Sailing on Historic Schooner Yacht in Salem, MA

Sailing on a Historic Schooner Yacht in Salem, MA: A Detailed Review

If you’re visiting Salem and craving a different perspective, a sailing trip aboard a historic schooner might be just the thing. This tour offers a chance to glide along Salem’s coastline on a vessel built in 1939, with the wind in your hair and the sights unfolding around you.

Although I haven’t personally taken this cruise, the glowing reviews and detailed information paint a compelling picture for anyone seeking a relaxing, scenic adventure on the water.

What we love about this experience is the authenticity of sailing on a vessel that’s nearly 85 years old, and the spectacular views of Salem’s coastline and nearby islands. The chance to help hoist the sails or take the wheel adds a dash of hands-on fun.

However, one potential consideration is that the tour operates in all weather conditions, so it’s wise to dress appropriately — and be prepared for the possibility of less-than-perfect weather.

This sailing tour is perfect for couples celebrating a special occasion, families, or anyone who simply loves being on the water. If you’re after a unique, laid-back way to see Salem from a different angle, this tour fits the bill nicely.

This experience made our article of The 3 Best Boat Tours & Cruises In Salem.

Key Points

• Authentic Vintage Vessel: You’ll sail on a beautifully restored classic schooner built in 1939, built by General George Patton himself.
• Scenic Coastal Views: Expect unobstructed vistas of Salem’s coastline, nearby islands, and historic homes on Marblehead.
• Flexible Schedule: Multiple departure times allow you to pick a slot that fits your day.
• All Weather Operation: The tour runs rain or shine, so dress accordingly.
• Optional Drinks: Soft drinks are included, and a cash bar offers beer, wine, cider, and cocktails — perfect for relaxing after hoisting the sails.
• Educational & Entertaining Crew: The crew is praised for their knowledge, hospitality, and fun attitude, making the trip engaging for all.

In-Depth Look at the Experience

Boarding and Location

The adventure begins at 10 Blaney Street, adjacent to the Salem ferry building. Parking is available on the pier, but on busy days, arriving early is advised. The vessel, What and If, is a stunning piece of maritime history, with a wooden hull and four sails, perfectly maintained to reflect its 1939 roots. Boarding starts 15 minutes before departure, and the tour lasts around 2 hours, offering plenty of time to enjoy the scenery and the boat’s character.

The Itinerary Breakdown

Stop 1: Sunset Sail Salem
Setting sail from Salem’s harbor, this trip is not just about catching the sunset — though you might if timing aligns — but also about experiencing sailing as it was over a century ago. The crew hoists the sails, and you’ll get hands-on opportunities to help if you’re interested. Many reviews mention how engaging and personable the crew is, with one reviewer saying, “The crew was amazing, we made great new friends.” You can enjoy a variety of drinks from the craft beverage bar, which remains open until about 30 minutes before docking.

Stop 2: Sail around Salem Sound
The route takes you around Marblehead, showcasing historic homes and gorgeous coastal scenery. You’ll also pass near several islands, including Children’s Island and Misery Island Reservation. The crew is eager to share stories about these islands, adding depth to the experience — “ask the crew about the history of the islands,” one review suggests. Even if the weather isn’t perfect, many find the experience relaxing and scenic.

Additional scenic cruising around Salem’s islands and nearby areas provides opportunities for photos and enjoying the fresh sea air. Several reviews mention the spectacular views and the peacefulness of sailing with the wind, especially when the sails are hoisted and the engine is turned off.

What’s Included and What’s Not

Included are bottled water and the experience of sailing a historic vessel. Alcoholic beverages are not included but are available for purchase onboard, with a full bar offering beer, wine, cocktails, and cider. Many reviewers noted the quality of the drinks and the friendly attitude of the bartenders, making for a relaxed, social atmosphere.

The Crew and Atmosphere

The crew receives consistent praise for their knowledge, friendliness, and humor. From helping climb the rigging to explaining the ship’s history, they ensure everyone feels involved and comfortable. Several reviews mention how guests of all ages, from toddlers to grandparents, enjoyed helping with the sails or simply relaxing on deck.

Weather Considerations

Since the tour operates in all weather conditions, dressing in layers is wise. Reviews recount instances of wind, fog, or cloudy skies, yet most still enjoyed the trip immensely. If the weather is less cooperative, you might find the atmosphere even more atmospheric — perhaps fog adds a mysterious pirate vibe! Just be prepared for possible wind and chill, especially on the open water.

Duration and Group Size

The tour lasts approximately 2 hours, with a maximum of 28 travelers, keeping the group intimate enough for personalized attention from the crew. Booking about 30 days in advance is common, highlighting the popularity of this experience.

Pricing and Value

At $55 per person, this experience offers excellent value for a scenic, historical, and interactive sailing adventure. Compared to other Salem attractions, it’s a peaceful, memorable way to spend a couple of hours soaking in views and maritime history. The opportunity to help with the sails or take the wheel makes it a hands-on experience that adds to the value.

Authentic Reviews Reflection

Numerous visitors highlight the stunning scenery as a standout feature. One mentions, “Beautiful night and a beautiful boat,” emphasizing the visual appeal. The crew’s attentiveness and humor shine in reviews like, “They all went out of their way to make sure everyone had a good time,” and “The crew was very knowledgeable and welcoming.” Even weather-related hiccups didn’t dampen spirits; for example, a reviewer fondly called the foggy weather the “Pirate Experience,” turning what could be a disappointment into a memorable adventure.

Many reviewers appreciate the informative storytelling, which brings the vessel’s history alive, and the opportunity to interact — like helping hoist the sails — which makes the trip both fun and educational.

Who Should Consider This Tour?

This cruise is ideal for couples, families, or groups of friends looking for a laid-back, scenic outing. It suits those interested in maritime history, scenic photography, or simply a peaceful escape from bustling streets. For travelers celebrating a special occasion or seeking a unique way to appreciate Salem’s coast, this tour delivers in all those areas.

The Sum Up

Sailing on a nearly 85-year-old schooner offers more than just a boat trip — it’s an opportunity to experience Salem in a quaint, historic, and relaxing way. With its well-maintained vessel, friendly crew, and stunning views, this tour delivers a genuine maritime adventure that’s both fun and educational. The option to help hoist the sails or enjoy a drink from the bar adds a layer of engagement that many travelers find memorable.

At just $55, it provides great value, especially for those wanting to combine scenic beauty with a touch of history and hands-on fun. Whether you’re a sailing enthusiast or simply seeking a peaceful, scenic afternoon, this tour will leave you with stories to tell and memories to cherish.

FAQ

How long is the sailing trip?
The tour lasts approximately 2 hours, giving you ample time to enjoy the scenery and participate in the sailing.

Where does the tour start?
Boardings are at 10 Blaney Street, Salem, next to the Salem ferry building.

Is parking available?
Yes, there is parking on the pier, but arriving early on busy days is advisable to secure a spot.

What should I wear?
Dress in layers and wear comfortable clothing suitable for outdoor weather, as the trip runs in all weather conditions.

Are drinks included?
Soft drinks and bottled water are included; alcoholic beverages are available for purchase onboard.

Can children participate?
Yes, children must be accompanied by an adult. Child prices apply only when sharing with two paying adults.

Is the trip suitable for people with mobility issues?
The gangway may have steep inclines depending on the tide, so take care when boarding.

What happens if the weather is bad?
The tour operates rain or shine. If canceled due to poor weather, you’ll be offered a different date or a full refund.

This sailing trip in Salem offers a charming, authentic way to see the coast and enjoy some maritime history, all while savoring the fresh sea air. It’s a calming, engaging experience that combines natural beauty, historical charm, and a splash of adventure — truly a highlight for any maritime-minded traveler.