Amazing sailboat cruise around the lighthouse and very good story teller of the history of the…read morerivers and the Bay Area

Captain Melvyn and first mate Jamie made the cruise memorable. We had fantastic weather for our…read moresunset cruise on the Tranquility. They answered all our questions and pointed out interesting things along the way. They allowed one of our entourage to steer once we were out in safe waters - lucky for us, the river and bay were not crowded. We highly recommend this cruise. It was the highlight of our vacation weekend.

I bought a Travelzoo voucher for historic tour for 2, and it was a little hard to book since I'd…read morecall leave a message and then they'd call me, leave a message... if you have a voucher you can't book online and they don't have email. I will say something came up the day before my first selected date and they let me reschedule without penalty. But then it took a few more calls to rebook. Parking was a little confusing; parkmobile said you had to pay so we did ($8/day); didn't know if Kayak Annapolis customers had to or not. Aside from the parking and booking difficulty, we loved the tour. Just the right amount of history, paddling, and resting. We were lucky the day wasn't booked up so there were 4 of us total, and it was sunny and a little breezy too. They had dry sacs to put your belongings and tie to the kayak and water shoes if you forgot to bring shoes to get wet in. Megan did a great job, rehearsed corny jokes but kept it entertaining. They offered us juice, water and granola bars when we took a break across from the Naval Academy. I liked that we were able to go into the middle of downtown Annapolis. This is a true small local business, 100% just floating in the water, which is cool. Would recommend if you're in the area! The regular price isn't a bad deal either; or they rent kayaks hourly.

Great kayaking experience during 85° weather! Perfect day really! My tour was with one of the…read moreowners Pete who knows a lot of Annapolis history and has a great personality and humor. I look forward to going back and renting a kayak now that Pete has shown me the ropes.

This was an awesome event. To experience a captain and crew who are professional and humble made…read morefor a great day sailing on the Liberte. Looking forward to booking this sailboat for another memorable occasion. Thanks for an excellent time on the water.

Absolutely had a wonderful time on last sail of the season of the Liberte. They did a great job,…read morekept the drinks coming, and were very nice to us lovely bunch of women.

Our retired womens group booked the tiki cruise this evening. It was the best way to close out…read moresummer. The weather was gorgeous. They start off at Nautilus Point, go past the Maritime Museum, around into Annapolis Harbor, into Ego Alley, on to Spa Creek and back. It was frustrating fun. They have Bluetooth speakers, so bring your Playlist. It is BYOB, but they provide a big cooler to store drinks and they help keep the glasses filled. What a great time!

We had a crew of about 15 pile onto a boat and we couldn't have been happier with the experience…read more The boats are BYOB but the staff help serve you and tidy up throughout the experience. They will also take photos for your group and let you control the music. We were lucky to have Dan and Mike and it was just such a wonderful day!

The experience was great from start to finish. I mostly dealt with Keegan and he was very helpful…read morewith planning to helping work through minor issues on the boat. The boat, Lily Rose, was a beautiful, new Seawind 1170 catamaran. Keegan, and his colleague Ralph, really helped make our bareboat charter great.

Chartered a catamaran for a week in Nov 2024 from Sailaway Key West. Booked in March…read more Unprofessional outfit: boat we chartered was not available, but an on paper good alternative was offered. Then the price of the crew was increased. Excuse was that the person who we booked with in March was no longer with the company. Lot of work to redo all the work we had done in March to find the charter we wanted - anyone who has tried to book one knows it's much smoke and mirrors, the same boats are rented out by different outfitters, everything is a little different between each and it's hard to get a full picture of total cost, and to compare apples to apples and not something else. Document every conversation and detail of what you agreed upon with Sailaway (or any other company) or they'll change the game. Arrived in Key was as agreed upon. Boat reeked of sewage. Captain had been on the boat for ten minutes several days before our charter, that's it. Said it reeked then too, but didn't do anything about it. Captain had almost no contact with Sailaway, it was the first time they worked with them. Captain ended up calling marina engineer and it turned out that half of the boat had not been pumped out. Additionally, the captain's cabin bathroom was broken, and the toilet didn't flush. You can imagine. It all got fixed but it was a stinky hassle and we started our charter several hours late. Sailaway overcharged us in their electronic system and ghosted us upon repeated request to resolve. Jennifer, owner of the company, acted unprofessionally and winged it to provide a charter boat and an ok but inexperienced crew she had never met, nor taken the time to get to know. It came out all right by helping out on the fly, but Sailaway was disappointing and there was no communication with, nor support for the crew from them either. The situation would have been salvageable if Jennifer had responded to our emails and calls to resolve the issue and accept feedback as we asked her to do. But she didn't, which leaves us with a bad feeling about her and her company.

Went out on family fishing trip Nov 15, 2025. Excellent time. Everyone caught fish- even a 40 in…read morefish. Great service and music. Couldn't have been any better!!

Went out today from the Pasadena location, had a great trip!…read moreCaught our limit early and enjoyed some bottom fishing to finish out the day. Captain called me early in week to suggest leaving a bit early for better fishing, worked out perfect. Really impressed with captain and mate. Eric p

Captain Jim and his wife were wonderful! We booked a 2 hour cruise at the end of May for a team…read moreactivity. He was always quick to respond to any questions, his boat is beautiful, and his wife was so hospitable during our ride! She served us snacks and refilled our drinks, and narrated the sights for us as we cruised! They are both knowledgeable about the area and were wonderful tour guides through Annapolis and the Chesapeake. We will book a longer cruise next time. In my research, it's hard to find a boat that is NOT a fishing boat in the area. (Fishing boats are great, but are usually not for lounging and not that pretty.) Captain Jim's boat is super sleek and meant for cruising! More than enough space for 6 adults to spread out. You won't be disappointed!

Absolutely wonderful! Captain Jim was amazing, and the boat was immaculate! We did a 2 hour cruise…read moreout of Kentmorr and up to Thomas Point Shoal Light. Then we went through Ego Alley in Annapolis and underneath the Bay Bridge. We have lived in the area for decades, but learned so much about that area that we didn't know! Captain Jim is knowledgable, accommodating and wonderful! Five enthusiastic stars!

Omg super fun time each time I go out the Captain is great the 1st mate great and they work to…read moreensure you have fun , learn to fish (if your new to fishing ) and catch fish ---fishing can be fickle but you'll never go wrong with this team

My crew had such a great time with Captain D! He has a great deal of patience and humility…read more This is the perfect venture for a small group. He's definitely wanted to ensure we caught a lot of fish and had a lot of fun. I really appreciated the efforts he went to ensure this. Extremely knowledgeable. I can't wait to go back out