Do I need sailing experience to join the trip?

No prior experience is necessary; Captain Evan will guide you throughout the sailing adventure.

Where does the sailing trip start?

All tours depart from 31st Street Harbor on J Dock in Chicago.

What should I bring on the boat?

Bring layered clothing, sun protection, water, and a light jacket depending on the season.

Is food or drink provided?

Food and drinks are not included, so consider bringing your own refreshments.

Can I customize the sailing itinerary?

You can communicate preferences with Captain Evan before your trip to tailor your experience.

Are group bookings available?

Yes, Captain Evan welcomes small groups for private and special occasion sails.

Experience Thrilling Chicago Sailing Adventures with Captain Evan Toczyl | Boat Tour | Water Activities

Adventure Brief

Explore Chicago from the water with Captain Evan Toczyl, a 100GT Masters Captain offering engaging 3-4 hour sailing adventures from 31st Street Harbor. Discover the city skyline and Lake Michigan’s natural beauty on a trip tailored to your pace and interests.

3–4 hours

moderate

From $321.00

Set sail from Chicago’s iconic 31st Street Harbor on J Dock, where Captain Evan Toczyl, a seasoned 100GT Masters Captain, invites you to explore the city’s stunning waterfront like never before. This 3-4 hour sailing adventure offers a hands-on experience aboard a well-equipped vessel, blending the excitement of open water navigation with the sweeping urban skyline views that define the Windy City. Chicago’s Lake Michigan shoreline stretches wide here, framed by sandy beaches and punctuated by architectural marvels, making this trip a unique way to see the city from a fresh perspective.

Under Captain Evan’s expert guidance, both novice sailors and seasoned adventurers can expect a safe, educational, and truly memorable outing. Whether you’re eager to learn the ropes or simply want to relax and soak up the lake breeze, this experience is customized for your group’s pace. You’ll glide past Lincoln Park and the Navy Pier, while the tranquil waters play against the hull, creating a rhythm only the lake can offer.

The area’s distinct maritime history and dynamic role in Chicago’s leisure culture come alive on this trip. Chicago Harbor is a favored spot for locals and visitors alike, historically important as a trading point and now a prime destination for water recreation. Captain Evan adds a personal touch with his years of master-level expertise, ensuring your journey is not only scenic but educational about Lake Michigan's ecology and sailing nuances.

This sailing excursion stands apart in the Chicago outdoor scene by marrying urban adventure with the serenity of the lake, offering a rare balance of city energy and natural calm. Ideal for small groups, friends, families, or corporate outings, it’s a chance to unwind yet feel the pulse of the city from a new vantage point. With flexible communication prior to your trip, Captain Evan ensures your questions are addressed to craft an experience tailored to your interests.

For visitors staying in Chicago, this sailing tour adds a refreshing alternative to the typical city itinerary. It’s also an excellent way to celebrate special occasions or simply disconnect from the bustle without venturing far. As the sun dips lower, casting golden hues across the water, you’ll appreciate how this adventure captures the essence of Chicago’s connection to the Great Lakes.

Whether seeking a peaceful afternoon or an invigorating hands-on sailing lesson, Captain Evan Toczyl’s Chicago Harbor expedition is a standout water activity that blends expert leadership, engaging education, and unforgettable lakefront views. Prepare to chart a course where urban backdrop and natural beauty meet in perfect harmony.