Best September Anniversary Travel Ideas

Portland, Maine

Kenneth C. Zirkel /Getty Images

Whether it's your fifth wedding anniversary, your 20th, or the anniversary of your first date, traveling together is a great way to celebrate it. And September is the best time of year to hit the road: Kids are back in school, weather is not as hot as in the summer, attractions aren't as crowded, rates are down from summer highs, and the crispness of fall can be felt in the air.

01 of 09

Make Your Way to Maine

Portland Head Light at dusk
 Enzo Figueres/Getty Images 

Winter comes early to Maine, so if you chill easily, visit in September. Foodie couples will want to check out Portland, recently named Restaurant City of the Year by Bon Appétit.

Fresh lobsters drawn from Casco Bay, wild blueberries, and cheese are among the best-known local Maine foods. Whether dining along the waterfront or cocooning in one of Portland's most romantic hotels, you're in for a memorable anniversary visit. 

In addition to the city's many restaurants, shoppers will find unique stores offering jewelry, pottery, and clothing in downtown Portland.

Outdoors lovers have plenty of choices, too. Great Pond is a 125-acre freshwater pond with a boardwalk that many couples like for an Instagram shot. In Robinson Woods, you can bike and hike on trails. Audubon runs guided kayak and canoe trips in Scarborough Marsh. Or take a sunset walk to see the Portland Head Light. 

Couples starry-eyed with love should make their way to Bar Harbor for the annual Acadia Night Sky Festival, which takes place right after Labor Day.

02 of 09

Spend September in San Juan

Wall at Castillo San Felipe del Morro, a 16th-century Spanish fort in San Juan, Puerto Rico.
 Joel Carillet/Getty.

San Juan has bounced back from devastating Hurricane Maria in 2017, and the Caribbean city's appealing culture, hotels, restaurants, casinos, golf courses, and spas lure lovers.

This destination's soft sand beaches will entice you to frolic in the warm turquoise waters or settle into a lounge chair with an icy piña colada.

Still, you'll want to explore the streets of Old San Juan and visit windswept El Morro fort overlooking San Juan Bay; for centuries it served as the harbor sentry. Across the bay, the Bacardi Rum Distillery welcomes visitors to tour its facilities and sample premium rums.

Head to bioluminescent bay at the southern end of Puerto Rico, rent a kayak for two, and watch the waters light up with glow-in-the-dark critters.

03 of 09

Book a Trip to Prague

High above the city, Prague Castle looms.

Cooler weather and sparser crowds make Europe the best bet for a September anniversary trip. 

Visit the highest point in the city where Prague Castle maintains its medieval flair. The city’s number-one tourist attraction, it's reachable by tram, funicular, and foot.

You'll also want to stroll the Charles Bridge, which crosses the Vltava river to the historic Mala Strana district on the west bank. River traffic, historic statues, and sellers along the way all vie for attention.

Take the train to the countryside and check into Chateau Mcely, a restored hunting lodge of the gentry. For a special treat, dine privately in the Gold Room. Its long oval table is dressed with candles, crystal, and fine china, and a dedicated waiter serves you alone.

04 of 09

Choose Buenos Aires

High Angle View Of Cityscape Against Sky
 Alan Brutenic / EyeEm/Getty Images 

Known as the Paris of South America, cosmopolitan Buenos Aires attracts lovers in search of beauty, elegant architecture, great food, nightlife, and the sensual tango, all at affordable prices. 

You'll want to wander Recoleta Cemetery, where Eva Peron and other Argentine luminaries repose. The massive necropolis is distinguished by elaborate marble and granite mausoleums, religious sculptures, and paths to wander.

Nights in Buenos Aires will make you feel truly alive. After dinner in the Palermo Viejo neighborhood, walk hand-in-hand on quiet cobblestone side streets under 100-year-old oak trees.

Then make your way to a milonga, where locals dance the tango. If you can't manage the footwork, admire it from a 1940's style club table.

Consider combining your Buenos Aires stay with one in Mendoza's wine country. Known for producing big, mellow Malbec wines, Mendoza offers visitors a range of touring and tasting opportunities at its 800-plus wineries.

Continue to 5 of 9 below.
05 of 09

Catch a State Fair

new york state fair day
New York State Fair

If you are one of those couples who said your vows around Labor Day, you're in luck. Many state fairs run through the September holiday, and others (in Massachusetts, Virginia, Tennessee, Kansas, New Mexico, Utah, Oklahoma, and Texas) take place later in the month. Not only are state fairs fun, but they're also very affordable. Come for the stuff-on-a-stick, stay for the rides and evening entertainment.

Instead of wasting a fortune trying to win a giant stuffed animal at a midway game, devote the cash to booking a better hotel room, and splurge on a bottle of champagne to toast the years.

06 of 09

Attend Oktoberfest in Munich, Germany

Oktoberfest celebration, Munich
 Michelangelo Gratton/Getty Images

Beer and festivity await in Munich, home to the world's best-known suds festival, which traditionally begins the third week in September and extends into the beginning of October. Admission is free to the festival as well as to the dozens of beer tents. Just be aware that each is a bit different and draws a different crowd (and there will be crowds). 

Oktoberfest accommodations book up early (sometimes a year in advance), so make hotel reservations soon.

07 of 09

Plan a Gourmet Getaway

charlotte inn marthas vineyard
Susan Breslow Sardone.

Inns and hotels that belong to the Relais & Chateaux group represent the highest standards of hospitality. Each one of the properties, which are located all over the world, is unique and charming in its own way. 

In addition to top-notch service and beautiful decor, guests can expect meals that are exceptional in both taste and presentation. It's no wonder that many couples choose a Relais & Chateaux to celebrate an anniversary or another special occasion.

Let the inn know in advance that you're coming for your anniversary and book a dinner on site. Then leave it to the kitchen to prepare customized delights and surprises.

08 of 09

Honor Your Anniversary in Asheville

Blue Ridge Parkway.
 Fine Art Images by Rob Travis Photography/Getty Images

At the southern end of the Blue Ridge Parkway, Asheville celebrates creativity from traditional Appalachian culture—bluegrass music and mountain crafts—to avant-garde art and performance.

A favorable climate and range of elevations also mean that there’s always something in bloom, and it feels good to be outdoors in September.

Acres of groomed hiking and biking trails, cultivated gardens, and exquisite bonsais await visitors to 434-acre North Carolina Arboretum, laid out by Frederick Law Olmstead.

No trip to Asheville is complete without a tour of Biltmore Estate. A National Historic Landmark, it is America’s largest home. Opened in 1895 by a Vanderbilt scion, the French Renaissance-style mansion contains 250 preserved period rooms and is surrounded by gardens. 

On the first Friday in September (and every first Friday from April through December), stroll the galleries and museums in the Downtown Asheville Art District when they remain open till 8 p.m. 

Continue to 9 of 9 below.
09 of 09

Treat Yourselves to a Tahiti Trip

Floating bungalows in Tahiti

TripSavvy / Lauren Breedlove

If you didn't have the honeymoon of your dreams, perhaps you can correct that with an anniversary trip to dreamy Tahiti this September. Its warm waters are dotted with romantic overwater bungalows

Or instead of limiting yourselves to one resort or island-hopping by plane, sail through French Polynesia on a Paul Gauguin cruise that calls at Moorea, Bora Bora, and other exotic ports in addition to Tahiti. And bring home some black pearls as a precious souvenir.