There's nothing like taking a trip together to create a bond between a mom and her adult daughter. But a stellar multigenerational women's getaway needs a few key ingredients: a beautiful destination, an itinerary that includes a good mix of activities, including relaxation — and, in my opinion, spending a little time apart each day.
Greenville, South Carolina
A friendly town in hilly upstate South Carolina, Greenville offers a supremely walkable downtown with browsable shops and an urban oasis at Falls Park on the Reedy River, where a 345-foot-long suspension bridge hung by a single cable and a big grassy lawn beckon. Get fixings for a picnic at Caviar & Bananas, a gourmet market and sandwich shop with delectable main courses and desserts. Consider a fascinating historical or culinary walking tour through downtown with Greenville History Tours, led by historian John Nolan (or take his driving tour, in a comfy van). You can also stroll around Greenville on your own to enjoy the public art — nearly 100 works that include Dale Chihuly's Rose Crystal Tower — and learn to pour your own soy candle under the tutelage of a master at Magnolia Candle. Then wind down with wine and flatbreads at Foxcroft Wine Bar. Search flights into Atlanta or Charlotte, North Carolina, as well as Greenville-Spartanburg International Airport for the best airfares.
Where to stay: The new Springhill Suites Greenville Downtown has an indoor-outdoor pool and room rates ranging from around $125 to $175, depending on the time of year. Swamp Rabbit Inn is a modern six-bedroom bed-and-breakfast that sits right along Greenville's best cycling trail, with bikes available for rent; rates are $135-$200 a night.
Winter Park, Florida
Towns that you let you park your car on arrival and forget about it the rest of your trip are my favorites. And the upscale town of Winter Park — just north of downtown Orlando — is precisely that kind of place. Start by getting the lay of the lakes. You're surrounded by the natural Winter Park chain of lakes fringed with stately homes. Pontoon cruises with Scenic Boat Tours take your through shaded canals and within a few yards of the gracious lawns of mansions, with gorgeous views at every turn. Park Avenue, full of adorable cafes (like the breakfast staple, Briarpatch) and stylish boutiques is a pleasant place to wander. Also on Park Avenue, the Charles Hosmer Morse Museum of American Art is home to the largest collection of glassworks by Louis Comfort Tiffany, who wintered in the area ($6 for adults, $5 for adults 60 and up; closed Mondays). Every Saturday morning, a wonderful farmers market spills out from Winter Park's historic train depot, where you can catch the SunRail commuter train to downtown Orlando for more exploring.
Where to stay: Depending on the size of your budget, you can situate yourself within walking distance to everything at the lovely Alfond Inn, on the campus of Rollins College and home to an exquisite collection of art. Rooms generally run between $200 and $300 a night. Or consider one of the many chain hotels in and around Orlando.