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Our Favorite Weekend Trips

Weekends are sacred for Travelzoo’s Deal Experts. During the week we’re on deadline publishing the best travel deals in the market in our Top 20 newsletter and negotiating exciting experiences with our Local Deals. So when the clock chimes 5 on Fridays, it’s not uncommon for us to hit the road immediately. And since we’re based in the biggest cities across the country, we look for peace and quiet when we get away on weekends.

Here’s a roundup of our favorite places for some rest and relaxation away from the city. For travelers, these are easy spots to add on to big-city stays:


  • An hour-and-a-half drive from New York City and two hours from Philadelphia, the Delaware Water Gap is a stunning natural phenomenon surrounded by a wealth of hiking trails and campgrounds. Hiking routes ranging in difficulty, some of which overlap with the Appalachian Trail, offer stunning views of the ribbon carved in the mountain ridge by the Delaware River. The 70,000-acre Delaware Water Gap National Recreation Area offers opportunities for boating, swimming, fishing, biking and rock-climbing. The area has a rich history and is home to Native American archaeological sites as well as structures from the colonial period. -- Andrea Kahn
  • Newport, R.I., is a charming New England town complete with the history and delectable seafood of a port town and the opulence of its residents’ yachts and summer homes. Stunning mansions are open for tours -- these magnificent structures were once the summer homes of the 20th century’s most famous last names: Vanderbilt, Astor, Widener. The International Tennis Hall of Fame is also in Newport. As is Touro Synagogue, known as the oldest still-standing synagogue in the United States. -- Arielle Chorney
  • Stowe, Vt., is known as a ski destination, but we loved using it as a picturesque home base for exploring the state’s quaint towns and covered bridges. As an added bonus, Stowe is much closer to airports in Boston and Manchester, N.H. Plus, discounted rooms are easier to find in off-season as hotels have space. -- Josh Gershenson
  • The South Fork of Long Island is home to eight historic villages that make up The Hamptons, a popular seaside resort for affluent New Yorkers and Hollywood celebs. In addition to clean, uncrowded beaches, The Hamptons’ hamlets offer upscale shopping, dining and nightlife rivaling those found in the city. Get there via a luxury coach bus, the Long Island Railroad or by car in less than two hours for a weekend escape from the concrete jungle. -- Elisabeth Barker


  • Less tourist-riddled and more laid-back than Key West, Islamorada (pronounced eye-la-more-ah-dah) is South Florida locals’ alternative to the Florida Keys. A car ride of less than an hour and a half from Miami will take you to pristine beaches, panoramic water views, thatched-roof outdoor bars and an authentic island-hideaway feel. Head to Islamorada Fish Co. for arguably the best key lime pie ever (encrusted with nuts on the bottom), or spend a few hours at Robbie’s feeding the 50-100 tarpon fish swarming the waters under the dock. Find a restaurant serving fresh-caught fish and crack open a Key West Sunset Ale. -- Angela Tablac
  • Atlanta is often thought of as the heart of the South, but there are plenty of side trips to take where you can experience real southern hospitality. Head northeast for an hour and a half and you’ll find the charming town of Athens. Best known as the hometown of the band R.E.M. and the University of Georgia, the town has plenty to offer visitors. Stroll the quaint main street and poke around the eclectic art galleries, check out some live music at one of the many venues or wander around the redbrick buildings of the university. And bring your appetite – Athens has become a serious foodie town in recent years. -- Annalisa Henderson
  • When visiting Austin and San Antonio areas, getting out west of the city to the Texas Hill Country is totally worthwhile. I took a Brit out that way and he loved the drive and the scenery, the ranches, the cows … and there’s tons of wineries. Texas makes some lovely wines and many people are surprised to hear that. -- Rebecca Gindele
  • It’s easy to avoid the major beaches along Florida’s West Coast -- if you know where to go. (Oh, and by the way, Florida’s West Coast boasts much better sand than the Eastern side, and less surf.) Cruise past Clearwater Beach and St. Pete Beach to the quiet little stretch of good sand on Pass-A-Grille Beach at the southern tip of St. Pete Beach. Or head to Fort De Soto, often rated one of the best beaches – it even has a “dog beach.” Tired of the beach scene? Head north of Clearwater to Tarpon Springs to check out the sponge docks and dine on yummy Greek food. -- Angela Shannon


  • If you don’t mind a bit of a drive from Chicago, head west to the mighty Mississippi and spend an evening or two in Dubuque, Iowa. Just a few miles past the well-known quaintness of Galena is a classic river city that’s still thriving, thanks to major employers like John Deere and IBM. They keep the downtown surprisingly active with plenty of bars and restaurants on hand including the one-of-a-kind Paul’s Tavern, whose main decorations are the taxidermied hunting trophies “collected” by the previous owner over the past half-century or so. Attractions like the National Mississippi River Museum & Aquarium keep the days interesting, stays at the rumored Al Capone hideout of the recently renovated Hotel Julien are recommended, and when you’re within distance of the world’s shortest, steepest railroad, you probably shouldn’t pass that up either. -- Karl Klockars
  • Lake Geneva, Wisc., is to Chicagoans what I imagine Cape Cod is to Bostonians or the Jersey Shore is to New Yorkers. The adorable town has a timeless, Main Street USA vibe, with trendy boutiques, foodie-approved restaurants and come-one-come-all bars lining the well-kept streets. But the real action is on the water -- don’t miss the popular tour boats that take wide-eyed visitors on a journey past the opulent mansions that line the shore. Buy your tickets, then duck into Popeye’s across the street from the marina -- not the fast food chicken place, but a casual, convivial seafood joint loved by locals and tourists alike. -- Wendy Wollenberg
  • Some of my favorite vacations spots in the Midwest are the beach towns along the west coast of Michigan. It’s the perfect escape from the hustle and bustle of the city. I planned a family summer vacation over a long weekend for eight adults to Saugatuck. Although the town boasts several charming B&Bs, I opted for a vacation house rental where we could make ourselves more comfortable, and not to mention, save a few bucks. We stayed in a large townhouse that was in an ideal location -- across the street from the water and about three blocks from downtown. We spent a whole day just exploring the art galleries and boutique shops that Saugatuck is known for. My family visited the local fudge/ice cream parlor every single night we were there. One morning took a ferry to the neighboring town of Douglas to visit the beach where it was easy to spend the entire day sunbathing. The beach was clean, pleasant and relaxing. This was the perfect long weekend getaway that reminded us why summer in the Midwest is pretty awesome. -- Gia Teolis
  • Don’t discount Milwaukee, often seen as the Second City’s Second City. But with good reason, locals fiercely love their town, which makes for the perfect side trip from Chicago. It’s a straight shot up I-94 (don’t forget a stop at Mars Cheese Castle), about a 90-minute ride each way. There you’ll be greeted by breweries big and small, lively festivals in the months where the weather’s above freezing, a vibrant restaurant scene with a focus on farmland produce (and cheese) and even a bronze Fonz statue downtown. What’s not to love? -- Hilary Solan


  • International visitors will know Seattle and Vancouver, but they may not have heard of the idyllic, rugged, beautiful chain of Pacific Northwest islands known by locals as just “the San Juans.” It’s a 1.5-hour drive from Seattle; board a ferry and cruise through the Strait of Juan de Fuca to Friday Harbor on San Juan Island, a great jumping off point for whale watching, fishing trips or exploring other nearby islands. Time truly stands still here. -- Kelsey Mesher
  • Capitola is a small town outside of Santa Cruz -- it’s a beautiful little beach town with bright buildings along the water and just a nice respite from the bustle of the Santa Cruz boardwalk. -- Megan Edelman
  • Crested Butte is a gorgeous mountain town with ski and hiking trails for all abilities and a cute downtown. It’s more remote than the ski resorts clustered around Denver, about 4.5 hours away, so it’s easy to feel like you have the mountain to yourself. Travelers can fly into Gunnison, a 30-minute drive or shuttle ride away. -- Kelsey Rexroat
  • I know Solvang isn't the best kept secret for a getaway from Los Angeles, but I wanted to vouch for it as I took a day trip on Saturday to redeem a Travelzoo wine deal. For $19, I got two wine flights at Curtis Winery paired with chocolate truffles. I also got a bottle of the house Syrah to bring home. The wine room was cute and quaint, and the servers were very knowledgeable and accommodating. We drove up to Solvang along the Pacific Coast Highway, marveling at the jagged coastline, high peaks and surfers in the ocean. The right turn off the coast into the mountains was the most amazing part of the drive. Once we were in Solvang, it felt like we were transported into Tuscany. The green rolling hills and miles of quaint farmland and vineyards were so beautiful. It was a nice escape from the crowds and traffic of LA. -- Mary Walker Baus

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Tips by

Deal Expert, Chicago
Friday, April 26, 2013
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Hilary Solan