Portland is an easy 2 hour drive from downtown Boston. If you are driving to Portland, there are a number of city parking lots where you can leave your car before boarding a ferry or water taxi to get you to the island.
The Portland Jet Port is a modern airport with a large number of direct flights to most of the US east coast cities. Information on airlines and schedules can be found at the website for the airport. The Portland airport is approximately 10 miles from the ferry terminal to Diamond Cove.
In addition to the Portland Jetport, many travelers find it cheaper and/or easier to fly into Boston or Manchester NH. If you fly into Boston, Concord Coach Lines, is a luxury bus service that runs hourly from the bus pick-up area outside the baggage claim at Logan Airport. Transit time to the Portland Bus & Amtrak station is roughly 2 hours. The same buses also run from the Portland Station to Amtrak’s North Station, in downtown Boston, and to Logan Airport regularly. A schedule for Concord Coach Lines can be found here.
Amtrak also travels from Boston to Portland on the service known as the “Downeaster”. The train departs Boston’s North Station (not the South Station where most other Amtrak trains arrive) and travels to the Portland Transportation Center – transit time is approximately 2.5 hours. If traveling Southbound to Portland there is also service from Brunswick and Freeport. For more information you can visit www.amtrakdowneaster.com
There is no regularly scheduled ground transportation from Manchester NH to Portland and most travelers depend on car rentals from Manchester to make the 1.75 hour drive.
The most important public transportation provider is Casco Bay Lines- the ferry service that serves the islands. They operate a modern and clean fleet of large ferries. You can also hop aboard a number of tours that wind through the hundreds of islands in the Casco Bay. The cost and the schedule (which varies greatly by season) can be found at their website.
Water taxi services are available, too, if you’re not inclined to take the ferry or if the ferry schedule doesn’t match your own schedule. Check out Portland Express Water Taxi or Casco Bay Water Taxi.
The Greater Portland Transit District runs Metro bus service around the area. A one-way fare costs $1.50, and you can also purchase 10-ride passes for $13.50 and day pass for $5.00. You can purchase tickets at a number of locations, including the Casco Bay Lines office. Bus schedules and routes are posted on the Metro bus website home page, on the left side of the page.
Once on the island, you will find that Diamond Cove is a “walking/bike riding” community. Private motorized vehicles are not allowed in Diamond Cove, so you’ll need to walk, or ride a bicycle. The homeowners association operates a small bus to meet all boats and deliver passengers and freight to their homes. Some homeowners use electric golf carts to get around.