1. Get away for a perfect weekend! Charter 44' Catalina Sailboat
  2. Get away for a perfect weekend! Charter 44' Catalina Sailboat
  3. Get away for a perfect weekend! Charter 44' Catalina Sailboat

Get away for a perfect weekend! Charter 44' Catalina Sailboat

4 reviews
5 bookings

Sail around the Herring Bay and surrounding area onboard this beautiful sailboat! Charter this 44' Catalina sailing yacht for up to 6 people. Rates as low as $590 per day. Rates: • Weekend/Holiday Full Day: $800  *** Weekday Special $590 (Monday through Thursday)*** What You Can Expect: This Catalina 445 is a very spacious and comfortable sail boat.  Perfect for four people but can squeeze six. Easy galley, two heads two spacious cabins for $800 per weekend day in North Beach, Maryland.  This vessel has all of the latest safety equipment and the USCG Captain is a certified US Sailing Coach, certified by US Safesport (https://safesport.org/) and he has the highest training for off-shore sail racing including the Volvo Ocean Race. A typical cruise would be a 19 mile sail to Annapolis for one night, 20 mile sail to St Michael for the next night, and a sail back to her slip the next. We only do day or over night charters. Three Day and Two Nights for a weekend for $2700.  Three Day and Two Nights (Weekday $2400) Your Captain is a Professional Sailor – with over thirty years of racing and over 30,000 miles of offshore racing experience and another 60,000 cruising. Recently he co-authored an article that discusses the issue of “Sending in a Second” that discuses the possibility of creating a methodology for assisting a person in the water by sending in a second crew member.  He is certified as a United Nations Field Security Coordinating Officer, UN Paramedic, USCG Captain and US Sailing Coach. These accomplishments followed service in the United States Army, 25th Infantry Division (Light) Headquarters in the Plans and Operations Cell (G-3) in Hawaii.  This is important as the Captain and the vessel meet all offshore racing safety requirements that go beyond the minimum standards.    Day rates start at six hours. If you have any questions, we can answer those through GetMyBoat’s messaging platform before you pay. Just hit, “Request to Book” and send us an inquiry for a custom offer.

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


Professional Sailor - with over thirty years of sailing and over 30,000 miles of offshore racing experience. Throughout my career I have developed safety and training protocols on vessels ranging from Panama Super Max Freighters to my favorite vessels ranging from 130 luxury sailboats, Volvo, Clipper to 40-foot racer cruisers and Swans. Utilizing my lifelong experience as a yacht racer I am training teams to prepare and compete in numerous inshore, offshore and ocean races. Recent Racing 2020 - Annapolis NOODS - 1st Place - J 35 2020 – The Hook Race – Navigator, Tactics, Watch Capt. CC 41 2020 - Heineken Regatta, Coaching, Navigator, Tactics, Volvo 65 - Sailing Poland (MAPFRE) 2019 – Down the Bay Race, Annapolis to Hampton – Velocity Racing, Catalina 445 2019 – 12 Meter World Championships175th NYYC Regatta, American Eagle, Spinnaker Trimmer 2019 – RORC 600 – Coaching, Incident Response 2019 – Heineken Regatta, 12 M, Stars and Stripes – 1st place Runners Tactics 2019 – Ft. Lauderdale – Key West, Watch Capt. – Coaching 2018 – Annapolis – Bermuda, Captain, Navigator, Velocity Racing 2018 – IC 37 – Development Program Coach, NYYC

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April 2021
May 2021
June 2021
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4 reviews

5.0 out of 5!

  • Listing Accuracy

  • Departure & Return

  • Vessel & Equipment

  • Communication

  • Value

  • Itinerary & Experience

13 photos have been added by reviewers who booked this listing.
  1. AB

    Everything was exceptionally done. Captain Jack was professional, communicative, and fun. All of my guests loved the experience and had a great day on the Bay. We will sail with him again.

  2. PK

    Wonderful experience with Jhon on his Velocity. We had wonderful day . We had lots of fun. Jhon is best Captain. We will be back again. Thanks Jhon and wife for hosting our family.

  3. AL

    We had a great day on the water with Jack! He is an absolute expert sailor with a gorgeous sailboat. He was accommodating from beginning to end and I definitely would go on his boat again. I highly recommend Jack and I am glad I connected with him through this website. Shoutout to first mate Jeff!

  4. OY

    My friends and I had an absolute amazing time! Captain Jack was an amazing host, super caring, very experienced and very welcoming. He took us sailing and took us to a beach bar and the whole day was fun from start to finish. I 100% recommend this Charter!

Features & Details

  • Wi-Fi
  • Life jackets/required safety gear
  • Bar
  • BBQ
  • Bluetooth
  • Climate Control
  • Galley Stove & Oven
  • Cabin
  • Toilet
  • Wheel steering
  • Bimini
  • Bow Thrusters
  • Autopilot
  • Chart Plotter
  • Dinghy
  • Dodger
  • Single Engine
  • Fuel type: Diesel
  • Generator
  • Berth
  • Head

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

Full refund up to 6 days prior.

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