PORTLAND

We love exploring Maine and we are so excited for our friends and family to have Maine adventures of their own! Please feel free to reach out to Abigail or Danny for any recommendations.

Getting Around:

Portland is a very walkable city. Ubers are easy to come by in the city and renting a car is not necessary unless venturing further up the coast.

Eat & Drink:

Portland is an amazing city for food. Lobster, seafood, and so much more.

Eventide Oyster Co. - Known for their oysters & brown butter lobster roll on a bao bun.

Twelve - Run by the same Chef as Chebeague Island Inn. Try the croissant lobster roll!

Evo - Also run by the same Chef as Chebeague. Incredibly creative Mediterranean.

Leeward - Fresh pasta and creative small plates. Great wine & cocktails.

Duckfat - Best french fries you have ever had. Best dipped in their chocolate milkshake.

Terlingua - Tex-Mex-inspired BBQ.

Fore Street - A Portland classic.

Island Creek Oysters - Stop by the outdoor patio for fresh oysters & wine.

Bite Into Maine - Food truck at Portland Head Light with 6 kinds of lobster rolls.

Becky’s Diner - Nothing finer! Iconic diner along the working waterfront.

Cong Tu Bot - Low key spot for Vietnamese comfort food.

LB Kitchen - Counter-serve spot with breakfast and healthy salads and bowls.

Standard Baking Co - Homemade breads and pastries

Smalls - Market with coffee, sandwiches, and natural wine.

Gelato Fiasco - Favorite ice cream in Portland. Don’t miss the dark chocolate.

Portland Zoo - Dive bar with great music & beer selection.

The Jewel Box - Cocktail bar with funky candlelit vibe.

See & Do:

Portland is a great city to walk around, with tons of restaurants, shops, breweries, and ocean views. There are also many day trips that can be taken from Portland using a rental car or Uber (reserve return trip in advance).

Portland Head Light - Stunning all day but especially at sunset.

Portland Paddle - Rent kayaks and paddle around Casco Bay and the islands.

Eastern Promenade - Path along Casco Bay great for running and walking.

Breweries - Allagash, Maine Beer Co., Rising Tide, Lone Pine, Oxbow, Wild Root Kombucha, the list goes on…

Portland Art Museum - Centrally-located museum with a wide selection of work by Winslow Homer.

Wolfe’s Neck Center - Walk or jog around this stunning sustainable saltwater farm. Pre-book an Uber for your return to Portland.

Wolfe’s Neck Woods State Park - Hike around this woodland preserve with stunning rocky coast views. Pre-book a return Uber.

Day Trip to Chebeague Island - Bike around the island, play golf, and have a picnic at one of the two beaches.

Day Trip to Peak’s Island - Take the Casco Bay Lines out. Bike around the island, explore galleries, and stop for ice cream and lobster rolls.

Day Trip to Kennebunk - 40 minutes south of Portland, a coastal town with shopping, restaurants and sandy beaches.

Shopping at Freeport Outlets - 25 minutes north of Portland, shop the outlets and visit the giant boot at LL Bean.