a walkable thoroughfare filled with boutique shops, old-fashioned candy stores, antique dealers, and cozy cafés.
• Get inspired by Galena’s national acclaim—this town has been ranked among the most beautiful small towns in the U.S. by *Forbes* for good reason.
• Take in panoramic views from Horseshoe Mound Preserve, where you can see across Illinois, Iowa, and Wisconsin all in one breathtaking lookout.