Regardless of where you are on the map or what fall looks like to you, there’s something undeniably romantic about the season; so take advantage by planning a few fall-friendly trips. Don’t worry about approaching the boss—these easy getaways can be done in the convenience of your 2-day weekend. Let’s see which romantic spots made the list:


Pacific Northwest: Whistler, BC
Take a drive (or a short flight) to the snowy summit of Whistler where you’ll instantly fall in love with its picturesque, snow-capped setting.

It’s a date:
Plan a day on the slopes and then enjoy a quintessential après-ski at the famous Dusty’s bar. A hot toddy and some local live tunes are always on the menu.

Where to stay: Nita Lake Lodge
Perch up on the side of a lake in one of Whistler’s most charming hotels. When it snows, it seriously looks straight out of a holiday movie.


West Coast: Healdsburg, CA
A stone’s throw away from Napa, Healdsburg combines wine country charm with California cool. Take a short flight and drive from any West Coast city, then get ready to load up on vino and locally sourced fare.

It’s a date:
Make a beeline to Bergamot Alley for a night of unique wine tasting, plenty of beer, games and live music. Don’t pass up their famous grilled cheese! If you want a more intimate experience, check out Dry Creek Kitchen for some serious seafood and California-style dishes.

Where to stay: H2
The little sister to the famous Healdsburg Hotel, H2 offers a younger, hipper vibe. Spacious rooms with electric art and a modern pool have your off-time covered.


Mid-West: Hocking Hills, OH
Run for the hills, literally. Ohio’s popular nature getaway falls among the state’s incredible rock formations. Opt for a woodsy outdoor experience or a more luxurious, relaxing itinerary.

It’s a date:
If you crave adventure, visit the Hocking Hills State Park for a scenic winter hike. For indoor date ideas, hole up at the GlenLaurel Spa and enjoy their hot tubs and whirlpools. Also, get your fill at Rhapsody restaurant where culinary students test out inventive dishes while you listen to live tunes.

Where to stay: Glenlaurel Inn and Spa
Check into this Scottish-inspired inn to enjoy staying in cozy, tucked-away cottages in the middle of the woods.


East Coast: Newport, RI
This majestic spot by the sea, normally popular during the summer months, keeps its allure even in the snow. Famous mansions and incredible seafood are just two of this trip’s most popular take-aways.

It’s a date:
Explore the town’s sought-after Armory Antique Marketplace, expansive bird sanctuary or take a tour of the mansions. Afterwards, take a load off at the lobby bar of the The Chanler mansion. Staying in the historic hotel is always an option, but even a seasonal drink provides a proper taste.

Where to stay: Castle Hill Inn
Take a break at the Castle Hill Inn, a seaside oasis with a New England vibe. Enjoy access to a private beach from your individual cottages.


South: The Keys, FL
For the sun-worshippers, there’s still warmth way down south in the Florida Keys. Hop on a jet or a jet ski to get there, so you can start enjoying tropical drinks, exotic tastes and a touch of Cuban culture.

It’s a date:
There’s so much to do in the Keys, but our recommendation is to make the most of what the ocean has to offer. Go snorkeling or deep sea diving and explore historic shipwrecks off the coast. At night, take in the breathtaking sunset at Mallory Square and finish off the day with dinner at Latitudes restaurant for a feet-in-the-sand-while-feasting experience.

Where to stay: Casa Morada
Take shelter in this quaint boutique hotel located along the beach. Enjoy free yoga and water-friendly activities.

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