Jake

4.9/5 stars 41 reviews
  • Phone Verified
  • 20
    Years Boating

About Jake

“I am a former Merchant Mariner holding a 2nd Mate Unlimited License. I grew up sailing dinghy sailboats and previously owned and lived aboard a 36ft. cruising ketch which I cruised from New England to the Bahamas. My Lippincott 30 Sloop is sailed on the Chesapeake Bay and is at a marina on the West River in Galesville, MD. I have enjoyed getting boaters on the water in my two years with Boatbound and have met lots of great people through this service. ”


Aboard since 2014

From Shady Side, MD

Reviews of Jake (41)


  • Great boat and a beautiful sail. Jake and his wife were terrific hosts and took the time to get us comfortable with the boat in advance of our sail. We'll definitely plan to do this again.


  • Fine experience overall! Would’ve loved more wind. Jake (10)- on time, thorough, easy to contact and work with. Shady Lady (8)- comfortable, easy to operate with a great headsail; a little tired.


  • Jake's boat is great for the bay and is a great guy to rent from


  • Jake was an incredible host. He did a great job explaining all the details of the boat, was super responsive, and was flexible on scheduling. We had a great experience and a great time on the boat!

    The Lippincott 30 was perfect for an overnight sail with 4 people. Given its size, I wouldn't try to sail with more than 4 adults. The amenities were simple, but all you really need for one night!


  • Excellent sail; excellent skipper.


  • Nice boat in great location. Boat was clean, well equipped and sailed great. Jake was accommodating, gave a thorough overview of the boat, and quickly got us on our way.


  • Beautiful boat in great quiet marina - perfect for the bay!


  • Awesome owner, boat, and trip. Highly recommend.


  • Great boat and great trip. Jake was accommodating, easy to work with, and gave us some great advice on fun destinations.


  • Excellent sail in good wind. Shady Lady is a solid sailboat, steady and easy to keep on track. Jake's guidance on operating the boat is thorough, very helpful, and provided in a very friendly way. Great host and a lively sail.


  • Great experience! Shady Lady is a great boat and Jake offered tremendous support for our sailing experience!
    The boat was in great conditions when we got it and everything worked well during the 2 days we had it.


  • We had a wonderful experience wth Jake and Shady Lady. The boat is very well equipped and Jake was able to give some great advice on local spots to stop. I would highly recommend taking Shady Lady out for a trip on the bay.


  • Jake provided us nice boat. He gave us a comprehensive and clear briefing about the boat and a hassle free rental process. If you are lucky enough to rent this boat, make sure to have enough time to drive to Shady Side. Pier is easy to find, but roads are a bit slow to travel.


  • Judd showed up on time and took the time to take me through the boat controls and where all the safety equipment was stored. Boat runs well and is big enough to handle chop on the bay. All in all a great experience and
    would rent from him again anytime.


  • Had a great time on Jakes boat. This is boat is fast for a 30 footer. Everything worked as advertised. Looking forward to next years rental.


  • As always Jake and the Shady Lady were top notch!


  • Jake was very friendly, accommodating, and had good recommendations for locations to sail to. The sailboat was wonderful and was exactly what we were looking for. I would def. recommend Jake and his boat to anyone.


  • Jake, Thanks for the use of your boat "Shady Lady".
    You have a well equipped safe boat and give a great orientation.
    We Had a blast and appreciate being able to step on a boat and GO!
    We enjoyed Annapolis and an overnight on the hook in the bay just north of your home harbor.
    Hope to use your boat again.
    Thank You!


  • My family and I had a great experience chartering from Jake. He was patient, flexible and laid back, and gave me and my wife a helpfully thorough briefing of his boat. He also suggested an excellent anchorage on the Rhode River, which was protected from the elements and perfect for a paddleboard excursion to a small island he pointed out on the chart. In the morning - after a nighttime thunderstorm - he was thoughtful enough to motor out to check on us. Thanks, Jake!


  • Jake was great. He met with me and showed me the boat. He answered all my questions. We sailed out the West River and into the bay and then anchored in the West River for a few hours and relaxed. We had a great time. The motor and sails worked flawlessly. If I was pressed to complain about anything it would be that bottom of the boat needed to be cleaned. Would definitely rent again.


  • We had a fabulous day on Jake's Sea Chaser. He met us on time and went over the boat's operation. The Sea Chaser is a great boat, very clean and operated well. We cruised the Rhodes River around the Smithsonian Environmental Research Center and then down to Deale for lunch on the water. The Sea Chaser was a great boat, easy to operate and comfortable for four of us for the day. Jake was extremely easy to deal work with, communicated well and was very personable. We really enjoyed our day. We would highly recommend renting from Jake.


  • Great boat and superbly outfitted for cruising the Chesapeake! My family (four of us) and I did mostly day sailing. We were comfortable on this roomy and well outfitted boat. Jake gave us a great orientation, everything was east to find and very functional. Boat is easy for one person to sail and in great condition. Galesville is a great central location to explore north and south along the Chesapeake. Would love to rent this vessel again anytime.


  • Awesome location, awesome boat, , awesome owner. Jake met our party at the docks, on time. The boat was clean, in good working order and made for a fun cruise around the area. On our day on the water, we traveled up the Rhode River, back out into the Chesapeake and up past the Annapolis Naval Academy. Jake again was back at the docks, on time, to when we returned the boat. Highly recommended.


  • Jake and the Shady Lady were perfect for our cruise. We spent 4 days on the Chesapeake Bay, dropping anchor in Annapolis, St. Michael's Bay area and Rhode River inlet. The Shady Lady was more than equipment to handle the sleeping, cooking and BR facilities. The genoa and mainsail were more than enough to handle the various wind we encountered. The second night a short squall rolled through but the Shady Lady held tight, and the rest of the trip we didn't worry about the anchor at all. Great boat, great owner. I recommend this boat.


  • Once again, Jake and the Shady Lady do not disappoint! We had an absolutely lovely time cruising the Eastern Bay over July 4th weekend. We spent two nights at anchor grilling out on deck and watching the fireworks all across the horizon. The Shady Lady had everything we needed for the trip. Jake had a few maintenance challenges prior to our trip (sails needed to be repaired), but he was very communicative about the situation upfront and offered to refund our money if we wanted to cancel instead of play it by ear. We'd been looking forward to the trip all summer and didn't really want to cancel, so Jake worked hard to coordinate the repairs despite being out of town on vacation, so that we could go on our 3-day Chesapeake cruise as planned. He got a friend to pick up the repaired sail and drop it off at the marina and was on-call to help us make sure we had the Genoa rigged properly.


  • Couldn't ask for a nicer boat or a more accommodating owner. My first time on a Lippincott 30 and I was impressed by how roomy and well designed it is. We hit some fairly rough weather coming back and she felt solid and confidence-inspiring. Jake went out of his way to make our trip go smoothly on very short notice. We'll be back.


  • A wonderful day on the water! Jake was responsive, punctual and extremely helpful. He even kept the boat in the water an extra few days to allow us one last sail before season's end. We'll definitely see Shady Lady again come springtime!


  • My brother and I took out Shady Lady for a weekend in October. The boat was clean, well appointed, and fun to sail. I highly recommend working with Jake who was most accommodating to our needs. Also, the location works to get out to the Bay in a reasonable time and close enough to go to St. Michaels, Annapolis, or even Oxford. Enjoy! Jonathan


  • This was our second 3 day rental of Jake's Lippincott 30 sailboat. We liked it so much last year, we decided to do it again this year! Well, as last year, it was a very good experience.

    The boat was in very good shape, and Jake met us at the dock at the agreed upon time. He also answered all our questions, and offered that we could call him anytime if we had questions during our trip. We will definitely rent this boat from Jake again!


  • The Shady Lady is a comfortable and clean sailboat in great condition.
    The sails are in great shape and she has a nice cruising genoa.

    Her owner Jake was great and very helpful.
    I was interested to book his Shady Lady on short notice for the weekend and it was not a problem. Jake was very responsive and flexible to make it happen.
    Shady Lady is well equipped with everything what is needed for a pleasant journey on the Chesapeak Bay. The grill works great and we had an awesome BBQ in the evening.

    I can highly recommend renting Shady Lady from Jake and I am looking forward to chartering her again!


  • The Shady Lady is such a solid boat. Clean, tidy, comfortable, and we'll appointed. The owner, Jake, was fantastic throughout the entire chartering process. He was communicative, pleasant, available, and professional. I look forward to chartering Shady Lady again and recommend this boat and owner to all Boatbounder's!


  • Both the Shady Lady and her owner Jake were fantastic! Jake provided helpful advice in advance about possible destinations for our weekend cruise, then met us at the dock on Saturday morning to go over everything. The Shady Lady was just perfect for a weekend with two couples aboard. She's an older boat, but very well maintained with a new engine. We had good wind and sailed nearly the entire time, turning on the engine only to dock and anchor. Jake has all the things you might need aboard, including a gas BBQ grill which makes for a perfect summer dinner on the water. We'll definitely be renting from Jake again.


  • Absolutely great boat. I have been on a few cruisers with various friends and I can say that this is a rare, well-organized gem. Everything is in its place and everything works. Jake's pre-rental briefing was extremely thorough and the boat is equipped to handle all manner of bay cruising. Jake offered many welcome recommendations and advice. He carefully answered all my questions beforehand and remained attentive to our text messages throughout our cruise without being overbearing.

    We were aboard for three days around the bay and two nights at anchor. We even managed to time our arrival to St Mikes to join our friends for lunch at Foxy's! We comfortably slept four below the first night and two below + two in the cockpit the second night. Knowing how comfortable sleeping along each side of the cockpit was, we could easily sleep six in separate bunks next time.

    My crew had nothing but praise for Shady Lady's equipment and comfort. Our favorite accessories were the propane grill on the stern and the sun shower for taking hot showers on deck after a dip in the bay.

    All in all, it was a perfect Boatbound experience and I look forward to renting this boat from Jake again in the future!


  • We rented the Shady Lady for 4 days and our trip couldn't have been better! First, a big thanks to Jake for the suggestions on where to go. We are not from the area but Jake gave a few ideas of where to go. We ended up sailing to Annapolis, which was fantastic and also spent two nights on the hook in the Rhode River. The boat was in the exact condition that Jake describes (which is very nice) and Jake was just a phone call away when we had questions.

    We used an Iphone and Garmin Bluecharts for navigation. There are paper charts on board.

    The Shady Lady sailed well, even when blowing 15-20 knots. We ended up using just the headsail and she was under full control.

    I would highly recommend renting from Jake and hope to be back next year!


  • We truly enjoyed sailing on the Shady Lady. From Galesville, the Bay is easily accessible. The vessel was clean and in great condition. Jake was very helpful and answered all my questions. The marina has a nice restaurant with facilities as well. Overall, it was an excellent experience which I hope to repeat soon!


  • The Shady Lady is a old graceful lady. She will sail faster than she will motor. It did not use a lot of diesel for our 5 day trip. There are many small modifications Jake made to make things a little easier like loop fasteners at the mast and by the winches to easily hold that extra part of the halyard and sheet. Keeping our electronics charged was easy with his supplied 12volt usb charging port. The anchor held well and I was surprised how clean it came up ie not covered with muck. The head took some getting used to. There is wind sock in the V berth and 2 screens to cover the hatches for mosquitoes


  • We had a great time. Jake was extremely helpful and friendly, and recommended a great anchorage. Looking forward to renting with him again.


  • I highly recommend renting the Shady Lady from Jake. The boat is immaculate, very well kept up, and sails perfectly. Jake did a great job of orienting me to the boat, and my daughter and i had a great day sailing around Chesapeake Bay. I am really looking forward to renting from Jake again, hopefully next time for a multi-day trip.


  • We had a great sailing weekend on the Shady Lady. This is a great boat, very well maintained and that does well under sustained wind (20 kn). She is well equipped too.
    Jake is a very helpful and responsible owner in addition to being a very pleasant person. Last but not least, Galesville strategic location offers a lot of great sailing options, North, South or Eastern shore of the Bay. I’m looking forward to my next sailing adventure with the Shady Lady!


  • I just got back from a great 3 day rental of the "Shady Lady", Lippencott 30. It was an excellent experience all the way around. The owner, Jake was very prompt, and helpful with pre-trip information and planning, and gave a thorough training and practice sail the morning of the rental.

    The boat was in great condition, and sailed and motored well. One note is that it does not have a Chartplotter on board, so bring your hand-held or favorite phone marine navigation app (Mine is Navionics for the IPhone and it worked well) to keep away from the many shoals in the Chesapeake.

    The Shady Lady was a really nice base for an extended cruise across to St. Michaels for the 2 of us. We heartily recommend the Shady Lady, and will definitely come back again next year for more bay cruising!


  • Had a great experience on the Shady Lady. The morning of our rental the boat was prepped for us and ready to go and Jake went above and beyond to ensure we were comfortable with every aspect of the boat. I'd absolutely recommend the Shady Lady to anyone interested in renting a very well maintained and easy to handle to handle boat. She was truly a pleasure to sail and we definitely intend to rent from Jake in the future!