Portland’s sailing scene offers three standout experiences for maritime enthusiasts.
The historic Maine Windjammer tour packs serious value into its 2-hour trip, letting you work the sails while soaking up local seafaring history – perfect for hands-on travelers.
For a more intimate experience, Scovare Yachts runs excellent private charters that let you set your own pace through Portland’s waterways.
The 90-minute harbor tour hits the sweet spot, combining essential sights with expert narration at a reasonable price.
We especially love the Windjammer tour for its authentic sailing experience and the way it connects visitors to Portland’s maritime roots.
The private Scovare charter wins points for flexibility and personalized attention.
Let’s explore these top-rated sailing tours that showcase the best of Portland’s coastal heritage.
Key Points
- Traditional Maine-built windjammer sailing tour offers a 2-hour scenic experience with opportunities to participate in sailing activities.
- Private sailing charter by Scovare Yachts provides a personalized tour of Portland’s waterways with live commentary and local guidance.
- 90-minute sailing tour of Portland’s waterways offers city views and complimentary food and drinks, though may be limited by low wind conditions.
- Sailing experiences range in duration from 2 hours to 90 minutes, catering to different preferences and group sizes.
- Sailing tours depart from various locations in Portland, including the Maine State Pier and Willamette Park, accommodating different access needs.
Portland Maine Traditional Windjammer Sailing Tour
The Portland Maine Traditional Windjammer Sailing Tour offers visitors a chance to experience the beauty of the Maine coast from a unique vantage point. This 2-hour sailing tour aboard a traditional, Maine-built windjammer departs from the Maine State Pier in Portland, Maine.
With a maximum capacity of 45 travelers, the cruise provides an intimate and relaxing atmosphere. Guests can bring their own snacks, refreshments, and alcoholic drinks to enjoy during the tour.
They’ll have opportunities to hoist sails or steer the ship, while the crew provides historical context and navigational insights. Sightseeing highlights include lighthouses, seals, and seabirds. The schooners are equipped with life jackets for adults and children, ensuring a safe and enjoyable experience.
With an overall rating of 4.5 from over 222 reviews, the Portland Maine Traditional Windjammer Sailing Tour is praised for its friendly and knowledgeable crew, beautiful scenery, and serene atmosphere.
The tour is recommended for families and individuals seeking a peaceful outing on the water.
Read our full review: Portland Maine Traditional Windjammer Sailing Tour Review
Book now: Check availability
Private Portland Sailing Charter
A popular option for visitors to Portland is the Private Portland Sailing Charter offered by Scovare Yachts, Inc. This private tour provides a unique opportunity to experience the city’s waterways from the comfort of a sailing yacht.
With a rating of 4.5/5 based on 3 reviews, the charter offers live commentary, a local guide, and private group participation.
The tour departs and returns to the Boat Ramp Dock in Willamette Park, located at 800 S Idaho St. While the tour isn’t wheelchair accessible, it’s stroller accessible, and service animals are allowed. Participants are advised to dress appropriately, as the tour operates in all weather conditions.
Customers have praised the charter, with one reviewer describing it as a “beautiful day” with an “informative and fun” captain.
Another commenter enjoyed “sailing and manning the tiller,” highlighting the interactive nature of the experience. The reviews have been verified, ensuring the authenticity of the feedback.
Read our full review: Private Portland Sailing Charter Review
Book now: Check availability
90 Minute Sailing Tour of Portland
For those seeking a more intimate sailing experience in Portland, the 90 Minute Sailing Tour offers a captivating exploration of the city’s waterways. Priced from $99 per person, this tour accommodates up to 6 travelers and includes a driver/guide, live commentary, and complimentary food and drinks.
The tour departs from the left side dock at the boat launch area in Willamette Park, with a start time of 3:00 PM.
Reviewers have praised the knowledgeable Captain Chris and the tour’s entertaining aspects, as well as the beautiful views of the city. However, some passengers have expressed disappointment with the lack of sailing experience due to low wind conditions, and have suggested better communication regarding the actual services provided.
The tour isn’t wheelchair accessible, but infants can participate while seated on laps. The 90 Minute Sailing Tour offers a unique opportunity to explore Portland’s waterfront from a different perspective, though guests should be aware of potential limitations in sailing experience.
Read our full review: 90 Minute Sailing Tour of Portland Review
Book now: Check availability
The Sum Up
Portland, Maine offers a range of sailing experiences for visitors. From traditional windjammer tours to private charters and shorter sightseeing cruises, there’s something to suit every interest and budget. Whether you’re a seasoned sailor or a first-time seafarer, these excursions provide an opportunity to enjoy the stunning coastal scenery and maritime heritage of this picturesque city.