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Best results for

Sailing in Castine, ME

Showing 1-19 of 19 results
Lobstering Sail Past Rockland Breakwater Lighthouse

Lobstering Sail Past Rockland Breakwater Lighthouse

Help haul lobster traps aboard one of Maine's last sailing lobster boats

5.0 • 306 reviews
$91/ person
1918 Schooner Day Sail on Penobscot Bay from Camden

1918 Schooner Day Sail on Penobscot Bay from Camden

Sail aboard a historic schooner with cushioned seating and crew-led local stories

5.0 • 252 reviews
$68/ person
Camden Sunset Sailing Cruise

Camden Sunset Sailing Cruise

Sail at sunset aboard a 49-passenger windjammer

4.9 • 2.9K reviews
$74/ person
Rockland Harbor Sailing Tour Past Breakwater Lighthouse

Rockland Harbor Sailing Tour Past Breakwater Lighthouse

Help raise the sails and try steering along Maine's rugged coast

5.0 • 306 reviews
$75/ person
Penobscot Bay Schooner Day Sail in Camden, Maine

Penobscot Bay Schooner Day Sail in Camden, Maine

See Maine's coast from the deck of a schooner

5.0 • 261 reviews
$64/ person
Private Sailing Charter in Penobscot Bay

Private Sailing Charter in Penobscot Bay

Host your celebration, gathering, or team event aboard a private schooner

5.0 • 106 reviews
$1,325& up
Fall Foliage Cruise in Rockland

Fall Foliage Cruise in Rockland

Sail through fall colors and search for an island lobster-feast setting

4.9 • 133 reviews
$1,548& up
Private Half-Day Sailing Charter in Rockland, Maine

Private Half-Day Sailing Charter in Rockland, Maine

Explore Penobscot Bay on a private sail shaped around you

5.0 • 306 reviews
$2,247/ boat
Camden Sunset Sail With Live Acoustic Music

Camden Sunset Sail With Live Acoustic Music

Sail to live acoustic music as evening settles over the water

5.0 • 252 reviews
$85/ person
Afternoon Cruise on Penobscot Bay

Afternoon Cruise on Penobscot Bay

Take the helm and help sail a wooden ship on Penobscot Bay

5.0 • 106 reviews
$58/ person
Camden 2-Hour Windjammer Day Sail

Camden 2-Hour Windjammer Day Sail

Sail Maine's rugged coast aboard a tall ship with wide decks and seating

4.9 • 2.9K reviews
$53/ person
Fall Foliage Sailing Cruise From Rockland

Fall Foliage Sailing Cruise From Rockland

Sail through fall color toward an island lobster feast

4.9 • 133 reviews
$1,548/ cabin
Private 55' Ketch Sailing Charter in Rockland

Private 55' Ketch Sailing Charter in Rockland

Set your own course across Penobscot Bay, with the option to explore an island preserve

5.0 • 306 reviews
$3,157
Camden Sunset Sail on Penobscot Bay

Camden Sunset Sail on Penobscot Bay

Watch sunset colors unfold across Penobscot Bay aboard the Schooner Surprise

5.0 • 252 reviews
$73/ person
Sunset Sailing Cruise in Camden

Sunset Sailing Cruise in Camden

Help raise sail as sunset views unfold across Penobscot Bay

5.0 • 252 reviews
$117/ person
Private Penobscot Bay Sailing Charter from Rockland

Private Penobscot Bay Sailing Charter from Rockland

Relax on your own private ketch or lend a hand with the sailing

5.0 • 306 reviews
$1,284/ boat
Sunset Sailing Cruise on Penobscot Bay

Sunset Sailing Cruise on Penobscot Bay

Sail into the evening aboard Charm on scenic Penobscot Bay

5.0 • 106 reviews
$69/ person
2-Hour Camden Sailing Cruise

2-Hour Camden Sailing Cruise

Coastal views and local insight past Curtis Island Lighthouse

5.0 • 252 reviews
$106/ person
Full Moon Sailing Cruise in Camden

Full Moon Sailing Cruise in Camden

Watch sunset and moonrise from Penobscot Bay with live acoustic music

5.0 • 252 reviews
$87/ person
Castine Things To Do
SailingBike Rentals13National Parks11Boat Tours10Sunrise and Sunset Tours9
More
  • Kayaking Tours8
  • Bike Tours5
  • Car Rentals4
  • Farm Visits3
  • Fishing Charters3
  • Trolley Tours3