If you’re looking for a deep-dish pizza, world-class hockey, or a walk through Millennium Park, we can help you see—and eat—it all with a Chicago vacation package. There’s always something to do here in the crown jewel of Illinois, from a walk on Navy Pier to the gorgeous boutiques on the Magnificent Mile. Pardon our pun, but we’re sure “The Windy City” will “blow” you away!
Does your family thrive on challenges? Multiple escape rooms now pepper Charlotte, and near the intersection of the city’s two interstates, you’ll find Escape Kings. This family-friendly attraction lets those over 10 years of age test their collective wits by escaping from Aztec Ruins and Kings Quest rooms. The puzzle clues are for all ages, and escape is neither too hard for kids nor too easy for adults. To avoid disappointed faces, pick up tickets for escape rooms, Segway tours and other family-friendly activities in advance.
It’s worth noting that if the original price isn’t always posted for these types of deals, so you may not know exactly how much you’re saving (or if you’re saving at all). And while Groupon does post the percent savings (and it’s often 50% off or even higher), some critics point out that the “original” prices for Groupon deals and other discount sites are occasionally inflated to make the deals look better.
Why: Canada, eh? The good news is, our neighbor to the north(west) has a favorable exchange rate of .80 cents to the U.S. dollar. So luxury hotels like the Fairmont Pacific Rim in the naturally stunning city of Vancouver are super affordable. The city is one of the most ethnically and linguistically diverse cities in Canada: 52% of its residents have a first language other than English. “Van” is literally set within a rainforest, so nature enthusiasts will love walking along the waterfronts with views of the nearby mountaintops. For the culturally curious, I suggest weaving your way through the cobbled streets and shops in the historic Gastown neighborhood. Don't miss Kimprints, a shop supporting underprivileged street artists, or the Ok Boot Corral, a local bootmaker who has been in business since 1833. For an unexpected insider experience, get your sea legs on to go fishing for what’s in-season with sustainable seafood supplier, Organic Ocean. Afterward, you can bring your fresh catch to the kitchen of the Fairmont Pacific Rim to make fresh sushi. And let’s be real: What’s sushi without homemade sake? Check out Masa Shiroki, an artisan sake maker on Granville Island, for his locally made bubbly sake. Watch Oh the People You Meet's video for more insider tips on Vancouver.
Why you’ll love it: For tweens and teens, this getaway is a perfect fit; it’s 35 miles east of Los Angeles, but without all the traffic and commotion, so they can explore on their own without parents worrying. Claremont Village is home to over 150 shops and restaurants (don’t miss the I Like Pie Bakeshop or the frozen treats at 21 Choices) and where you’ll want to spend your evening. The Raymond M. Alf Museum of Paleontology and Folk Music Center are local favorites to visit, and there are events going on every week throughout the summer.

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Break up a day at the beach with an outing to the Cayman Islands National Museum. The colonial-era building depicts the island's natural and cultural history in 3-D displays, murals and videos. Or spy colorful blue iguanas at the Blue Iguana Recovery Program, located in the Queen Elizabeth II Botanic Park. A 90-minute guided tour is suitable for the entire family, and if grandma doesn't share the kids' fascination for lizards, she can always enjoy the native flora in the park instead.
St. Augustine, FL: Strolling through St. Augustine, you will sometimes have a hard time believing that it belongs to the 21st century America. From the 17th century Castillo de San Marcos on the western shore of Matanzas Bay to the lavish historic Hotel Alcazar that today hosts the Lightner Museum of Victorian times, St. Augustine has retained the elegance and charm of its past and preserved its historic treasures with lots of love and care. Stroll through the cobblestoned streets of the Old City, St. George, Hypolita and Charlotte Streets, and have a cup of coffee in one of the many quaint shops. Visit the Ximenez-Fatio House built in 1798, an architectural gem that showcases the life of 19th century Florida. A visit to the St. Augustine Alligator Farm Zoological Park and pristine beaches of Anastasia State Park will show you that some things are timeless and never change.
Where to stay: Tanque Verde Ranch is celebrating its 150th anniversary this year, and they’re offering a special $150-per-night family stays for the entire summer. The family-owned property provides an authentic wild west experience with horseback riding and much more, through Arizona’s most breathtaking desert landscapes of the Rincon Mountains. The $150 for the 150th special includes breakfast and free use of the pool and general facilities. A kids camp, great for ages 4 to 12, is available for an extra fee, as is horseback riding, biking, and guided hikes.
Why: For an affordable and sun-soaked vacation, southern Portugal’s Algarve region should be hot on your radar. The city of Albufeira boasts a beautiful climate, fabulous beaches, inexpensive apartment-style hotels and a central location within the Algarve. There are over 100 different restaurants, bars and nightclubs, and Albufeira even has a charming Old Town with traditional Portuguese streets and plazas within the city center. The prices for both food and wine are extremely reasonable; be sure to sample the wines of Portugal. While summer remains the busiest and most popular time to visit, I love visiting in late spring — the weather is pleasant and sunny, there are fewer tourists and hotel rates are very affordable. Albufeira also offers easy access to nearby towns such as Loulé, with its famous market and an authentic slice of Portuguese culture. Rent a car to see the church of São Lourenço in Almancil, famous for its exquisite blue tile. Head north of Lagos to see Ponta da Piedade, with its towering red rock formations against the sea. Play a round of golf in one of the many beautiful courses in the Algarve. The place to stay: the Epic Sana Algarve overlooking Praia da Falésia, where you can bask in the sun at one of its five outdoor pools and indulge at the beautiful spa.
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