With summer quickly approaching, I’ve started dreaming of a vacation to Bailey Island, Maine, a tiny island located in the Casco Bay about an hour from Portland. Jolian and I stumbled upon it a few years ago while driving through the area and immediately fell in love. We even got married there. If you ever get a chance, visit this magical little place. You’ll fall in love with it too.
VOYAGE: If you’re looking for a relaxed, inexpensive, authentic Maine vacation, visit the tiny island of Bailey Island located in the Casco Bay. We love to rent one of the cabins at The Driftwood Inn (cabins starting at $675/week). The Inn has been open for over 100 years and I’m pretty sure not much has changed since then. It’s rustic, but so charming. You’ll feel like you’re 12 years old again at camp (in a good way!). Walk down the bluff from the inn and you’ll stumble upon the rock formation that looks like giant stairs leading down to the sea. Get your fill of lobster and clam chowder at The Giant Stairs Seafood Grille, Cook’s Lobster House, Estes Lobster House, and our favorite spot, a tiny little restaurant on the road to Cundy’s Harbor, Block & Tackle. Go for lunch and order the lobster roll and fish sandwich. (Mackerel Cove and lobster photos by Jacob Pritchard; The Driftwood Inn photo from here)
SUITCASE: It’s Maine – pull out your stripes and let your prep flag fly. 1. Ahoy Headwrap $35 | 2. Big Baggu in Seahorse $12 | 3. Endpoint Dress $118 | 4. Sperry Top-siders in Dark Spearmint $98 | 5. Seersucker Stripe Pestemal $49