Adventure Collective
null - Boston

2hr Sunset Sail on When And If

Salemeasy

Difficulty

easy

Duration

2 hours

Fitness Level

Suitable for most fitness levels; minimal physical activity required

Overview

Join Sunset Sail Salem for a 2-hour private sunset cruise in Salem, Massachusetts. Experience breathtaking views, peaceful waters, and the magic of dusk as you glide across the ocean in an intimate setting. Perfect for romantic evenings, special celebrations, or simply unwinding after a day of exploring Salem.

Sailing
Salem, Massachusetts

2hr Sunset Sail on When And If

$55 Adult, $35 Child | Summer Sunsets on a Stunning Classic Schooner

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Adventure Photos

2hr Sunset Sail on When And If photo 1

About This Adventure

2 HR. Sunset sail departing daily.

Enjoy the sunset from the water aboard the gorgeous 1939 wooden schooner built for General George S. Patton.

Built with the dream to sail around the world 'When the war is over, and If I live through it," When and If is over 80 years young with her destiny as yet unfulfilled.

Come and be part of her story! Take a turn at the helm, help raise sail or simply relax and enjoy the views of the gorgeous North Shore coastline at Sunset.

We will cast off, motor out to where we can safely raise sail, and as soon as the sails are set we will shut off the engine and see where the wind takes us! Your journey ends with your safe return to the dock 2 hours later.

Please arrive at the dock 15 minutes before your scheduled departure time.

What's included:

  • 2 hour Sunset Sail
  • The services of your Captain and Crew
  • Your spot on When And If; with capacity for up to 28 people you'll be sharing the boat with our other lovely guests
  • Coolers stocked with bottled water and seltzer water
  • Full bar on board (credit card preferred) Please note that as we are a licensed premises we cannot permit you to bring alcohol on board but we're sure we'll have something you'll love!

Adventure Tips

Arrive early for the best sunset views

Getting to the harbor early will give you ample time to settle in and find a great spot to watch the sunset unfold.

Dress in layers for changing weather

Even in summer, evenings can be cool near the water, so bring layers to stay comfortable throughout the cruise.

Bring your camera or smartphone

Capture the stunning sunset colors and scenic views during your sail—don’t forget your device's charging cable!

Book in advance during peak season

Sunset sails are popular, especially in summer and fall, so reserve your spot early to secure your preferred date.

Local Insights

Wildlife

  • Seagulls
  • Herring

History

Salem has a rich maritime history dating back to the 17th century, and this sailing trip offers a glimpse into its historic nautical culture.

Conservation

Sunset Sail Salem emphasizes eco-friendly practices by minimizing waste and promoting responsible marine tourism to preserve the coastline’s natural beauty.

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Adventure Hotspots in Boston

Frequently Asked Questions

Recommended Gear

Weather-appropriate clothing

Essential

Wear comfortable, layered clothing suited for outdoor conditions on the water.

spring|summer|fall|winter specific

Sun protection

Essential

Bring sunscreen, sunglasses, and a hat to protect yourself from the sun during your sail.

spring|summer|fall|null specific

Camera or smartphone with extra batteries

Capture memorable moments and panoramic views of the sunset and coastline.

Light waterproof jacket

Be prepared for potential splashes or cooler air with a lightweight waterproof layer.

winter|spring|fall|null specific