Islamorada, Fla., from Miami: Islamorada is one of the top sportfishing spots in the world, and it’s less than two hours from Miami by car. There are plenty of snorkeling and swimming experiences available here as well. And if hitting the warm Gulf waters isn’t your thing, this small Florida Keys town has boutiques, galleries and plenty of snap-worthy sunsets that melt across the horizon. Plus, there’s always the draw of grabbing a frozen fruity cocktail and just chilling out on the beautiful beaches. Hotel pick: Chesapeake Beach Resort(Photo: Oyster.com)
Labor Day weekend feels like the last real weekend of summer, so we suggest celebrating with a bang. If you are still stuck on the fence on where to go, now’s the time to decide. From quick back-to-nature getaways to 24-hour party cities, we’ve got our top spots for your last long weekend of summer — no matter where you live. Oyster.com scouted out the best weekend destinations for those traveling from Miami, New York City, Chicago, Los Angeles, San Francisco, and Washington, D.C.; all of our picks are reachable from the designated city in under three hours — by car, flight or train — so book your quick trip and pack your bags!
Islamorada, Fla., from Miami
Hotel pick: Chesapeake Beach Resort
New Orleans from Miami
Unfortunately, some areas of southeast Louisiana are still recovering from the floods, but New Orleans has remained relatively dry this time around, so Miami locals looking to get a break from the beach should hop on a two-hour flight to The Big Easy. Here, they can trade the funky and flashy vibes of The Magic City for live jazz in the historic French Quarter and bowls of homemade jambalaya. You can spend the weekend getting your voodoo on or hunting spirits on a ghost tour, hop on a ferry for a quick cruise of the Mississippi River, visit quirky museums, and appropriately taste and sip your way through the streets as you admire New Orleans’ historical architecture.
Hotel pick: Bourbon Orleans Hotel
Portland, Ore., from Los Angeles
Things can get pretty hot out in the desert around Labor Day, so we suggest grabbing some respite in Portland, where high temps average around 76 degrees. You’ll still find healthy and delicious dishes at restaurants that pride themselves on being hyper-local and farm-to-table, cute vintage shops, Powell’s Books (one of the best brick-and-mortar bookstores left standing), crafty cocktail bars — and, of course, the famous Voodoo Doughnut. Plus, easy access via the aboveground public train isn’t too shabby either.
Hotel pick: McMenamins Kennedy School
Sayulita Nayarit, Mexico, from Los Angeles
If you are looking to unplug and unwind, look no further than Mexico’s Sayulita Nayarit. This sleepy and relaxed fishing village is a great place for a quick city detox. Aside from the amazing food and picturesque beaches, visitors can also take advantage of yoga classes and snorkeling, try their hand at wind sports, or go on hikes through the jungle. Trust us, it’s well worth the three-hour flight.
Hotel pick: Haramara Retreat
Wilmington, N.C., from Washington, D.C.
Popping down to North Carolina’s most accessible coastal city of Wilmington will reward you with fresh air, friendly southern smiles, a lively riverwalk and stone’s-throw access to three different beaches — Wrightsville, Kure and Carolina. This cute and historical spot’s brick-lined downtown streets are home to several boutiques, eateries and spectacular views across Cape Fear River. History buffs will love visiting places like Battleship North Carolina and the Bellamy Mansion, while nature-lovers will enjoy strolling along the river and visiting the Airlie Gardens. This town is also famous for being haunted — as well as being the filming location for TV shows and movies like Dawson’s Creek, One Tree Hill, A Walk to Remember and Empire Records, to name a few.
Hotel pick: Hilton Wilmington Riverside
Virginia Beach from Washington, D.C.
Less than an hour flight and D.C. dwellers can start their Labor Day weekend festivities in Virginia Beach. A big military town, Virginia Beach is also a perfect spot to go if you’re looking for that quintessential seaside holiday. There are long stretches of sandy beaches, tons of water sports, dolphin cruises and even a lighthouse. However active (kayaking, hiking) or relaxed (lounging on the beach or strolling the boardwalk) you want to be, you’ll find it here.
Hotel pick: Hilton Virginia Beach Oceanfront
New York’s Finger Lakes Region from New York City
Sometimes you don’t need to look any further for great long weekend trips than your own state. Labor Day weekend is a fantastic time to head upstate for New Yorkers. Take the 90-minute flight to Ithaca and then hop in your car, hitting up some of the small towns along the Finger Lakes; you’ll either be catching the tail end of summer — meaning you can hike while dipping in and out of swimming holes — or you’ll glimpse the leaves as they just start to turn, when it’s almost just the right time for a warm cider. This region is one of the leading producers of craft cider, and mapping out visits to the local breweries and cideries makes for a great activity.
Hotel pick: Hope Lake Lodge
Philadelphia from New York City
If you love the city life, but just want to experience it in a different city, hop on the 90-minute Amtrak to Philadelphia. Here you can visit the kooky oddities at the Mutter Museum, walk along America’s oldest residential street, Elfreth’s Alley, peep the Liberty Bell, catch some amazing artists at galleries like Arch Enemy Arts, and make it your mission to find the city’s best Philly cheesesteak. This place is easily walkable and packed with a host of arts, culture, delicious food and historic roots.
Hotel pick: The Rittenhouse
New York City from Chicago
From one famous pizza city to another, hopping on the metal bird over Labor Day could help you solve the mystery of whose pizza style is king. It’s also a perfect opportunity to explore the city — or, if you’ve been here done that, branch out and discover another borough, like the ever hip and trendy Brooklyn. On par with some of Manhattan’s best museums, there you’ll find the Brooklyn Museum as well as the Brooklyn Botanical Garden, massive Prospect Park, and tons of new restaurant choices. In Queens, you can head to Flushing where you’ll find authentic Asian eats and the haunting remnants of the 1964 World’s Fair site.
Hotel pick: Wythe Hotel
Louisville from Chicago
Louisville is just a quick one-hour flight from Chicago. While much of Kentucky is filled with small towns and horse farms, Louisville is metropolitan and hip. While you are here, you might want to check out a horse race at Churchill Downs, go zip-lining or brave it up at the Cave Hill Cemetery. There are also fantastic restaurants, a lively bar scene, historic district and, of course, a famous baseball manufacturer.
Hotel pick: Seelbach Hilton
Big Sur, Calif., from San Francisco
San Franciscans, hop in your car this Labor Day for a scenic two-hour journey (or longer with holiday traffic!) and you’ll end up high on the mountain in Big Sur. The low-key vibe here means you can soak up some quiet time over the long weekend. Or use the peace to write your novel — or at least a few journal entries. Visit the Sykes Hot Springs for a hike and a soak, marvel at some of the breathtaking oceanside views while you try to spot seals and whales, or just get lost in nature for a few days.
Hotel pick: Post Ranch Inn
Las Vegas from San Francisco
For the opposite of reconnecting with nature, jump on a 90-minute flight to Las Vegas and get wild. Soak up the energy of the Strip, play your cards right and treat yourself to some of Sin City’s best restaurants, pools and spa treatments. Three nights in Vegas can seem like an eternity, which makes it feel like a perfect bang-for-your-long-weekend-buck getaway.
Hotel pick: Wynn Las Vegas
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Last-minute Labor Day: Easy trips from five U.S. cities
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