Pineapple Ketch Sailing Trip
Kennebunkport, Maine Coast
About This Activity
The Pineapple Ketch is Kennebunkport's most recognizable vessel — a beautifully restored 38-foot Downeaster ketch with vibrant red sails and a black hull that locals call the 'Pirate Ship.' Sail down the Kennebunk River into the Atlantic, cruising up the coast to Cape Porpoise past grand Ocean Avenue estates (including Walker's Point), rocky lighthouses, and harbor seals on the ledges. Sails depart from the Nonantum Resort dock at 95 Ocean Avenue.
Seasonal note: Sailing season May-October from Nonantum Resort dock; sunset sails especially popular
See This in an Itinerary
This activity appears in 10 of our curated itineraries.
Best 10 Days in Maine Coast — Romantic
Portland → Kennebunkport → Midcoast Maine
Best 10 Days in Maine Coast — Romantic & Walking Tours
Portland → Kennebunkport → Midcoast Maine
Best 10 Days in Maine Coast — Photography & Romantic
Portland → Kennebunkport → Midcoast Maine
Best 10 Days in Maine Coast — Adventure & Romantic
Portland → Kennebunkport → Midcoast Maine
Best 10 Days in Maine Coast — Nature & Romantic
Portland → Kennebunkport → Midcoast Maine
Best 14 Days in Maine Coast — Romantic
Portland → Kennebunkport → Midcoast Maine
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