Find The Best Boat Rentals in Rock Hall

Rock Hall Reviews

1. ML

   Martha

   50ft Catamaran Charter with Water Toys - Annapolis, MD

   We intentionally booked a late afternoon cruise around the Chesapeake so we would return around sunset to get great views and photos. Kristal was super responsive in preparing us and Captain Wayne and his 'first mate' Mish were super helpful with capturing the perfect photos. We would definitely book again!

2. JA

   Joey

   Enjoy the best views of Annapolis, MD aboard this beautiful Lydia dinner yacht

   Booked a private yacht charter along the Island Princess for 3 hours and had a great experience! Captain Steve was kind, accommodating, and knowledgeable during our journey! Would 100% recommend! Thank you!

3. 

   Elisabeth

   Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese

   Charles & Renee were amazing! We booked last minute and enjoyed an awesome afternoon on The Optimystic in Chesapeake Bay!! We can’t wait to sail again!! Charles is an excellent Captain and host. A good teacher as well! Have an awesome winter!! See you in the Spring!! Charlie, Beth and Sam (Class of 2026) ⚓️⚓️⚓️

4. DL

   Dylan

   Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese

   Had the best time. Great boat and experience. Communication,knowledge, and time was phenomenal. A+

5. 

   Megan

   Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

   Captain McCoy made us feel right at home from the start. He is incredibly friendly and welcoming, and he handled our large group of ladies very well! He is a host and a captain! The boat itself was even better than expected, and Captain McCoy helped us enjoy all the amazing amenities (the speaker, the mounted cameras for group pics, the giant beanbag chairs for lounging on the bow). We will book with him again!

6. JS

   Jen

   STARZ -Lagoon 42 Catamaran in Chesapeake Bay

   I highly recommend Chronic Sailing! We did a 4 hour charter out of Annapolis as a bachelorette party. Captain Steve and Sarah were so accommodating and made our time so memorable. We are so appreciative. They made everything so easy- from booking to sailing and making memories with us. The STARZ catamaran boat was incredible! It fit our big group comfortably and gave us a little bit of luxury as we lounged and enjoyed on the bay. Again, this was a great experience for all of us and I would love to use them again!