WORLDWIDE
This is the shortlist you would send a friend: 15 history sailings worth the money, each with its price, what the crew serves and the one thing to know before you pay.
Review of San Juan’s two-hour sunset sail, with fortress views, local history, drinks, practical meeting tips, and honest value advice.
“What an incredible experience! The sunset sail was intimate, relaxing, and absolutely beautiful. Our captain was interesting, knowledgeable, and genuinely funny—he brought so much personality to the trip and made the whole experiRead more”
See Lisbon at sunset from a small sailboat, with Vinho Verde, local history, blankets, and landmark views along the Tagus.
“The entire tour was well-paced, organized, and stress-free, which I attribute to the excellent planning and attention to detail of our guides Pedro and David The weather was perfect Tour highly recommended!”
Tour Dublin’s Jeanie Johnston tall ship for a moving 50-minute lesson on famine-era voyages, passenger stories, and life below deck.
“Ronan was amazing! Thank u so much for the experience”
Sail Lisbon at sunset for two hours with Portuguese wine, river views, landmark stories, blankets, and a friendly two-person crew.
“The Sunset sail was fantastic. It was a beautiful evening with clear blue sky to start. Pedro was a fantastic guide, sharing facts about the sights we were seeing, historical context, as well as his personal stories about growing up and living in Portugal. The Vinho Verde was flowing. When it got colder as the sun set, lovely warm cozy blankets were passed around. I would 100% recommend this activity.”
Sail from Nydri on an 8-hour Greek history cruise with cave swimming, village walks, snorkeling, and a beach BBQ for $88.
“The crew was very nice and funny. The whole tour was very nice. A very nice experience.”
Sail Camden Harbor and Penobscot Bay aboard historic Appledore II, with hands-on sailing, coastal views, blankets, and drinks for purchase.
“It was a beautiful day on Penobscot Bay! Would have enjoyed more commentary on the surroundings to make the cruise more interesting and educational. Captain and crew were very friendly.”
Sail San Juan Bay on a small authentic sailboat, with Old San Juan views, drinks, local history, and a six-person maximum.
“Captain Ivan the owner gives a great experience and is an awesome conversationalist, me and my wife enjoyed sailing with him.”
Sail Salem Sound aboard a historic schooner with hands-on crew, sunset views, island history, and drinks available for purchase.
“I really hate to write this review because others seemed to have a better experience. I booked on Viator a couple of months ago. I showed up at the harbor early and waited. There was no boat, no other people waiting. I double checked the address, I was in the right spot. Two minutes before the event was to start, I popped into the Salem Ferry building. She confirmed I was in the right place but that she didn't see the ship. I called the number through Viator, went straight to voicemail. I sent two messages to the operator via Viator and never got a response. Filed for a full…”
Sail Key West aboard General Patton’s historic schooner, enjoy drinks, wildlife, hands-on sailing, and a beautiful sunset cruise.
“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.”
Review of Lisbon’s two-hour small-group yacht cruise, with historic commentary, landmark views, one drink, pricing, tips, and practical details.
“This was an amazing small-group sailing experience on the river. Miguel and Rui were fantastic - safe sailors and great company. Would definitely go again next time I'm in Lisbon.”
Sail Salem aboard the historic Schooner Fame for 100 minutes of harbor views, hands-on sailing, maritime stories, and a licensed onboard bar.
“Fantastic value! Captain Mike and his crew were very friendly, they engaged everyone on board the Schooner! Great time.”
Sail Charleston Harbor aboard Mystique with a private skipper, dolphins, historic waterfront views, drinks, shade, and room for six.
“We had a wonderful morning sailing experience. Will and Sam were fantastic as the captain and crew of the Mystique - they made us feel welcome and comfortable, were so knowledgeable about the history of Charleston, made sure we saw several dolphins, and were just fun to visit with in general. They also went above and beyond, helping us get my son’s sweatshirt back that he left on the boat. We would highly recommend this experience for any group/age. It was a perfect morning!”
Review of Charleston’s private 43-foot sunset sail with BYOB drinks, dolphins, Battery views, Fort Sumter, and the Ravenel Bridge.
“What a great night! The boat was beautiful and Adam and Walker were both friendly, fun and informative. We loved our cruise and celebrated a birthday on board. Sunset was beautiful and we will definitely be booking again.”
Sail Lisbon’s Tagus at sunset with local skipper Rui, two glasses of wine, landmark views, and a relaxed group of up to 10.
“Ne pas vouloir me prendre pour 5 minutes de retard….160 euros”
Review of Charleston’s private Mystique sailing tour, with dolphins, Fort Sumter, historic homes, flexible timing, and practical booking tips.
“Very nice crew! We did see dolphins. Boat was clean and the crew had a lot of knowledge about the area.”
Pick a rig, a coast or an afternoon.
