Luxury for Less: 5 Posh Things To Do in Portland Maine for $20 or Less

Looking for affordable things to do in Portland, Maine? My list focuses on posh treats that are all under $20! 

​Some links within this blog post are affiliate links, which means we are paid a small commission should you make a purchase . I was in Portland for the Women in Travel Summit and some of these experiences were the result of tours which were included in my conference registration fees.

The ultimate Portland, Maine, treat - a buttery lobster roll. I loved them!

Portland, Maine, is the kind of budget-friendly small city that frugal travelers such as myself are thrilled to explore. With a gorgeous ocean front location, compact streets which are easy to explore, and plenty of low cost attractions, you get great bang for your buck here. And if you want to feel a bit spoiled, you don't have to break the bank.  I've got five sumptuous, luxurious, feel-like-a-millionaire things to do in Portland, Maine, that all ring in under $20. In fact, some are even FREE! Get ready to indulge!

Free to $10: Tour Portland's Grandiose Customs House

I don't know about you, but I was born for a life of gilded gold leaf, expansive swaths of rare marble, and precious mahogany. Alas, my destiny is very often in conflict with my bank balance but at the Portland Customs House, a world of opulence is yours to soak in.

This gorgeous building was designed to impress upon ship captains and men of trade just how important and influential Portland was. Often, the Customs House was the only part of the city these men would see and their first impression would be a lasting one. The sumptuous interior is rich in detail and symbols. Mercury, Roman god of shopkeepers, merchants, travelers, traders, communication, and trickery, is strongly represented throughout the building - if you know where to look.

At one point, Portland was third only to Boston and Philadelphia in terms of its significance and size as a port. To appreciate Portland's importance, you have to keep in mind that back in the days of old, Portland was a full 1 to 2 days closer by ship to Europe than Boston. When you're shipping precious cargo, an extra day can mean all the difference. Goods like timber, fur pelts, salted fish, sugar cane, and molasses would leave the New World for Europe. The European ships brought in luxury goods, textiles, spices, tea, and an oft-forgotten kind of cargo - human beings, kidnapped and enslaved, forced into making the perilous Atlantic journey. The European ships were also often laden with Belgium paving stones to be used as ballasts while making the return journey. Those stones are still part of the Portland's waterfront streets today.

Greater Portland Landmarks occasionally offers tours which includes a visit to the Portland Customs House at a cost of about $10. You can see their events schedule and contact information for more details. And if you're particularly lucky or determined, you may just catch Jeffrey Porter (director of the US Export Assistance Center) giving a free tour. Jeffrey works in the Customs House - yes, it's still a fully operational federal building - and sometimes people try their luck to buzz into the building and catch him at a free moment. A more sound plan is to reach out in advance and ask super nicely - he might be able to tell you when he's free or when another group is coming through and you could tag along (You can reach him at 207-780-3756). 

Around $5 - $20: Feast on Made-In-Maine Cheese 

If you love a mix of classic and more unusual cheeses on your plate and are eager to try local delicacies like honey, jam, pickles, and salty snacks, a trip to Cabot Farmers' Annex should be high on your list. It's the loveliest spot for shopping in Portland, perfect for picking up adorable souvenirs (like a turquoise whale shaped butter dish) and yummy treats.

Cabot's has a great selection of local cheeses, from sharp cheddars to a port wine infused cream cheese style spread. Grab some chili honey, pickles, and savory crackers and you have the makings of a mighty fine hotel room cheese plate. Be sure to ask the staff about cheeses which are safe to keep at room temperature for several days if you're traveling without refrigeration. They've got a good selection of travel-friendly foods and are experienced at packing things up.

$8: Indulge In A Flight of Portland's Best Beer (and enjoy some live music too...)

I'm not going to lie. I'm not a big beer drinker. I'm not even a small beer drinker! It's just not my kind of beverage. But that doesn't mean I'm going to stop trying and nor should you, especially with the variety and hospitality on offer at the Rising Tide Brewing Company.

Rising Tide brews a variety of different beer styles, including some seasonal selections, and odds are very good there'll be something you like on the menu. A good place to start is their $8 tasting flight, which gets you four samples, each a generous four ounces. 

I love that Rising Tide has an open and bright tasting room. It's a little thing but there are so many craft breweries out there that seem to think a gloomy, rustic tasting area somehow makes their beer taste better. About once a week, the tasting room features FREE live music. If your travel schedule is flexible, check out their events page to see when there'll be music and what beers are available. With a little luck, the schedule might just correspond with their list of FREE brewery tours. In general, the free tours operate Monday – Thursday 3 pm, Friday & Saturday 1 pm, 3 pm, and 5 pm, and Sunday 1 pm and 3 pm. Free tours, free music, and cheap beer samples is a winning travel combination in my books. And there's usually a well priced food truck in Rising Tide's parking lot to accommodate hungry guests.

My visit to Rising Tide was part of a broader tour put on by the Maine Brew Bus. If you're looking into Portland Maine tours, I would highly recommend this one! ​I was lucky to be a participant as part of my registration for the Women in Travel Summit. There are a lot of breweries near Portland Maine and they put together a great itinerary to help us discover several of them. 

$12 (or sometimes free!): Take in the Old Masters at the Portland Museum of Art

Image courtesy Trip Advisor

Image courtesy Trip Advisor

Image courtesy Trip Advisor

Few small cities have so fine an art gallery as Portland. And few small art galleries have done so fine a job in their curation as the Portland Museum of Art. The museum is actually three buildings, beginning with a stunning modern interior, with clean lines and great light. It's connected with two further historic buildings, each with its own distinct style and character. I've seen similar buildings-merging-into-other-buildings styles and none have pulled it off as elegantly as the Portland Museum of Art. This really matters, because museums - and especially art museums- can be both intimidating and overwhelming. Here, it feels natural.

The Museum has a sound collection of Maine artists (including several pieces by Winslow Homer), American artists (Whistler, Singer Sargent), and European masters (Renoir, Picasso, Monet, Degas). They also host special exhibits. During my visit, the feature was an exhibit on sustainability in the Caribbean as expressed through modern art and it was EXCELLENT. 

Words don't do justice to this lovely art gallery. I highly recommend a visit and, if possible, one on Friday nights. That's when the Portland Museum of Art's admission drops from $12 to absolutely nothing from 4:00 pm to 8:oo pm. You know how much I love freebies!

If have a flexible travel schedule, Portland is the place to explore on the first Friday evening of each month. Not only is the Museum free, but that's when the city's monthly "First Friday"event happens. Many museums, galleries, and shops are open late (and sometimes have special treats too!)

Around $20:  Savoring a Portland Maine Lobster Roll

While a $20 sandwich wouldn't normally make the grade as a cheap meal option, all bets are off when lobster is available. Most restaurants in Portland offer some kind of lobster dish on their menu. While I wouldn't exactly say no to any of these delicacies, I'd argue that a classic lobster roll is the only way to go in terms of delivering the most powerful flavor punch. And in Portland, this gourmet goodie rings in at a reasonable $20 or less.

It's a personal preference, but in general I like to get my lobster rolls from a restaurant that specializes in seafood. My theory is that they'll be less inclined to skimp on quality and quantity when lobster is their signature showcase product - and you're less likely to get lobster meat that's been sitting around, waiting for a sale. But that's just me!

I was very content with the $19 lobster roll at The Highroller Lobster Co - large chunks of meat, toasted buns, and a choice of mayo or drawn (melted) butter for the purists. They also offer funky flavors for the more adventurous, including charred pineapple mayo and curried ketchup.  Other well reviewed spots include Eventide, the Portland Lobster Company, and Bite Into Maine, a food truck located next to Fort Williams lighthouse park in Cape Elizabeth. In short, if you're in Portland Maine, lobster should be at the top of your foodie experience list!

Note that the price of lobster fluctuates according to market demand and that many Portland restaurants (including Bite Into Maine and the Portland Lobster Company) are closed in winter. 

Exploring Portland Means Low Prices and High Indulgences

This was my third visit to Portland, Maine, and my longest as well. But each time I'm in town, I always feel like the time is too short and I need to come back again and again to explore further afield. It's an underrated, under-priced destination that's cozy and plush all year round and it should be on everyone's travel bucket list.
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PS: My Portland, Maine, hotel of choice is the AC Hotel Portland Downtown/ Waterfront by Marriott. I loved that it was on a quiet street but still just steps from the water, with lots of top restaurants and coffee shops just a block away.