Schooner Yacht Tour: Salem's Historic Sail

Experience a sunset sail on the historic schooner yacht When And If in Salem, Massachusetts. Built in 1939 by General George Patton, this beautifully restored classic yacht offers a unique opportunity to sail into the past. Open to the public for the first time, don’t miss out on this unforgettable adventure!

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • Sunset Sail Salem - Set Sail aboard the historic and brilliantly maintained classic North Shore sailing schooner yacht! Experience a sail on Salem sound as it would have been in the early 1900’s in classic yacht comfort. The majority of our sails are 2hrs and yes we do actually go sailing! Once the sails are set, we open our craft beverage bar,…
What's Included
  • Bottled water
What's Not Included
  • Gratuities
  • Alcoholic beverages
Additional Information

Embark on a voyage in the stunning locale of Salem, Massachusetts aboard the schooner yacht, When And If. Originally commissioned in 1939, this magnificent vessel was the brainchild of North Shore’s very own, General George Patton. Its creation was spurred by Patton’s infamous declaration, ‘When the war is over and If I live through it, Bea and I are…

Location
10 Blaney St
Blaney Street
The When And If is docked at 10 Blaney Street in Salem, MA. Most days there is ample parking at the dock but just in case, we recommend arriving atlas 30 minutes prior to departure to ensure enough time to find parking.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.9
(172 Ratings)
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Stephanieyoung60
Dec 5, 2025
Highlight of the girl's trip! - This was one of the biggest highlights of our girl's trip. From the time we got there the crew was amazing. They were so fun and kind. We were able to steer the ship with the captain and hoist the sails. The sailing was so fun and relaxing. They also had a full bar on board. They told us the history of the boat and great chats. You will not regret booking.
Review provided by Tripadvisor
Chelsey951
Nov 4, 2025
Don't Miss This Sunset Cruise! - My friend and I booked a sunset cruise and were on the Marimar Schooner. The crew was wonderful, kind and knowledgable and made the trip fun. We enjoyed taking photos (and having our photos taken), yummy dark and stormy cocktails and chatting with other passengers and the crew. The evening was stunning and we felt like we got to experience a part of Salem outside of the witch history. We would recommend this cruise to anyone that loves being on the water and appreciates these historic schooners. Can't say enough about this adventure!
Review provided by Tripadvisor
Globetrottermelissa
Nov 3, 2025
October sunset sail on the When & If - I had a great time on the When and If sunset sail cruise on Sunday, 10/26. It was chilly, being late October, but the passengers and staff were in great spirits despite this! The boat staff was very friendly and knew their way around the boat. It was my first time on a sailboat and was really cool to see how the sails are operated. They offered drinks for purchase which was nice, and I also bought a commemorative long-sleeve T. The history of the boat was also very cool, having been commissioned by General George Patton, it felt like we were getting to enjoy a little piece of American history.
Review provided by Tripadvisor
G7790tucindys
Oct 10, 2025
Magical Sail - This was the absolute highlight of our trip to Salem! The When and If Schooner is a gorgeous piece of history cared for by a caring, professional, and exuberant crew who are passionate about sharing their love of tall ship sailing with everyone! We were welcomed and instructed in emergency procedures and basics of sailing when we boarded and soon we were invited to help raise the sails! It was amazing to work with the crew to get her underway! Definitely a once in a lifetime chance. We were offered wool blankets to take the chill off and invited to walk about the deck, take a turn at the wheel, and visit the cabins below deck as we sailed. The crew shared stores with off, offered us history of the area and an adult beverage, including hot spiked cider. There were only 8 guests sailing with the crew of 3, so we all got to visit, talk, learn, and hoist as we sailed the harbor and admired the sunset for 2 hours. I would strongly recommend this opportunity to everyone and anyone. 1939 wooden tall ships are a piece of history that you can enjoy today.
Review provided by Tripadvisor
Theresa_h
Oct 10, 2025
Sailing in Salem - Great crew, fun ride. Staff was super knowledgeable. I felt safe on the boat. Love the hot apple cider and wish they had medium sized shirts.
Review provided by Viator
Janice
Oct 10, 2025
Sailing on historic vessel - The yacht was amazing. 1939 schooner designed by John Alden for General Patton. Many original parts. The crew, Captain Tyler, Kate and Chaos Cos were knowledgeable and enthusiastic. We were encouraged to raise the sails. I did and it was very fun to be part of the experience. We were blessed with good sunny weather. Overall so worth it!
Review provided by Tripadvisor
Krista_e
Oct 9, 2025
A Splendid Day! - Riding a schooner is a MUST if you come to New England! You can get a tiny feel of what travel was like in colonial days. Being something new to me I was a little nervous about the experience in the beginning, but having the opportunity to help hoist the sail was just what I needed to get my mind off my silly fears. Kos and Kate were such knowledgeable crew ladies and talked to each one of us, pointing out different light houses along the way. My husband and I, both were so very grateful for this unique opportunity.
Review provided by Viator
Estefania_m
Oct 9, 2025
Friendly, Amazing - Very nice and relaxing experience! The crew were very helpful and welcoming! A very romantic setting for couples as well.
Review provided by Viator
768bucks
Oct 7, 2025
Fantastic - It was a fantastic time my wife and I were really pleased with the whole experience from start to finish the crew was amazing
Review provided by Tripadvisor
U6535mzstephaniek
Oct 7, 2025
Sail - We had such an amazing afternoon sailing. K & K were amazing hosts and it was such a fun and relaxing way to round out a busy few days in Salem.
Review provided by Tripadvisor
From $55
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).