The 10 Most Romantic Fall Getaways

Planning a romantic getaway for two this fall? Look no further! Here, we've compiled a comprehensive list of the top 10 destinations in which to enjoy the season's bounty throughout the U.S.

By Dave Singleton

omewhere between the summer's swelter and winter's chill, you get a chance at having fun fall dates that are unlike any you'll experience at other times of the year. So why not make the most of all the things that make dating in the fall a sexy, surprising experience?

I've combed through options across the country to find what I consider to be some of the best romantic fall weekend getaways. From New England-based fall
Your senses will swoon in the heart of the southwest.
foliage expeditions to northern California wine country tours to sunset-filled romantic excursions in the Florida Keys, these 10 places offer a warm, romantic welcome for new couples looking to fall into something more serious than just a hot summer fling!

1. Chicago, IL — the Windy City will sweep you off your feet
Catch the Windy City in autumn, when it's a town of fresh breezes and vibrant outdoor scenes that are perfect for holding hands and strolling with your new amour. Before the icy chill of winter descends, this "toddlin' town" that Frank Sinatra sang about is full of romantic bed-and-breakfasts/hotels, colorful neighborhoods, and fantastic restaurants perfectly suited for couples.

Top romantic spots to check out include the Ferris wheel at the famous Navy Pier, where you can hang out at the Chicago lakefront while enjoying drinks, views of the water… and each other. Some couples swear by the music at Joe's Be-Bop Café & Jazz Emporium. Others head to a different part of town and ascend nearly 100 floors up to visit the Signature Room on the 95th floor of the John Hancock Center. Then, take a romantic, horse-drawn carriage tour (starting at the corner of Michigan and Chestnut streets) of Chicago's best sights. Other romantic spots include the darkly lit Geja's Café for fondue and the atmospheric Il Mulino.

2. Santa Fe, NM — your senses will swoon in the heart of the southwest
When some people think of New Mexico, the images that come to mind include cowboys in Albuquerque and aliens in Roswell, but true romantics that are "in the know" conjure up Santa Fe's alluring spiritual and sensual charms instead. Fall is a great time to enjoy this Land of Enchantment — the crowds that bustled in for opera season in August have departed, the lines at popular restaurants are faster, the weather is perfectly crisp… and in late September, the local foliage starts to turn a brilliant shade of gold.

You and your honey can stroll down Canyon Road to visit the area's myriad art galleries, many of which host wine receptions that are open to all visitors, especially on Friday evenings. Talk about a perfect way to kick off a weekend getaway! The most romantic restaurants in the area include: Restaurant Martin, Geronimo (the fireplaces in every room make the entire place glow!), Café Pasqual's, and the Rosewood Inn of the Anasazi, which offers romantic diners the opportunity to spoon in their lodge for a night or two.

Maybe it's best to think of a fall visit to Santa Fe as more of a romantic and spiritual renewal rather than just a mere getaway. You'll definitely feel that way if you choose to visit Ten Thousand Waves, a unique mountain spa resort nearby that serves as both a day spa (where you can get a couples' massage followed by soaking under the stars in a premium private tub, like Ichiban) as well as being a destination spa, where couples, families and their pets can stay at a charming bungalow-style suite.

3. Middleburg, VA — tour Virginia's scenic country estates and wineries
Nothing says autumn more than foliage tours in Virginia, which is known to have some of the most brilliant changes of season throughout the United States.

Bucolic Middleburg, VA is about an hour west of Washington, D.C., but its small village surroundings nestled in the foothills of the Blue Ridge Mountains — replete with trees, horses, wineries, shops and restaurants — will make urban lovebirds feel like they've flown the big-city coop for a true country escape. In many ways, this area's as close to visiting the fabled English countryside as you and
You can take your sweetie for long walks through the area's parks.
your sweetie can get without actually crossing the ocean!

Couples can enjoy the cozy 18th century fieldstone tavern atmosphere found at the Red Fox Inn and the Goodstone Inn (a historic 265-acre plantation farm converted into a luxury retreat), or enjoy a French bistro dinner for two in a relaxed country setting at The French Hound. Take the opportunity to pass a leisurely afternoon into the early evening together by exploring the local wineries (which are plentiful), where the settings for the tastings are as delicious as the wine itself.

4. Sonoma, CA — toast your new love in Sonoma's famous wine country
Couples who either live nearby or have a yearning for the elegance and fine vintages that are characteristic of northern California's wine country will be drawn to charming Sonoma. Located about 40 miles north of San Francisco, Sonoma boasts many incredibly delicious restaurant options, where you can savor food from some of the top foodie chefs in the country. Or, enjoy being pampered in one of the area's relaxing spas, where you and your new love can indulge in massages and saunas, many of which also provide lodging where you can unwind after days spent exploring amid the scenic countryside — either by car, foot or bicycle. Check out the list of Sonoma wineries here, which include Chateau St. John and the Kendall Jackson Wine Center.

Some of the most notable places to visit nearby include the Fairmont Sonoma Mission Inn & Spa, a classic wine country resort in operation since 1926; Calistoga Ranch, an exclusive, indulgent and romantic hideaway set on 157 acres of vineyard, garden, forest and mountain views, The Harbor House Inn, where redwoods meet the Pacific Ocean; and The Honor Mansion, a Victorian mansion originally built in 1883 that features suites and cottages equipped with private hot tubs and fireplaces.

5. Boston, MA — experience the sporty side of autumn while gazing at the Charles River
Boston in the fall is a city surrounded by sophistication overflowing with indoor activities (such as candlelit meals, museums, and shops) to fill your days, but exploring the city outdoors is at its best during this time of year. You can take your sweetie for long walks through the area's parks, plan picnics beside the Charles River for watching the teams rowing on the water, sit and talk in the gorgeous indoor courtyard of the Isabella Stewart Gardner Museum — and if you're both feeling sporty, watch the New England Patriots kick off football season at Gillette Stadium or see the Red Sox pitch their last few baseballs for the year at Fenway Park in September.

While there are plenty of great romantic hotels in downtown Boston, nearby Cambridge (home to prestigious Harvard University) is actually a great lodging choice for couples to consider. It's lower-key than Boston proper, yet also full of great restaurants and shops. Looking for some of the best places to romance your sweetie? Try booking a table at Bondir, Ten Tables, or Salts Restaurant — all located in Cambridge.

Two places to consider stowing away with your new love for the night include the Hyatt Regency Cambridge, which is situated so close to the Charles River that you can actually sneak down for a sunset make-out session by the water before hitting the hotel's top-floor restaurant, which revolves to offer 360-degree views of the Boston skyline; another great option is the Hotel Marlowe, with its sexy vibe and whimsical decor.

To continue reading and see our picks for the next five romantic getaway spots to visit this fall, click here.

Dave Singleton, an award-winning writer and columnist for since 2003, is the author of two books on dating and relationships. Send your dating questions and comments to him at

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