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Portland, the largest city in Maine, is a common port for East-Coast cruises starting out of New York City.
This charming seaside city is filled with fun things to do. But when you only have five hours to see it all, it’s hard to know where to begin. To make the most of your short time in Portland, consider taking a tour from a local company. If you’re cruising, there will be plenty of shore excursions offered through your ship. Typically, you’ll find an itinerary that covers all of the hottest local attractions.
For example, Carnival offers a tour called Portland Highlights and Kennebunkport. In just five hours, you get to take in the top sites, and you’ll still have a bit of time afterward to wander on your own. Here’s what you’ll see.
Portland Overview
Your tour begins with a drive through Portland itself. You’ll coast along the seaside in a motor coach, taking in the local streets, including some of the most affluent homes in the area. Your guide will tell you about the rich history of diversity and how the homes along the water were once considered undesirable for this exact reason. Today, they are some of the most sought-after abodes in the state.
As you drive along, you’ll catch a glimpse of the stone fortress built to defend the city against the Red Coats, as well as the observation tower that boasts views of the entire city, though you won’t get a chance to test that theory for yourself, as there simply isn’t time to stop here.
As you drive through the heart of the city, you’ll see the home of Henry Wadsworth Longfellow, as well as hear old folk tales of other homes in the community, such as the heavily adorned Wedding Cake House that was built for a bride as her wedding gift many moons ago.
Portland Head Light
The first official stop on the tour is to the most photographed lighthouse along the East Coast, Portland Head Light. Looking as picturesque as the many postcards on which it’s been featured, the little lighthouse stands tall as a beacon to sailors passing along the coast of Maine.
You’ll have about 30 minutes to take pictures amid the craggy canyons and rushing waves. A small gift shop offers trinkets and a few locally crafted items at shockingly affordable prices. Snap a few photos, grab, and souvenir, and head back on board the motor coach for the next leg of your five-hour tour.
Kennebunk and Kennebunkport
Next, your tour will take you on a rural drive to see the summer homes of the rich and, well, richer. A few decades ago, the state offered plots of land for $20,000 each. While the land was reasonably priced, it came with a catch: You had to build a home with a certain price tag. The intent was to attract only the upper-middle class to the area. The plan was successful, and most of the homes exceeded the expectations.
After about a 45-minute drive from Portland Head Light, you’ll arrive in Kennebunk. The charming little community looks like something out of a Nicholas Sparks novel, and you half expect to see Ryan Gosling strolling the streets hand-in-hand with Rachel McAdams. Colorful cottage-like shops and restaurants line both sides of about a three-block radius and include everything from candy and coffee shops to kitschy souvenir stores and upscale artists’ havens.
You’ll get a chance to take in the shops after a short drive through nearby Kennebunkport. If you’re here in the summer months, you’ll see surfers riding the waves on the local beaches, while families gather outside their summer homes for a bonfire and a glass of wine. The brightly colored “cottages” are far more lavish than any typical upscale community and make you long to be one of the next generation of family members who are sure to inherit the tradition.
Perhaps the most notable—okay definitely the most notable—local family is the Bushes, who have been spending their summers here for many decades, long before father and son took on the presidential roles of numbers 41 and 43. Like everyone else, they paid $20,000 for their plot of land that stretches like a peninsula into the ocean. The locals tell stories of spotting the secret service in town and George Sr. jumping from airplanes like they are part of their own family histories. It’s just a fact of living here. You will run into one or the other at some point in your lifetime.
Once you’re done your drive, you’ll get about an hour or so to sweep through the Kennebunk shops. If you don’t dawdle, this should be plenty of time. There are an obscene number of stores catering to fashionable canines (my own got several new shirts). And we even had time for a quick snack at one of the popular coffee shops.
Pro Tip: Be sure to have a whoopie pie, the state dessert. Rumor has it the famous cakes came to be after a woman, tired of the icing coming off the top of the cakes she would wrap in a kerchief for her husband’s lunches, placed an extra piece of cake on top of the icing. When her husband opened his lunch to find the icing still in place, he yelled, “Whoopie!”
Back in Portland
Once you’ve wrapped up your visit to Kennebunkport, you’ll arrive in town with about two hours to spare before you need to be back on board the ship. This will give you plenty of time to walk around the Old Port, which is only about a 10-minute walk from the cruise ship terminal itself. You’ll find lots of one-of-a-kind shops, as well as plenty of places to try the local seafood.
If you’ve only got five hours in Portland, Maine, this is the perfect way to take in the best the area has to offer. What other must-see sights do you recommend? Visit the Wanderlust Wayfarer Facebook group to share your ideas.