1. Annapolis/Chesapeake Sail Escape with Classic Captain--and Classic Boat!)
  2. Annapolis/Chesapeake Sail Escape with Classic Captain--and Classic Boat!)
  3. Annapolis/Chesapeake Sail Escape with Classic Captain--and Classic Boat!)

Annapolis/Chesapeake Sail Escape with Classic Captain--and Classic Boat!)

2 reviews
4 bookings

Enjoy a private sailing adventure in Annapolis, Maryland-America's Sailing Capital!  Welcome aboard my lovingly restored, classic 38' . She is NOT a cookie-cutter, plastic floating condo but is a real yacht with a rich teak interior, a newly rebuilt engine and many other upgrades. Rates: We offer private 3 hour tours twice daily tours daily and a 2.5 hour sunset sail every day AND 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. Despite what the listing states, we are NOT on the Potomac! This is a professionally-operated full-time service now in its sixth season--in full compliance with Coast Guard regulations for your safety fully and is insured for up to six passengers, meets or exceeds all Coast Guard regulations and is always operated by your highly skilled and Coast Guard licensed Merchant Marine Officer. This is not a hobby or recreational boat that occasionally takes paying guests. We offer sunset sails including overnight stays at our resort marina with pool (2-4 guests). The boat is easily accessible with ample parking just minutes from downtown Annapolis.  We can answer your questions through GetMyBoat before you pay. Just hit, “Request to Book” and send us an inquiry for a custom offer--but remember we are a full-time professional operator in full compliance with laws and fully insured. We also collect and pay mandatory county taxes! Don't take the risk of sailing with a hobbyist who may or may not be licensed or insured or who is illegally taking more than six on an uninspected vessel. Before you entrust your safety--and pleasure--ask about experience and legality and insurance! 

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

Owner:Captain

With over 40 years of professional boating experience I am happy to take you and your private party of up to six guests on a FUNtastic and relaxing sailing tour 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

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

Reviews

2 reviews

5.0 out of 5!

  • Listing Accuracy

    Awesome
  • Departure & Return

    Awesome
  • Vessel & Equipment

    Awesome
  • Communication

    Awesome
  • Value

    Awesome
  • Itinerary & Experience

    Awesome
5 photos have been added by reviewers who booked this listing.
  1. KB
    Kierra

    Captain Paul was amazing. His teammate Cynde was awesome and together, they made the perfect team for a family Mother's Day excursion. Whenever I am in the Annapolis area, I will DEFINITELY be re-booking with Captain Paul, an excellent Captain and Annapolis native (and expert!) With Captain Paul, expect a beautiful vessel, intriguing Annapolis history lesson, and laughs from start to finish. Booking with Captain Paul is really your best bet. DO IT!

  2. AZ
    Ariel

    Amazing day at sea for our anniversary! Captain and crew were amazing, fun, engaging and accommodating! We will definitely be booking another trip!

Features & Details

Length
38ft
Year
1980
  • Life jackets/required safety gear
  • Cabin
  • Wheel steering
  • Inboard Engine
  • Cabin
  • Dodger
  • Wheel steering
  • Single Engine
  • Inboard Engine
  • Fuel type: Diesel
  • Dodger
  • Inverter
  • Single Engine
  • Berth
  • Fuel type: Diesel
  • Head
  • Inverter
  • Furling Headsail
  • Berth
  • GPS
  • 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 welcomed when guests are reserving the sunset sail or a full daysail. Please provide very specific details about your desired trip and I will provide you with a quote.

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