When it comes to Chicago group travel and celebrations, nothing beats swapping crowded bars for an open deck, your favorite drinks, and the city’s skyline as your backdrop. With Sailing Chi, you’re not just renting a boat, you’re stepping aboard a high-end, BYOB floating celebration curated by passionate locals who know every iconic curve of the lakeshore.

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Meet the Captain Behind the Wheel

Captain Charles loves two things: sailing and sharing his favorite city’s skyline with locals and visitors.

Charles and the Sailing Chi crew are more than just guides; they’re a not-for-profit, volunteer-run community sailing program dedicated to making Chicago’s sailing scene accessible and unforgettable. Their mission? To combine safety, fun, and personalized experiences, all while supporting a vibrant sailing community.

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Whether you’re brand new to sailing or a seasoned pro, their roots in Chicago’s boating culture mean you get more than just a ride, you get insider tips, warm hospitality, and a crew who treats your celebration like their own.

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Option 1: BYOB Luxury Sailboat with Private Captain

Perfect for bachelorette parties, birthdays, or a Chicago summer group getaway, this 37’ luxury sailboat offers four hours of lakeside magic. A USCG-certified captain navigates while you sip your favorite drinks, stretch out on the plush deck, or float on the Lily Pad in the warm summer sun.

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You’ll enjoy:

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• - Complimentary snacks and drinks

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• - Bluetooth speakers for your curated playlist

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• - A swim platform with floaties and noodles

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• - Kitchenware, fridge, and a private bathroom (no extra fees, no surprise charges)

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Anchor at the lively Playpen for a social party scene or choose a quieter cove for laid-back lounging. Either way, you’ll have skyline views that’ll make your group photos pop.

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Option 2: Expansive Luxury BYOB Yacht Cruise

If you believe bigger really is better, Chicago’s largest private sailing yacht is calling your name. With ample deck space, multiple lounge areas, and an itinerary tailored to your group’s vibe, this experience is ideal for milestone birthdays, corporate outings, or any occasion worth going all out for.

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Bring your own drinks and bites, or let Sailing Chi handle provisioning. Whether you want to swim, dance, or simply relax with the skyline gliding by, your captain will make sure your trip is smooth, safe, and exactly how you imagined.

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Why Sailing Chi Is Different

Plenty of companies can rent you a boat. Sailing Chi gives you:

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• - Authenticity: A volunteer-run, community-focused sailing program with deep Chicago roots.

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• - Customization: From party coves to quiet sunset sails, every trip is designed for your group.

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• - Value: No hidden captain’s fees, docking charges, or surprise deposits, just straightforward fun.

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And with over 500 five-star reviews in eight seasons, their reputation sails ahead of them.

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Plan Your Chicago Sailing Celebration

Whether it’s a bachelorette weekend, a friends’ reunion, or a family day out, Sailing Chi transforms your Chicago group celebration into an unforgettable on-water experience. From the deck, the city skyline feels even more magical, and your only job is to soak it all in.

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So gather your crew, pack your drinks, and let Captain Charles and his team show you Chicago like you’ve never seen it before.

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Plan Your Chicago Party on Batch

You can plan your party with just a few clicks on Batch! Get ready to make some memories you can bring home with you and celebrate all weekend long with a good group of friends! Here at Batch, we’ve made it our mission to simplify party planning and make booking experiences easier for any celebration! Whether you’re a local to the area or just looking for good party vibes, there’s endless fun to be had when you download the Batch app free of charge!

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Book your party today using our Nashville, Tampa, Scottsdale, Savannah, Chicago, Austin, Las Vegas, Miami, Palm Springs and New Orleans marketplaces or browse all destinations on letsbatch.com. Discover the best local crafting experiences, delicious dining, private group classes, live shows and more that would add to the vibes of your party on Batch.

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