1. Sail Escape with Classic Captain (...and boat!)
  2. Sail Escape with Classic Captain (...and boat!)
  3. Sail Escape with Classic Captain (...and boat!)

Sail Escape with Classic Captain (...and boat!)

2 bookings

Welcome aboard my lovingly restored 38' sailboat in America's Sailing Capital. Rates: I offer private 3 hour tours twice daily tours daily and a 2.5 hour sunset sail every day or customized trips just for your party. SIX GUEST MAXIMUM! The price varies by number of person and weekday or weekend/holiday. What You Can Expect: Enjoy a FUNtastic sailing escape with a locally-grown skipper who grew up boating right here on these waters. It's not just a sailing adventure, but a real Chesapeake experience with your captain who will share his experiences on the Bay with you. Just 35 miles east of the Nation's Capital in historic Annapolis, "Non Sea Quitter" is perfect for mini-escapes and longer trips. This is a professionally full-time service now in its fifth season. The boat is fully insured for tours, meets or exceeds all Coast Guard regulations and is always operated by your highly skilled and Coast Guard licensed Merchant Marine Officer. We offer sunset sails including overnight stays at our resort marina with pool. "Non Sea Quitter" is easily accessible with ample parking just minutes from downtown Annapolis. We also provide advanced cruising, navigation/seamanship training and consulting.

Captain is included.
A captain is provided by the listing owner to host and operate the trip.
6 guests
Cruising Monohull


With over 40 years of boating experience my goal is to help you realize your boating dreams and I do this mainly by taking you and your private party of up to six guests out for FUNtastic and relaxing sailing tours from Annapolis on Chesapeake Bay. I've cruised tens of thousands of miles on hundreds of different sail and power boats from Maine to Florida, the Bahamas, Virgin Islands and Gulf of Mexico. Each season I take hundreds of happy guests out on the Chesapeake. I hope you'll join me.

Check Availability

March 2021
April 2021
May 2021
  • Select a date to check availability.

Features & Details

  • Life jackets/required safety gear
  • Cabin
  • Wheel steering
  • Inboard Engine
  • Dodger
  • Single Engine
  • Fuel type: Diesel
  • Inverter
  • Berth
  • Head
  • Furling Headsail
  • GPS

Approximate Location

You’ll get directions to the departure location when you make a booking.

The boat's approximate location on a map

Cancellation Policy

90% refund up to 14 days prior.

Additional Terms & Information

I offer only CAPTAINED charters and the prices shown include those services and all taxes. This is a full-time professional service and the boat is always operated by a licensed mariner in accordance with federal law. The boat is documented for coastwise trade and is fully equipped and insured to carry passengers for hire. The maximum number of guests is six. No illegal drugs or marijuana are allowed. A full deposit is necessary in advance and if severe weather causes a cancellation, we issue a raincheck for rescheduling. A partial refund may be provided at our discretion if guests are unable to reschedule. Overnights aboard are only allowed when guests are reserving the sunset sail. Please provide very specific details about your desired trip and I will provide you with a quote.

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