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.

We went on a 2 hour sunset boat ride with Tyler, to celebrate my daughter's graduation from…read morecollege. Tyler was amazing!! Even from the beginning when I was inquiring about booking-he took time to explain everything and the cost is so reasonable compared to other charters. Plus, you get the opportunity to have it all to yourself for you and your loved ones. Tyler is such a nice guy and he made it so special for us. He remembered that we were there to celebrate my daughter and told her congratulations. I barely mentioned that in my phone call so for him to remember it-that was so amazing! He took us all over. I feel like we literally saw everything there is to see. We were able to play our country music, drink our champagne and wine. It was such a beautiful and comfortable boat. We can't wait to return and hopefully Tyler will still be available to take us out.

Wanted to go out on the Chesapeake Bay for Memorial Day weekend with some friends and we decided to…read moregive Peake Charters a call. Best decision we could have made! Tyler, the Captain of the boat, set us up with an awesome afternoon. Started with some wake boarding and tubing. Then, we got some dinner to go from a local restaurant, so we could anchor out and relax a bit. Would recommend to anyone, we had a very good time.

We sailed up the Severin River in Annapolis on the Cabernet II. Beautiful clean very well…read moremaintained ship. Highly recommend. 1st class experience.

Took the cruise around the Naval Academy. Decent price $25 and not overcrowded. Had a beer onboard…read more Enjoyed the experience and would recommend it.

This yacht is extremely beautiful. With a very professional staff. The "dock happy hour" was…read moreAMAZING to say the least. JRocx I would like to THANK YOU for the wonderful evening. I can't wait to host a girls night out on the weekend with my friends . Thanks again for the awesome experience!

What better way to get around than on the water. I would commute via water if there were a way to…read morewhere I live. In Annapolis, there is! So try it out. Starting out at $2 you've got nothing to lose and it is a super fun way to beat the heat and enjoy that sea breeze while watching the shoreline pass you by. They have a fairly high capacity, we were a group of 6 and all fit plus more. So go cruise Annapolis

We have used the taxi for years to ride from the boat to town dock…read more During a week long stay on mooring #17, a matter arose where I needed to drive back to Baltimore to grab some missed packed medical supplies. Unfortunately it was all ready 8pm and the last taxi stopped at 10pm. Capt. Phillis went above and beyond her service. She assured me her taxi would be waiting to take me back to the boat. It was a big comfort during my 2hr round trip drive. Thanks a million to all the fine and pleasant captains especially Capt. Phillies. ​

Scenery, Scenery, Scenery! Gorgeous view of the water. Fresh Air, Amazing Sunset and the fulfilling…read morebreeze. It's a Vibe!

Beautiful place with great views and nice restaurant. Staff were very friendly and accommodating.read more

My brother and his wife and and my wife and I very recently completed a three hour Sunday morning…read morecharter. We thought the charter was well worth the money. The Captain and one crew member were really excellent. They made sure to cover critical aspects of the boat and abide by all the safety precautions. I actually timed the charter and we were on the water under sail for almost exactly 3 hours. We got there a little early, and the process of familiarizing us with the boat took a few minutes, so the entire process was probably closer to four hours. The boat was clean and in great shape. Some of the electronics we're not working but that was not an issue for our charter. We were provided with basic cold drinks and bagged treats as well as a bottle of wine. We own a Catalina 22 sailboat so we were familiar with sailing, but sailing a Catalina 42 Mark II was a lot different. I was thrilled that the captain offered me the opportunity to sail and tack the boat for an extended period, of course under his watchful eye and guidance. In short it was a very memorable experience and we had a blast! The wind and weather were perfect.

Went out on a whim and scheduled this party boat out of Annapolis this summer - we had never heard…read moreof them (well come to find out they are new!) and truly didn't know what to expect... It was such a FUN evening! Watching the sunset from the water, the drinks were flowing (loved that it was BYOB, we brought a cooler for us, but they already had one on the boat as well!) and being on the water... doesn't get much better IMO Can't recommend this party boat enough! The captain and the owner, Trevor, were responsive and helpful in booking and finding the location of where the boat docks. Would be so fun to bring the girls back for a gals night or even a bachelorette party. Can't wait to book again this summer and maybe even for the air show Ps - make sure you use the bathroom before you leave bc there isn't really one on the boat haha

Amazing experience for my bachelorette party with Captain Jamie and his deckhand Devin. It was a…read morevery personalized experience and Devin even helped us capture some amazing photos along the way!!! Highly recommend to anyone looking to celebrate an event or just cruise along the beautiful water. It was S O MUCH FUN and super affordable !!!