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Guided City Tours


Indulge in exciting urban exploring throughout America's favorite destinations! Cloud 9 Living's collection of guided city tours are the perfect way to combine sightseeing & tourist attractions with interests like art, culture, food, wine, history, hauntings, beer, sweets, architecture & more.


  • "I had an awesome time! The guides were great! Dave truly knows his Chicago history, architecture, and is guaranteed to make you smile and laugh, even if you become exhausted. The whole staff was fantastic. Truly professional and a fun sense of hum"
    Architectural Kayak Tour
    John S
  • "The history and information provided by both the tour guide and the businesses that we stopped at was much more than I expected and was very interesting. This was a gift for 2 other friends and they were thrilled with the fun and knowledge."
    Boston Chocolate Walking Tour
    Sandi M
  • "It was a great tour and our guide Amber was terrific. We learned about the food and also the history of the neighborhood. Very fun. "
    Walking Food Tour of Chicago
    Mel S
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  • Explore the ins and outs of America's favorite places on unique guided city tours from Cloud 9 Living!

    Dive into the rich sights, sounds, tastes and overall feel of the most impressive urban spreads in the US of A! Cloud 9 Living is your one-stop shop for connecting both locals and visitors alike with fascinating things to do in sought-out destinations.

    With an extensive collection of outings available, it's easy to find guided city tours that are perfect gifts for men and women (or even yourself as a lucky experience gift recipient)! Excursions may include walking, biking, buses, Segways, boats, helicopters, kayaks, or other fun forms of transportation — allowing you to get the most up-close, personal and unforgettable views of famed city attractions. And even better still, there are countless topics and activities in which you can immerse yourself: food and wine, art, architecture, history, beer, hauntings, local hot spots, desserts, culture, and much more! Many city tours also offer combinations of such features — so while you may primarily be sampling fine vino on a wine tour, you're likely to enjoy plenty of sightseeing along the way, from stop to stop.

    Get to know either your own stomping grounds or make the most of a visit with guided city tours that feature the guts and glory of a magnificent metropolis! Traverse past various tourist attractions, capturing them on camera. Take a historical tour to hear fascinating stories of the immigrants that built a city's neighborhoods, making them what they are today. Check out historical landmarks and buildings, marveling at their design, construction and preservation. Explore urban art and culture like never before. And much, much more.

  • Delight in guided city tours that invite guests to indulge in any number of tantalizing topics.

    Discover which restaurants are best-kept secrets. Learn the origins of legendary family recipes. Chat with local chefs about menu creation. Sneak a peek behind the scenes of culinary magic. Hear tall tales of famous patrons who used to frequent certain hot spots. Find out how chocolate or other tempting desserts are made. Sample ethnic fare from a variety of diverse neighborhoods. And many more engaging food tour topics to satisfy hungers of all sorts.

    Wet your whistle in a way that makes traditional sightseeing even more sensational! Escape to a vineyard for a wine sampling tour, learning how such fine fermentation goes from grapes to your glass. Relive the not-so-dry spell of the Prohibition era, and try the cocktails that came with it. Take a local brewery tour, complete with fun facts about the art of craft beer. Or paddle along a river to earn your pints! Wander along the renowned Kentucky Bourbon Trail, going where the spirits lead. With compelling guided city tours like these, plus plenty of others nationwide, a feast of food (and drink) for thought awaits!