The 5 Best (and Unbelievably Affordable) Places to Travel in May

Home to the state’s Urban Bourbon Trail, baseball, bluegrass, museums and the first event of horse racing’s Triple Crown, Kentucky’s largest city—which sits on the Ohio River—has been called one of the friendliest cities in the country. Pro tip: Spend a perfect weekend day in town by filling up on Southern staples at The Porch before popping into Woodford Reserve’s distillery for a tour and tasting. In early May, the Kentucky Derby is Louisville’s big draw. Need we say more? Extravagant hats, fancy dresses and ice-cold mint juleps are all staples of the Kentucky Derby at the iconic Thoroughbred track Churchill Downs. Now in its 145th year, it’s said to be the greatest two minutes in sports. During the rest of May, when the Derby crowds have cleared out, you can enjoy Louisville’s other famed cocktail, the old-fashioned, on Whiskey Row. Evan Williams Bourbon Experience, Angel’s Envy, Jim Beam Urban Stillhouse and the Peerless are just a few of our favorite distilleries located in this thriving part of downtown.

Where to stay: Celebs like Elizabeth Taylor and past presidents alike have rubbed elbows at the luxurious Brown Hotel, a Louisville historic landmark full of traditional treasures that’s just three miles from Churchill Downs. For a more budget-friendly option, check out the original 21c Museum Hotel, an art lover’s destination in its own right that’s also downtown.

Clearwater is that quintessential fry-on-the-beach vacation you can take advantage of starting in early spring, especially when this barrier island beach town boasts a reported 361 days of sunshine each year. With May temps in Florida hitting the mid-to-sometimes-high 80s, you can get a kick-start on that awesome summer tan even before Memorial Day weekend—or spend your time on the water, where highlighted activities include kayaking, stand-up paddleboarding, or even swimming with horses (!) in neighboring St. Petersburg. If you’re soleil-averse, you can soak up the region’s rich craft beer culture instead of the sun. In fact, there are over 30 breweries that make up the St. Pete/Clearwater Craft Beer Trail, all less than an hour’s drive. 

Where to stay: Looking for a place that’s a quick getaway for you and mom this Mother’s Day? (Hint: If you haven’t bought her a card yet, it’s coming up on May 12.) The posh Wyndham Grand Clearwater Beach has an exclusive experience for mom’s special day with a fashion accessory brand you both love—Kendra Scott. On May 12, the accessories powerhouse is debuting a mobile, one-day-only pop-up of her popular Color Bar to celebrate the big day, meaning you can get mom—and yourself—something special. As an added bonus, the resort also has a Kendra Scott “Jewelry Borrowing Box,” which allows guests to try out some stylish baubles on loan during their stay, regardless of when you visit in May.

It’s impossible to get bored in this gorgeous and impressive walled Provençal town. Once home to the Roman Catholic Church, the historic Palais des Papes—a gothic 14th-century palace where the pope once lived—is still a major draw and the reason this UNESCO World Heritage Site is known as The City of Popes. Here you’ll find lots of tiny cobblestone streets and charming squares overflowing with good eats just a short drive from the lavender fields that the South of France is made of. Well that, and the good, cheap wine pretty much everywhere you go.

Where to stay: This is one place where you’ll want to splurge, and after one look at La Divine Comédie, you’ll be OK eating ramen for a month to make it happen. Set in a private garden in the center of town, just steps from the Popes’ Palace, this urban oasis has stylish interiors to rival its lush outdoors. But the pièce-de-résistance, you ask? The enchanting poolside spa and wellness area that houses a hammam and sauna.

Some of our favorite things to do in the valley include hot air balloon rides, olive oil tastings and exploring a museum dedicated to hand fans—yes, you read that right. But despite all these great activities, we all know and love this California wine region for its juice. When it comes to planning a wine-focused itinerary, you’ll want to sip and play croquet on the courts at Sonoma-Cutrer Vineyards, tour the 140-year-old stone cellars—with a glass in hand—at Simi or just savor the yummy pinot noirs and Chardonnays at the tasting room at La Crema. With relatively low fares into SFO from across the country this month, according to SkyScanner, you can be enjoying wine country in no time. Plus, this month marks the third annual Signature Sonoma Valley, from May 16 to 19, a long weekend full of vino tasting events coupled with exclusive access to vineyards as well as the growers and vintners themselves. Guests who attend each year get access to hard-to-find vintages or wines from the private collections of legendary winemakers and get a behind-the-scenes look at the winemaking process. This year’s agenda promises to keep the wine flowing at a Large Format Bottle Party, at which you can you to chow down on refined food and pairings from six distinct appellations at “Icon: A Grand Terroir Tasting,” or enjoy as much Sunday bubbly and bacon as you can at “Bubbles + Brunch.” With events priced at as little as $65, you’re probably already pushing checkout on your ticket in another browser tab. The best part? It all takes place in one of the country’s—and world’s—most beautiful and dynamic wine regions, Sonoma Valley.  

Where to stay: Located on a 50-plus-acre ranch, this tiny house-style cottage is a Sonoma steal, priced at $150/night on HomeAway. Meanwhile, if you’re looking to splurge, the Fairmont Sonoma Mission Inn & Spa offers posh digs, a Michelin-starred restaurant, one of the Sonoma’s finest spas.

This small New Hampshire town might seem like the most quiet and slow-paced destination on this list, because it totally is. Lebanon—on the banks of the Mascoma River in the Upper Valley—is insanely New England (in the best possible way) and a great getaway if you just need a little R&R. The scenic region is also perfect for spring vacationers that want to spend some much-appreciated time outdoors. As the temps rise, there’s boating, biking or exploring the local parks. Besides, it’s an easy drive from much of the Northeast and flights are a steal no matter where you’re coming from right now. Did we mention idyllic, 70-degree days that will lure hikers to lace up their boots and hit the trails, too?

Where to stay: The Residence Inn by Marriott Hanover Lebanon has comfortable, contemporary digs with rates right around $160 a night, even on the weekend. Meanwhile, the Trumbull House Bed & Breakfast—a 1919 clapboard house on 16 acres in nearby Hanover—has classic New England charm. We also found some stunning riverfront Airbnbs…if you appreciate that kind of thing.