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
(169 Ratings)
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Joego3668jp
Aug 28, 2025
Amazing sunset experience - My wife and I found this while looking for things to do in Salem on our drive from Philly. It was an amazing experience! I haven’t been on a boat in a few years so I wasn’t sure how I would do on it but no sea sickness. It does move around a decent amount and probably depends how windy it is, I was also a little nervous as the wind can push the boat so it’s “bowing” (not sure if that’s the right word) to the one side and is up on an angle but still not too bad! The crew is also amazing, very friendly, accommodating, and personable. The lady (Cass I believe) was a great conversationalist and bartender, made great dark and stormies as well as bay breezes. If you come to Salem, this is a necessity!
Review provided by Tripadvisor
Amber
Aug 26, 2025
Relaxing and beautiful experience! - A relaxing sail around the wharf! Drinks were available for a nice treat while exploring. Very picturesque and serene! Take pictures!
Review provided by Tripadvisor
S3893dttanyam
Aug 25, 2025
Sunset Experience - Such an amazing evening on the Malabar X! The crew made sure we had fun, were safe, and enjoyed sharing information about the area! Can’t wait to do this again!
Review provided by Tripadvisor
Alesha_f
Aug 13, 2025
Must do activity! - Be prepared to hoist the sales! So cool that we got to help! The crew members were super friendly, the ride was great!
Review provided by Viator
Foodiera
Aug 5, 2025
Outstanding captain and crew! Go! - What an outstanding captain and crew! We went on a sunset cruise and it was our first time on a sailboat. The captain gave very clear directions before we set sale with respect to safety, and I was highly appreciative as I had no idea what I was doing. The two crew members were absolutely phenomenal and took care of all of us. What I really liked is how they took the time to speak to each and every individual to get to know us and they were very knowledgeable, kind, and friendly. I highly recommendthis trip as they restored a 1930 yacht and it was quite a memorable experience. I’m definitely going back!
Review provided by Tripadvisor
Faith_h
Aug 5, 2025
Excellent atmosphere. ... - Excellent atmosphere. The staff was amazing. I brought a 69 year old man and they couldn't have been any nicer. They not only explained everything about the ship but allowed him to raise the sails and even steer the ship..... it was Excellent and Iook forward to doing again witht a bigger group for friends... Thank you......
Review provided by Viator
Michael_z
Jul 31, 2025
Fun evening excursion for the whole family - This was a fun sailing experience and 2 hours was the right amount of time for an excursion at the end of a long tourist vacation day. The sunset view from the boat was really beautiful. The crew was fun and it was a nice touch allowing guests to raise the 4 sails. My daughter and I raised one together and she thought it was awesome.
Review provided by Viator
H2924tmjanag
Jul 29, 2025
Sunset on a sailboat - Crew was awesome and informative. Sights were great. Bare feet is the way to go. Definitely check out below. Drinks were mixed perfectly 😎 I could’ve stayed out longer and sailed further!
Review provided by Tripadvisor
541heatherd
Jul 27, 2025
BOOK IT !! THIS IS AN AWESOME EXPERIENCE !!!! - AMAZING EXPERIENCE! I took my kids ages 18, 16, 13 & my 12 yr old niece. All 3 of the crew members were really nice & let the kids help with raising & lowering the sails…it was something the kids will remember forever! GREAT MEMORIES & BEAUTIFUL PICTURES TO REMEMBER OUR TRIP!
Review provided by Tripadvisor
Z389aoholliec
Jul 25, 2025
Amazing sunset cruise! - Beautiful historic boat. Crew made the trip so much fun starting with our daughters getting to raise the sails. Would highly recommend.
Review provided by Tripadvisor