Sunset Sail on Historic Schooner in Key West

Beautiful ship with a friendly and fun crew! Everyone on board was so kind, social and they kept the beverages coming! An absolutely beautiful evening with a beautiful sunset view (we also saw some dolphins!) 10/10 would recommend this for anyone visiting Key West!

Captain Andy and the crew were wonderful - helped answering questions about “When and If”, the cruise and how they sailed the boat. “when and If” was custom built for General George Patton and has quite a history. Don’t forget to explore below deck to see the true beauty of this twin masted schooner. The cruise itself was awesome and the relaxation of moving through the water under sail cannot be understated … not to mention the spectacular sunset! This is a “must do” item for your visit to Key West!

My husband and I thought this would be a fun change from a standard dinner/party boat and booked this on our recent trip to Key West. It was overall a good time and the staff were awesome, but there are a few things I didn't expect that I want other people to know before booking this cruise. There are tons of sail boats cruising around in front of Mallory Square in the calm harbor waters during sunset and that's what I thought this cruise would be, however, this boat leaves from Stock Island. To have an unobstructed view of the sunset we had to sail about 45 minutes out into the gulf in open water. It was a fairly breezy day and the waves were 3-4ft. For most of our sail the boat was cruising at a steep angle and rocking enough to splash some waves on to the front seats. It was really difficult to get up and move around (I didn't except to use the bathroom which felt scary, and I had worn a dress which made it worse, lol). By the time the sun was setting, I had to think hard about not feeling sea sick. I'm a Florida native and have spent plenty of time on the water. I know this is a sail boat which means some waves and wind, but I was hoping for a smooth sail in the harbor. There was nothing on the website or in the reviews that mentioned all of this, so I just want anyone else who books to be able to account for this (and not wear a dress, lol). The boat was neat though and the sunset was gorgeous of course. Thanks to the crew who were fun, helpful, and engaging.

We did our research and wanted a beautiful scooner, made out of wood, neither crowded nor a party boat. This one experience surpassed our expectations! Great history behind this gorgeous and well cared vessel. The captain and crew were very welcoming, caring, and knowledgeable. Highly recommend it!!!

So much fun! Great time on a historic ship! Would recommend this to anyone who wants to get out to see the sunset or looking for an enjoyable evening.