Summer vacation usually means a trip south for us Midwesterners, but this year, I recommend trying something different! While Florida and South Carolina are classics, consider going north during the warmest time of year. I was recently in beautiful Maine hosted by Visit Portland and The Maine Beaches, and I can’t stop singing its praises. This state was absolutely beautiful, and now I have so many suggestions for places to visit in southeastern Maine. Check out my itinerary for the perfect summer vacation in this northerly state!
Day One: A Warm Welcome to Portland
Explore the Waterfront
After flying into the Portland airport, spend the rest of your afternoon in the Old Port neighborhood. This district is home to the working waterfront, where you can watch fishermen cast their nets and see water taxis circling the docks.
Try a Classic Seafood Dinner
There’s nothing like a traditional seafood dinner right on the water! On the first night, Boone’s Fish House & Oyster Room was the fare of choice—it’s been overlooking Portland Harbor since 1898!
Relax at the Hotel
No one would fault you for staying at the restaurant to take in the views, but don’t forget to settle into your hotel tonight. I stayed at the charming Regency Hotel & Spa and enjoyed a drink at their Armory Lounge!
Day Two: Sights in the City
Walk the Beautiful Arts District
After breakfast at the hotel’s Eighteen95 Restaurant, get out on the town! I loved walking through the city’s vibrant Arts District and visiting the Portland Museum of Art. For a smaller city, the art scene is certainly exceptional. Check out Creative Portland and download their app for the latest events and guides!
Have Lunch at Shipyard Brewing Co.
Shipyard Brewing is a top lunch spot in Portland, a city known for an abundance of breweries. In addition to an amazing variety of fine brews, the food is delicious! You can’t go wrong with their wings or flatbreads.
Spend an Afternoon Sailing
Here’s a Maine trip idea you can’t do just anywhere! An afternoon of sailing with Portland Schooner Co. is just what you need to make your vacation extra special. It’s absolutely stunning out on the water, and you might even catch glimpses of Portland’s six lighthouses.
Attend an International Cooking Demo
It’s been a high-energy day, but the day’s not over quite yet. Finish off your first full day in Maine with a hands-on international cooking demo with EN-NOBLE. My class learned to cook calulu a peixe, a five-star dish from Angola!
Day Three: History and Hearty Food
Have Donuts at a Local Cafe
It’s another big day for your summer vacation in Maine—start it off right with some donuts! Eighty8 Donut Cafe is a winner, with lots of yummy, beautifully-decorated desserts.
Immerse Yourself Portland History
Visiting a new place is a fantastic chance to learn a bit of history. And the best way to take a look into the past is with Portland by the Foot. Their Hidden Histories Walking Tour tells often untold stories about the indigenous leaders, European colonizers, and historical figures who made Portland what it is today. Our tour guide did an incredible job showing us the city!
Try Oyster Shucking
Want a real Maine experience? Come down to Maine Oyster Company and try shucking these mollusks for yourself. It’s more complicated than you might think! After learning this new skill, be sure to try one of their amazing lobster rolls before you leave.
Visit an Early English Settlement
After lunch, it’s time to leave the city and head out to the Maine beaches! But don’t run straight to the water just yet. Make sure to tour Old York first, one of the earliest English settlements in the United States.
Explore the Dunes on the Waterfront
Okay, now it’s really time for waterfront views! The Dunes on the Waterfront resort with its charming luxury cottages is the perfect jumping off point for lots of complimentary different activities, including kayaking, boating, biking and simply watching the tides roll in. My group took a complimentary pontoon ride!
Stay for Dinner and a Show
Close out the night in style with dinner at Jonathan’s and a show at Ogunquit Playhouse. I had the seafood pasta (topped with lobster!) at the restaurant and loved the production of Come From Away (a musical set in nearby Newfoundland).
Day Four: Nature Trails and Beach Views
Wake Up to Mornings in Paris
It’s our last full day, so we’re starting off with an adorable local coffee shop. Mornings in Paris in Ogunquit serves house-roasted coffee and a range of French-inspired products.
Visit the Wells Reserve at Laudholm
It’s time for another beach visit! The Wells Reserve at Laudholm is absolutely stunning, with clear waters and several conservation initiatives to keep the area teeming with wildlife. The waterfront homes are beautiful as well.
Eat Lunch in Kennebunkport
If your lengthy walk along the beach has you hungry, stop by legendary the Clam Shack. This bite-sized restaurant Kennebunk staple serves fresh and fried seafood. I was sure to try their award-winning lobster roll. Delicious!
Take a Scenic Drive in Kennebunkport
After lunch, take a drive around town to see all the beautiful old-money homes along the water. You can even see parts of the Bush family property!
Make Your Own Scent at Sea Love
We all love a souvenir, but how about one that’s an experience, too? At Sea Love, you can create your very own custom scent. I took home my very first fragrance diffuser. Such a unique way to bring the memories home with you.
Walk Downtown and the See the Local Beaches
We have time for one more museum and beach visit! Tour downtown Biddeford and be sure to make a stop at the Biddeford Mills Museum. You’ll learn about the local mills and take some fantastic photos at Saco Falls. Afterward, head to Old Orchard Beach to catch one last sunset in Maine.
Sit Down for Dinner at Joseph’s by the Sea
Another gorgeous day in the books! Wind down with dinner and ocean views at Joseph’s by the Sea. The ambience is exceptional, and the seafood is noticeably fresh. If you have room for dessert, swing by Fielder’s Choice for a helping of rich ice cream.
Day Five: Wrapping It Up
End With a Sunrise Walk
We might have a flight to catch in a few hours, but our summer vacation in Maine isn’t over quite yet! Wake up at the crack of dawn to watch the sunrise over the water.
Enjoy One More Breakfast at CREW
You’ll need your energy for your upcoming travel day, so sit down for a delicious breakfast at CREW. This Ogunquit favorite serves an excellent brunch, but also features local live music later in the day.
How Will You Spend Your Maine Vacation? Let Me Know! You don’t need to scour the internet for Maine trip ideas. My itinerary from Visit Portland and the Maine Beaches has you covered for your next trip. I loved the chance to visit this gorgeous state and be pampered with experiences that began with a welcome reception for fellow travelers and me from Ballast Events and Experience Maine Culinary. See more of my trip or let me know your thoughts on visiting Maine over on Instagram!