About Shore Leave
Our Place
We've got a small cottage at 61 West Shore Road on Bailey Island. It's nothing fancy, but we love it here — quiet street, water views, and the best sunsets.
The setup:
- 2 bedrooms, 1 bathroom — room for a couple friends or a small group
- Living room overlooking the water
- Large deck where we spend most of our time
- Kitchen has what you need
- Wi-Fi (but you might not want it)
- We'll have linens and towels ready
Cool thing: Almost every night, the schooner Alert does a sunset cruise right in front of our place. Grab a drink, hang on the deck with us, and watch it sail by.
About Bailey Island
Bailey Island is a little island community in Harpswell, Maine, connected to the mainland by the Cribstone Bridge. It's got working lobster boats, rocky shores, and that classic Maine vibe.
Not much happens here, which is kind of the point. Good for resetting, exploring the coast, and eating too much seafood.
What We Like to Do
🚶 Walking Around
West Shore Road is quiet and perfect for walks. Cook's Lobster and Ale House is a short walk from us. Sun-drenched (cute spot) is nearby too.
🦞 Lobster Runs
We hit up Cook's a lot. There are also tons of other lobster pounds and seafood shacks all over the island.
⛵ Watching the Alert
The schooner does sunset cruises almost every night, right in front of our place. Never gets old.
🏛️ Portland Runs
Portland is 30 min if you want to explore. Brunswick is 10 min. But honestly, we mostly just hang on the island.
🥾 Giant's Stairs Trail
Cool hike right on Bailey Island — rocky coast, good views. Worth doing once.
🌅 Sunsets on the Deck
The main event. We're west-facing, so every night is the show. Bring your own drinks.
What to Bring
(Alex/Kathleen — update with your packing list)
Stuff to pack:
- Layers — Maine weather is unpredictable
- Rain jacket and decent shoes for walking
- Sunscreen
- Groceries and drinks (not much on the island)
- Whatever else you need
Good to know:
- Arrive Friday afternoon, leave Sunday
- Be cool with the neighbors
- No smoking inside
- Clean up after yourselves
- (Add more rules here if needed)
Getting There
Address: 61 West Shore Road, Bailey Island, Maine
About 30 min from Portland. You'll cross the Cribstone Bridge to get to the island (it's iconic — you'll see). West Shore Road is easy to find once you're over the bridge. Text us if you get lost.
Nearest Airport: Portland International Jetport (PWM)
Driving Time:
- From Boston: ~2.5 hours
- From Portland: ~30 minutes
- From Brunswick: ~20 minutes
Full address and navigation instructions will be sent after your reservation is confirmed.