Charter a sailboat from Belmont Harbor

Outfitter Chicago Sailing

Details Choose from a fleet of 23 sailboats that can accommodate up to 12 passengers.

What you get Wind in your hair, an iconic skyline, and a professional captain to keep you in line (and onboard)

Wallet damage $525 to $735 for a three-hour daytime sail depending on boat size; $90 a person or $150 a couple for a fireworks sail on Wednesdays or Saturdays

Tip Don’t be that guy with black sneakers and a bottle of red. White soles and white wine only.

Standup paddleboard at Kathy Osterman (Hollywood) Beach

Outfitter Chicago Paddle Co.

Details: Rentals (including board, paddle, leash, and life preserver) are first come, first served. If you’re more of a pack person, you can reserve a spot in a group trip, like Rise & Grind, the popular sunrise paddle followed by coffee on the beach.

What you get: A serene trip and a killer tan

Wallet damage $30 an hour

Tip Roll with it. Literally. The less you fight for control of a wave, the less likely you are to demonstrate your best belly flop.

Kayak or canoe the Skokie Lagoons

Outfitter: Chicago River Canoe and Kayak

Details: The Winnetka boat launch is on the south side of Tower Road, just west of Forestway Drive.

What you get: A self-guided escape (boat, paddle, and life vest included) from the city, with wetland wildlife galore

Wallet damage: $15 an hour for a single kayak; $20 an hour for a canoe or tandem kayak

Tip: Keep an eye out for a pair of bald eagles nesting across the river from the launch site.

Reel in a big one on Lake Michigan

Outfitter: Endorfins Charter

Details: The 53-foot Diazepam holds six passengers and departs from Montrose Harbor daily.

What you get: Captain John Oberman’s boat is bigger, faster, and decked out with more swanky marine electronics than other local charters. Or so he says.

Wallet damage: $1,000 for six hours. Those state-of-the-art fish-finding radars don’t come cheap.

Tip: Captain John will tell you to take motion sickness prevention pills the night before the trip. Do everyone a favor and listen to him.

Scuba dive at a shipwreck

Outfitter: Windy City Diving

Details: A 34-foot catamaran for up to six certified divers leaves from Burnham Harbor for half-day weekend trips 10 miles offshore.

What you get: Titanic vibes, thanks to more than a dozen wrecks, including the Buccaneer, a 1925 merchant ship 72 feet down

Wallet damage: $130 a person for a two-tank dive

Tip: Don’t go expecting to see pretty fish. They aren’t the main attraction here.

Jet Ski at 31st Street Harbor

Outfitter: Chicago Water Sport Rentals

Details: Before jetting off, you’ll receive an orientation, a life vest, and—by request only—a wetsuit.

What you get: A view you won’t forget—perfect for a #humblebrag selfie

Wallet damage: $99 to $125 an hour

Tip Look for the LED billboard truck parked on a barge floating in the harbor that broadcasts Cubs or Sox games.

Party on a yacht out of Belmont Harbor

Outfitter: Chicago Party Yacht

Details: The 60-foot Martini (up to 35 guests) runs daily private trips.

What you get: Basically anything you want. This is a choose-your-own-adventure cruise helmed by a licensed captain.

Wallet damage: BYO and a three-hour minimum for $2,600. Catering packages and holidays are extra.

Tip: You can live out your spring break fantasies at the booze-soaked spread of docked boats (i.e., the Playpen), where you get a front-row seat to the best parade of butts in town.