Wanderwoman Diaries

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Road Trip Getaways: The US Edition

Lately, the skies have felt a little less friendly. With an increase in plane-related incidents, even the most seasoned travelers are second-guessing their next flight. But here’s the thing—travel doesn’t have to include a TSA line, a cramped seat, or the uncertainty of air travel. Some of the most exquisite, restorative, and jaw-droppingly beautiful getaways are just a scenic drive away. Whether you’re in the mood for a boutique wellness retreat, a Michelin-starred culinary escape, or a weekend of total seclusion in nature, I’ve curated the ultimate list of elevated road-trip destinations from seven of the most cosmopolitan cities in the U.S. Think vineyard stays, coastal hideaways, and five-star resorts nestled in landscapes that feel worlds away—without ever stepping foot in an airport. Buckle up (preferably in something vintage and chic), and let’s hit the road.

From nyc: hudson valley, ny

Vibe: Rustic-chic farm-to-table bliss with a side of vintage treasure hunting
Just two hours from the city, the Hudson Valley is the perfect remedy for New York’s constant buzz. Check into the ultra-charming Wildflower Farms, Auberge Resorts Collection, where you’ll be surrounded by rolling meadows and the scent of woodsmoke from your private cabin. Spend your days sipping biodynamic wines in the Shawangunk Wine Trail, indulging in farm-to-table feasts at Blue Hill at Stone Barns, and strolling the charming streets of Hudson for curated vintage finds.

From boston: watch hill, ri

Vibe: Coastal elegance meets New England charm
Just a quick drive from Boston, Watch Hill is home to the breathtaking Ocean House, a five-star resort that embodies the quintessential New England seaside experience. With its stunning ocean views and luxurious accommodations, this historic hotel offers a perfect blend of relaxation and refinement. Spend your days lounging on the private beach, indulging in rejuvenating treatments at the spa, or savoring fresh, locally sourced seafood at Coast, the hotel’s acclaimed restaurant. For an exclusive experience, take advantage of their private beach cabanas or join a wine tasting curated by the hotel sommelier. In the evenings, take a stroll along the charming coastal streets, and watch the sun dip below the horizon—there's no better way to unwind after a day of indulgence.

From Miami: Islamorada, FL

Vibe: Barefoot luxury and crystal-clear waters
Two hours south of Miami, Islamorada offers all the tropical bliss of the Caribbean—without the passport. Stay at The Moorings Village, a private beachfront resort with 18 secluded cottages, lush palm groves, and zero crowds. Spend your days paddleboarding over turquoise waters, enjoying a private beach picnic curated by Chef Michael’s. Enjoy an elegant waterfront dinner at Pierre’s, a stunning colonial-style restaurant serving French-Caribbean cuisine with breathtaking sunset views over Florida Bay. Cap off your evening with a tropical craft cocktail at The Green Turtle Inn, a beloved island staple with an upscale yet relaxed vibe.

From la: ojai, ca

Vibe: Bohemian wellness meets understated luxury
Ojai is what happens when wellness and effortless luxury have a love child. Just a 90-minute drive from LA, it’s a haven for those who love organic wine, elevated spa experiences, and spiritual rejuvenation. Stay at the Ojai Valley Inn, a five-star sanctuary with apothecary-style spa treatments and an award-winning golf course. Spend your morning exploring the town’s charming boutiques and art galleries before indulging in a farm-fresh meal at The Dutchess , a beautifully designed bakery-turned-restaurant offering a fusion of Burmese and California cuisine with locally sourced ingredients. Spend your weekend hiking to Meditation Mount, enjoying wine tastings at Ojai Vineyard, known for its artisanal blends, and shopping for handmade ceramics and ethically sourced crystals in the town’s dreamy boutiques.

From Philadelphia: Bucks County, PA

Vibe: Countryside charm with historic elegance
Just an hour’s drive from Philadelphia, Bucks County offers a sophisticated yet peaceful retreat, blending rolling vineyards, historic estates, and charming river towns. Stay at The Inn at Barley Sheaf Farm, a luxurious country estate set on 100 acres, offering refined accommodations, a spa, and gourmet farm-to-table dining. Spend your afternoon strolling through the quaint streets of New Hope, browsing upscale boutiques and art galleries before enjoying a scenic drive along the Delaware River. For an unforgettable dining experience, head to The Golden Pheasant Inn, where French-inspired cuisine, a romantic riverside setting, and impeccable service create the perfect evening out in Bucks County. End your evening with a handcrafted cocktail at Stella, a stylish riverside bar with sweeping views of the Delaware.

From chicago: lake geneva, wi

Vibe: Gatsby-era elegance with lakeside charm
Just a 90-minute drive from Chicago, Lake Geneva is the perfect blend of relaxation and refinement, offering stunning waterfront views and a rich history of Gilded Age mansions. Stay at The Grand Geneva Resort & Spa, a luxury retreat with a world-class spa, championship golf courses, and lakefront activities. Spend your day exploring the charming downtown, then enjoy an upscale meal at Sopra Bistro, a cozy yet refined eatery known for its seasonal, globally inspired dishes crafted with local ingredients. End your evening with a craft cocktail at The Baker House, a 1920s-style mansion-turned-lounge with live jazz and an extensive wine list.

From Atlanta: Savannah, GA

Vibe: Southern charm and historic elegance
Just a short two-hour drive from Atlanta, Savannah offers a perfect blend of southern hospitality, rich history, and timeless beauty. Stay at the luxurious Perry Lane Hotel, where elegance meets comfort in the heart of the historic district. Stroll through the cobblestone streets, exploring the city’s iconic squares like Forsyth Park, and immerse yourself in the city's captivating architecture. For an unforgettable dining experience, indulge in the Southern-inspired cuisine at The Grey, a beautifully restored 1938 Greyhound bus terminal turned restaurant. Don't miss a charming evening at The Collins Quarter, where you can enjoy a cocktail in a cozy, inviting atmosphere while people-watching on Abercorn Street.

From austin: marfa, tx

Vibe: Art-world darling meets desert mysticism
Marfa is an otherworldly escape that feels like a Wes Anderson film come to life. About a six-hour drive from Austin (trust me, it’s worth it), this high-desert town is home to minimalist art installations, designer boutique hotels, and a mysterious phenomenon known as the Marfa Lights. Stay at the ultra-chic Hotel Saint George, dine at The Water Stop for impossibly good craft cocktails, and lose yourself in the surreal landscapes of Chinati Foundation’s outdoor exhibits.

From san francisco: big sur, ca

Vibe: Cliffside romance and cinematic landscapes
There’s a reason Big Sur has inspired countless poets, artists, and Instagram feeds. Just a three-hour drive from San Francisco, this rugged stretch of the California coast is pure magic. For a stay that’s as breathtaking as the scenery, check into Post Ranch Inn, where your eco-friendly cliffside suite has floor-to-ceiling ocean views. Drive the Pacific Coast Highway at golden hour, book a sound bath at Esalen Institute, and dine at Sierra Mar, a restaurant that makes you feel like you’re floating above the sea.

From Seattle: San Juan Isles, WA

Vibe: Coastal charm meets Pacific Northwest serenity
A scenic ferry ride from Seattle takes you to the picturesque San Juan Islands, an idyllic destination for relaxation and exploration. Stay at the luxurious Rosario Resort & Spa on Orcas Island, where you can enjoy stunning views and rejuvenating spa treatments. Spend your days kayaking through clear waters, exploring local art galleries, and hiking to the top of Mount Constitution for sweeping island vistas. For a refined dining experience, indulge in the farm-to-table offerings at Duck Soup Restaurant, known for its seasonal menu highlighting fresh, locally sourced ingredients in an intimate, cozy setting. Don’t miss a wine tasting at San Juan Vineyards, where you can sip local wines made from estate-grown grapes while soaking in the peaceful island ambiance.You’ll also want to check out The Orcas Island Distillery for an artisanal spirit tasting to round out your culinary experience.

From Charlotte: Highlands, NC

Vibe: Mountain luxury with a refined touch
Just a three-hour drive from Charlotte, Highlands is a hidden gem in the Blue Ridge Mountains, offering crisp mountain air, lush landscapes, and an elevated escape from city life. Stay at Old Edwards Inn & Spa, a European-inspired retreat where rustic charm meets modern indulgence, complete with a world-class spa and infinity-edge heated pools. Spend the day exploring scenic hiking trails like Whiteside Mountain, then indulge in fine dining at Madison’s, the inn’s farm-to-table restaurant featuring locally sourced ingredients and an impeccable wine list. For a nightcap, visit The Ruffed Grouse Tavern, an intimate lounge with handcrafted cocktails and a cozy fireside ambiance.

From Salt Lake City: Sun Valley, ID

Vibe: Rugged elegance and alpine luxury
A five-hour drive from Salt Lake City, Sun Valley offers a secluded yet sophisticated getaway with breathtaking mountain landscapes and an elite après-ski culture. Stay at Sun Valley Lodge, an iconic retreat favored by Hollywood’s elite, where you can unwind at the spa or take in the views from your plush suite. Spend your days hiking or skiing Bald Mountain, followed by a meal at The Roundhouse, a stunning mid-mountain restaurant accessible only by gondola, offering upscale comfort food with panoramic views. End your evening at The Duchin Lounge, a stylish cocktail bar with live jazz, expertly crafted drinks, and an old-Hollywood feel.


Sometimes, the most rejuvenating journeys don’t require a passport—just a willingness to slow down and savor the beauty of the present moment. Whether it’s a scenic drive along the rugged coastline of Big Sur or a moonlit swim in the warm waters of Islamorada, these destinations invite you to embrace the art of mindful travel. So take a deep breath, let go of the need to rush, and remember: luxury is not just about where you go, but how you feel when you get there.