Featured Destinations
Portland
Urban boating in Maine begins and ends when you reach the waters of Portland Harbor. Nowhere else on the Maine coast will you find more shoreside entertainment opportunities along with a concentration of waterfront amenities. And this is a big-time harbor, with plenty of ocean-going traffic, as well as small craft commercial and recreational boats.
Two distinctly different shoreside options are along the edges of the harbor. First, there is the busy, glitzy, more urbanized Portland side of the harbor. Alternatively, you can opt for a berth on the more retiring, family-oriented South Portland shores—still a city but much more spread out. Either way, you will find the harbor itself busy with commerce on a grand, international scale, plus a sizable crowd of tour vessels and scads of recreational boats going everywhere at all times of the day and night. From superyachts to jet skis, you will find fellow cruisers amid these waters—in which the wakes rarely calm down throughout the summer season.
While both cities are well-established destinations, Portland is the better-known tourist stopover, with hundreds arriving by land and sea every day. Intent on being a multicultural beacon with a wide variety of enclaves all over town, Portland allows you to step from the dock directly onto the streets and take in some handsome, historic architecture, a multitude of restaurants, various shops and attractions, or just generally enjoy a diverse urban scene. In more traditional South Portland, the options are decidedly fewer, more laid-back and somewhat more scattered, but nonetheless appealing.
Near the docks, Commercial Street and the Old Port neighborhoods are the centerpieces for most waterborne visitors, with activities extending well inland and uptown these days. The city also has a growing Arts District, a modest walk uptown from the marinas.
Many new restaurants and shops have clustered around the Portland Museum of Art on Congress Square, making the extra effort to get there worthwhile. Indeed, neighborhoods like Munjoy Hill, Thompson’s Point, City Hall Plaza, Marginal Way, Forest Avenue, Deering Oaks and others offer striking diversity and most are worth a daytime visit, especially if you’ve got your best walking shoes with you, or you chose to take advantage of the city’s bus system.
Across the harbor in South Portland, the vibe is toned down. There are several marinas for transient sailors and the modest sights and amenities ashore keep the pace easy. Even with South Portland’s somewhat industrial look and bulk commercial ships transiting the waterfront waters with some frequency, the city is well aware of its casual visitors—which doesn’t include cruise ship enthusiasts.
The city’s self-awareness begins with the massive petroleum storage tanks on its shoreline, which are eye-catching because artists have painted murals on them, creating what is by far Maine’s largest outdoor art exhibit. Add to that the Spring Point Shoreway Trail and associated Greenbelt Walkway — paths that run along many waterfront neighborhoods — and it’s hard to resist stopping here. Popular among runners, walkers, bicyclists and in-line skaters, the trail system also connects with the popular angling spot, Fisherman’s Point, as well as with Bug Light Park, both at the heart of the southside waterfront.
Throughout Portland Harbor, it’s important to remain aware of its commercial roots and traffic. It’s among the busier oil trans-shipment ports on the East Coast and also hosts a deep-sea, commercial fishing fleet that comes and goes at all hours of the day and night. Tug-and-barge traffic is likewise busy. Predictably, the U.S. Coast Guard has a significant presence here, with facilities on the South Portland side and operations that include pollution abatement, search-and-rescue, ship inspection, navigation aids maintenance and ice breaking duties. Year ’round, these waters can be pretty active.
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Things to See and Do
In Portland, many visitors head for the Old Port neighborhood, the city’s oldest district. The area encompasses vibrant blocks of waterfront and wharves, cobblestones and brickwork, and is an easy walk from just about any Portland marina. Gourmet markets and specialty shops are clustered around venerable Exchange Street, the core of the Old Port, where professionals, college students and visitors of all ages populate the bistros, coffeehouses and bars. The shops are diverse, numerous and attractive, offering everything from local pottery and imported textiles from Africa to gourmet dog biscuits and the inevitable T-shirts and mugs.
Uptown in the Arts District, we hope you’re in the mood for culture. View the latest installations at the Portland Museum of Art (7 Congress Square Plaza; 207-775-6148), where you can spend hours seeing exhibits featuring world-famous artists such as Degas, Matisse, Picasso and Renoir. For local flavor, there are permanent exhibits by Winslow Homer, Dahlov Ipcar and Andrew Wyeth, three painters with strong ties to Maine. The museum’s Susie Konkel Pass grants free admission for anyone 21 and under.
Want to catch the latest Maine arts hopefuls? Check out the free exhibits by Maine College of Art students at the Institute of Contemporary Art (522 Congress St.; 207-699-5029), near the midtown Arts District. Elsewhere, dozens of one-of-a-kind galleries dot the side streets and main drag of midtown Congress Street. Wander around and you just might find the perfect piece to take home for a permanent memory of your Maine cruise. Get a customized one-of-a-kind nautical gift from Chart Metalworks (1 Pleasant St.; 207-221-6807), which turns charts into jewelry, cuff links and the like.
For some “play time” a little farther from the waterfront, call the Portland Stage Company (25 Forest Ave.; 207-774-0465) for information on a live performance or let the Portland Sea Dogs (271 Park Ave.; 800-874-9300) take you out to the old ball game. This minor league Boston Red Sox affiliate features both day and night games at handsome Hadlock Field.
The independent bookstore may be an endangered species in some places, but not in Portland. Visit the “fiercely independent” Longfellow Books (1 Monument Way; 207-772-4045), where you can get new and used literary pieces. When possible, they also feature readings by Maine authors. For readers with a penchant for independent publishers, PRINT: A Bookstore (273 Congress St.; 207-536-4778) is the place to go for readings, author signings, new releases and the like. And Carlson Turner Antiquarian Books & Bookbindery (241 Congress St.; 207-773-4200) has more than 40,000 tomes for sale, having been around more than 30 years. You also can’t go wrong with Sherman’s Maine Coast Book Shop (49 Exchange St.; 207-773-4100), where they’re packed, literally, to the ceiling with stuff, including old maps. Handy to the waterfront, their friendly and helpful staff knows where everything is located, so just ask.
In South Portland, parks, beaches and walkways are the prime source of fun. Need to cool off? Follow the Greenbelt to Willard Beach, easily Portland Harbor’s favorite swimming attraction. Another must-see on the SoPo (as locals call it) side of the harbor is Fort Preble, a 19th century edifice started in 1809 and added to as the century went on and as wars came and went. It’s adjacent to the Spring Point Lighthouse, which you saw on your way into the harbor and can be visited at close range. At nearby Bug Light Park, whose namesake lighthouse you also saw on the trip in, is SoPo’s handsome, ship-like memorial to the 236 Liberty Ships built on the waterfront here during World War II. For more information on the South Portland’s nearly 30 walkways, outdoor exhibits and parks, contact the city’s parks department (207-767-7670).
Back in Portland, there’s plenty more for history buffs. Greater Portland Landmarks (93 High St.; 207-774-5561) offers daily walking tours of Portland and is in charge of preserving the 1807 Portland Observatory, a lighthouse-like tower that overlooks the city at the east end of Congress Street. The Observatory is open to guided as well as self-guided tours. Alternatively, you can take a trolley tour or a ferry ride via Portland Discovery Land & Sea Tours (170 Commercial St.; 207-774-0808), which has been escorting visitors around town and nearby waters for more than 20 years.
In recent years, both cities have made it easier to get around via bicycle, with designated paths and zones, maps and such. Nearest to the waterfront, rent a bike at Portland EnCYCLEpedia (6 Commercial St.; 866-857-9544) or farther inland, check out CycleMania (65 Cove St.; 207-774-2933). While you’re pedaling around, don’t forget to ride over the Casco Bay Bridge between Portland and South Portland, which has a terrific bike and walking path, plus a picturesque view of the entire harbor from the center span.
While it’s a bit of a hike to get to, younger crew members will appreciate the playground and wading pool at Portland’s Deering Oaks Park, a shady 51-acre, Olmsted-designed parcel that’s popular with locals and visitors alike. Kids will also enjoy the nearly 100-year-old attraction of Maddy’s Theatre (250 Thompson’s Point Road; 207-828-1234), known up until 2021 as the Children’s Museum & Theatre of Maine. There are still hands-on exhibits that will enchant minds of any age, plus workshops and of course plenty of theatre opportunities and acting classes. City buses regularly go to the Thompson’s Point area, which includes the Portland Transportation Center (100 Thompson’s Point Road; 800-872-7245). From the Center you can catch either a train or bus to various points in New England and elsewhere
To entertain the whole family, Lucky Catch Cruises (170 Commercial St.; 207-761-0941) offers a 90-minute trap-hauling excursion with some hands-on fun for anyone in the mood. Odyssey Whale Watching (170 Commercial St.; 207-775-0727) also sails out of Long Wharf and includes deep-sea fishing and scenic cruises with musical outings on weekends. If you want to see Casco Bay’s outer islands, Casco Bay Lines (56 Commercial St.; 207-774-7871) offers scheduled ferry service to many of the most popular islands and welcomes nonresidents to tag along. The mail boat run and sunset excursions are especially popular. The Portland Sea Taxi (72 Commercial St.; 207-879-2562) is another option.
Back on terra firma, get on track at the Maine Narrow Gauge Railroad & Museum (58 Fore St.; 207-828-0814), which has railroad heritage exhibits and 3-mile train excursions along the edge of Portland’s Eastern Promenade. The area’s known as The Prom and includes a huge park with an excellent view of western Casco Bay and outer Portland Harbor. Leashed dogs are welcome in the park.
Another place that piqued our interest is the Portland Fire Museum (157 Spring St.; 207-772-2040), housed in an 1837 firehouse. It’s the only one left standing in Maine that contains horse stalls. In addition to antique firefighting equipment, the exhibits include photographs, paintings and other artifacts. The highlight is a 1938 pumper truck. Hours can be quirky so call ahead.
Live music is available all over Portland and in a few places in South Portland. You can catch it in the streets, in coffeehouses and small clubs, and at the Cross Insurance Arena (1 Civic Center Square; 207-791-2200). Still, we think the best venue of all is the great outdoors. Find out what type of music is playing where is the Portland Public Library (5 Monument Square; 207-871-1700). Another melodic option is Portland Symphony Orchestra (50 Monument Square; 207-773-6128), which is just one of the many productions to be seen at Merrill Auditorium (20 Myrtle St.; 207-842-0800).
Featured Marinas
DiMillo’s Marina
207-773-7632Fore Points Marina
207-517-4860Maine Yacht Center
207-842-9000Portland Yacht Services
207-774-1067South Port Marine
207-799-8191Spring Point Marina
207-767-3254
Restaurants and Provisions
Get your city’s name in a big-time publication and life will never be the same. Ever since Bon Appétit magazine named Portland its “Restaurant City of the Year” for 2018, foodies worldwide have been flocking to eateries all over town. Portland does indeed have a wide assortment of cuisines for a wide range of budgets. And some restaurants do sport very high quality offerings. But a crush of restaurants trying to locate in Portland has meant lots of comings and goings of places to eat.
Over in South Portland, that city has its share of good chow houses. But most food-o-philes end up eating somewhere in the “big brother” of Portland Harbor.
Dominating the waterfront and just steps away from the Old Port, there is venerable, DiMillo’s (207-772-2216), the on-site, floating restaurant of the namesake marina. This prominent ferry-turned-eatery just off Commercial Street highlights the best of Maine. Lobster is the specialty, but they also serve other great seafood concoctions, steaks and Italian dishes.
If you’re on the go or ready to settle in, Gilbert’s Chowder House (92 Commercial St.; 207-871-5636) provides many versions of its award-winning, namesake menu item, along with various other seafood specialties. If you care about top-drawer corned beef hash, do not miss Becky’s Diner (390 Commercial St.; 207-773-7070), which is open for breakfast at 6 a.m. and serves dinner until 9 p.m. Other menu items are quite tasty, too.
For a long-time fixture just off Commercial Street, try J’s Oyster (5 Portland Pier; 207-772-4828), which features a traditional oyster bar and lots of other seafood options. There is often a bit of a wait because they don’t take reservations and it’s that popular. If seafood isn’t at the top of your list, you’ll find the ever-popular Flatbread Company (72 Commercial St.; 207-772-8777) near the Casco Bay Ferry terminal and featuring award-winning pizza, salads and (what else?) flatbread creations. Nice views, too. Next door, try Ri Ra Irish Restaurant & Pub (72 Commercial St.; 207-761-4446) for Irish fare and live music.
For a constantly-varying menu and cocktail list, go to Central Provisions (414 Fore St.; 207-805-1085), which is only a block from the waterfront and always seems to be among the top 10 restaurants in town. Also a block from the waterfront, another perennial award-winner is Fore Street Restaurant (288 Fore St.; 207-775-2717), which uses ingredients from Maine farmers, fishermen, foragers and cheesemakers with excellent, nationally-recognized results.
Back on the waterfront, Scales Restaurant (68 Commercial St.; 207-805-0444) weighs in with an outstanding reputation for both seafood and terrestrial creations. If you’ve never had citrus-scented french fries done in duck fat, check out Duckfat (43 Middle St.; 207-774-8080), where you can also get excellent sandwiches, milkshakes, sausages and more.
Barstool quarterbacks will bask in the athletic atmosphere at the Fore Play Sports Pub (436 Fore St.; 207-780-1111), featuring two floors of televisions as well as hands-on games: air hockey, foosball and darts. A Maine original brewer, Gritty’s Brew Pub (396 Fore St.; 207-772-2739) has been pulling in the crowds for handcrafted ales, pub food and a welcoming atmosphere since 1988. Located in two other Maine cities, Gritty’s Portland location includes a gift shop.
Still looking for upscale? Check out Union Restaurant (390Congress St.; 207-808-8700), which is located in the new Press Hotel. Serving all three meals daily, it regularly gets rave reviews from locals and visitors alike.
Fans of Asian cuisine will be inspired by Portland’s selection. Sushi lovers from the waterfront and elsewhere have been patronizing Sapporo (230 Commercial St.; 207-772-1233) for years, focusing on a wide-ranging Japanese menu. Farther west and just off Commercial Street, more sushi can be had at Benkay Japanese Restaurant (16 Middle St.; 207-773-5555), which also offers affordable daily specials. For Chinese, take-out or eat-in, try Zen Chinese Bistro (45 Danforth St.; 207-775-6888), which is a little farther inland from the waterfront but worth the effort. Back in the Old Port, Tandoor (88 Exchange St.; 207-775-4259) serves authentic North Indian lunches and dinners.
For Mexican food, head farther away from the waterfront and try popular Taco Escobarr (548 Congress St.; 207-541-9097), where gluten-free dishes are available along with more traditional offerings. And as long as you are already on Congress, head over to Cheval (58 Pine St.; 207-772-1110) for a sell-proclaimed “brasserie” serving Spanish and French-inspired cuisine, using whatever is locally in season.
Fueling a coffee habit is easy in the general vicinity of the Old Port district, as well as elsewhere around town. Start with one that seems to have taken Portland by storm, Coffee by Design (67 India St.; 207-780-6767), with three storefronts in town. The India Street outlet is closest to the marinas. Also in the Old Port is local favorite Bard Coffee (185 Middle St.; 207-899-4788), where it’s fun to watch the busy pedestrian traffic. We counted at least another half dozen coffee shops around town, so you should never be without your cuppa joe.
Sweets have inspired all sorts of specialty outlets in Portland. Start with Gelato Fiasco (425 Fore St.; 207-699-4314) for a wide variety of the icy concoctions of Italian heritage. If you’re not in the mood for something cold, a few short steps away is the Old Port Candy Company (422 Fore St.; 207-772-0600), featuring fudge and all of the favorite confections from your youth, plus some Maine-centric options. With exclusively gluten-free offerings, Bam Bam Bakery (267 Commercial St.; 207-899-4100) has a devoted and passionate clientele, with tasty treats for just about anyone. For the traditional summertime cold treat, you can choose between two locations of Beal’s Ice Cream (12 Moulton St.; 207-828-1335), which offers more than 100 locally-made flavors and frozen concoctions for your pleasure. Their original Veranda Street spot near the Maine Yacht Center is also in operation.
In South Portland, dining options are fewer and will depend largely on where you’ve chosen to tie up. For instance, if you’re at South Port Marine, you can grab some quick bites to eat at nearby Taco Trio (60 Ocean St.; 207-767-9055), where the burritos are as good as the namesake menu item. Also from South Port Marine, it is a relatively easy walk to some excellent shopping areas, too. A modest walk inland will take you to the laudable Q Street Diner (9 Q St.; 207-767-0299) where you can get a sumptuous breakfast all day long.
Next door to Sunset Marina, dock and dine at a longstanding favorite, the Saltwater Grille (231 Front St.; 207-799-5400), where their spectacular views complement their varied menu, with choices of lobster pizza, seafood jambalaya and some vegetarian options. The Saltwater Grille has been around for nearly 30 years and it has a crowd of loyal regulars who delight in everything from old-school, casual dishes to eclectic, seafood-leaning entrees. Sharing is encouraged.
Patrons of Spring Point Marina would be wise to head to the on-site restaurant, North 43 Bistro (1 Spring Point Drive; 207-747-4009), which features American fare with interesting twists. The upscale ambiance and creative American fare for lunch or dinner feature the best of seasonal ingredients, both surf and turf. If you’ve got wheels, check out David’s 388 (388 Cottage Road; 207-347-7388), which has been serving award-winning, eclectic American fare since 2007.
Time to restock the larder? Portland Harbor is noted for providing specialty goods, which may be a smart move before moving on to less-developed parts of Maine. In Portland, one of the top shops on the waterfront is Harbor Fish Market (9 Custom House Wharf; 207-775-0251), where the sheer variety and volume are impressive. The popular Italian specialty store, Micucci’s Grocery (45 India St.; 207-775-1854), is loaded with wines, deli meats, olives and lots more. People from all over Maine come to Portland specifically to shop at Micucci’s.
A short cab ride away from the waterfront is Trader Joe’s (87 Marginal Way; 207-699-3799). In the vicinity are two other supermarkets Hannaford (295 Forest Ave.; 207-761-5965) and Whole Foods (2 Somerset St. 207-774-7711). In South Portland, Shaw’s (180 Waterman Drive; 207-799-8149) and Hannaford (50 Cottage Road; 207-799-7359) are two of many conveniences within easy walking distance of South Port Marine.
For nautical needs, it’s back to Portland and several top-drawer outfits. For nearly 170 years, mariners have trusted Chase, Leavitt & Co. (144 Fore St.; 207-772-6383) for their aquatic requirements. Check out the chart room, where you can get all assorted navigational tools, cruising guides (like this one!), plot books, paper charts and much more. In addition, their Life Raft Service Station is excellent for making sure you’re prepared for the worst.
A much wider array of supplies — and we mean just about anything — will be found at Hamilton Marine (197 Presumpscot St.; 207-774-1772), where some rigging services are also available. They’re located about a mile north of Back Cove in Portland’s East Deering neighborhood, so you will need ground transportation to get there from the Old Port. This large discount chandlery, which is well-respected in Maine, also has shops in Searsport, Rockland, Southwest Harbor and Jonesport.
Marine clothing, hardware and related items are also in good supply from West Marine (127 Marginal Way; 207-761-7600), which is next door to Trader Joe’s, where you can pick up some groceries. Take just about any brand diesel engine or generator for service by the expert technicians at PowerProducts Systems (432 Warren Ave.; 207-797-5188), a Volvo Penta specialist in service, parts and sales.
If you don’t have a bike and would rather save the cab fare, check out Greater Portland Metro (21 Elm St.; 207-774-0351), which has buses running all over the Portland, South Portland and Westbrook area. It’s particularly useful for getting to South Portland’s Maine Mall (364 Maine Mall Road; 207-828-2063), where shopping options are too numerous to contemplate. Buses start running early in the morning and continue well into the night.
