Halifax is a city that loves to sail. Its harbor, dotted with historic ships, vibrant waterfront, and scenic coastlines, makes for an ideal setting for sailing adventures. Whether you’re interested in a romantic sunset cruise, a hands-on sailing experience, or an evening under the stars, Halifax offers options that cater to all tastes. Among our favorites is the JFarwell Sunset Wine and Cheese Yacht Sailing — a small-group cruise that combines stunning coastline views with local wines and cheeses, perfect for a leisurely evening. We also appreciate JFarwell Adventure Yacht Sailing for its eco-friendly, wind-powered approach, which is ideal if you want to get hands-on with sailing. For those craving a lively atmosphere, the Tall Ship Silva Sailing Cruise with Live Music offers a classic tall ship experience with entertainment and the chance to assist in raising sails. With such a variety, Halifax truly stands out as a prime sailing destination.
Quick Overview
The list below covers sailing tours in Halifax that range from romantic sunset sails to energetic tall ship adventures. Highlights include wine and cheese cruises, moonlight sails, and eco-friendly wind-powered experiences. Whether you prefer a private yacht, a family-friendly tour, or a public tall ship cruise, each offers a unique angle on Halifax’s maritime charm. Now, let’s explore each in detail.
1. JFarwell Sunset Wine and Cheese Yacht Sailing
At number 1, the JFarwell Sunset Wine and Cheese Yacht Sailing offers a beautifully curated 2.5-hour cruise during Halifax’s most scenic time of day. This small-group tour, limited to just 10 people, provides a cozy, intimate setting to enjoy the spectacular coastline views as the sun dips below the horizon. What makes this experience stand out is the inclusion of four sampling glasses of local wine, paired with cheese boards featuring Nova Scotia’s best cheeses. The crew, well-versed and friendly, shares insights about the local area, making it both relaxing and educational.
Guests consistently praise the personalized service and memorable views, with reviews highlighting how Captain Ryan and crew went above and beyond, especially for special occasions like birthdays. The combination of scenic sailing, wine tasting, and charming small group makes this a top pick for romantic evenings or quiet getaways. The only caveat? The price at $148.32 per person is a bit on the higher side, but the exclusivity and quality justify it. This tour is perfect for couples or anyone wanting a refined, memorable night on the water.
Bottom Line: An elegant, intimate way to enjoy Halifax at sunset, ideal for romance or special celebrations.
2. JFarwell Adventure Yacht Sailing in the Halifax Harbour
For around $81.58, the JFarwell Adventure Yacht Sailing provides a more active and eco-friendly way to experience Halifax Harbour. This is Halifax’s only wind-powered sailing tour, giving you a chance to truly feel the wind in your hair and learn the basics of sailing. The 1.5-hour trip is perfect for those curious about how sailing works — you can opt to help with the sailing tasks or just sit back with the scenery.
What makes this tour stand out is its small, intimate group of 12, and the opportunity to get involved with the crew, making it especially engaging for families or curious travelers. Reviews mention that Ryan and Colin are fantastic, and kids particularly enjoy doing the sailing tasks. Modern equipment onboard adds to the comfort, and the views of Nova Scotia are stunning from the deck. The tour’s value lies in its participatory nature, giving you a genuine sailing experience without the crowds or high cost.
Bottom Line: Best suited for those who want an authentic, eco-friendly sailing adventure with hands-on involvement and beautiful harbor vistas.
3. JFarwell Moonlight Yacht Cruise from Halifax Waterfront
A romantic choice, the Moonlight Yacht Cruise offers a 90-minute sail along Halifax’s illuminated skyline. It’s a perfect way to wind down after a day of sightseeing, with the nighttime ambiance creating a different perspective of the city. The small group, with just 48 reviews and a 5/5 rating, makes it cozy and personal, with serene views of Halifax’s landmarks bathed in moonlight.
You’ll sail past George’s Island, enjoy music onboard, and have the option to purchase craft beer, wine, or spirits. The relaxed atmosphere, with blankets available if it gets chilly, makes it ideal for a casual evening out. Guests remark on the beautiful harbor views at night and the attentive crew that makes sure everyone is comfortable. The cost at about $74.13 per person makes it accessible and worthwhile for a memorable night under the stars.
Bottom Line: A relaxing, intimate cruise perfect for couples and small groups wanting a peaceful, scenic night sail.
4. JFarwell Private Yacht Wine & Cheese Sunset Sail
For those seeking privacy and a tailored experience, the Private Yacht Wine & Cheese Sunset Sail offers a 2.5-hour cruise with a private boat. Starting at 1599 Lower Water St., this experience includes four Nova Scotia wines, cheese, and snacks, all while cruising the scenic coastline and Northwest Arm. It’s a customizable tour, making it perfect for romantic evenings, anniversaries, or small celebrations.
What really elevates this experience is the ability to personalize the itinerary—perhaps to include landmarks like Dingle Tower or lush parks. The yacht’s elegant setting and the opportunity to savor local wines while watching the sunset lend a luxurious feel. Reviews highlight the private setting and attentive service, making it ideal for travelers wanting exclusivity.
Bottom Line: A luxurious, customizable sailing experience suited for romantic getaways or special occasions.
5. Tall Ship Silva Sailing Cruise Ft. a Live Musician
At number 5, the Tall Ship Silva Sailing Cruise offers a classic schooner experience with a lively twist. For just $40.36, you get a 2-hour tour that includes the chance to help hoist sails, tie knots, or just relax while enjoying Halifax’s waterfront sights. The ship, often with sails up during the trip, also features live music, adding to the festive atmosphere.
Guests often mention the interactive nature of the trip, with crew sharing interesting tidbits about the harbor and landmarks like Fort George and McNab’s Island. The reviews praise the friendly crew and the musician Gary, who enhances the relaxing vibe. The tour’s affordability makes it a good pick for families or those new to sailing who want a lively, engaging experience.
Bottom Line: A fun, interactive, and musical take on sailing, suited for families or anyone wanting a lively vibe and classic tall ship charm.
6. Halifax: Tall Ship Harbor Sailing Cruise with Live Music
This 2-hour afternoon cruise on the Tall Ship Silva provides a transportive experience with the chance to help hoist the largest sails in Halifax Harbor. Starting from downtown Halifax, it’s a great way to see the city’s highlights from the water while enjoying live musical entertainment.
The tour is slightly more relaxed and offers good photo ops, especially of the harbor bridge, Cable Wharf, and Georges Island. The crew’s friendliness and the opportunity to participate in sailing make it more engaging than a typical boat ride, and the live music sets a lively tone. The experience is priced at $42 per person, making it a good value for an interactive sailing outing.
Bottom Line: A lively, participatory sailing experience with entertainment, perfect for visitors wanting both sightseeing and engagement.
7. Halifax: Sunset Wine and Cheese Sailboat Cruise
Combining sailing, wine tasting, and sunset views, the Sunset Wine and Cheese Sailboat Cruise offers a refined experience for about $117 per person. Over 2.5 hours, you’ll cruise the harbor, enjoying Nova Scotia wines and cheese while watching the sunset behind Dingle Tower.
The tour emphasizes learning about the local wine industry, making it both relaxing and educational. The sailboat provides excellent vantage points of the waterfront, and the small group size enhances the intimacy of the experience. This cruise is best suited for wine lovers and those celebrating special occasions.
Bottom Line: A sophisticated, scenic cruise for wine enthusiasts wanting a tranquil, picturesque evening.
8. Halifax: Summer Breeze Sailing Tour with Cocktail
Ideal for summer days, the Summer Breeze Sailing Tour is a 2-hour relaxed cruise with a custom local cocktail or mocktail. It’s a laid-back option that passes by landmarks like George’s Island and Point Pleasant Park, offering maximum comfort and enjoyment.
This tour is perfect if you want to combine sailing with refreshing drinks and scenic views. The two reviews both rate it 5/5, emphasizing the relaxed atmosphere and passenger involvement. It’s suited for travelers who prefer a casual, summer-focused outing, especially if they enjoy a drink or two.
Bottom Line: A chilled, scenic cruise perfect for warm days and those who want to sip while enjoying Halifax’s coastline.
9. Private Luxury Catamaran Moonlight Party in Halifax
For the ultimate luxury experience, the Private Luxury Catamaran Moonlight Party offers a premium, private cruise for up to 12 people. Priced at $990.81, it features the newest boat in the fleet, The Reverie, with lounging areas, water views from the nets, and a full setup to enjoy the halifax harbor at night.
This experience is tailored for special celebrations or those wanting a luxurious, private outing. The deck layout maximizes comfort and views, and the onboard music system adds a party atmosphere. Reviews highlight the boat’s elegance and the serene moonlit setting, making it worth the splurge for a memorable, exclusive event.
Bottom Line: The perfect choice for private celebrations, romantic evenings, or a once-in-a-lifetime luxury cruise.
$990.81 per group (up to 12)
How to Choose Your Halifax Sailing Experience
When picking your ideal sailing trip, consider your budget, timing, and interests. If you’re after a romantic sunset, the Sunset Wine and Cheese Yacht Sailing is a top choice. For a hands-on adventure, Adventure Yacht Sailing offers an eco-conscious, participatory experience. Family travelers or first-timers may prefer the Tall Ship Silva cruises, especially with live music and sails.
Budget-conscious travelers will find good value in the Harbor Sailing with Live Music, while those celebrating special occasions might enjoy the private yacht or luxury catamaran options. Keep in mind the best times tend to be during warm months from late spring to early fall, with sunset cruises especially popular.
Booking early is recommended, particularly in peak summer months, to secure your preferred date and experience.
Final Thoughts
Halifax offers diverse sailing experiences that suit all preferences—from romantic sunset cruises to energetic tall ship adventures. If you’re looking for a refined, private experience, the Private Yacht Wine & Cheese or the Luxury Catamaran Moonlight Party fit the bill. For a lively, interactive outing, the Tall Ship Silva cruises promise fun and music. Budget travelers will appreciate the value of the Harbor Sailing with Live Music, offering a classic Tall Ship experience at a reasonable price.
No matter your choice, Halifax’s sailing scene invites you to enjoy the water from a new perspective. Booking early and considering your personal interests will ensure a memorable experience on the harbor. Dive in and set sail—you won’t regret it!