Provincetown Sailing Tour on Historic Bay
Treat yourself to a memorable afternoon sail
From$63/ personincl. taxes and fees
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Discover what we've curated for you
Treat yourself to a memorable afternoon sail
Discover what we've curated for you
2 hours
Maximum 41 people
Afternoon Sail at Cape Cod
Treat yourself to a memorable experience on an afternoon sail. Spend 2 hours on the water during this outing.
Cancel at least 24 hours in advance for a full refund. Full refund if the operator cancels due to weather or unforeseen circumstances. No-shows will be charged in full.
9 Macmillan Pier, Provincetown, MA, United States, Massachusetts
This locally-owned family business has been delighting sailors for over 30 years, and their reputation speaks volumes. Captain Bob and his crew strike that perfect balance of being knowledgeable and professional while giving you space to simply enjoy the experience. Multiple reviewers mention how refreshing it is that the crew doesn't talk non-stop but remains available to answer questions and share their obvious expertise. The 73-foot schooner is spacious and well-maintained, giving you freedom to move around and find your perfect spot, with the bow being a favorite perch once the sails are up. The sunset cruise gets consistent praise as a highlight of Provincetown visits. Bring your own wine, cheese, and snacks to make it special, and keep an eye out for seals near the lighthouse. The two-hour duration feels just right, and the pricing is repeatedly mentioned as very reasonable. One practical tip from a regular: try to book when there's good wind for the full sailing experience. The warm, welcoming atmosphere combined with breathtaking harbor views makes this an experience people return to year after year.
The sunset cruise was such a memorable experience - perfect for both couples and families. The crew clearly knows what they’re doing and gives you the freedom to make the experience your own, including exploring around the boat once the sails are up. Highly recommend packing your own wine and cheese, and taking them up on the opportunity to grab the bench seat cushions and sit up at the bow.
Anusha Purakayastha
September 24, 2025
The sunset cruise was such a memorable experience - perfect for both couples and families. The crew clearly knows what they’re doing and gives you the freedom to make the experience your own, including exploring around the boat once the sails are up. Highly recommend packing your own wine and cheese, and taking them up on the opportunity to grab the bench seat cushions and sit up at the bow.
Anusha Purakayastha
September 24, 2025
