Continuing on my itinerary sharing streak, it seemed like a good time to share this one for a trip I took last fall to Maine. Reading back through it I’m realizing this trip was mostly dedicated to eating lobster. This was an easygoing and fun long weekend that included a little bit of activity (one bike ride and a ton of walking), and a lot of time on patios with amazing views and food. We went in late September, and it was perfect crisp fall weather. But I think this trip would also work well for a summer weekend escape or a cozy late fall getaway.

Thursday

11:15 am: Arrive in Portland, Maine

12 pm: Check in/drop baggage at Canopy on Portland waterfront.

1 pm: Lunch at Duck Fat (In Old Port, reservations not available, 15-minute walk from hotel. Order the duckfat fries, obviously). 

2 pm: Walk around and shop in Old Port (Charming cobblestone streets in a historic neighborhood. Stop in Blanch + Mimi.) 

3:30 pm: Uber to have a beer on the patio at Allagash Brewery. 

6:30 pm: Uber to return to Old Port for Dinner at Eventide Oyster Co. (Reservations not available, order the lobster roll trio and the oysters.) 

8 pm: Post dinner drinks at Blyth & Burrows (Speakeasy-esque cocktail bar with sailor themed cocktails in Old Port).

Friday

8:30 am: Grab coffee and donuts at The Holy Donut (Gourmet house-made donuts from Maine potatoes.)

9:15 am: Take ferry to Peaks Island.

10 am: Rent bikes to explore the island. (Take the loop the entire way around the island—it’s not that far and the views are more than worth it.)

1 pm: Stop for lunch at the picnic tables overlooking the water at the Island Lobster Company. (Lobster rolls from caught-that-day lobsters and whoopie pies.)

2:30 pm: Catch ferry back to Portland, pick up bags at hotel, Uber to Kennebunkport. (Note: Once you get to Kennebunkport, Ubers are hard to find. Ask at the Inn for driver recommendations, and be sure to schedule something for your return trip to the airport.)

4 pm: Check into The Kennebunkport Inn, walk around Kennebunkport, drinks on the rooftop at Batson River Brewing & Distilling.

7 pm: Dinner at Earth at Hidden Pond (Reservations required and prix-fixe menu. It’s pricey, but totally worth it just for the gorgeous experience.)

Saturday

9 am: Grab breakfast sandwiches and coffee at HB Provisions. (I really loved this little general store and ended up here every morning because I’m an early riser and it was the first spot in town to open.) Explore and shop in downtown Kennebunkport and Dock Square. 

11:30 am: Walk down towards Walker’s Point (2.3 miles along the water).

12 pm: Stop at Mabel’s Lobster Claw (Make reservations, and order the clam chowder and the lobster roll.)

1:30 pm: Continue on walk—cute shops across from Mabel’s (Happynest and Dannah), gorgeous beaches and homes along the walk, turn around at Walker’s Point.

3 pm: On the return walk, stop at the historic Colony hotel for a snack/drink by the pool overlooking the water.

4:30 pm: Continue walk back to the Inn, and enjoy drinks and music on the patio of the Inn (or by the fire, depending on time of year).

7 pm: Dinner at Hurricane (Reservations required—this place gets VERY busy. The baked stuffed lobster is just as amazing as it sounds.)

Sunday

9 am: Breakfast bowls and coffee at Fiafia.

10 am: Leave Kennebunkport for Portland airport.

12 pm: Depart Portland.