The Best Boat Rentals Near Havre de Grace

42ft Party Yacht Best of Baltimore 2024-25 Winner!

Captain Brian was amazing! He was so helpful, professional, and made sure everything went smoothly for me and my guests. The weather was perfect, and he was very accommodating to make sure we had the best experience possible. We had so much fun out on the water! I truly appreciate how easy and enjoyable he made the whole trip. It was such a fun and memorable experience I’m definitely looking forward to booking again and would absolutely recommend anyone to book with him.

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) ⚓️⚓️⚓️

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

What an enjoyable experience! Captain Joe was always attuned to our wishes, making an extra effort to make this afternoon pleasant for all. His company is very agreeable. We wish we could relive yesterday's feeling of complete relaxation over and over!

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

HIGHLY recommend Capt Joe for a fantastic sailing experience out of Rock Hall. Joe worked with us to get a last-minute booking when another booking fell through. He and his crew are experts and you will not be disappointed. He let us take the helm and participate as much or as little as we wanted to. Sol Searcher is a beautiful, well-equipped boat - plenty of comfort and speed (wind dependent of course.)

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

What a gorgeous day on the water aboard Sol Searcher! Captain Joe was an awesome host for our day! Peaceful, serene and exactly what we were hoping for to bring the summer to a close. What a lovely world we have to enjoy when we step away from the hustle of life and take the opportunity to take in all that it has to offer. Thank you Capt’n Joe for a wonderful sailing experience. Until we meet again, Loretta and Greg

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

For our wedding anniversary, I wanted to try to do something that we'd never done before. Getting a chartered boat for a day cruise along the Chesapeake Bay was certainly a memorable way to spend the day, in no small part due to the efforts of Cap'n Joe. The weather was wonderful, which he had nothing to do with, but he took us on a wonderful round trip on the Bay so we could get back to our son on-time in the evening. The vessel was magnificent! It was well worth the expense and was honestly impressive. I'd definitely do this again with friends. Simply outstanding.