Salem’s waterfront offers three standout sailing experiences that showcase the city’s maritime heritage.
The Privateer Schooner Tour on the Fame tops our list – it’s a well-organized 30-passenger voyage that brings colonial seafaring history to life.
The historic schooner When And If delivers a comfortable, relaxed experience with convenient scheduling and onboard refreshments.
For those interested in local lore, the 90-minute Salem Sailing Cruise combines water views with tales of the city’s haunted past and witch trials.
We especially recommend the Fame’s tour for its engaging crew and historically accurate storytelling.
The When And If earns points for its flexible scheduling and welcoming atmosphere.
Let’s explore these distinctive sailing options in detail.
Key Points
- Experience Salem’s rich maritime history aboard the privateer schooner Fame, with a 5-star rating and a maximum capacity of 30 travelers.
- Explore the North Shore on the historic schooner When And If, built in 1939 by General George Patton, accommodating up to 32 passengers.
- Set out on a 1.5-hour sailing cruise on the schooner yacht When And If, offering views of Salem’s iconic landmarks and a “Ghosts, Graveyards, and Gallows” tour.
- Enjoy a memorable sailing adventure with warm cider, soda, snacks, and a full bar on the privateer schooner Fame.
- Suitable for families, excluding children under five, and ideal for couples or special occasions on the historic schooners in Salem.
Privateer Schooner Sailing Tour in Salem Sound
The Privateer Schooner Sailing Tour in Salem Sound offers visitors a unique opportunity to experience the maritime history of Salem. Aboard the schooner Fame, guests can help hoist the sails and steer the boat, while the crew provides historical insights and even fires a cannon during the tour.
With a maximum of 30 travelers, this 5-star rated experience boasts a remarkable 99% recommendation rate from past guests.
The tour departs from Finz Salem, though parking and traffic can be challenging, especially on weekends in October. Onboard, guests can enjoy warm cider, soda, and snacks, as well as alcoholic beverages.
While the tour isn’t wheelchair accessible, it’s a great option for families, with the exception of children under five. Reviewers consistently praise the crew’s friendliness and knowledge, as well as the stunning views of the coastline and sunsets.
Whether you’re a history buff or simply seeking a memorable sailing adventure, the Privateer Schooner Sailing Tour is a must-do activity in Salem.
Read our full review: Privateer Schooner Sailing Tour in Salem Sound Review
Book now: Check availability
Sailing on Historic Schooner When And If in Salem, MA
Nestled along the picturesque shoreline of Salem, Massachusetts, the historic schooner yacht When And If offers visitors a unique opportunity to experience the region’s rich maritime heritage. Built in 1939 by General George Patton, this iconic vessel sets sail along the North Shore, providing guests with unobstructed views of Salem’s coastline.
With multiple departure times available, travelers can easily fit this experience into their schedule. The tour includes bottled water, gratuities, and a full bar for purchase on board, ensuring a comfortable and convenient journey.
Accommodating up to 32 passengers, the When And If is ideal for couples or special occasions, boasting a 5.0 overall rating from 124 reviews.
Despite the vessel’s accessibility limitations, the crew is praised for their knowledgeable and friendly guidance, making the experience enjoyable for all.
Whether you’re seeking a relaxing outing or a celebration on the water, the When And If promises a memorable sailing adventure in Salem.
Read our full review: Sailing on Historic Schooner When And If in Salem, MA Review
Book now: Check availability
Salem: Historic Schooner Sailing Cruise
Sailing along the picturesque coastline of Salem, Massachusetts, the historic schooner yacht When And If provides visitors with a unique opportunity to experience the region’s rich maritime heritage.
This 1939 classic wooden schooner offers 1.5-hour cruises that allow guests to step back in time and witness the town’s storied past from the water. During the tour, passengers can marvel at the Witch House, the Old Burying Point Cemetery, and other historic sites that dot the Salem shoreline.
With a capacity of just 49 passengers, the When And If offers an intimate sailing experience. Guests can choose to relax on the deck and take in the scenery or lend a hand by assisting the crew with sailing duties.
The schooner’s Ghosts, Graveyards, and Gallows cruise is particularly popular, providing an atmospheric journey through Salem’s haunted history. At $35 per person, this sailing adventure is a must-do for anyone seeking to explore Salem’s maritime legacy.
Read our full review: Salem: Historic Schooner Sailing Cruise Review
Book now: Check availability
The Sum Up
Sailing through the historic Salem Sound offers visitors a unique experience. Aboard the classic schooners, travelers can enjoy the maritime heritage of the area while enjoying scenic views and a peaceful journey. Whether it’s the Privateer Schooner Tour, the schooner When And If, or the Historic Schooner Sailing Cruise, these sailing excursions provide an unforgettable way to explore the coastal charm of Salem, Massachusetts.