Sailing on Historic Schooner Yacht in Salem, MA

If you’re visiting Salem and love the idea of spending a couple of hours on the water, a sunset or daytime sail aboard a historic schooner might just be the perfect addition to your trip. This tour, provided by Sunset Sail Key West, offers a chance to glide along Salem’s shoreline on a beautifully restored vessel built in 1939—yes, the same year as General George Patton’s military career.

What caught our eye is how highly rated this experience is—people seem to love the genuine charm of the boat and the friendly, knowledgeable crew. Plus, the unobstructed views of Salem’s coast and the chance to help hoist the sails make it feel more like a real adventure than just a sightseeing cruise. However, a quick note for anyone sensitive to weather: since it operates in all conditions, you’ll want to dress appropriately and be prepared for a bit of wind or chill, especially on the water.

This experience is best suited for couples, groups celebrating special occasions, or anyone looking for a relaxing yet engaging way to see Salem from the water. If you enjoy scenic, laid-back outings with an authentic maritime vibe, this tour should definitely be on your list.

Key Points

• Authentic Sailing Experience: You’ll board a classic schooner built in 1939, offering a true maritime feel.
• Flexible Schedule: Multiple departure times make it easy to fit into your day.
• Great for Special Occasions: Perfect for celebrating or just enjoying a romantic outing.
• Beautiful Views: See Salem’s coastline, Marblehead, and nearby islands from the bay.
• Drink Options: Soft drinks and bottled water are included, with a cash bar for cocktails, beer, and wine.
• Weather-Resilient: Operates in all conditions, so dress accordingly.

An In-Depth Look at the Experience

Boarding and Location

The tour begins at 10 Blaney St., Salem, MA—just next to the Salem ferry building. Parking can be limited on busy summer days, so arriving early is wise. Boarding starts about 15 minutes before departure, giving you time to settle in and get excited. The vessel, the “What and If,” is a stunning piece of maritime history, lovingly maintained, with a fresh coat of paint and gleaming wood that instantly transports you back to the early 20th century.

The Itinerary Breakdown

Stop 1: Sunset Sail Salem – This is the heart of the experience, where you truly get to feel like a sailor. Once onboard, the crew hoists the sails, and the boat begins its glide across Salem Sound. As many reviews highlight, the crew is both knowledgeable and engaging, sharing the history of the vessel and the area. Guests are encouraged to participate—help with hoisting sails or simply enjoy the tranquility of sailing.

Stop 2: Navigating Salem Sound – From here, you’ll cruise around Salem’s coast, enjoying unbeatable views of historic homes on Marblehead’s Neck. The captain and crew often share stories about the area’s history, islands, and notable sites. This is also the part where you get an unobstructed view of Salem’s skyline and the nearby islands like Children’s Island and Misery Island Reservation.

Additional Sights – Depending on the weather and timing, the boat might sail around the islands, offering a different perspective of Salem’s maritime environment. Many reviews mention the spectacular sights of historic homes and the chance to see wildlife, sometimes including whales—yes, whales! Several travelers found the views breathtaking, especially at sunset.

Onboard Comfort & Amenities

While the boat is classic and charming, it’s also functional. Soft drinks and bottled water are included, which is great for staying hydrated during the cruise. For those wanting a drink, a cash bar offers beer, wine, cocktails, and cider—perfect for toasts or just relaxing with a beverage. The crew is attentive, making sure everyone feels comfortable, whether they’re up at the wheel or just enjoying the scenery.

The Sails and the Crew

Many reviews rave about the crew’s friendliness and expertise. They are quick to answer questions and make everyone feel included—whether helping with the sails or explaining the boat’s history. One reviewer noted, “The crew was amazing, friendly, attentive and gave us the history of the boat,” which captures the general sentiment.

The sailing aspect is genuine, not just a boat ride—most trips are around 2 hours, and you’ll actually be sailing, not just motoring. It’s a laid-back atmosphere, great for relaxing and soaking in the views. Be aware that the sails are hoisted, and guests are encouraged to participate, which adds to the authentic feel.

Weather Considerations

The tour operates regardless of weather, which means you could be facing a chilly breeze or even rain. Most reviews mention dressing in layers—bring a jacket, especially if you’re doing a sunset or evening cruise. Several travelers note that even in less-than-perfect weather, the experience remains enjoyable thanks to the crew’s hospitality and the boat’s cozy charm.

Duration & Group Size

At roughly two hours, the tour strikes a great balance—long enough to unwind and see plenty of sights, but not so long that you feel overstayed. With a maximum of 28 travelers, the group size is intimate enough for everyone to participate and ask questions but still lively enough for a social vibe.

Pricing & Value

At $55 per person, this sailing trip is reasonably priced considering the experience. You’re paying for authentic sailing, stunning scenery, and access to a historic vessel. Many guests find that the value is high—especially given the friendly crew, the beautiful views, and the chance to participate actively in sailing the boat.

A few reviews mention that the open bar is an added plus, with drinks available to purchase, making it a fun, relaxed outing. The fact that the trip is booked about 30 days in advance suggests it’s popular, so planning ahead is wise, especially during peak season.

Who Is This Tour Best For?

This experience is perfect for those who enjoy scenic, leisurely outings with a touch of history and authenticity. Couples celebrating a special occasion will find it romantic, but it’s also great for friends or solo travelers who want to enjoy a peaceful sail. It’s especially suited for anyone interested in maritime history, stunning coastal views, or simply a relaxing trip on the water. While not specifically marketed as family-friendly, children who are comfortable on boats and under supervision will likely enjoy the open-air sailing.

Final Thoughts

Sailing in Salem aboard the “What and If” offers a unique way to experience the North Shore’s coastline. It’s a chance to see Salem’s historic homes, nearby islands, and wildlife from a perspective that most land-based tours can’t match. The crew’s warmth and knowledge make the experience more than just a boat ride—they make it memorable.

At a reasonable price, with flexible departure times, and the opportunity to participate actively, it’s a great pick for those looking to add some maritime adventure to their Salem visit. Just remember to dress for the weather, arrive early, and prepare to enjoy a relaxing, scenic cruise on a classic vessel.

FAQs

Is this tour suitable in all weather conditions?
Yes, it operates in all weather, so dress appropriately for wind, rain, or sunshine.

What’s included in the price?
You get a 2-hour sailing experience, bottled water, and the chance to enjoy unobstructed views of Salem’s coast.

Are alcoholic beverages available on board?
Yes, a full bar is available for purchase, including cocktails, beer, wine, and cider.

How early should I arrive?
Arrive at least 15 minutes before departure to allow for boarding and parking, especially during busy summer days.

Can I participate in sailing the boat?
Absolutely. Sails are hoisted during the trip, and guests are encouraged to help if they want to.

What’s the group size?
The maximum number of travelers is 28, ensuring a cozy and engaging atmosphere.

Is this tour family-friendly?
Children are welcome if accompanied by an adult, but keep in mind the boat’s steeper gangway and outdoor setting.

How far in advance should I book?
Most trips are booked about 30 days ahead, especially in peak season.

What’s the best time of day for this tour?
Multiple departure times are available, but sunset cruises are particularly popular for the stunning views.

If you’re after a memorable, authentic sailing adventure in Salem, this tour offers a wonderful blend of history, scenery, and relaxed fun. Whether you’re a seasoned sailor or just looking to enjoy some peaceful coastal views, it’s a voyage worth considering.