5 Romantic Road Trips in Cities Across America

Reconnect during lovely escapes to blissful hideaways, such as historic Savannah, Georgia and outdoorsy Whitefish, Montana.

Smiling African-American couple drinking wine and enjoying a meal in a café

by NEA Member Benefits


Devoting your life to education has definite rewards but there are significant challenges, too. It can be a constant struggle to balance the classroom with your home life. If you’re like most educators, you feel as if you’re being tugged in a million different directions and everyone wants your complete attention. Walking that tightrope can make anyone feel stressed out and tired.

With all of that responsibility resting squarely on your shoulders, it’s important to schedule some downtime so you can reconnect with the one you love. It’s important to put the two of you first, and one way is to take a vacation, no matter how short, and get away from it all. Here are five romantic road trips that can help you unwind.

1. Romance flavored with history and art in Savannah, Georgia

Live oak trees dripping with moss, gurgling fountains, purple wisteria draping over a front porch—even the setting in Savannah is romantic. After a leisurely breakfast at Roussell’s Garden bed and breakfast, take a carriage ride through the Historic District or a Footprints of Savannah walking tour that traces black history in the city. Then, get in line for a fried chicken lunch at Paula Dean’s restaurant, The Lady & Sons.

Do you share a love of art and literature? Appreciate the 4,000 works of art in the Telfair Museums. Later, indulge in a romantic dinner at The Olde Pink House. Or, explore Bonaventure Cemetery made famous by John Berendt’s book Midnight in the Garden of Good and Evil, followed by a visit to the childhood home of writer Flannery O’Connor.

Nearby Tybee Island provides a change of pace, if you’d rather spend more time dipping your toes into the sand. Make Tybee Island Inn your romantic headquarters.

Plan your trip: Visit Savannah | Explore Georgia

Driving distances: 2 hours from Jacksonville, Florida and Charleston, South Carolina | 3 hours 30 minutes from Atlanta, Georgia | 4 hours from Orlando, Florida and Charlotte, North Carolina | 5 hours 30 minutes from Montgomery, Alabama

2. Get away to a Northern Rockies wonderland in Whitefish, Montana

 If outdoor fun inspires romance, this Northern Rocky Mountain town delivers in spades. On a trip to Whitefish, enjoy winter activities such as skiing and snowshoeing, or visit in summer to explore Glacier National Park, only 30 minutes away. With easy access to hiking and biking trails, outdoor lovers will find something to do year-round. Want to make your arrival special? Take Amtrak’s Empire Builder from Seattle or from Chicago/Minneapolis.

With a charming downtown shopping area, staying at the value-priced Firebrand Hotel makes sense. Do you share a love of golf? Grouse Mountain Lodge is your place to stay. For lunch, enjoy the made-from-scratch menu at Loula’s Café.

Plan your trip: Explore Whitefish | Visit Montana

Driving distances: 2 hours 30 minutes from Missoula, Montana | 4 hours from Coeur d’Alene, Idaho | 4 hours 30 minutes from Spokane, Washington | 5 hours from Bozeman, Montana

3. Wine and cherries flavor the romance in Traverse City, Michigan

Photo courtesy of Traverse City Tourism

 Wineries, cherries and freshwater beaches inspire the romance in Traverse City. Explore the lighthouses, beaches and trails along Grand Traverse Bay on Lake Michigan. Don’t miss a climb on the dunes at Sleeping Bear Dunes. Or stop to photograph a covered bridge on Pierce Stocking Scenic Drive. Arrive in winter to share a snowshoe walk, downhill or cross-country skiing and a seat by the fire. In the spring and summer, tour a vineyard and enjoy a picnic lunch or dinner.

The Oviatt House bed and breakfast makes a good in-town location. Would you rather sleep in a vineyard? Consider Chateau Chantal, offering sunset jazz concerts in the summer. Or go completely romantic with a night on Sailing Yacht Scout. Tasting cherries is a must, so order the Brie smothered in cherry sauce at Sleder’s Family Tavern.

Plan your trip: Traverse City Tourism | Pure Michigan

Driving distances: 3 hours from Lansing, Michigan | 4 hours from Elkhart, Indiana | 4 hours 30 minutes from Detroit, Michigan | 5 hours 30 minutes from Chicago, Illinois

4. Romantic recreation in Stowe, Vermont

Photo courtesy of Greg Petrics/Stowe Mountain Resort

 You probably recognize Stowe as a winter skiing destination or for prime New England leaf-peeping drives. But there are many ways to bond with your sweetie in Stowe. Go ziplining, mountain biking or snuggle underneath a warm blanket for a sleigh ride. In the summer, sit on the grass of a rolling meadow listening to the music from the Vermont Symphony Orchestra. Settle in for a romantic stay at Fiddler’s Green Inn. Or splurge with a getaway at Stowe Meadows. And, of course, you can’t come to Stowe without dining at the Trapp Family Lodge. Yes, the Trapp Family from The Sound of Music.

Plan your trip: Go Stowe | Vermont Vacation

Driving distances: 30 minutes from Montpelier, Vermont | 3 hours 20 minutes from Boston, Massachusetts and Albany, New York | 4 hours from Portland, Maine

5. California wine country meets the Old West in Paso Robles

Photo courtesy of Juice Media/Travel Paso Robles Alliance

For a more affordable wine getaway, forget Napa and head straight to Paso Robles in Central California. This trip comes with the ambiance of an Old West ranching community. Sip wine at the in-town tasting rooms before venturing to the vineyards. How should you visit? Take your choice of self-drive, bike, van or limo tours. For a behind-the-scenes look at grape growing, take Steinbeck Vineyards’ crash course on a 4-wheel-drive tour. 

You’ll find value luxury accommodations downtown at Paso Robles Inn. Drive over to the coast for a tour of Hearst Castle or spend a morning soaking at River Oaks Hot Springs. For the freshest of meals, Thomas Hill Organics serves up deliciousness picked straight from their farm.

Plan your trip: Travel Paso | Visit California

Driving distances: 2 hours from Santa Barbara, California | 3 hours 30 minutes from Los Angeles, California | 4 hours from Sacramento and San Francisco, California

Get Inspired!

Subscribe to the NEA Travel Newsletter to get tips on where to go on your next vacation and exclusive member deals.

Save on your next road trip