Great Itineraries

Great Itineraries

If You Have 1 Day

For a comprehensive one-day tour of the Blue Hill Peninsula, without spending all of it in an automobile, start with a stroll around Blue Hill and hike up Blue Hill Mountain, for 360-degree views. Then drive 45 minutes to Stonington via panoramic Caterpillar Hill and Deer Isle bridge for lunch in one of the restaurants over the harbor, followed by a walk around town. In the afternoon, drive back to the mainland, taking scenic Route 175 through Sargentville, Sedgwick, and Brooklin before crossing the Blue Hill Falls bridge and driving west on Route 172 to Route 177 and South Penobscot. Continue on to Castine for an exploratory tour through town.

If You Have 3 Days

If you have three days on the peninsula, stay in Blue Hill. Visit the town's shops and galleries your first morning, then take the afternoon tour to neighboring Brooklin, home to the world-famous Wooden Boat School, and Brooksville, where you can find the Sow's Ear Winery. On Day 2, climb Blue Hill Mountain for 360-degree views of the peninsula, then head to Castine and take the town walking tour—be sure to see historic homes like the Ives House and landmarks like the Abbott School and the Unitarian Church. On Day 3, explore Deer Isle and Stonington to learn about the region's rocky past at the Deer Isle Granite Museum and Settlement Quarry.