Top Salem Sailing Trips

Crew was fantastic. It was an amazing experience to go sailing on a schooner and to be out on the ocean with no engine noise or exhaust, no wake from a propeller, experiencing sailing as it has been done for centuries and millennia before the modern era. Truly a relaxing and a must-do life experience. I highly recommend it and would live to do it all over again myself!

Great experience and time sailing the harbor

This is the second year that we have gone out on the When and If, this time on a private charter for all of my family. It was a wonderful experience and the crew was the best!

My family and friends went as group of 13 on a beautiful sunset cruise to celebrate my sister’s birthday. The boat is stunning and the crew is so accommodating. It was a perfect trip, everyone loved it. Thank you!

Fabulous! This experience far exceeded my expectations. The captain and crew were fantastic. It was fascinating watching how they brought the sails up and down, and how they navigated. They even let some volunteers help if they wanted to. The two hour cruise went so smoothly. I am definitely going to come back next summer!

The crew was friendly and hospitable and the ride was fun! Just the right amount of time. If going on an outing in September you may need a light jacket!

My wife and I went on a sunset cruise last night with some friends, and we could not have had a better time. Seth (captain), Remy, and Shawn (crew) we’re excellent. Great guys, fun to be around, and super attentive. Remy is a cocktail master, all juices are fresh squeezed to order.The boat is 80+ years old, in perfect condition, and has a great feel to it. We went out around Baker’s Island and saw a beautiful sunset. Exceeded all expectations, incredibly relaxing.If you’re reading this review and you’re on the fence, all I can say is do it, you’ll be glad you did. We will be going out again this summer.

We did a private 3-hour sail with a backcountry swim stop for 5 locals. We loved the crew, and everything about our trip was perfect. We appreciated the attention to health and safety during the pandemic. I'm a travel agent here in KW and will absolutely be recommending this to my clients!

Fun time. Great crew. Patton's boat.

We had an excellent time. The crew were knowledgeable and engaging, and made the excursion a lot of fun.

We had such a wonderful time sailing with the crew on the When and If! We sailed on a windy day, which really helped us to see the skill and care the team took to insure a safe and fun experience for us all. The views were absolutely beautiful, and each member of our family had a fantastic time.

We had a great fun time. Knowledgeable crew who were all about safety and showing us a good time

This was so much fun and very relaxing! Make sure to bring a jacket because it gets chilly on the water, and maybe a hat/beanie.

Amazing crew- very adept at handling the boat and sails. Felt confident we were safe the entire time even with the amount of wind that was coming in. Fantastic bar. Would do it again

Incredible, captain was incredibly knowledgeable and kind. His staff poured great drinks and kept them flowing. He also made sure a bachelorette party had the opportunity to do an epic photo op at the helm of the boat. And was diligent about watching out for the safety of all aboard.

The Crew was very good at keeping the ship and everyone onboard safe. They made everyone feel welcomed and answered all our questions. Gave us excellent instructions at the beginning to the end of our trip. The crew took time to share their experiences with sailing that made the trip more exciting. Our whole family enjoyed the sailing trip and would recommend it for your family time together. To the Crew thank you for the great experience.