Cruise or Race on the Chesapeake Bay on this Fast Sloop

 5.0 (4)

Cape Fear 38 (2002)


  • 38 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 and experience the beauty of the Bay as you glide through the water. 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.


  • Manufacturer
    Cape Fear
  • 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

4 Reviews

  • Yann
    Sept. 3rd, 2023

    It was a fantastic sailing experience with Greg & Gary. We felt very safe all along and they both made us feel home on their boat. It was a beautiful family time with our kids and friends, and we can only recommend to go for it if you are considering sailing with Greg & Gary. Thank you Greg & Gary!

  • 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: 82.4%
Response time: within 29 hours
Message owner

Location and Destination Guide

Usually this boat operates around Pasadena, MD.

Home to the US Naval Academy is one of the best places to jump on board your own sailboat charter in Annapolis, MD 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.

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.