Long Weekend Trip Ideas
Have a long holiday weekend coming up or just looking to use up some vacation days? Although we would love to spend a month traveling, quick trips can be just as fun if you pick the right place. So head out of work early, beat the traffic, and find yourself at one of our favorite long weekend getaway destinations.
Shelter Island, New York
This small 29-square-mile island is a relaxing destination, with its quiet bays, dirt roads, and quaint eateries. Shelter Island, often known as the “un-Hamptons,” is a peaceful and charming place known for its Zen vibes and chill attitude. Take a short ferry ride and check into the Chequit (pronounced CHEEK-wit by locals), a 145-year-old inn that has an updated take on the building’s Victorian heritage and high society heyday. The hotel is convenient for visitors because it’s located just a short walking distance from plenty of shops and restaurants.
Snag a reservation at celebrity hotelier Andre Balazs’ Sunset Beach restaurant, with a menu celebrating the French Riviera and coastal Italy featuring dishes such as niçoise salad, creamy burrata, and bouillabaisse. It’s a place to see and be seen; enjoy good food, an extensive wine list, and a beautiful sunset (we recommend requesting a reservation on the top deck for the best views). Across the street is Crescent Beach — the island’s most popular beach — a lovely curve of sand, calm ocean, and picnic tables. To explore the natural beauty of the island away from the crowds, rent a kayak from Shelter Island Kayak Tours and escape the noise in the calm creeks and harbors.
Temecula, California
An easy drive from San Diego and Los Angeles, Temecula is a wine country hidden gem. With a Mediterranean climate and stunning vistas, it’s no wonder that Temecula was nicknamed “a tourist’s secret paradise.” The terroir (wine growing environment) here produces award-winning wine grapes, mainly Italian and Spanish varietals like Sangiovese, Tempranillo, Pinot Grigio, and Barbera. With delicious wine, farm-to-table food, Tuscany-esque views, and small-town friendliness, Temecula makes an awesome weekend getaway.
Book your stay at the beautiful South Coast Winery Resort and Spa, situated on 63 rolling sun dappled acres. Because it’s one of the few hotels on a working winery, guests can take behind-the-scene tours and step off their patios right into the vineyard. An ideal way to explore the valley and wine country is by booking an all-inclusive Grapeline Wine Tour, a four-hour wine tasting tour hosted by a wine country insider complete with cheese and fruit and deluxe transportation. Spend some time exploring Old Town Temecula, with its historic buildings, charming antique shops, and a farmers market every Saturday from 7:30 a.m. to 12:30 p.m. Feeling adventurous? See the valley from a completely different angle by soaring high above the hills in a hot air balloon. California Dreamin' is on of Southern California’s top rated hot air balloon companies and the memories from the experience are sure to last a lifetime.
Gulf Shores, Alabama
Just a few hours drive from New Orleans, Atlanta, and Panama City Beach, Gulf Shores is perfect for a long weekend away. Located on the southernmost tip of Alabama, it’s one of the South’s best-kept secrets and the perfect place for white sand, sun, and fun all year round. The area boasts a myriad of hiking trails and outdoor activities, fresh-from-the-boat seafood, and plenty of wildlife. While there are a few hotels, the majority of visitors choose vacation rentals situated in high-rise condominium complexes with pools and beach access.
Gulf Shores’ beaches are perfectly white and powdery as they are made of tiny quartz crystals that came from ancient Appalachian Mountains. If fishing is your thing, more than 100 charter boats head out into the green-blue waters daily with the promise of an awesome catch — it’s rare to head home empty-handed. The area is also home to the nation’s first and largest organized artificial reef program. Made of recycled bridge material, the reefs attract white trout, flounder, redfish, mackerel and cobia; and if you venture further from shore, you can expect tuna, snapper, grouper and wahoo. To enjoy some good ole southern food, head to LuLu’s. What was once a small burger and beer joint, is now a huge entertainment complex with a beach, ropes course, volleyball courts, live music, a couple of bars, and the restaurant serves up to 4,000 people daily. You’re going to want to try the cheeseburger served with a fried green tomato on top, an order of its famous seafood gumbo, or the fresh Gulf red snapper sandwich. End a day by taking a sunset catamaran with Sail Wild Hearts and admire all the beautiful colors, keeping an eye out for dolphin pods.
Poconos Mountains, Pennsylvania
This idyllic region in northeastern Pennsylvania is the perfect antidote to the hustle and bustle of Philadelphia and New York, each just two hours away. Always popular for honeymooning couples, today the Pocono Mountains also attract families and groups of friends to its town-and-village-dotted woods and hills. Within 2,400 square miles and across four counties, the Poconos host hundreds of miles of hiking trails, dozens of golf courses, nine state parks, two national parks, and numerous historic sites. With ski areas, sprawling mountain resorts, and quaint inns, there’s enough to please travelers in any season. Reserve your stay at Hotel Fauchère, a boutique inn that offers extraordinary dining and historical lodging experiences. The inn opened in 1852 by Louis Fauchère, thenmaster chef at Manhattan’s Delmonico’s Restaurant and creator of American classics such as eggs Benedict, lobster Thermidor, and the Delmonico steak.
Although the Poconos region attracts more visitors when the weather is warm with its zip lines, the Appalachian Express Mountain Coaster, and a nearby resort with two water parks, ski season is a big draw. Camelback Mountain has 37 lighted trails, terrain and snow-tubing parks. Amid the shops and restaurants in small towns such as Hawley (which inspired the song “Winter Wonderland”), Lackawaxen, Milford, and Stroudsburg, you’ll find fascinating local history and charming Victorian architecture. The Zane Grey Museum — full of the famed Western novelist’s memorabilia — is a striking clapboard-sided farmhouse and a must-visit during your long weekend.
Richmond, Virginia
Richmond, one of America’s oldest cities, has been the capital of Virginia since the Revolutionary War. Having also served as the capital of the Confederacy during the Civil War, it is covered extensively in museums and the southern perspective is prevalent on 13 sites within the city’s Battlefield Park. Back in 1780, when Richmond became Virginia’s capital, 12 acres were appropriated for public buildings, including a capitol and executive mansion. Now known as Capitol Square, visitors can tour the Virginia Capitol building designed by Thomas Jefferson, home to the western hemisphere’s oldest continuously operating legislature (it’s where the Bill of Rights was ratified).
Grab a bite to eat at Millie’s Diner, and though there’s usually a wait, it’s worth it for the indulgent specials, cozy atmosphere, and tableside jukeboxes. Book a room at the Jefferson, Richmond’s “grand hotel,” a Beaux-Arts beauty that’s been in operation since 1895. The Jefferson has hosted 13 presidents and a long list of celebrities. Nearby is the Virginia Museum of Fine Arts, which showcases 35,000 pieces of rare 20th century works, elaborate Asian carvings, and a four acre sculpture garden – plus admission is free for its ongoing exhibitions! If the weather allows, take advantage of the 550 acres of shoreline and islands in the James River Park System where you can bike, hike, fish, and connect with nature.
Sioux Falls, South Dakota
Sioux Falls is located in the heart of America at the junction of Interstates 90 and 29, and within a day’s drive of most major Midwestern cities. The Big Sioux River pours 7,400 gallons of water per second over sparkling rose quartzite waterfalls in the middle of the city. Falls Park is the crown jewel of Sioux Falls, with more than 123 acres to explore and a five-story lookout tower from which you can admire the whole park. While there is a lot to do and the city is expanding, the residents here are dedicated to maintaining a sense of hospitality and small-town charm.
In the summer, rent a bike or take a walk along the bike trail corridor that circles the city to enjoy more of that fresh Midwestern air. While you could spend your entire weekend enjoying the outdoors, Sioux Falls also offers a vibrant food and art scene. Check out the Sculpture Walk, which is the largest and most recognized annual exhibit of public art sculptures in the country – and all of the sculptures are for sale if you want to take one home with you! With more than 700 restaurants, there’s plenty to choose from, but our recommendation is Phillips Avenue Diner for some classic all-American diner food. Once situated in a small airstream trailer, it now operates in a classic brick and mortar retro diner building. If history is your thing, pay a visit to the Old Courthouse Museum, a historic building constructed from Sioux quartzite. Inside are permanent and rotating exhibits about the history of the region, beautiful architecture, and stunning murals. Despite its size, there’s so much to explore of this small city.
San Juan Island, Washington
The San Juan Islands are made up of 172 ferry-accessible islands and are perfectly positioned for a serene getaway. Situated on the Salish Sea, between Seattle and Vancouver, the islands offer temperate weather year-round making it perfect for a weekend away. If you’re looking for beautiful views, abundant wildlife, awesome kayaking and hiking trails, art galleries, and farm-to-table restaurants, then you’ve come to the right place. The cellular dead-zones and slowed-down pace make the islands popular with nature lovers and tech billionaires alike. The most popular island of the San Juan Islands is the actual island of San Juan (but it still has a tiny population of less than 7,000), where the main village is Friday Harbor, and the most traffic you’ll see here is for boarding the ferry.
There are no chain restaurants or stores to be found on this historic and charming island, so spend a day strolling around the incredibly walkable streets and popping into small boutiques and cafes. Take a drive to Lime Kiln Point State Park, which is across the Haro Strait from Vancouver Island, Canada and a great place for spotting orcas when the weather is amenable. However, the best way to see some whales is by taking a tour, like San Juan Excursions, which will provide you with an informative and entertaining trip and plenty of wildlife! Finish your day by grabbing a bite to eat at Downriggers, and enjoying the view overlooking the harbor where you can enjoy fresh Pacific seafood and creative cocktails.
Colorado Springs, Colorado
About 70 miles south of Denver, Colorado Springs is an outdoor enthusiast’s paradise. Nestled at the foot of Pikes Peak (the second most popular mountain in the world, and the number one most visited on the continent with 500,000 visitors annually), Colorado’s second largest city is home to plenty of outdoor activities, cool points of interest, and one of the country’s three Olympic training centers — it’s hard to decide where to start. A great jumping off point is the city’s Garden of the Gods, a spectacular free public park with towering red rock formations that soar up to 300 feet. There are 15 miles of hiking trails, guided walking and Segway tours, bike lanes, rock climbing points, and a world-class museum that celebrates the ecology, geology, and culture of the park.
Snag a room at the rustic and timeless Outlook Lodge where numerous hiking trails with breathtaking views are right outside your door. Grab a slice of pizza at Fargo’s, one of the world’s largest family pizza restaurants that attracts bus-loads of tourists and members of the community alike. Besides all the hiking and biking, there are plenty of other things to check out, like the Cheyenne Mountain Zoo, America’s only mountain zoo. Hand-feed giraffes and budgies as you take in the sweeping alpine views. There is also a host of exceptional museums to spend a few hours in, such as the Colorado Springs Fine Arts Center and the Colorado Springs Pioneer Museum. Also be sure to check out the U.S. Air Force Academy, one of Colorado’s largest tourist attractions, that welcomes more than one million visitors annually. The Academy and its iconic and stunning Cadet Chapel — a 150-foot structure all-faiths house of worship for the cadets — are open to visitors daily.
