Olivia & Sam
Things To Do
Prouts Neck Cliff Walk
Experience the ocean views that inspired artist Winslow Homer on this breathtaking walk along the edge of the Prouts Neck peninsula. Pass the Prouts Neck Yacht Club, the historic Winslow Homer Studio, and the Prouts Neck Bird Sanctuary.
Fort Williams Park
Fort Williams Park is the triumphant endpoint of our favorite Maine road race, the TD Garden Beach to Beacon 10K. The race was founded by Olympian and Bowdoin College alumna, Joan Benoit Samuelson. Admission is free to visit the lighthouse and old forts and parking is available within the park.
The Holy Donut
Frankly, you haven't lived until you've tried a handmade, potato-based donut from The Holy Donut. Go for the dark chocolate sea salt, and pair it with an iced coffee with coffee ice cubes (like Olivia), or add a second donut for extra calories (like Sam).
The Front Room
Serving new American comfort food, The Front Room is one of our favorite brunch spots. When we can't decide between savory or sweet, we order both! Try the Eggs Benedict with ham and house-made hollandaise and the Silver Dollar Pancakes with Maine blueberries and real maple syrup.
Forage Market
This is one of our favorite casual spots to enjoy bagels and coffee with friends. We recommend the salt bagel with vegetable cream cheese, but you really can't go wrong with any of Forage's wood-fired bagels or breakfast sandwiches!
Tandem Coffee and Bakery
This former 1960's gas station turned bakeshop is an iconic Portland eatery. Grab-and-go, or stay and enjoy your espresso with a fully loaded biscuit.
Roma
We dined at Roma for the first time to celebrate our engagement, and it quickly became a favorite! Limited seating, cozy fireplaces, and home decor create the sensation of enjoying a delicious Italian meal in your living room.
Eventide Oyster Co.
For the lobster lover, a trip to Maine is not complete without a Brown Butter Lobster Roll from Eventide Oyster Co. Pair it with one of the many local brews on tap.
Empire Chinese Kitchen
We can't say enough about Empire, and are drooling just thinking about the delicious dumplings and savory small dishes! Enjoy your family-style Dim Sum with our favorite cocktail, the Dragon's Milk.
Maine Beer Company
Maine Beer Company is located 15 miles north of downtown Portland on U.S. Route 1. Play darts and drink hoppy beer in the tasting room. The pizza is killer, too. If you have time, continue north to visit L.L.Bean and the outlets in Freeport.