12 Perfect Getaway Ideas for Friends

When everyone is grown up and has his/her own lives, it’s important to set aside time to reconnect—so why not travel together?

It’s special when a group of friends can find the time to get away for a while and do fun things together. When everyone is grown up and has his/her own lives, it’s important to set aside time to reconnect—so why not travel together?

Yes, together. Traveling to a major city with a group of friends has never been easier. Oakwood Worldwide has fully-furnished apartments that offer guests the opportunity for everyone to get together in a comfortable environment. A spacious living room is great for hanging out, while the kitchens are perfect for storing snacks, cooking a meal—or several meals—together, in addition to stocking the necessities for early evening drinks or nightcaps.

If you’re in need for great group travel ideas, here are some themed suggestions in some of the country’s biggest cities.

Picnic basket with unlabelled bottle of wine leaned against in, a red-checkered cloth napkin and two full wine glasses
Enjoy a group picnic with some bottles of wine you picked up on your wine tour. (©iStock)

Wine or Beer Lovers Getaways

There are over 400 wineries in Napa Valley, California and to even tour just a handful of them, you’ll need a to set aside at least a few days to sample their fermented offerings. Indulge in great wine, decadent meals and more just an hour outside of San Francisco!

Long Island Wine Country has distinct flavors of merlot—the region’s most popular red grape—and a wealth of wines for being a relatively young hub for viniculture. Hop the Long Island Rail Road from Penn Station in Manhattan for leisurely ride to the North Fork Wineries for easy access to wine tours.

The craft beer scene is thriving in Chicago, so much so that they have an annual Chicago Craft Beer Week in May. Participating bars, restaurants, pubs and craft beer-sellers offer celebration-specific pricing for rare beers and special events.

North Texas is also a hot spot for unique brews. The Dallas Brew Scene is aiming to make people more aware of the regional craft beers and list a bunch of different events going on in the area, as well as conduct tours on their Dallas Brew Bus.

Nteliseng Skhela as Rafiki in "The Lion King" on Broadway
Nteliseng Skhela as Rafiki in "The Lion King" on Broadway (©Joan Marcus)

Creative Culture

Pop culture lovers rejoice when it’s time for the Chicago Comic and Entertainment Expo, C2E2, held annually in April. This convention unites fans with stars of television, film and comics through panels, autograph sessions, in addition to hundreds of exhibitors and artists. Toys, video games, comics, exclusive content, special screenings and more await those with tickets to this weekend of wonderment.

Los Angeles is the West Coast’s epicenter for film and the city has festivals year-round showcasing independent movies, short films, forgotten gems of the past and foreign films, among dozens of other themes. The Los Angeles Film Festival screens over 100 feature films, offers panels and screens short films made by high school students each June. A qualifying festival for various prestigious awards ceremonies, you could be among the first to see the next big thing in cinema.

Out-of-town theater lovers can cross a bunch of shows off their lists when in town for multiple days. With most Broadway and Off-Broadway productions running eight performances a week—with matinees usually on Wednesday, Saturday or Sunday—it’s possible to see approximately 10 different shows in just one week. There are 2-for-1 ticket offers during the designated Broadway Week and Off-Broadway Week throughout the year, when you can snag great seats for half the cost.

Celebrate the Fourth of July in the nation’s capital! In addition to taking a few days to scope out the Smithsonian, National Archives and other great museums in the city, there are so many patriotic events to enjoy, such as the National Independence Day Parade and the “A Capitol Fourth” concert that ends with a grand finale of fireworks over the National Mall.

Cowboys on horseback chase a bull in a rodeo ring.
Cowboy hats are optional attire at the rodeo. (Courtesy lifeofpix.com)

Sports and Friendly Competition

For over 100 years, the Pasadena Tournament of Roses has brought us the Rose Parade—marching bands, equestrian units and floats decorated completely using floral elements—and Rose Bowl Game, the oldest college bowl game where a Big Ten Conference team plays a team from the Pac-12 Conference annually in January. This unofficial holiday celebrates community and the best of college football. Lodging in Pasadena can be tough to find close to all the Rose Bowl action, so consider staying in Los Angeles, which is only about 10 miles away.

Since 1896, the Fort Worth Stock Show & Rodeo has been wowing audiences with heart-racing rodeos—including bull riding—and livestock exhibitions showcasing horses, poultry, cows and more during January and February. There’s a livestock auction, an art show competition for youths (to win awards, college scholarships or cash prizes), as well as huge parade.

Marathon lovers who enjoy running for a great cause can sign up for the Big Sur International Marathon. With six hours to finish the scenic jaunt from Big Sur to Carmel, this marathon is an official Boston Marathon qualifier and certified by USA Track & Field. There are additional running events surrounding the marathon including a 5K, 10.6-miler and more.

While the Marine Corps Marathon, or MCM, takes place in October—where participants pass some of the most iconic monuments in D.C.—MCM hosts a generous handful of runs throughout the year of varying distances and challenges including its Turkey Trot, Run Amuck, Quantico Tri and others. Teams of three to five runners can compete in the Marine Corps Marathon. Members must register individually before a team entry form can be filled out. There are a number of 5Ks in the D.C. area hosted by other entities including the NOVA Jingle Bell Jog, March for Marrow DC 5K Run & Walk and more.


Spacious living room at Oakwood at the Nash in NYC (Courtesy Oakwood Worldwide)
Spacious living room at Oakwood at the Nash in NYC (Courtesy Oakwood Worldwide)
Make plans with your friends to take time for yourselves this year. By staying at an Oakwood Worldwide property for extended stay trips—three-nights, seven-nights or even longer—in locations like Chicago, Dallas, Los Angeles, San Francisco, New York City and Washington, D.C., you’ll have a reliable, comfortable home base to come back to each night after fun-filled days of adventures and memory-making.