Windsong Charters

What an amazing experience! The boat was absolutely beautiful, clean and well maintained. Krystal and Darren were wonderful, kind and helpful. They made us feel welcome. My only regret is not doing a longer charter. 10/10 would recommend.

I can't say enough positive things about Captain Dave and his First Mate, Krystal. It was a reunion day with my cousins, and it was perfect. Smooth boating, well thought-out route in and around the Annapolis harbor. Boat was clean and well organized. Only accolades from all my family members. Thank you!

Boat rocked. Would follow wherever you dock.

I cannot speak more highly of my experience with Windsong Charters - 10/10! I had originally booked a different boat for my bachelorette party and they cancelled on us the day before, but it turned out to be the BEST blessing in disguise!! The crew was absolutely fantastic (super chill, fun, clear, accommodating, the list goes on) and the boat was beautiful and stocked with floats and anything you may need - even two adorable french bulldogs on board! We had the most phenomenal time - THANK YOU!

Great boat, captain and crew!

Amazing trip!

Our party had an amazing time out on the water with Captain and crew. Would definitely recommend this boat to anyone looking for a great day out on the water !

Fabulous day with fabulous crew (Kristal and one other) and Captain Derek. They were amazing from beginning to the end. Highly recommend!!! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ Great boat with really fun water toys…snorkel, floats, paddle boards, etc… such a fun day for my daughter’s 21st birthday with her friends!!!

We had an amazing time! Kristal was quick to respond to our day-of request for a charter. Great hospitality and even included complementary sparkling wine. The boat toys were fun and relaxing and just what we needed to have a great time. We will definitely book again!

Very nice experience and very professional crew. Looking forward to do it again

Beautiful boat, excellent crew, adorable dogs, family and I had a great day on the water!

Amazing boat, perf for our bachelorette party of 9. Put simply, it was just a total blast. And cutest seafaring dogs ever.

I had an incredible time on the 50' catamaran! It offered ample space for everyone, including those less comfortable with the water. The design featured multiple lounging areas, ensuring comfort whether you’re swimming, using the standing boards, or just relaxing. The catamaran’s layout made it easy to enjoy both the sun and sheltered spots. Highly recommend for a luxurious and versatile boating experience. Thank you for making our day unforgettable!

The boat was super spacious and filled with an array of water toys that were a crowd favorite at my sister’s bachelorette party!

Great time. Wonderful captain and crew. Woukd definitely book again

Late writing this review (sorry!) but our group had an amazing experience! The boat was clean and had everything we could need, the dogs were friendly and adorable, and the communication was very timely and reassuring considering we were dealing with some bad weather! I cannot wait to use this boat and captain again!

Great boat and great crew.

This was an incredible experience. The captain and crew made sure we had everything we needed, brought us to a lot of cool and fun spots, and having the adorable dogs was a bonus. It was the perfect day and cannot thank you enough!

Great experience on a beautiful boat with 2 of the cutest puppies in the area. Highly recommend booking with them.

Clean full amenities lots of extras very relaxing, smooth sailing

We had a ball on the boat. Everyone was extremely professional and accommodating. It was the highlight of the bachelorette weekend! We can’t wait to come back!

We chartered on May 17th 2024 for a bachelor party From start to finish, this charter was top notch. From the catamaran to the captain to the staff. The boat was spotless, the crew and captain were the Best. If you want to have a great day on the water, you wont be disappointed with Windsong Charters

The boat was awesome - plenty of room and lots of fun things to do.

The best boat day ever!!!!!! We rented this boat for a bachelorette party and they took such great care of us! We sailed and swam and had the best time! 10/10 will be back!

Our experience on this catamaran was amazing! I did a 3 hour rental for my husbands birthday and I can't wait to do it again. We took a water taxi to the boat Saturday morning and was immediately greeted by an extremely friendly crew, they even put up a happy birthday sign! We loved everything about our time on the boat, the only thing I regret is not booking for a longer time slot. If you're debating booking, just do it, you wont regret it!

We rented this boat for my sister's bachelorette party and had the BEST time! Seriously it was the highlight of the weekend -- especially Frankie and Sammy! Cannot recommend this crew enough -- everything was perfect.

I cannot say enough great things about our boat day with Jamie & Kristen!!! We booked this boat for our friend’s bachelorette party and it was absolutely perfect. Jamie and Kristen went above and beyond to make our trip soo much fun! The boat is huge and has a ton of space to lay out, a huge kitchen and table space, and lots of fun water toys like paddle boards and floats. I would 100% book again & hope to be back soon!!

captain was knowledgeable and friendly. wonderful trip

Nicely equipped with water toys. Comfortable seating options for a variety of people.

My group had the best time with Windsong Charters. Everything was exactly as described and we had a wonderful day. Whether it was the ample, high-quality boat toys, the adorable little ship pups, or the extremely friendly and warm boat crew, it was all amazing. We will be back!

I had a great experience being on this boat for my Birthday! Not only with my friends but Deren the captain,Kristal and Abby took great care of us. I felt very welcomed and appreciated of their service. I recommend to book with them for your next celebration. 10/10 would book again

I’m not sure we’ve ever had a more perfect Saturday! Captain Deren and Kristal were delightful, kind, and let us build our own adventure. Want to be chill, and just float around? This is the place for you. Want to sightsee? Yup, they’ve got you. Want do be a daredevil and jump off the top? You can do that too! A combo of both (what we did) they are more than willing!

This “back to school” adventure was the perfect combination of relaxing and adventurous for us. Extremely reasonably priced and

Great professional crew and captain

We enjoyed ourselves! A great time was had. I will be renting again. Thank you!

We had the most amazing day on our chartered boat ride! Captain John and Jason were absolutely fantastic — professional, fun, and incredibly attentive from start to finish. Captain John made everyone feel safe and relaxed while still keeping the energy high, and Jason went above and beyond to make sure we had everything we needed.

One of the highlights was stand-up paddle boarding in the most beautiful, calm water. They made it easy and enjoyable for everyone, whether you were experienced or tr

We couldn’t have asked for a better charter experience, Captain Deren and the entire crew were excellent!

Thanks for everything. From greeting us at the dock, to stepping onboard and our day on the boat was top notch. Great for families. Tons of things for kids to do while we set sail. See you guys soon

This was the BEST boat charter ever!!!! Will absolutely be using again. Comfy shaded area, plenty of room. Crew was absolutely amazing! 10000% recommend

It was the best time. Crew amazing !!!!