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    Sailing Lessons

    Is Jack Sparrow your hero? Do you dream of sailing the open seas with nothing but the wind at your back? Whether you're a rookie mariner or a seasoned veteran, this sailing class has it all. Each lesson is custom tailored and taught by a USCG certified sailboat captain, and the hands-on approach to sailing instruction allows you to maximize your potential while increasing your ability to sail safely and confidently. After this sailing lesson, you'll feel Magellan-like confidence and be ready to sail around the world!
    Sailing Lessons

    Montrose Harbor, Chicago

    • Learn the fundamentals of sailing, such as tieing basic knots, balancing the boat, and tacking
    • Learn terminology for recreational boating as well as safety procedures
    • Practice your skills on the water with a USCG Certified sailboat captain
    • All levels welcome
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    A Getaway Sail (Weekend)

    (7)
    You haven't tasted luxury until you've experienced a summer sail on a private charter. Picture this: you've got your sunglasses on, an ice cold beer in your hand, and NOTHING on your mind! During this Getaway Sail, you'll have two full hours to put your worries behind you and embrace the Lake Michigan breeze. Experience Chicago from a totally new perspective as you witness the Chicago skyline, Navy Pier, Soldier Field, and the Museum Campus, all from the comfort of a boat! You can relax on the front nets, lounge in the bean bags, help sail and steer the boat, or straight up destress! All Phenix charters will include the services of a U.S. Coast Guard Licensed Captain, and some trips also have an additional crew member. Bring up to 5 of your friends or family members to share this experience of a lifetime with you!
    A Getaway Sail (Weekend)

    111 N Lake Shore Dr, Chicago

    • Come aboard a private charter for the best day of your summer
    • See the Chicago skyline, Navy Pier, Soldier Field, and more from the waters of Lake Michigan
    • Bring a bottle of wine or a couple of beers to relax in luxury
    • Make memories of a lifetime with friends, family, or your special someone
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    7 positive reviews
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    Sunset Dinner Cruise

    (17)
    What does a night out in Chicago need? Dinner? Dancing? Maybe a glimpse of the city's charm and beauty? Have it all on this Chicago Sunset Dinner Cruise. Aboard a three-hour luxury cruise on Lake Michigan, you'll encounter attractions such as Navy Pier and Soldier Field as you dine on a lavish, all-you-can-eat buffet! See spectacular views of the city skyline, while being entertained by a singing ship staff and a live DJ spinning your favorite songs. The sumptuous all-you-can-eat buffet is complete with everything to keep your stomach satisfied. As you enjoy your meal in the elegant setting of the ship's dining room, you'll be entertained by the colorful characters of the ship's cabaret. Let the city enchant you with a wonderful night out!
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    Sunset Dinner Cruise

    600 E Grand Ave, Chicago

    • See spectacular views of the Chicago skyline aboard a luxury cruise on Lake Michigan
    • Encounter attractions like Navy Pier and Soldier Field
    • Be treated to a sumptuous all-you-can-eat buffet, complete with a carving station
    • Enjoy the entertainment of a live DJ
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    17 positive reviews
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    Architectural Tour

    (31)
    Part adventure, part history lesson. If only school had been this fun! This tour will have you paddling through the heart of Chicago as you take on the urban canyon that is the downtown Chicago River. Along the way, your guide will fill you in on the history of the area, pointing out architectural points of interest and other oddities that will make this journey almost as intellectually satisfying as it is visually riveting. All told, you'll spend several leisurely hours on the water, getting a light upper body workout that will leave you feeling rejuvenated and limber. Whether you've never kayaked before or you're an experienced pro, you'll love this intimate introduction to the city's history.
    Architectural Tour

    1220 W LeMoyne Ave, Chicago

    • Kayak across the city on the Chicago River during this energizing adventure tour
    • Learn about the history and architecture of Chicago as you paddle by several famous sites
    • Let a certified instructor show you the ropes during a safe row
    • Feel adrenaline of adventure consume your senses and fuel your sense of wonder
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    31 positive reviews
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    Intro to Sailing

    Have you ever looked out on Lake Michigan and seen hundreds of sailboats and said to yourself, "I wish I could do that?" Now you can! Enjoy striking views and breathtaking sunsets. Learn to sail and experience the thrill of a lifetime as the wind catches your sails. Use your time for a relaxing sail on Lake Michigan, or as a hands on class. You'll learn what it takes to sail a boat from professionals who are passionate about sailing in this hands-on course. Experience world-class sailing at its best while the breathtaking Chicago skyline sparkles on the horizon.
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    Intro to Sailing

    Belmont Harbor, Chicago

    • Learn the basics of how to sail on Lake Michigan
    • Enjoy the fun, friendly, and safe environment aboard a sailboat
    • Watch the Chicago skyline sparkle on the horizon
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    TikiSail with Fireworks

    (6)
    Chicago TikiBoat's TikiSail is the premiere party sailboat of the Chicagoland Area, and they want to take you out on Lake Michigan for some fun! There's no better way to see the beautiful Chicago skyline than with a few of your closest friends on a 34-foot luxury sailboat. And at the end of the day, you'll be treated to a fantastic firework show that will leave you breathless. This is the perfect activity for an anniversary, birthday party, or just a regular old weekend getaway. Your experienced captain will know exactly how to provide you with the right atmosphere, whether you're looking for a quiet, intimate evening or a blowout party. So what are you waiting for? Get out there and cut loose!
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    TikiSail with Fireworks

    400 E Monrore St, Chicago

    • Head out to Lake Michigan on one of Chicago's premier party boats
    • Enjoy great views of the Chicago skyline and a dazzling fireworks display from the comfort of a luxury sailboat
    • Party in style with your closest friends
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    6 positive reviews
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    Tiki Pontoon - Morning

    (6)
    Chicago TikiBoat's Tiki Pontoon is the premiere party boat of the Chicagoland Area, and they want to take you out on Lake Michigan for some fun! The Tiki Pontoon is the original Chicago TikiBoat. It comes equipped with a sundeck, Bluetooth enabled stereo, complimentary grill with 3 bags of fuel, and even a waterslide! And of course, you'll also be provided with a cooler and ice for all the booze you'll bring to keep the party going. As if all that weren't enough, you'll also get to see some fantastic, unforgettable views of the famous Chicago Skyline, and even choose where you want to boat to end up. So what are you waiting for? Get out there and cut loose!
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    Tiki Pontoon - Morning

    400 E Monrore St, Chicago

    • Head out to Lake Michigan on one of Chicago's premier party boats
    • Enjoy a fun ride in the sun and some incredible views of Chicago's skyline
    • Check out the sun deck, Bluetooth enabled stereo system, and waterslide
    • Party in style with all of your closest friends
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    6 positive reviews
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    Fox River Valley Wine Tasting Room Trail

    These aren't your parents wines! Step out into the scenic Fox River and the beautiful old towns that supported the economy based on river and rail transportation. While the days of steamboats and locomotives are in the distant past, you will find wonderful wine tasting rooms in these towns. Sample wine made from grapes grown in Illinois and around the Midwest. You'll experience flavor and aroma profiles that differ drastically from wines made in California and Europe. Visit three tasting rooms along the Fox River and indulge in a gourmet lunch along the way. You'll enjoy a day outside of the normal loop and see some sights off the beaten path. Break the mold and shock your folks by bringing back one of these bottles to the next family dinner.
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    Fox River Valley Wine Tasting Room Trail

    Hotel on the Magnificent Mile, Magnificent Mile

    • Enjoy a scenic day exploring the wineries and vineyards of the Fox River Valley
    • Visit three tasting rooms and learn the different flavor profiles of the region
    • Indulge in a delicious lunch along the way
    • Spend a day drinking wine and learning the history that surrounds the area
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    Lakefront Bike Tour

    What's the best way to enjoy Chicago? You need to be on the streets and by the water, listening to the sounds of cars, boats, and the serene Lake Michigan. Go and experience Chicago's sites, while enjoying the outdoors on a great bike tour. As you enter this urban safari, bear witness to the great architecture of the Windy City, beaches, lagoons, gardens, and animals. You'll even ride through the famous Millenium Park, Navy Pier, and Lincoln Park Zoo. Chicago should be seen from the streets not from afar -- looking at you Sears Tower.
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    Lakefront Bike Tour

    Navy Pier, Chicago

    • Ride a bike through the streets of Chicago, passing through sites like Millenium Park, Navy Pier, and Lincoln Park Zoo
    • Enjoy a guided tour on this urban safari
    • Explore Chicago like a native
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    Tiki Pontoon with Fireworks

    (6)
    Chicago TikiBoat's Tiki Pontoon is the premiere party boat of the Chicagoland Area, and they want to take you out on Lake Michigan for some fun! The Tiki Pontoon is the original Chicago TikiBoat. It comes equipped with a sundeck, Bluetooth enabled stereo, complimentary grill with 3 bags of fuel, and even a waterslide! And of course, you'll also be provided with a cooler and ice for all the booze you'll bring to keep the party going. As if all that weren't enough, you'll also get to see some fantastic, unforgettable views of the famous Chicago Skyline, And for the grand finale, you'll be treated to a fantastic firework show that will leave you breathless. So what are you waiting for? Get out there and cut loose!
    No available dates to book.
    Bucketlist to hear about new dates first!
    Tiki Pontoon with Fireworks

    400 E Monrore St, Chicago

    • Head out to Lake Michigan on one of Chicago's premier party boats
    • Enjoy great views of the Chicago skyline and a dazzling fireworks display
    • Check out the sun deck, Bluetooth enabled stereo system, and waterslide!
    • Party in style with all of your closest friends
    BOOK NOW ← Back
    6 positive reviews

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