Sailing on Historic Schooner Yacht in Salem, MA

If you’ve ever dreamed of feeling the wind in your hair while gliding across the water on a charming, vintage vessel, this sailing experience in Salem might just be what you’re looking for. Operating aboard the beautifully restored 1939 schooner What and If, this trip offers a glimpse into maritime history combined with stunning views and a relaxed vibe. Whether you’re celebrating a special occasion or just craving a peaceful escape on the bay, this tour manages to strike a perfect balance of fun, history, and scenic beauty.

What truly makes this experience stand out are three things: it’s an authentic sail on a vessel built in an era when sailing was both a livelihood and a leisure activity, the crew’s deep knowledge and friendliness, and the opportunity to enjoy unobstructed views of Salem’s coastlines and nearby islands. That said, the tour does operate in all weather conditions, so dressing appropriately is wise—wind and sun protection are key if you want to stay comfortable.

One potential consideration is that, depending on the weather, the sails may not always be fully hoisted, and the trip could be partially powered by engine. For some, that could slightly alter the sense of traditional sailing, but most reviewers find it doesn’t detract from the overall charm. This tour is ideal for couples, families, or friends who appreciate history, scenic cruises, and a touch of adventure on the water.

Key Points

• Authentic vintage vessel built in 1939 offering real sailing charm
• Scenic routes around Salem Sound, Marblehead, and nearby islands
• Relaxed, small group experience with a maximum of 28 travelers
• Informative crew sharing local history and boat insights
• Flexible departure times allowing for personalized schedules
• Drinks available onboard including soft drinks and a full cash bar

An In-Depth Look at the Salem Schooner Experience

Setting Sail on a Classic Schooner

The tour begins at 10 Blaney Street, next to the Salem ferry building, making it easy to access whether you’re staying in Salem or arriving by ferry. The vessel itself is a beautifully maintained piece of maritime history, built in 1939, with a wooden hull and four sails that evoke an earlier era of sailing ships. It’s clear from the reviews that the crew takes excellent care of it—“Thesis was in such great condition,” said one guest, highlighting the vessel’s pristine state and attention to detail.

Boarding usually begins about 15 minutes before departure, and there’s parking available on the pier. It’s best to arrive early on busy summer days to secure a spot, especially since the boat limits its number of passengers to 28, ensuring a more intimate and engaging experience.

What to Expect During the 2-Hour Trip

The journey typically lasts around 2 hours, with the itinerary covering several key highlights:

• Sunset Sail Salem: While most sails focus on daytime cruising, many reviews mention the magical quality of sailing during sunset. As the sails are hoisted, the crew opens a craft beverage bar, offering cocktails, beer, wine, and cider, which many reviewers say adds to the relaxed, celebratory atmosphere.

• Sailing Along Salem Sound: The majority of the experience is about gliding smoothly across calm waters, with the crew actively involved—helping raise sails, steering, and sharing stories. According to reviews, guests love the chance to take a turn at the wheel and learn about the boat’s history.

• Scenic Coastal Views and Islands: The tour explores Marblehead, where you’ll see historic waterfront homes, and visits Children’s Island and Misery Island, with the crew sharing stories about their significance. Several guests appreciated the “spectacular sights of historic homes” and the unique island history.

• Wildlife Spotting and Nature: A few reviews mention seeing whales and other marine life, which shows how captivating a day on the water can be, even with some weather hiccups.

The Experience on Deck

The deck is the main attraction, offering both comfort and adventure. Many visitors mention how well-maintained and charming the schooner is, with a cozy, authentic feel. The crew’s friendliness and knowledge make the experience more meaningful; they’re eager to share stories, answer questions, and involve guests in sailing activities.

“The crew was very knowledgeable, welcoming, and entertaining,” said one reviewer, capturing the warm, hospitable atmosphere. And with drinks available until 30 minutes before docking, you can toast the sunset with a glass of your favorite beverage.

The Crew and Service

The crew receives high praise for their professionalism and friendliness. They’re described as “knowledgeable, hospitable, and fun,” making the trip more engaging. Many reviews also mention how they go above and beyond—encouraging guests to help with sails or explore the boat, which adds a hands-on element that many find memorable.

Weather and Conditions

While the trip operates in all weather, adverse conditions might affect the sailing experience. In some cases, the sails may be partially powered by the engine, but most reviewers agree this doesn’t diminish the atmosphere—“despite being under power most of the time, it was a fantastic outing,” said one. It’s wise to dress in layers and bring windproof gear, especially for sunset or evening sails.

Pricing and Value

At $55 per person, this tour offers a very reasonable price for a two-hour, scenic sailing adventure. When you consider the vessel’s historic charm, the crew’s expertise, and the unobstructed views, the value feels justified. The inclusion of soft drinks and bottled water further sweetens the deal, and the cash bar allows for added indulgences if desired.

Booking and Availability

Most travelers book about 30 days in advance, which speaks to the tour’s popularity, especially during peak summer months. Multiple departure times provide flexibility so you can pick one that fits your schedule—perfect for those who want to combine this with other activities around Salem.

Accessibility and Practical Tips

The schooner’s gangway might have steep inclines depending on the tide, so travelers with mobility concerns should plan accordingly. Children are welcome but must be accompanied by an adult, and service animals are permitted. Since the trip is outdoors, dressing in layers and bringing sunscreen or rain gear is recommended.

Who Will Love This Experience?

This sailing tour is ideal for couples seeking a romantic adventure, families wanting a fun, educational outing, or friends looking for a unique way to explore Salem’s coastline. It’s especially suited for those interested in historical vessels, scenic views, and a relaxed atmosphere. If you enjoy engaging guides and a chance to actively participate, this trip delivers on all fronts.

The Sum Up: Is This the Sailing Trip for You?

This historic schooner experience offers more than just a boat ride; it’s a window into the maritime past mixed with modern comfort and lively storytelling. The combination of a vintage vessel, knowledgeable crew, and stunning scenery makes it a standout activity in Salem. It’s perfect for travelers who cherish authentic, scenic moments and enjoy a bit of maritime history with their cruise.

If you’re after a relaxing yet engaging outing, and don’t mind a little weather-dependent flexibility, you’ll find this tour to be worth every penny. It’s a great choice for those who want a memorable, scenic adventure that combines the charm of the past with the beauty of Salem’s surroundings.

FAQs

Is this tour suitable for children?
Yes, children are welcome if accompanied by an adult. Kids will enjoy the chance to see the boat and participate in sailing activities if they wish.

What should I wear?
Dressing in layers is recommended since it can get breezy on the water, especially during sunset or evening sails. Bring a windproof jacket and comfortable shoes.

Can I help with the sails?
Absolutely. Many guests find helping raise the sails to be a memorable part of the experience, and the crew encourages participation.

Is there a bar onboard?
Yes, a cash bar is available, offering cocktails, beer, wine, and cider. Soft drinks and bottled water are included in the ticket price.

Are the sails always hoisted during the trip?
Not necessarily. The sails are hoisted when wind conditions allow, but sometimes engines are used if the weather isn’t ideal for traditional sailing.

What are the departure times?
Multiple departure times are offered to fit different schedules, with most sails lasting around 2 hours.

How early should I arrive?
Arrive at least 15 minutes before your scheduled departure to allow time for boarding and parking.

What happens if the weather is bad?
The tour operates rain or shine. If weather conditions are unsafe or too poor to sail, the trip may be canceled or rescheduled, with full refunds offered.

This sailing adventure in Salem offers a practical blend of history, scenic beauty, and relaxed fun, making it a must-try for anyone eager to see Salem from a different perspective. Whether you’re celebrating, seeking tranquility, or just love the water, this tour delivers a memorable maritime escapade.