Even independent travelers welcome the chance to hop aboard guided tours here in Kennebunkport, Maine. That’s because these adventures on water and land introduce you to our local way of life and open up perspectives you might otherwise miss. We hope all of our Yachtsman Hotel & Marina Club guests have the chance to experience Kennebunkport in unique ways, and we’re happy to reserve your spot on one of our favorite guided tours.

Schooner Eleanor Sailing Tours

When you stay at the Yachtsman Hotel & Marina Club, you’ll be perpetually reminded that the “action” in our port town happens on the water. Don’t miss out! The traditional gaff rigged schooner Eleanor has been part of our coastal town’s fabric since Captain Rich Woodman built and launched this majestic vessel in May of 1999. He’ll be your guide on a scenic, two-hour sailing trip. Kick back and relax or help set the sails, as the wind’s whims determine your course out on the open Atlantic. Daily departures are available late May through early October. Our favorite sailing is at 4:30 p.m. during the summer season, when the light on the ocean is golden, and you can bring your favorite happy-hour beverages on board.
43 Ocean Avenue, Kennebunkport, Maine, 207-967-8809

Rugosa Lobster Tours

You’ll appreciate every morsel of Maine lobster even more once you’ve joined a working lobsterman on this lobster boat adventure. Learn all about what it takes to catch these crafty crustaceans: You can even help haul traps on your 60- to 90-minute tour of Kennebunkport’s picture-perfect lobstering grounds. Cruise down the Kennebunk River and out to sea aboard an authentic wooden lobster boat on your choice of three daily outings, Memorial Day weekend through Columbus Day. Here’s a little secret: There’s a fourth, BYOB tour for adults only on July and August evenings. Just ask, and we’ll help you prep for your voyage.
95 Ocean Avenue, Kennebunkport, Maine, 207-468-4095

Intown Trolley

Want to efficiently see all of Kennebunkport’s most famous scenes? In just 45 minutes, these hourly-departing trolley tours offer the perfect guided introduction to our town’s historic attractions, scenic vistas and natural wonders. The narration is both entertaining and informative, as you travel past landmarks like Spouting Rock, Blowing Cave and the Walker’s Point home of George H.W. and Barbara Bush. Tours are available daily from Memorial Day weekend through Columbus Day. Already know your way around Kennebunkport? You can opt to hop on and off this nostalgic trolley all day and take control of your sightseeing destiny.
21 Ocean Avenue, Kennebunkport, Maine, 207-967-3686


More Guided Tours and Adventures Near Kennebunkport: