Gliding across Lake Michigan, the sailing party watches the sun sink beneath the Chicago skyline. As the last rays fade from view, the city's skyscrapers throw their light onto the lake's surface. The captain steers the ship past Grant Park and Millennium Park, and then veers out toward Navy Pier, where the ship's passengers find a prime viewing spot for the Saturday-night fireworks show.
In addition to charters like these, the captains of Go Sailing Chicago—all holding US Coast Guard Master Captain licenses and certifications from the American Sailing Association and US Sailing—furnish beginner through advanced sailors with sailing gloves and life jackets before leading hands-on instruction in proper seamanship. Launching from DuSable and Monroe Harbor, and sometimes other points along the lakeshore, Go Sailing Chicago's four-boat fleet meets or exceeds the safety standards set down by the USCG and the most persnickety of ship-in-a-bottle builders.
With about a decade's experience in starting up rowing clubs across the country, Row America is well versed in bringing the sport to a new audience. Its introductory Learn to Row classes teach sculling and other techniques to beginners whose only watercraft knowledge may have come from watching old Love Boat reruns. But Row America also serves more experienced athletes, who may dream of competing in the Olympics like founder Howard Winklevoss's sons did in 2008, with clubs for high schoolers and adults.
In 1935, Albert Borgstrom, a Swedish immigrant and carpenter by trade, set about constructing a 65-foot wooden yacht. He named the ship The Wendella and charged visitors $0.25 to ride through the city and listen to a guide expound on the sights. This simple vessel ended up being a steppingstone, and 75 years later, guests still ride along, now craning their heads back at the jagged opalescent silhouette of Trump Tower and the beehive curves of Marina City. Beneath the evolving skyline, the fleet has expanded to six vessels, which are now run by Albert's grandson, Michael Borgstrom. Wendella staffs a dedicated, in-house education department to keep the city's history alive and make sure that people continue to believe in water so it doesn’t disappear. On special excursions, the crew stocks the boats with wine for tastings beneath the stars or points the vessel through the verdigris waters of the lake to watch evening fireworks shows.
The party-loving minds behind Yacht Party Cruises wanted a creative way for locals and tourists to explore a city's late-night atmosphere. Eventually they launched a fleet of luxury yachts into the waters of eight of North America's most lively urban waterfronts. On each vessel, festivities abound as DJs spin everything from hip-hop to Sinatra, inviting passengers to shake a leg in between trips to the full bar or buffet lined with hot appetizers. All yachts boast extravagant details such as wraparound decks, fireplaces, or a glass atrium that hangs above the dance floor offering dancers a direct view of the man in the moon's game of solitaire. Guests can also step onto the decks for fresh air or panoramic views of city's skyline.
Shoreline Sightseeing has been whisking passengers along Lake Michigan since 1939. Traveling down the reverse-engineered Chicago River, Shoreline’s architecture tours explore the history of the city’s landmark buildings—from the Great Fire of 1871 to the work of famed architects Mies van der Rohe and Jeanne Gang. Colorful bursts illuminate the sky during fireworks cruises, and nighttime tours allow for glimpses of lit-up buildings. Skyline tours drift into Lake Michigan, giving passengers a chance to espy the whole city, and water taxis connect visitors from one destination to the next, speeding between Navy Pier, the Museum Campus, and the Willis Tower.