"Zoom out. What’s the big picture here? Inspired by his love for the water and a hope for more people to experience the Chicago River, Ron Silva founded this boating company in 2012 with late business partner Greg Krueger. What started as a business with just two electric Duffy Boats has since grown to encompass more than 25 vessels with seven types available, ranging to hold anywhere from four to 26 guests. All boats and routes were thoughtfully chosen to reflect the team’s M.O.— to offer guests a simple and fun way to boat privately on the river. From where do you sail? Guests can set sail from four locations throughout the city (with a fifth launching this summer). Three loop locations include Marina City (300 N State), Chicago Water Plaza (151-155 W Wacker Drive) and the Chicago Riverwalk (11 W Riverwalk St), and in Avondale at Rockwell on the River (3057 N Rockwell St). This season, a new lakefront dock at 400 East Monroe Street will offer private Cycleboat cruises. How does it work? Cruises are booked by the hour for electric boats and yachts, and 90 or 120 minutes for Cycleboats. Though each boat can be operated by the party (so long as drivers are 21+), captains and accredited tour guides are available for hire (at $75/hour each, with a two hour minimum). Any tips? To enhance the experience, bring along some sailing accompaniments like décor and playlists (a Bluetooth speaker is aboard every vessel). All cruises are BYOB for food and drink. Why should we go? Consider these cruises an excellent chance to round up that group of friends or coworkers for a low-key eve on the water—it just may be the perfect way to escape the city while still taking it in." - Nicole Schnitzler