Chesapeake Bay, US Boat Rentals & Yacht Charters

Chesapeake Bay Reviews

1. 

   Lauren

   Charter 42' Lagoon Catamaran in Annapolis, MD

   We had an amazing day on the bay with Captain Adam! He was super communicative leading up to the trip, providing amazing instruction to make it as easy as possible to get aboard. While on board the vessel was very clean and comfortable and he and his team were knowledgeable about the area. Highly recommend! They’re lovely!

2. AD

   Aliah

   Party Cruises & Fishing Trips in Virginia Beach

   a sweetie pie ! I had a great trip!

3. TM

   Thomas

   New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

   This is a great boat and we had an absolute blast. worth every penny!

4. DC

   Donte

   New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

   From start to finish, the entire experience was seamless and professional. There was zero chaos—everything ran like clockwork. The crew was exceptional: friendly, attentive, and incredibly knowledgeable about the Chesapeake Bay and Annapolis. The yacht itself was spotless and in pristine condition. From the moment we arrived, the crew went above and beyond—helping us load in, beautifully setting up our catering, keeping our group refreshed with drinks and snacks, and later packing up leftovers and loading them into our car. Every detail was handled with care. If you’re considering a yacht rental, don’t hesitate—this experience was truly top-notch. We’re already looking forward to booking again!

5. KB

   Kathy

   40' Robbins Deadrise Trawler Boat Rental in Rehoboth Beach, Delaware

   We rented a boat with Captain Brian to scatter my sister and brother-in-law’s ashes. From the first message, Captain Brian always returned my messages as soon as possible and always answered my questions. On the boat, Captain Brian (Wes) was so kind! He explained everything to us and was very compassionate. I would use him again and will suggest him to my friends! Thank you Captain Brian (Wes)!

6. EB

   Ellie

   40' Robbins Deadrise Trawler Boat Rental in Rehoboth Beach, Delaware

   Wes is a pleasure to work with, he's responsive and communicative during the booking process and the excursion. The boat was very clean and well appointed. On board, he's a conscientious professional; the purpose of my trip was to scatter flowers in honor of my recently deceased mother - Wes made me feel very comfortable going through my own emotions. I highly recommend Wes and I would charter a boat from Wes again.