PWM airport is 10 minutes from downtown Portland. If you're staying downtown, there is no need to rent a car, as the city is walkable. In general, you will be able to Uber/Lyft from the airport to downtown Portland, to the CTC Ferry in Yarmouth, or to your hotel. However, if you are arriving late at night (after 9:00 PM), you should plan to arrange a taxi beforehand.
Boston Logan Airport is about 2 hours from Portland. Once in Boston, you can rent a car and take the scenic drive up the coast, or take a bus or Amtrak from South Station to Portland.
Chebeague Transportation Company departs from Cousin’s Island in Yarmouth, ME. It’s only 15 minutes and lands right at the base of the Inn. If you’re driving, you’ll want to park in the satellite parking lot on Route 1 in Cumberland, and then take the complimentary shuttle to the ferry. If you’re taking a cab or Uber from the airport or bus station, you’ll want the cab driver to bring you to the end of Wharf Rd on Cousin’s Island, Yarmouth, Maine.
Schedule & Directions for CTC: Tickets must be purchased in advance (please see Q&A for more information).
Casco Bay Lines departs from Portland and is a scenic ride that stops at four islands along the way with an audio tour, taking about 1.5 hrs to get to Chebeague. This is a great option if you have the leisure of time and want to experience Casco Bay (but not on our wedding day). This ferry lands at Chandler’s Cove which is on the other side of the island. It’s about a 15 minute drive from Chebeague Island Inn.
Schedule & Directions for Casco Bay Lines: Tickets do not need to be purchased in advance but they recommend arriving at least 30 minutes before (please see Q&A for more information).
Fogg's Water Taxi provides privately booked transportation for up to 6 people from Maine Wharf (72 Commercial Street) in Portland to Chebeague Island. They ask that arrangements/reservations be made 24 hours in advance. Please contact them at (207) 415-8493.