Private Daysail on When and If with Sunset Sail Salem in Massachusetts

Set against the dramatic backdrop of Salem's historic waterfront, Sunset Sail Salem offers a chance to experience the North Shore waters from a vessel that embodies both elegance and intimacy. Their Private Daysail on the classic sailboat When And If invites adventurers to chart a course through shimmering harbor currents, with the freedom to choose an itinerary or craft a personalized voyage. Whether you’re celebrating a special occasion or simply craving an escape on open water, this experience transforms a day on the sea into a custom-crafted adventure.

Launching from Salem harbor, the trip takes you past iconic sights like Salem’s bustling waterfront, with views of colonial-era architecture and the rolling Atlantic beyond. The boat itself, a vintage classic vessel, offers a blend of nostalgic charm and seaworthy performance, making every sail feel both historic and exhilarating. As you slip through calm waters, the crew ensures a seamless experience, guiding you through the basics of sailing or simply allowing you to relax and take in the sea breeze.

This adventure is perfect for those who want an exclusive, personalized outing on the water. It’s suitable for all levels of adventurers, with the opportunity to learn a few sailing tips or just soak in the scenery. The trip can be tailored to include wildlife sightings, such as harbor seals or seabirds, or a quiet picnic on deck at sunset. Sunset Sail Salem’s commitment to a sustainable approach ensures that your journey remains as environmentally responsible as it is unforgettable.

Whether you're here for a day or a weekend in Salem, the private daysail on When And If offers a unique way to connect with the region’s maritime history and natural beauty—delivering both adventure and a moment of peace amid sea and sky.