Whether you opt for the classic nautical decor of the Anita Dee I or the Art Deco design of the Anita Dee II, your private charter (able to handle 50-400 passengers) will navigate the lakefront in opulent style. Both yachts boast formal, enclosed dining decks and roomy dance floors perfect for corporate outings, and the Anita Dee II features a grand piano at salon level and a helipad on the observation deck. Rates run $875-$2,325 per hour, subject to increase for summer holidays and special events.
Many cruise lines offer architectural and historical tours of the city, but Chicago Line Cruises was the first to employ expert docents, beginning in 1982. While the guides educate, passengers enjoy complimentary Starbucks coffee, lemonade, fresh-baked muffins and cookies as they wend through the city's waterways. Docents are also available for group tours and private charters for an extra fee. Adult tickets cost $32.
Once a winning member of the Australian Admiral's Cup team, the 53-foot Bumblebee racer now hosts up to 40 passengers for memorable private charters. She's the newest addition to the Chicago Sailing Club, which steers sailboats ranging from fleet J/22 keelboats to the stately 47-foot cutter Parvenu. Seasoned hands can rent a vessel for a day out on the water, while greenhorns get up to speed with comprehensive instruction. But anyone is welcome at the club's Tuesday Night Barbecue where like-minded enthusiasts socialize over burgers and brats. Rentals are $45-$125 per hour, $75-$650 per hour for charters.
Just past the blue awning at the Michigan Avenue Bridge you'll find comprehensive architectural tours certified by the Chicago Architecture Foundation. When the First Lady fleet isn't ferrying travelers up the river, the ships often double as floating chapels. The dock's convenient proximity to downtown hotels makes it a popular choice for rehearsals, receptions or wedding ceremonies framed by the sparkling city skyline. Architectural tours cost $26-$28, and private cruises run $740-$990 per hour.
What else could you name a 96-foot luxury yacht but El Presidente? This lavish vessel served as a patrol boat during World War II and has since hosted several U.S. Presidents, including Roosevelt, Kennedy and Clinton (even Nixon made it aboard). The teak- and mahogany-trimmed salon still sports many of its original furnishings, as well as gifts from foreign heads of state. El Presidente is available for private charter at $2,800-$3,200 for a three-hour tour, but also hosts a $95 Sunday Brunch buffet catered by Taste America.
On the 36-foot sloop Crescendo, passengers can relax as they trawl the lake or man the helm themselves. For those who don't know a jib from a jigger, qualified instructors offer sailing and racing courses for singles or groups on Saturday and Sunday mornings. The less athletic can board the 77-foot schooner Red Witch for Friday Night "Whale Watching" (Happy Hour) or Music Mondays where folk musicians regale guests with live ballads, sailing lore and sea-shanties. Charter the six-passenger Crescendo for $140-$165 per hour, bring plenty of friends on the Red Witch for $300-$675 per hour, or grab special event tickets for $35-$175.
Ever wonder how the Chicago River Lock operates? Mercury Chicago's Urban Adventure Cruise hits the usual architectural high points, and then steers curious sailors through the lock system to show them how it works. In addition, the crew offers a few unusual options like Richard Crowe's Supernatural Cruise and the Canine Cruise, a dog-friendly excursion complete with water bowls and a newspaper-lined head. No reservations are necessary, so stop by and see if you can guess which boat Vince Vaughn captained in "The Break Up." Adult tickets cost $20-$39.
Instead of more take-out in front of the TV, try Mystic Blue Dinner Cruises for a change of scenery. As the sleek 160-foot 500-passenger vessel sails north, enjoy a three-course meal at your private table, prepared onboard daily and served buffet-style. At midnight on Fridays and Saturdays, the luxury liner transforms into an aquatic nightclub where DJs flood the decks with hip-hop, R&B and dance mixes while partygoers pick at finger foods. Grab a seat or spot on the dance floor for $25-$80.
Sister ship to the Mystic Blue, the Odyssey offers similar brunch, lunch and dinner options, only jazzier. Rather than DJs, this 700-passenger vessel spices up its meals with live piano, show tunes and swing and jazz standards compliments of the Mike Frost Group. After enjoying your roasted duck confit to the bopping strains of Coltrane, don't forget to wander by the Captain's bridge, open throughout most of the cruise, and say ahoy to the skipper. Get tickets for $50-$107.
You've done dinner and disco cruises, absorbed our rich architectural tradition and even tried your hand at sailing. So what's left? Ply the lake with Captain Eddie Landmichl on one of his relaxing fishing expeditions. Cast your line for Coho Salmon, Chinooks or Lake Trout and rest easy knowing that Landmichl has 35 years experience on his side, so the big one will have to work that much harder to get away. All equipment is supplied, and back at the pier he'll even clean and ice your catch for you. Outings cost $600 for a half day or $780 for a full eight hours.
Sometimes you want to ogle the city skyline at a leisurely pace; other times you just want to go fast. Thank goodness for SeaDog, whose ships sport 2000 horsepower turbo-charged engines that whip you down the shore at a frantic 30 knots. They move so fast, in fact, that tours depart as often as 50 times a day. A word of warning: Choppy waters can make for a wet ride, and eating at top speed is discouraged, but you'll be having too much fun to care. Tickets cost $20-$30.
For those tired of flagging cabs in downtown congestion, Shoreline Sightseeing operates river taxis with frequent departures from Navy Pier to the Sears Tower, Equitable Plaza and Shedd Aquarium. In addition, seafarers can board for seasonal specials like the Halloween Floating Hayride, The Octoberfest Lunch Cruise and the Mackinac Race Cruise, which catches yachts at the start of this traditional 333-mile course. Toast to Tuesday outings with hors d'oeuvres, music and a cash bar let weary workers cut loose well before Friday rolls around. Taxi tickets run $3-$13 and architectural; lake tours cost $14-$29.
The 600-passenger Spirit of Chicago serves up lunch and dinner buffets with a Broadway twist. After the plates have been cleared, diners are treated to "Red Hot Rhythm and Blues," a live musical revue of pop and Motown hits followed by DJs and dancing. Tailor your unique trip further with enhancements like the Wine and Cheese Package or the Sweetheart Package with champagne, souvenir glasses and a half-dozen roses for a night your significant other won't soon forget. These melodic cruises cost $60-$112, plus a reservation processing fee.
It's hard not to feel like a swashbuckler aboard Chicago's official Tall Ship Ambassadors, the Windy and Windy II. Both of these 150-foot four-masted schooners sail on skyline cruises, and captains even let guests trim the sails and take the wheel (no word yet on swabbing the deck). Besides tours and private charters, the Windys offer week-long sea camps for ages 15-22 where deckhands get an in-depth look at the mariner's life, as well as pirate-theme cruises with cannons blazing. Start your adventure for $27-$45 or charter a tall ship for $2,195-$3,195 per hour and a half.
Wendella Boats began giving guided tours of Chicago's river and lakefront in 1935, possibly making it the city's oldest sailor. Since that one boat operation, it has expanded to include a Chicago at Sunset tour that takes in the Buckingham Fountain Water and Lights Show, wine tasting tours catered by Kafka Wine Company and a busy RiverBus fleet. Ferry docks abound at Madison Street Bridge, Reid-Murdoch Center, the Wrigley Building and River East Plaza. Adult tickets cost $22-$57 and RiverBus rides $2.
