Cruise or Race on the Chesapeake Bay on this Fast Sloop


Canadian Sailcraft 40 (1992)


  • 40 feet

  • 6 guests

  • 2 cabins

  • 1 heads

  • Captained



This boat is available to charter for 1/2 days or longer for groups of up to six people. Enjoy a day or overnight sail to the Eastern Shore. Experience the beauty of the Bay as you glide through the water and anchor in a creek. Longer overnight cruises down the Bay are also available where you will visit Rock Hall, Annapolis, St. Michaels, Oxford and other areas on your trip. On the water look for the twig and stick nests of the Osprey atop the channel markers and if you're lucky you will see a hovering Osprey spot a meal diving up to a meter in depth to grab the fish in its talons. To reduce drag the fish is pointed head first into the wind as it is carried off.

Team building and racing outings are available as well. This will truly be an experience that you won't forget!

The CS 40 was designed by the famous America's Cup Designer Tony Castro. He was able to take all that he learned about performance and translate it into an excellent cruiser/racer.


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


  • Stereo AUX input mp3 hookup
  • Stove / grill
  • Autopilot
  • Radar
  • Air conditioning
  • Refrigerator
Navigation & Safety
  • Autopilot
  • Radar
  • Chart plotter
  • GPS
  • VHF Radio
  • Depth finder
  • Life jackets
  • Fire extinguisher
  • First aid kit
  • Binoculars
  • Stereo AUX input mp3 hookup
  • CD Player
  • Speakers on deck
  • Stove / grill
  • Air conditioning
  • Refrigerator
  • Freezer
  • Warm water
  • Cockpit table
  • Overnight stay

3 Reviews

  • Lauryn
    Aug. 31st, 2020

    We had the most Amazing experience with Greg and Gary on their racing boat. We all got the chance to sail and they were great with our kids. I highly recommend them.

    Aug. 26th, 2020

    It was a wonderful trip. Greg and his brother Gary are experienced sailors and did a good job letting my husband and 8-year old grandson help. I highly recommend them.

  • André
    Oct. 12th, 2015

    Great service, was friendly and hospitable the whole time even though we showed up a bit late. Have a nice big tan to remember the day by :)

Boat Owner


Member since October 2015

I've been sailing now for over 50 years an racing sailboats for 40 years. I have raced to Bermuda twice and have raced Annapolis to Newport RI. 5 times. My goal is to ensure that the folks that come out on my boat have a great time and can participate as much as they want in the sailing of the vessel to include taking the helm. When booking please feel free to ask questions so I can tailor the outing to your needs.

Response rate: 85%
Response time: within 29 hours
Message owner

Location and Destination Guide

Usually this boat operates around Pasadena, MD.

Home to the US Naval Academy, Annapolis, MD is one of the best places to jump on board your own sailboat charter and feel the ocean spray! Sailo offers a great selection of monohull, motorboats and catamarans.


Anchored deep in the Chesapeake Bay, Annapolis is the perfect place to jump aboard a sailboat and spend some time on the water. Although this isn’t the open sea, there is lots of opportunity to let the wind fill the sails and experience the thrill of sailing.

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.
Please select dates:
Boat From $580 per half day
Total* Select dates
*excludes Sailo's service fee
per half day (4h)


What type of yacht should I charter?

No matter what type of yacht you choose to charter, we know that you will have a fantastic time on the water. If you are more about the journey, and want a relaxing time aboard, then choose from one of the many sailboats on the platform. If you are more about the destination, and going fast, check out the powerboats on Sailo. For an exclusive experience, Sailo recommends chartering a luxurious yacht for the day. Finally, Sailo has access to many event boats as well for group outings from 50 - 1,000 guests. If you are still unsure, then just ask! more...

What should I bring?

Bring yourself, and some comfortable clothes suitable to the season you are going to be out on the water. Please keep in mind that it is often 10 degrees cooler out on the water, so a jacket or windbreaker is never a bad idea. We also recommend bringing a hat, sunscreen, and sunglasses, as well as a swimsuit if appropriate for your charter location. Please coordinate with your captain regarding any food or drinks that you wish to bring aboard. For term-charters, Sailo recommends using soft-sided luggage, and keeping it simple. more...

How long does a rental last?

The basic daily rental is structured as either a quarter-, half-, or full-day. A quarter-day is two hours, a half-day is four hours, and a full-day is eight hours. You can also discuss a custom trip with the boat by contacting the owner through Sailo. Most term charters (weekly rentals) are from Saturday to Saturday. Keep in mind that the boat generally needs to be back at the dock by Friday evening, and you will need to be off the boat on Saturday morning so they can prepare the boat for the next guests. more...