15 Weekend Getaways to Take This Summer

From Memorial Day to Labor Day, you have 15 weekends (count 'em) to make the most of your summer. Check out our getaway picks — then start packing!

Related To:

Photo By: Thinkstock

Photo By: Moment / Getty Images

Photo By: Getty Images

Photo By: Thinkstock

Photo By: Sandra Hintzman, flickr

Photo By: Brain Gratwicke, flickr

Photo By: Meinzahn

Photo By: E+ / Getty Images

Photo By: Panoramic Images / Getty Images

Photo By: Aurora / Getty Images

Photo By: Lonely Planet Images / Getty Images

Photo By: Lonely Planet Images / Getty Images

Photo By: Getty Images News / Getty Images)

Photo By: Thinkstock

Photo By: Panu Tangchalermku, flickr

Asheville, North Carolina

Take a scenic drive through the Blue Ridge Parkway and see why Asheville attracts creative types and vacationers alike. This eclectic town has a burgeoning River Arts District, boasts some of the nation's best craft breweries and is home to the iconic Biltmore estate, "American's very own Versailles." Start off with breakfast at the popular, farm-to-table Early Girl Eatery, which dishes up Southern comfort food with a side of retro charm. Next meander through galleries in the River Arts District before stopping at Wedge Brewery for a draft, a game of cornhole and a bite from one of the food trucks posted up outside. In the evening, enjoy live music at local haunt 5 Walnut Wine Bar or curl up with a book at the dog-friendly Battery Park Book Exchange and Champagne bar.

Cannon Beach, Oregon

Cannon Beach is best known for its majestic monoliths like Haystack Rock (an ideal beach selfie spot). However, its miles of serene beaches and a charming (yet refined) art scene make it one of the best resorts on the famed Oregon coast. Surf shops, galleries and wine bars line Hemlock Street. We suggest stopping by the Wine Bar at Sweet Basil's Cafe for bacon-wrapped dates, Willamette Valley wine selections and live music.

Finger Lakes, New York

Skip the Hamptons-bound jitney. Instead road trip to this scenic Finger Lakes region of upstate New York. Popular for its wineries (nearly 100 in all) and New England scenery (think: rolling hills, deep-blue vistas dotted by Amish farmland and charming small towns) -- life slows down as you follow paved two-lane blacktops along the slender lakes' shores. Follow the popular Cayuga Lake Wine Trail near Seneca Falls, where a host of 15 wineries (and four distilleries), scenic waterfalls and gourmet restaurants beckon you to stop. We like Maxie's Supper Club & Oyster Bar, a Cajun seafood restaurant and raw bar. Stop in before 6 p.m. to beat the crowds and be treated to half-priced raw oysters or start your meal off with their signature cornbread and honey butter and Southern-style fried green tomatoes.

Florida Keys

Why spend the weekend on one Florida beach, when you can island hop through the Florida Keys -- preferably in a convertible -- on scenic Highway 1 through Key Largo, Islamorada, Marathon and, last but not least, Key West. Each mile marker seems to bring a new slew of kitschy gift shops, snorkeling spots, and roadside fish shacks, but we recommend stopping for conch fritters at roadside seafood joint, Alabama Jacks on Key Largo, checking into Casa Morada on Islamorada (the half-way point between Miami and Key West) and touring the Ernest Hemingway Home on Key West.


Forgo the crowds at Barton Springs and instead cool off at Hamilton Pool Preserve, a lesser-known oasis. Approximately 23 miles west of Austin, this historic swimming hole was formed when an underground river collapsed. Hamilton Creek spills out over limestone cliffs to create a 50-foot waterfall. It's an approximately 10-minute "hike" from the parking lot to the pool so wear sensible shoes and leave the rolling cooler at home or you'll be cursing the stairs and uneven ground. If you're visiting Austin as well, Franklin Barbecue is worth the wait (we promise) and the landmark Allen's Boots has more than 4,000 pairs to chose from (along with hats, clothing and other accessories).

St. Michaels, Maryland

To enjoy a quiet weekend on the water, head to Maryland's Eastern Shore. Wander through the charming, historic town of St. Michaels (which dates back to Colonial times) popping into boutiques, stopping for a scoop at Justine's Ice Cream Parlour or capping off the day at Carpenter Street Saloon. The real attraction here is the water: spend the day sailing, jet skiing, kayaking or even crabbing. We suggest checking into the Inn at Perry Cabin -- yes, the one from "Wedding Crashers" -- or at least stopping by the premises for an aperitif and to see the sunset over the water from an Adirondack chair.

Washington, D.C.

The most obvious choice for a full-blown Fourth of July celebration? D.C.'s "A Capitol Fourth" concert doesn't disappoint with the National Symphony Orchestra providing the soundtrack for a spectacular fireworks display. Locals know it's not the only thing to see at night: Skip the crowds (and sweltering humidity) by taking an evening walking tour of the National Mall -- the brightly lit monuments and memorials are just as beautiful after dark.

Jersey Shore, New Jersey

The Jersey Shore, stretching from Sandy Hook to Cape May, has undergone major recovery efforts since Superstorm Sandy. The shore welcomes visitors looking for an All-American summer vacation filled with beaches, lighthouses, ice cream shops, amusement rides, mini golf, fishing and more. While there is still work to be done, downtown Asbury Park has been revitalized, as have most of the region's tourist-heavy destinations. Spend a day in the kitschy town of Wildwood, home to the widest beach in the state and a boardwalk that lives up to its namesake, or stay in nearby Cape May, known for its Victorian houses, historic lighthouse and gourmet restaurants. 

Kiawah Island, South Carolina

Just 21 miles south of Charleston, Kiawah Island is a coastal island and world-class golf resort. While beautiful Beachwalker Park is open to the public (and provides lifeguards, picnic areas and parking), we recommend staying at the 5-star Sanctuary Hotel or renting one of the homes or villas to access the slew of amenities the resort has to offer (including its top-ranked spa). Play a round of golf at Ocean Course (one of five award-winning golf courses on the island), enjoy tennis on clay or hard courts, canoe through marsh-lined creeks or simply spend a day at the beach enjoying more than 10 miles of pristine shoreline.

Pacific Coast Highway, California

Hop in a car, better yet make it a convertible, for a weekend road trip along the Pacific Coast Highway. Take a detour on the private 17-Mile Drive, which hugs the craggy coastline from Pacific Grove to Pebble Beach. The drive not only offers views of the picturesque seventh green, but also one of California's best known landmarks, the Lone Cyprus. Back on the PCH, stop a few miles south of Monterey in the artsy town of Carmel-by-the-Sea -- once home to photographer Ansel Adams and writer Sinclair Lewis -- where you can spend the night at the romantic Highlands Inn, a Hyatt resort overlooking the Big Sur coast. Following brunch at Mission Ranch, venture off historic Highway 1 for a luxurious overnight stay at Carmel Valley Ranch. Bliss out at the spa; tee off at the resort's golf course; or wander through fragrant lavender fields next to the vineyard. Don't miss the gorgeous views atop Sunset Point!

San Juan

Though it's not located on the continental U.S., increasing direct flights from the East Coast are making Puerto Rico a viable long-weekend option. Puerto Rico is also becoming a popular year-round destination, but visit before July if you don't want to chance a hurricane. Once you land on the island, check into the luxurious St. Regis Bahia Beach resort for a secluded-island vacation or stay put in the town of San Juan. We recommend strolling Old San Juan's colorful, narrow streets, checking out the live music and nightclub inside the El San Juan Hotel, and mingling with locals over live salsa at Nuyorican Cafe when not basking on the beach.

Rocky Mountain National Park, Colorado

Roughly 80 miles northwest of Denver lies the majestic Rocky Mountain National Park. Families should make Estes Park -- at the east end of the park -- their base camp to experience unbelievable views from the Estes Park Aerial Tramway (which climbs over 1,000 feet in less than five minutes), kid-friendly hikes like the easily-accessible Alberta Falls and after-dinner ghost stories at the infamous Stanely Hotel. Those looking for solitude from the summer crowds -- and who are willing to brave a challenging hike (12.6 miles roundtrip) -- will find solace at nearby Lawn Lake, as well as 13,000-foot granite peaks, catch-and-release trout fishing and wildflowers ringing the western edge of the lake.

Sonoma County, California

Escape up U.S. Highway 101 into Northern California's wine country for a weekend of good food and fine wine in Healdsburg, California (just 70 miles north of San Francisco). Start the weekend off at the Healdsburg Farmers Market where you can pick up Pug's Leap goat cheeses, a variety of bottled olive oils, fresh butter and other produce -- all sustainably grown on farms within 10 miles of the town's Spanish-style plaza. Flying Goat Coffee and food trucks are also on site if you aren't full from the vendors' food samples. With more than 150 wineries dotting the Wine Road (made up of the Dry Creek, Alexander and Russian River Valleys) refrain from ending up "Sideways" by renting a bike from Wine Country Bikes or joining one of their guided tours. Afterwards, dine at Charlie Palmer's Dry Creek Kitchen inside the minimalist Hotel Healdsburg -- a stylish and convenient choice to stay as well.

St. Louis

Ah, baseball. Nothing epitomizes summer leisure more than taking in a game that involves a stretch somewhere into its third hour. Cheer on the St. Louis Cardinals -- beer in hand -- fittingly, at Busch Stadium. Afterwards, check out Three Sixty rooftop bar perched atop the nearby Hilton St. Louis at the Ballpark -- one of the best rooftop bars in the country. You'll get a bird's-eye view of the ballpark, the soaring Gateway Arch and more -- all from 400 feet above downtown. If you haven't filled up on stadium fare, indulge in gourmet bites like mini lobster rolls or have a House Kit Kat Bar for dessert. We suggest making Moonrise Hotel -- a unique, boutique hotel property on the famous Delmar Loop -- your home base for the weekend.


Cap off the summer in Chi-town. Grab a grassy spot and picnic at Jay Pritzker Pavilion in Millennium Park for the annual (free) Chicago Jazz Festival, a favorite among Chicago's many Labor Day weekend festivals. Spend the day strolling along the glistening Lake Michigan shore, taking in the expansive skyline as you round the North Avenue Beach curve. If you have kids, treat them to one last fireworks show at the Navy Pier before school starts.

Shop This Look