Casco Bay: Portland Harbor around Orrs Island to Strawberry Creek Professional Review and Guide
"This is a leisurely four-day trip starting in busy Portland Harbor and traveling up to quiet Harpswell Sound and back, stopping on state islands. Overnight trips in the Casco Bay area cannot be treated as casually as they once were because the residents have become far stricter about nonresident parking, especially overnight. Because Portland is one of the busiest shipping ports in New England, however, be prepared to give wide berth to intimidating, five-story oil tankers delivering most of the state’s oil, fishing vessels, and barges. Also add ferry boats, tour boats, and fleets of racing yachts to the list of craft to reckon with.
Some sea kayakers consider such dodging a challenge. Others might want to opt for a launch farther north in the bay such as at Falmouth Foreside, Cousins Island, or Yarmouth out of shipping channels. Once out of Portland Harbor, you will be rewarded. Just a few miles out are deserted gems such as state-owned Crow, Jewell, and Little Chebeague, where you can camp, hike, swim, and explore in pristine privacy."