Sailing on Historic Schooner Yacht in Salem, MA

Imagine stepping aboard a beautifully restored vessel built in 1939, feeling the wind in your hair, and watching Salem’s coastline drift past. That’s exactly what this sailing tour offers. Whether you’re a sea lover or just looking for a relaxing way to see Salem from the water, this two-hour cruise on the schooner What and If offers an authentic maritime experience with a touch of history.

We love that this tour combines classic sailing charm with informative commentary from friendly crew members. It’s also a fantastic way to unwind, sip a drink, and absorb the sights of Salem’s harbor and nearby islands. That said, it’s worth noting that the boat’s boarding may involve some steep inclines depending on tide conditions, so a bit of agility helps.

This experience is best suited for couples celebrating a special occasion, small groups seeking a unique outing, or anyone wanting a peaceful, scenic journey with unobstructed views. It’s a relaxed, intimate adventure that offers more than just a boat ride—it’s a taste of maritime history right on Salem’s shores.

Key Points

• The tour features a beautifully maintained 1939 schooner built by General George Patton
• It offers an authentic sailing experience with options for optional beverages
• Great for celebrating special moments or enjoying a peaceful sightseeing cruise
• Views include Salem coastline, Marblehead historic homes, and nearby islands
• The tour offers multiple departure times, accommodating various schedules
• The price provides good value, especially with included bottled water and the chance to help with sails

Setting Sail on Salem’s Waters

The experience begins at the dock at 10 Blaney Street, just a short walk from Salem’s historic areas and conveniently next to the ferry building. Boarding typically starts 15 minutes before departure, giving you a moment to settle in and soak up the maritime atmosphere. Parking on the pier is available, but especially during busy summer days, arriving early ensures you’ll find a spot.

Once aboard, you’ll notice the What and If’s elegant, vintage design echoing the early 20th-century schooner style. The crew greets you with friendliness and knowledge, eager to share stories about the vessel’s history as well as local lore. This vessel’s unique story—being built in 1939 and associated with General George Patton—adds a layer of historical charm that makes the voyage more than just a scenic cruise.

What to Expect During the Tour

The sailing itself lasts approximately two hours, during which you’ll get the chance to sit back, relax, or even take a turn at the wheel if you’re feeling adventurous. The majority of the sail takes place on Salem Sound, providing sweeping views of the coastline, historic homes in Marblehead, and the various islands nearby, including Children’s Island and Misery Island Reservation. As one reviewer put it, “The crew was amazing, we made great new friends, and we would do this again the next time we’re in town.”

The itinerary is straightforward but packed with visual delights:

• Stop 1: Sunset Sail Salem – Here, the crew expertly handles the sails, giving passengers an authentic feel of early 20th-century sailing. The vessel is meticulously maintained, and the crew’s passion for sailing is evident. While most sails are around two hours, the focus is on quality and comfort—plus, a craft beverage bar is available for those who want to toast the moment. You can choose from cocktails, beer, wine, cider, or weekly specials, which are available until 30 minutes before docking.

• Stop 2: Navigating Salem Sound – The crew’s commentary enhances this part, as they point out sights and share stories about the islands and the historic homes along the coast. This is the perfect opportunity to snap photos and take in the scenic beauty from a different perspective.

• Additional Sights – Sailing around the islands gives you a closer look at Salem’s maritime environment. An especially popular feature is sailing around Marblehead’s historic homes, with one reviewer noting, “Enjoyed spectacular sights of the gorgeous historic homes built on the neck.”

Authentic Experiences and Comfortable Comforts

A big highlight of this tour is the combination of historic charm and relaxed comfort. The vessel is well cared for, and the crew is friendly and eager to share their knowledge. Many passengers mention how the crew made them feel at home, with comments like, “They were very informative, friendly, and made us feel right at home.”

Soft drinks and bottled water are included, offering a quick refreshment after a busy day of sightseeing. The full bar, available for purchase, usually features a selection of wines, beers, and cocktails—perfect for unwinding as you watch the sunset or the waves. A common sentiment from delighted guests is, “The open bar was a plus,” which adds value to the experience without breaking the bank.

Keep in mind that the tour operates in all weather conditions, so dressing appropriately is wise. If rain or wind is forecasted, bringing a jacket or layers will ensure you stay comfortable. Since the gangway and deck have some steep inclines depending on the tide, travelers with mobility issues should plan accordingly.

Who Will Love This Tour?

This sailing adventure appeals most to those seeking a peaceful, scenic escape with a dash of history and a splash of fun. It’s ideal for couples celebrating anniversaries, small groups of friends, or families with children (who are accompanied by adults). The intimate nature of the boat—with a maximum of 28 travelers—creates a cozy environment perfect for making new friends or quietly soaking in the views.

Travelers praised the experience as “breathtaking” and “relaxing,” often mentioning the excellent crew and beautiful scenery. It’s a perfect way to slow down and enjoy Salem from a different perspective, especially if you like the idea of helping with the sails or learning about sailing life.

Analyzing the Value

At $55 per person, this tour offers quite a bit of value. Given the scenic beauty, the chance to learn about the boat’s history, and the optional participation at the helm, it’s a memorable experience that doesn’t break the bank. The included bottled water and the opportunity to buy drinks add to the relaxing vibe, making it feel like a floating social event.

While some may wish for a longer cruise or more stops, the two-hour schedule strikes a good balance between time and value, especially since many reviews highlight how the crew’s friendly approach enhances the experience. Booking about a month in advance is typical, which suggests it’s a popular choice during peak season.

Final Thoughts: Who Should Consider This?

If you’re looking for a leisurely, authentic sailing experience on Salem’s waters, this tour delivers. It’s perfect for those who enjoy scenic views, maritime history, and small-group intimacy. Whether celebrating a special occasion or simply craving some quiet time on the water, you’ll find this voyage a charming highlight of your Salem visit.

Keep in mind that weather can influence the experience, so dress accordingly and plan for flexible scheduling. The combination of earnest crew, historic vessel, and stunning coastal scenery makes this tour a worthwhile addition for any traveler seeking a genuine maritime outing.

Frequently Asked Questions (FAQs)

What is the duration of the tour?
The tour lasts approximately 2 hours, providing ample time to enjoy the scenery and participate in sailing activities without feeling rushed.

Where does the tour depart from?
It departs from 10 Blaney Street in Salem, right next to the ferry building. Boarding begins about 15 minutes before scheduled departure.

Is parking available nearby?
Yes, there is parking on the pier. However, during busy summer months, arriving early helps secure a spot.

What is included in the ticket price?
Soft drinks and bottled water are included. The full bar is available for purchase, offering cocktails, beer, wine, and cider.

Can children participate in the tour?
Yes, children can join when accompanied by an adult. Child rates apply only when sharing with two paying adults.

What should I wear?
Dress appropriately for the weather—layers and waterproof gear are advisable, especially if rain or wind is forecasted.

Are there any physical considerations?
The gangway may have steep inclines depending on the tide, so travelers should be comfortable with some mobility challenges.

Does the tour operate in bad weather?
Yes, it runs in all weather conditions. If canceled due to poor weather, you’ll be offered a different date or a full refund.

Can I help with the sails?
Guests are often encouraged to participate, making the experience interactive and engaging.

How far in advance should I book?
Most travelers book about 28 days ahead, especially during peak season, to secure their preferred departure time.

Final Word

This sailing trip on Salem’s historic schooner What and If offers a charming, authentic way to see the coast from the water. It’s a relaxing, scenic escape that combines maritime history with stunning views of Salem and nearby islands. With friendly crew, a touch of adventure, and optional drinks, it’s suited for those who want a memorable, intimate experience without sacrificing comfort or authenticity.

If you’re someone who appreciates a blend of history, scenery, and small-group camaraderie—this is the kind of outing that will leave you with lasting memories. Whether you’re celebrating, seeking a peaceful retreat, or simply curious about maritime life, this tour provides a unique perspective on Salem’s waterfront.