I was looking for something fun and different to do to celebrate my wife's birthday. She has…read morealways had an affinity for sailing, so I began looking for something on the water. I found the Moon Shadow website and decided to book a trip. We brought mother couple, so there were four of us, along with Captain Glen and his wife Seray for our 2.5 hour cruise. The Moon Shadow is a beautiful, well-maintained sailboat. Our hosts made us feel very welcome. Glen helped us carry the food and beverages we brought along from the gate of the marina to the dock and let us use the small refrigerator in the galley. I was invited to connect my phone to Moon Shadow's sound system by Bluetooth, so was able to play my own music for the whole cruise. We lucked out and had perfect weather- clear skies, sunshine, and a nice breeze to keep us moving. We got going pretty good for a while. Glen and Seray were nice people, friendly, knowledgeable, and interesting to talk to. Bottom line is all four of us had a great time and plan to make this an annual event!

We had a great time even though Mother Nature was not cooperating with us. Just being out on the…read morewater was worth it and the boat was amazing. Thanks for a great day! Trish

Great service and well kept boats. Christina and Braydon were exceptional and very knowledgeable. I…read moresailed the 22ft Capri with Braydon and got a great education. I highly recommend BaySail.

We had a lovely sunset cruise with Captain Dave and boy was it lovely! We brought some little…read moresnacks and sodas and just enjoyed the bay with a wonderful host! Capt. Dave really was special and if when we go again, we will be asking for him! Took our 90 year old father and 87 year old stepmom and they were so helpful with everything. Truly a class act, from the captain to the whole staff!

My husband and I were visiting the area for a weekend anniversary trip and had a last minute…read morethought to get out on the water. Sundance was awesome! Fit us in to his busy weekend...last minute...and had a great time out for a quick sail. Experienced sailor and willing to tailor the trip to whatever your experience, comfort, or sense of adventure desires. Highly recommend!

From the owner: We love introducing people to the world of Sailing via our 90 minute Sailing cruises on the Upper…read moreChesapeake Bay. Bring your family, your best friends or come solo if you like. Or if so inclined spend an exciting 4 hour trip with us and go game a better sailor.

This was so cool! Kayaking in the Inner Harbor through Ultimate Watersports…read more Julie is such a great instructor. Lessons were easy and fun. Sights are set for Floatilla!!!

First of all, I apologize for not having better pictures. I was so excited to be able to something…read moreoutdoors after all this quarentine time that the first thing I did was jumping into the water. The staff is very helpful and friendly. Everyone here is wearing mask and disinfecting from pens to life vests. Affordable prices for 1 hour of fun. You can rent paddle boards, kayaks, sailboats and windsurfing. One of the best parts of this is that I only drove 30min out from Baltimore. The water is nice, not cold at all. There is enough room for plenty of people to be either paddling or kayaking. Make time and come visit the area

What a fun time this was. Highly recommend it for anyone in the fence. We were supposed to be…read moreracing on this Wednesday evening, but unfortunately due to the weather patterns, it wasn't possible. But that is fine, we still got to cruise around out there and we had some wing pick up eventually! Great company, nice crew, overall really enjoyable evening on the water. Stay at the hotel to get a discount on the tickets as well. Thanks captain!

We had a beautiful 2 hour sail! We had a great time with the fantastic friendly crew! Shout out to…read moreDelaney for being a great captain. And sharing so much info with us! I highly recommend!

Wonderful Hosts!!! A relaxing and fun way to spend a day. From start to finish Captain Tom took…read moregood care of us, regaling us with history and tales of the Chesapeake area. He really knows these waters.

Tom was an absolute pleasure! I just needed to get out on the water and enjoy the scenery and…read morethat's exactly what happened. Tom was very hospitable and gave some great history lessons. I'll definitely return!

Overall, the experience was beautiful…read more Clean boat Great crew, all 3 crew The atmosphere was welcoming. Came with my son. He had a great time

We had an absolutely wonderful time sailing on the Epiphany with Captain Jim and First Mate Josie!…read moreThey were both incredibly friendly, knowledgeable, and accommodating, making the entire experience feel effortless and relaxing. They were wonderful with our family, and our two-year-old even got the chance to steer the boat, which was definitely a highlight for him! It was the perfect way to spend the day, and we couldn't have asked for a better crew. We will absolutely be sailing with them again the next time we're in the area.

After a (really) short hike and reading my book on the beach for a while, I wandered down the beach…read moreto the Eastern Watersports rental tent! They offer kayaks (single and tandem), paddleboards, and more. For $25, I rented a single kayak for an hour and enjoyed exploring some more of the Hammerman beach shoreline and the bay. (You can rent for longer than a hour as well, but that's all I had time for yesterday!) You have to pay to enter the park itself ($3 for state residents, $5 for out of state residents), but you can enjoy the park and then also rent a kayak or a paddleboard! Great way to explore some of the bay!

How is it that after all my years in Baltimore I just learned about this place? My wife and I have…read morebeen looking for new outdoor activities during the summer of COVID and while exploring Hammerman beach we saw Eastern. Prices on their website looked very reasonable so we decided to give it a try. Renting a Hobie Cat from here is extremely easy. I had to pass a quick check out and then it was $40 to rent a Hobie Wave for an hour. There's no setup required, you just push it off of the beach and you're good to go. I'd never sailed a catamaran before but they are fun little boats and the Gunpowder River is a very nice area to tool around in. One thing that I wish Eastern would do is make their website/facebook page a little more helpful. The first time we tried to do a cat rental we came here on a Friday evening, only to learn that they only rent the Hobies on Saturdays and Sundays. I'd tried calling their phone number a couple of times as well but it always went straight to voicemail. I'm glad that I discovered them though and my wife and I are already discussing getting a season pass next summer. Edit: Within a few minutes of my review posting I was contacted by the owner to check what phone numbers I had called. Apparently they also do rent the Hobies during weekdays in September this year, not sure what the source of the confusion there was. Still, I was extremely impressed by the prompt response and attention to good customer service.

The Escape catamaran experience is what being on the Chesapeake is all about. The 42' boat is…read morecomfortable, clean, and spacious. The crew is friendly and knowledgeable about sailing and the Chesapeake Bay. The Escape can manage any type of outing with the proper planning. I couldn't recommend the experience more highly.

From the owner: Sailing vessel ESCAPE is a 43’ Leopard catamaran chartered out of Annapolis, MD. Give us a call and…read morewe will help you plan a great ESCAPE on our beautiful yacht. Sailing on the Chesapeake Bay is an adventure you will remember for a lifetime. Charters can be as short as a half day and as long as you want. ESCAPE has four queen bed cabins and each has its own private head/shower. The salon is bright and includes a full galley and dining area. The cockpit is outside and covered with plenty of seating. And there is still the deck and forward trampolines to relax on. Our posted rates include all taxes, cleaning and booking fees, nothing is added at checkout.