Set Sail in beautiful Salem, Massachusetts on the schooner yacht When And If. The When And If was built in 1939 for the North Shore's own, General George Patton. Patton built the yacht with his famous quote as the intent "When the war is over and If I live through it, Bea and I are going to sail around the world." Open to the public and available in Salem for the first time in her history, don't miss out on your chance to sail into the past on the beautifully restored classic yacht. Our 2 hour sunset sail includes soft drinks and bottled water, and a cash bar! Sit back and relax or lend a hand with the sails! This activity is good for all ages.
Posted By : Donna_T
I would highly recommend this crew! They were extremely friendly. Personalized conversation so that everyone felt included.
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Posted On : 2024-06-21 09:15:19 
Posted By : tamaracZ8931PN
We’d been wanting to sail on the When and If since seeing it in the distance during sunset walks along the Ft. Sewall overlook in Marblehead. The view from that perspective was stunning. Yet to see the setting sun reflected in the waves, feeling wind and sea spray while sailing on this gorgeous schooner was even better! Full bar with top quality, fresh juice mixers, broad variety of local craft brews & even an Argentinian red blend curated especially for the When & If. Thank you to Seth & crew, JP & Charlie, for a great and memorable time. We’re looking forward to joining the roster of repeat offenders😂
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Posted On : 2024-06-20 21:52:12 
Posted By : Karen_R_N1109
First of all the ship was beautiful. The crew were open and friendly. The drinks were strong. The views were gorgeous. It was just so cold. And that’s on us, we went at the end of September and I even had a light blanket. The cold made it a little uncomfortable. Just know you’re on the water and the end of the day. My only other sunset cruise was in St Thomas so total opposite. Totally worth it - just come prepared.
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Posted On : 2023-10-26 15:45:09
Posted By : colindS790QE
The boat is beautiful well taken care of. The crew is knowledgeable of the vessels history the area they sail and of passengers needs. I can’t say enough good things about our trip. I can’t wait to go again next year
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Posted On : 2023-10-03 13:28:28
Posted By : 566clarel
We had the pleasure of sailing on the When and If last week - it was a hot day! There was a nice breeze once we left the dock. The captain and crew were very attentive and fun. Would definitely recommend this to others!
- CFL
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Posted On : 2023-09-14 12:48:36
Posted By : leonoras5
This was the first time we were on the When & If for the schooner race in Glostah. It was a bright sunny day. They provided lunch and drinks. We came in 2nd in our division! Bravo to the hard workin crew! 👏
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Posted On : 2023-09-11 10:06:18
Posted By : Trek59190902965
This was our 4th sail with the fantastic crew and the splendid ship the When and If !! As always a fantastic sail. The ship, its history and beauty makes you feel like relaxed and very safe. Because of its size and weight the sail is always smooth. Great choice of adult beverages and a very entertaining crew makes sure you have a great time. No better way to spend a couple hours in the Boston area. Thanks to Seath and crew for making our day special !!
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Posted On : 2023-09-10 19:08:30
Posted By : NorthStar710123
Great experience. Terrific crew who let passengers help with sails if they wish. Relaxing. Would do again for sure.
Only drawback was tips. They ask for tips when you purchase tickets online. I figured that would suffice for the who trip. But the bartender specifically asked for ‘Bar’ tips and then stood on the exit ramp as we exited holding a boot for another tip. That was at least one too many of not two too many. Otherwise a great thing to do in afternoon or evening.
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Posted On : 2023-09-08 13:48:18
Posted By : 790pamelas
Every summer my friends and I charter the When and If for a sunset sail. We are usually a group of 30, and we love the fact that there is enough seating for everyone without being cramped and still easy to move around to visit with different friends. We all bring a finger food item to share and the crew puts down mats for us to use as a buffet....the crew is so friendly and helpful...always smiling and getting into the festive mood. The sail is always awesome no matter how much wind we have...can't wait until next time!
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Posted On : 2023-09-07 14:56:26
Posted By : JeanneL405
This was a beautiful, relaxing sail. Comfortable. Friendly passengers. Staff was awesome and very experienced.
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Posted On : 2023-09-03 16:06:51
