Salem isn’t just about witches and spooky stories—it’s also a fantastic place to enjoy sailing experiences that showcase its waterfront charm. The coastline surrounding Salem, Marblehead, and Beverly has been a hub for privateers, pirates, and merchant ships for over 400 years. That’s why taking to the water here feels like stepping into a living maritime museum. Our favorite is the Schooner Fame Sailing Tour, which combines a hands-on approach with engaging storytelling, making it perfect for families and curious travelers alike.
If you’re after a slightly longer and more luxurious experience, the Sailing on Historic Schooner Yacht in Salem, MA offers a 2-hour trip aboard a beautifully restored vessel built in 1939—built during a time when Salem’s ships were the backbone of global trade. For a more budget-friendly option that still delivers a memorable sail, the Salem: Historic Schooner Sailing Cruise provides a 100-minute cruise with great views and a fully-licensed bar. Keep reading for all the details on each experience to help you choose your perfect match.
1. Schooner Fame Sailing Tour
At number one, the Schooner Fame Sailing Tour stands out for its lively, interactive style. For just over $50, you’ll hop aboard a replica privateer schooner for about 1 hour and 40 minutes. The crew actively involves passengers in tasks like raising sails and steering—ideal if you don’t want to sit back and watch. This hands-on approach makes the experience especially appealing for families or anyone who likes to get involved rather than just observe.
The route covers the Salem Historic Salem Sound, an area buzzing with pirate lore, privateer history, and stories of merchant ships that shaped New England. The crew shares colorful tales that make the past come alive—plus, you can shoot a cannon if you’re feeling brave. Reviews praise the engaging crew and the informative stories, with many noting how accommodating they are for seniors and children alike. The departure points at Pickering Wharf Marina are convenient for those staying downtown.
Bottom Line: This trip offers a true taste of maritime history with a fun, participatory twist. It’s perfect if you want a lively, educational cruise and don’t mind getting a little hands-on.
2. Sailing on Historic Schooner Yacht in Salem, MA
Number two on our list is the Sailing on Historic Schooner Yacht in Salem, MA. For around $55, you’ll spend about 2 hours aboard the What and If, a classic yacht built in 1939. This boat’s vintage charm is a big part of the appeal—sailing here feels like stepping back into the early 1900s. The vessel was even associated with General George Patton, which adds a bit of WWII history to your ride.
Boarding at 10 Blaney Street, you’ll enjoy unobstructed views of Salem’s coastline. The trip includes options for passengers to take the wheel, help raise sails, or just relax and soak in the scenery. An onboard bar offers cocktails, beer, wine, and cider, making it a relaxed way to toast the setting sun. Passengers often comment on the friendly crew and how the open bar enhances the experience. Sunset sails are particularly popular, as the views over Salem and the surrounding waters are spectacular.
Bottom Line: This tour suits couples or travelers celebrating a special occasion who want a more refined, classic sailing experience with the chance to participate or simply unwind.
3. Salem: Historic Schooner Sailing Cruise
The Salem: Historic Schooner Sailing Cruise ranks third for its affordability and straightforward appeal. At just $39 for about 100 minutes, it offers a relaxed, scenic trip on the Schooner Fame, a traditional gaff-rigged schooner. This cruise focuses on sightseeing—perfect if you want to see landmarks like lighthouses, waterfront homes, and forts from the water.
The cruise emphasizes simple pleasures: knocking back a rum punch or helping to raise the sails while enjoying views of Salem’s coast. Many reviews highlight the friendly crew and the opportunity to get involved in sailing, which makes the experience more engaging than just sitting on a boat. Since it’s a shorter cruise, it’s a good choice if you’re tight on time but still want a genuine sailing experience.
Bottom Line: Ideal for budget-conscious travelers or those with limited time, this cruise offers a relaxed, scenic view of Salem’s waterfront with the chance to participate in sailing activities.
How to Choose the Best Salem Sailing Experience
When deciding between these options, consider your budget, available time, and what kind of experience you’re after. If you want a lively, family-friendly adventure, the Schooner Fame Sailing Tour is a great pick. For those celebrating a special moment or seeking a nostalgic, classic yacht experience, the Sailing on Historic Schooner Yacht fits the bill. If you prefer a quick, affordable scenic cruise with a relaxed vibe, the Salem: Historic Schooner Sailing Cruise is worth considering.
Booking early is recommended, especially during summer months when Salem’s waters are bustling. Choose the time of day that best suits your schedule—sunset trips tend to be especially lovely, offering stunning views over Salem Harbor.
Salem’s waterfront offers a variety of sailing adventures that cater to different interests and schedules. Whether you’re eager to get hands-on with a historic privateer, enjoy a luxurious sail on a vintage yacht, or just relax with a drink and the views, the options above will add a memorable maritime dimension to your visit. For maximum fun, consider booking in advance to secure your preferred time—these cruises fill up quickly when the weather’s warm. Happy sailing!