3 components to a perfect vacation with friends

It’s our 20th anniversary! 

In 2004, I took a deputy business editor job at the Milwaukee Journal Sentinel. Somehow, I managed to meet, across departments and cubicles, the then-art director, Lonnie. On paper, we didn’t have much in common. In real life, we were instant besties. 

yoga class
Photo courtesy Rock Springs Retreat Center

Across the years and, now, across the miles (866, to be exact), we’ve supported each other through caring for our parents, career changes, health challenges, and through the aisles of the Bloomingdale’s on Chicago’s Magnificent Mile. Thanks to Lonnie, I now own several cashmere sweaters that I wouldn’t have treated myself to otherwise. 

We usually rendezvous at the Sheraton hotel that overlooks the Chicago River, settle into deep sofas with big cups of mocha, and define our current understandings of the meaning of life while the mist rises over the river, softening the glass-and-chrome skyline. 

If a girlfriend is involved, a getaway is close behind. I’d like to claim that I have conclusive expertise in this travel specialty, but I admit that my research is open-ended. There’s always another girlfriend’s getaway on the calendar, with Lonnie or my cousins or even an adult daughter, occasionally. 

Still, I’ve been around enough spas and tearooms to have a pretty good idea of what constitutes a great getaway with enough girlfriends to fill a short bus. 

The essential components are convenience, comfort and a confluence of interests. 

Convenience starts with choosing a venue that is equitably accessible for everyone so that meeting is the least adventuresome part of the trip. And once you are there, you want to be sure that the venue is easy for each member of the group to navigate. Resorts and city destinations work well for groups that encompass a spectrum of abilities. While some people want to walk everywhere, others want the option to grab a cab if they need to zip ahead to the next point of interest or break away back to the hotel. 

In winter, San Antonio is the perfect destination for a geographically scattered group. Choose a hotel that’s right on the famed River Walk, a shady loop around the city two stories below street level. There, you can pace yourselves through the seemingly endless choices of restaurants and shops that line the cool walkway. 

Recently, I spent nearly a week in San Antonio (my “girlfriends” for this trip were my daughter and her three daughters, ages 9, 8 and 3). The Westin Riverwalk afforded a leisurely breakfast at water level as the sun sent pastel rays through the trees that arch the river. When we walked straight out onto the San Antonio River Walk from the hotel’s lower level, a left turn led to the Briscoe Western Art Museum and a right turn led to the landing where we could board one of the flat riverboats that circle the river. 

Like Chicago in summer, San Antonio in spring offers the perfect combination of convenience and the second essential component: comfort. 

A deeply welcoming “home base” can serve as a center of gravity to anchor a successful girlfriends getaway. It could be a rented house or apartment, a hotel with alcoves for lengthy conversations or a resort that supports a mix of shared and private rooms. 

Beech Hill Farm
Beech Hill Farm. Photo courtesy Concord Chamber.

Small Towns, Big Fun 

Small towns in New England often mix charm with convenience and comfort, perfectly scaled for a weekend get-together. Great Barrington, Massachusetts, in the Berkshires; Concord, New Hampshire; and Rockport, Maine, each offer browse-worthy downtowns and restaurants that invite the depth of conversation that longtime friends crave. And with bed-and-breakfast inns adjacent to their historic downtowns, you can spend time talking and walking, not driving and striving. 

Sit under the patio lights on the front lawn of the Prairie Whale in Great Barrington and work your way through its samplers of local wines. From the restored Victorian Centennial Hotel in Concord, it’s a short walk to the Granite State Candy Shoppe, where you can fuel your exploration of nearby Main Street with maple sugar. In this capital city’s eclectic downtown, you’ll find one of the galleries of the League of New Hampshire Craftsmen with hand-thrown pottery, photography and more. 

Rockport, Maine, has a full spectrum of comfort, ranging from cozy bed-and-breakfasts to the oceanfront Samoset Resort, where you can center your getaway around your own cabin with views of the water from sunrise to sunset (and a kitchen for late-night popcorn). The Farnsworth Museum anchors downtown and merits a half day to explore its historic grounds and extensive collection of American art. 

group of friends kayaking
Photo courtesy St. Augustine, Ponte Vedra & The Beaches Visitors and Convention Bureau

Making Memories

And that brings us to the last essential component of a girlfriends getaway: confluence. The best itineraries have something for everyone and a chance to explore together. 

Destinations that offer an array of culture, history, soft adventure and affordable luxury hit all the right notes, says Barbara Golden, communications manager for the St. Augustine, Ponte Vedra and The Beaches Visitors and Convention Bureau in Florida. 

St. Augustine’s hip take on history positions girlfriends groups with the full spectrum of activities and relaxation. Conquistador-era fort? Check. Salt spa that pulls out the toxins lurking in your pores? Check. Guided moonlight kayak paddle through waters famously glowing with bioluminescence? Check. Early morning strolls along quiet streets lined with pastel cottages under Seussian palms? Check. Historic shopping plaza dotted with dining patios and shops that sell pottery and every type of hat you could imagine? Check, check and check. 

Golden, who has organized a girlfriends getaway or two for her pals (an occupational hazard), says that her go-to strategy is dinner as entertainment. Scour tourism websites well in advance for food strolls that link restaurants for each course, from drinks to dessert. Another pro tip: Split the bill for accommodations in advance and decide together how you’ll pay for meals and services so you don’t harsh your mellow with accounting at the table. 

The perfect getaway combines activities you all love with activities that are new to all of you. Shared new experiences build shared memories, and that’s what you’ll draw on when you are apart. 

“The most important thing about a retreat with a group of people is how do you slow down time?” asks Kris Intress, who founded the Rock Springs Retreat Center in northern Tennessee, which structures women’s retreats throughout the year. “It’s a little like going back to camp when we were kids. We had these experiences of doing karaoke when nobody cared, and how do you create those intense moments that everyone remembers?”

Top photo courtesy Visit San Antonio

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