I love playing travel advisor to my friends and family. And, after doing it for years, I've found that so many women my age aren't just looking for huge trip ideas, they're also looking for quick weekends away, and four-day excursions that don't consume their busy schedules. In fact, according to a study in the Independent, women aged 25 to 49 are responsible for over half the bookings for long-weekend getaways.
Related: 115 Best Destinations for a Quick Weekend Getaway
Charleston, South Carolina
Charleston, South Carolina, USA homes along The Battery.Although it's just forty minutes south, you'd think you stepped into New England with the Sanctuaryat Kiawah. One of my favorite resorts in South Carolina, The Sanctuary lives up to it's name, with sweeping views of the Atlantic, dune grass, gold clubs, large wide porches, and private beach access steps away. Plus, with restaurants, a spa, and shopping, it feels like it's own destination that's still close enough to Charleston for dinner reservations.
Related: The 5 Best River Cruises to Take in Your 40s
Healdsburg, California
It's a true one-stop shop, with everything worth doing sitting on or near the square. For a bite that the local's rave about, stop into Valette, run by a chef who grew up a town over in the building where his grandfather ran the bakery, and order the day boat scallops en croûte or a squid-ink pastry dome cut open tableside.
My biggest pro tip? Don't overschedule your time here. Two tasting rooms in a day is plenty, and the Saturday farmers market covers lunch if you grab a bench on the square. If you're looking for a vibe that feels distinctly local, come in spring. Harvest runs late August into October and it's the prettiest time of year, but rooms book out months ahead.
Related: These U.S. Destinations Feel Like Europe
Santa Fe, New Mexico
View this post on InstagramBishop's Lodge, an Auberge property on a historic ranch outside town, has horses and a spa built into the hills, while Rosewood Inn of the Anasazi puts you a block off the main Plaza with a fireplace in every room. The better value is a casita on the Historic Eastside with adobe walls, a private courtyard, and a kiva fireplace, which is exactly what you're picturing when you think of Sante Fe, and usually costs less than the hotels.
Related: The Fall Getaway That's Perfect for Your Personality Type
Mackinac Island, Michigan
The Inn at Stonecliffe and Hotel Iroquois are where I'd stay, and they're opposite trips. Stonecliffe is a $40 million rebuild of a 1904 estate on a wooded bluff, a twenty-minute carriage ride from the docks, so far past where the day-trippers reach, with pools and a wellness center right on property. Also right next door is the Woods Restaurant, which is decked out like a Medevial dining room, and was once the playground for the rich families at Stonecliff, with a bowling alley, bar, and dart boards. For a stay closer to town, go to Hotel Iroquois, which has forty-five waterfront rooms, and has been run by two families since 1904. The Carriage House downstairs is one of the best restaurants on the island, famous for whitefish broiled on the same pans the family's grandfather found in the '50s. Then walk down to the Pink Pony, the harborfront bar where crews have been celebrating the finish of the Chicago-to-Mackinac race since 1948. Get the Rum Runner on the patio, which is their own recipe of rums and fruit juice, served frozen (don't forget the floater).
For breathtaking views of the lake, walk thirty minutes uphill to Arch Rock, a limestone span over open Lake Huron. For the best sunset views, head to Windermere Point at the west end of Main Street. And while you're on Main Street, get fudge! Murdicks has been around for decades, and makes some of the best on the island (their peanut butter is what dreams are made of). More than a million people visit a year, most in a five-month window, so July and August belong to the day-trippers. September and early October are when I recommend people go, just know most of the island closes by the end of the month.
Chicago, Illinois
Chicago Cityscape from Chicago River Waterfront at Dusk. Small boats and tourist ferries cruising on the Chicago River towards the Michigan Lake. Chicago, Illinois, USA.The Pendry is in the old Carbide & Carbon Building, the green-and-gold Art Deco tower you'll notice from the river, and the lobby alone offers plenty of photo moments for the grid. My favorite hotel is the Langham, right on the river, because the service is the best in the city—it's held five stars for over a decade. Plus, the spa was Chicago's first to get five stars, and the architecture boat tour leaves from practically the front door. If you'd rather not spend on the room, rent a greystone in Lincoln Park or Old Town. Both are idyllic neighborhoods with ample access to the park, restaurants, Second City, shopping, and more. You can pick up a Divvy e-bike from anywhere, and ride through both neighborhoods at your leisure.
Sushi-san is a local fave, and the tuna crispy rice is what everyone orders. Aba has the prettiest rooftop in the city, and the food is just as good (don't forget the short rib hummus). Boka's had a Michelin star for years without any of the typical pretension. And if you're celebrating a milestone, book Smyth: three Michelin stars, and World's 50 Best just named it the best restaurant in North America. And trust us on this: one dinner should be a steakhouse, because nobody does them like Chicago, so try Maple & Ash for a trendy vibe or RMP Steak for the real deal. Just don't come in January or February.
Austin, Texas
View this post on InstagramEat at La Piscina, the Mexican spot on the Proper's pool deck, where a ceviche and a frozen margarita overlooking downtown set the immediate Austin vibe. Then go east to Bufalina for handmade pasta and the best natural wine list in the city, or Patrizi's, a Cherrywood institution for handmade pasta, where you order the Great Leopold or the family-recipe red sauce that's been passed down for generations. Don't overthink breakfast tacos, either. Find a trailer, order migas, and eat them standing up. or a real spa day, the Four Seasons takes outside bookings, and afterward you can take a lounge chair by the water and order a bourbon lemonade.
For fun, engage your inner 20-something and rent a paddleboard on Lady Bird Lake in the morning before the heat lands and drunkies come out. See live music at night without researching it first, because whoever's playing at whichever small club you walk into will be good—that was true a decade ago and I'd bet money it still is. Skip July and August because the heat is HOT.
Related: Inside the Detroit Michelin-Key Hotel That Brings the City’s Best Boutique to Your Door
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