Affordable Private Boat Charters

Hunter Marine Legend (1987)

Captain Conway

  • 36 feet

  • 6 guests

  • 2 cabins

  • 2 heads

  • Captained

Captain Conway


We offer Chicago's premier affordable luxury boat charters. We invite private groups of up to six passengers aboard the S/V Nightswimming for two to three hours based on our guests' needs.

While on board you can watch the sun set behind Chicago's skyline or watch a full moon rise out of Lake Michigan. You can also experience the Wednesday and Saturday Navy Pier Fireworks from the front row. Want to host your corporate outing? We can do it. Want to propose to your partner on a sailboat? Perfect! The annual Air and Water Show as well as Museum Campus, Northerly Island, and Soldier Field events are some other opportunities to experience the water. Or, maybe just sail with us because it's your Sunday Funday or you're on a staycation!​

Whether it's your first time, only time, or just the next time; we want your sailing experience with us to be the best time you have this Summer.


  • Manufacturer
    Hunter Marine
  • Model
  • Year
  • Guest Capacity
  • Cabins
  • Single Beds
  • Double Beds
  • Bathrooms
  • Number of engines
  • Horsepower per engine


The owner and master is a professional mariner with over 15 years of experience as a licensed USCG Master Captain. Their career has taken them from the Gulf of Mexico to Boston Harbor to the Willamette River to the San Juan Islands and Lake Michigan ever since 2010. They have commanded vessels from 8' to 148' and everything in between.


  • Stove / grill
  • Stereo AUX input mp3 hookup
  • Autopilot
  • Radar
  • Air conditioning
  • Sonar
Navigation & Safety
  • Autopilot
  • Radar
  • Sonar
  • GPS
  • VHF Radio
  • Depth finder
  • Life jackets
  • Fire extinguisher
  • First aid kit
  • Torch light
  • Binoculars
  • Stereo AUX input mp3 hookup
  • TV
  • DVD
  • CD Player
  • USB Connection
  • Speakers on deck
  • Stove / grill
  • Air conditioning
  • Refrigerator
  • Bed linen
  • Towels
  • Fresh water maker
  • Freezer
  • Inverter
  • Warm water
  • Cockpit table
  • Electricity

Boat Owner

Captain Conway

Member since February 2023

Response rate: 100%
Message owner

Location and Destination Guide

Usually this boat operates around Chicago, IL.

Renting a boat charter in Chicago is one of the best things to do in the summer months, whether you’re planning to party or just to escape the city heat. Find your perfect private boat rental with Sailo!

Despite being a long way from the sea, Chicago offers lots of things to do out on the water.

Customer Questions & Answers

Ask general questions about this boat. For questions related to a specific booking request click here to Message the Boat Owner directly.



Cancelation policy - Standard
Full refund if renter cancels 6 days or more before the trip start date.
No refund if renter cancels 5 days or less before the trip start date.