Portland, Maine: a getaway by land and sea

Roger Fasteson

Maine is known as Vacationland with good reason. The Pine Tree State evokes images of lobsters, lighthouses, sea breezes and a rugged rocky coast. It is a place known for rustic charm.

Portland, its largest metropolitan area, is also a place to experience a kind of casual elegance unique to Maine. It is a city with fine art, innovative cuisine, live performances, historical attractions and upscale accommodations.

Roger Fasteson

Portland by Land and by Sea is a four day, three-night getaway package that includes a one night city stay on the mainland followed by two nights relaxing at a private island enclave in a unique historic setting. 

It begins at the Portland Harbor Hotel, the city’s only AAA Four Diamond Hotel. It is in the restored historic Old Port district, just a block from one of America ’s oldest working seaports.

There is time to explore the city. Then hotel guests are taken by town car for a cruise on Casco Bay to the car-free Great Diamond Island. Golf carts await to escort passengers to the Inn at Diamond Cove.

The Portland Harbor Hotel

The Portland Harbor Hotel was renovated in 2017 with distinctive nautical design elements to reflect Portland’s heritage as a New England port city. It begins with the lobby’s kinetic sculpture of fish that appear to swim with the breeze.

Guest rooms and public spaces feature art by well-known Maine artists and artisans, from the Thomas Moser custom furniture to the framed nautical flags above the beds that were hand-crafted by Angela Adams. Monochromatic maritime photography by Jim Dugan hangs in public spaces of the hotel.

Should you want a refreshing drink, there is a pantry on each floor with a faucet that produces both plain and sparkling water. A variety of complimentary hot beverages -- including Starbucks coffee, hot chocolate, and Tazo chai latte -- may be selected from the large touchscreen.

There is casual fine dining at the hotel’s BlueFin North Atlantic Seafood Restaurant. When the weather permits, dining can be al fresco in the outdoor garden courtyard. The fire pit is a popular spot to relax with cocktails or a glass of wine. 

Maine native and Executive Chef Tim Labonte has created a menu inspired by fresh locally-caught seafood and ingredients from local dairies and farms. The traditional and innovative dishes change seasonally. 

Signature items include Maine Crab Cakes and a Lobster Roll Popover with lemon-thyme dressing. Halibut with kelp noodles, plankton and pulverized uni (sea urchin) was recently featured.

Chef Labonte recently won Maine Restaurant Week’s Incredible Breakfast Cook-Off with his Lobstah Hash.

Portland, Maine: where the action is

There are unique specialty shops and restaurants along the Old Port’s Commercial Street. The Arts District is centered on Congress Street, a culture center with museums, galleries, and historic sites like the Portland Observatory. 

Portland is a place to enjoy ballet, opera, symphony orchestra, and theater. Museum houses reflect Colonial times through Victorian and Industrial Age opulence. Visit early in the month for a First Friday Art Walk.

From the freshest seafood to the most innovative creations Portland is known for its culinary scene. Bon Appétit named Portland the foodiest small town in America and there are tours to prove it.

Maine became the first dry state in 1851, well before Prohibition began in 1920. Speakeasy-style bars still exist here. 

Portland is also known for the craft breweries, wineries and distilleries with tasting rooms and tours. Companies like the Brew Bus offer a variety of tours to places like D. L. Geary’s, the first post-Prohibition craft brewery east of the Rockies, and Ned Wight’s New England Distilling, where there’s a family history of producing rye whiskey, bourbon, gin, and rum that goes back to Wight’s great-great-great-grandfather, John Jacob Wight, during the 1850’s. 

Points of Interest

Enjoy a range of American, European and contemporary works at Portland Museum of Art. Reserve in advance for an exclusive tour of Winslow Homer’s home and studio on Prout’s Neck. 

Climb the 86’ tall Portland Observatory, America’s last standing maritime signal tower, for a bird’s eye view of the busy harbor. It was built in 1807 by Captain Lemuel Moody, who hoisted signal flags to alert subscribing ship owners and merchants that their ships and cargo were approaching.

Henry Wadsworth Longfellow House & Garden, at the Maine Historical Society, is the 19th-century poet’s childhood home. It was built 1785-1786 by his grandfather, General Peleg Wadsworth, and has been restored to the 1850s. Family furnishings and memorabilia are original.

Victoria Mansion is one of America’s best examples of Italian Villa style. It was built between 1858 and 1860 as a summer house for Maine-born Ruggles Sylvester Morse, who made a fortune in luxury hotels in New Orleans, and wife Olive. It was purchased by dry goods merchant J. R. Libby and is also known as the Morse-Libby Mansion. Over 90% of the furnishings are original.

Tate House (built in 1755), was the home of Captain George Tate, Maine’s last agent to supply he British Navy with Maine white pines for masts. It is the only pre-Revolutionary home in Greater Portland open to the public. There are period furnishings and herb gardens.

There are six lighthouses within a twenty-minute drive of the city. The most photographed, Portland Head Light in Cape Elizabeth, is the oldest lighthouse in Maine It was authorized by President George Washington. The lighthouse keeper’s quarters is now a museum that also includes the history of the adjacent Fort Williams, a military outpost for coastal defense.

The Inn at Diamond Cove: the serenity of an island getaway

A charter boat company offers service to the inn by the J.S. Kennedy, a 50 ft. decommissioned Navy UB85, or “Utility Boat,” from Boston built in 1985. It was named for Joseph S. Kennedy, who completed three different tours of duty with the U.S. Navy in both World War I and World War II. 

Cruise in the salt air past lighthouses, forts, lobster boats, and seabirds. You might even spot a bald eagle. The 30-minute cruise from the mainland stiops at Great Diamond Island, where a driver awaits with a golf cart to escort you to the inn. The tranquility and natural beauty of the island is accessible to residents and those who stay at the Inn at Diamond Cove or dine at Diamond’s Edge Restaurant.

The Inn at Diamond Cove has 44 well-appointed guest rooms and suites. All suites have a fireplace, kitchen, dining area, parlor, and a wide wooden balcony with a comfortable seating area. Suites can be connected to adjacent guest rooms to accommodate families or other groups.

The island can also be accessed by ferry, water taxi or private boat. There is a marina with deep water slips. Whether for a romantic getaway, an immersion in history, or as a family or group getaway, it feels worlds away.

This unique inn is in a meticulously restored army barracks that was part of the former Fort McKinley. This military base was built between 1891 and 1907 for coastal defense during the Spanish-American War. It was also used during World War 1 and World War 2,. It was retired from active Army duty in 1945 and passed to U. S. Navy in 1954. 

Before Diamond Cove was an army base it was popular as a retreat for writers and artists. Harriet Beecher Stowe and Henry Wadsworth Longfellow are among those who visited.

The Navy sold the property to a private investor in 1961. The fort was eventually sold to the developer who built the inn.

Unfortunately, the inn was gutted by fire just before completion in 2013. It was rebuilt, thanks to historic tax credits, and opened in 2015. It is on the National Register of Historic Places and a member of the Historic Hotels of America.

In tribute to the inn’s fire and rebuilding, a stained glass phoenix looms over the inn’s lobby fireplace. The phoenix is the emblem of the city of Portland, which was devastated four times by fire. Portland’s motto is “I will rise again.”

There is an outdoor pool with a cabana. Guests can also enjoy the walking trails, secluded beaches, complimentary bicycles, tennis, and yoga. A fire pit adds warmth to a chilly night. You can even test your skill at the hand-operated bowling alley.

Staff members will point out areas of interest to guests who request a golf cart tour. Often there are Adirondack chairs marking scenic places like Moon Garden, site of the former Engineer’s Wharf and a choice spot for watching for wildlife or sunsets over Casco Bay. Pleasant Cove Beach is known as Sea Glass Beach for the abundance of fragments that wash up. 

This is a place to relax and enjoy the serenity away from it all. Savor a leisurely breakfast, perhaps a lobster omelet, and dinner at the inn’s restaurant, where lobster rolls, crab cakes and an oversized pork chop with apple bourbon bacon chutney are top choices. Meals are served in the lobby area or al fresco on the patio, weather permitting.

Another night, dinner is in the waterfront Diamond’s Edge Restaurant, their free-standing restaurant in the former Quartermaster’s storehouse. It is open for lunch or dinner Tuesday-Sunday in the summer and for Sunday Brunch.

Be sure to try the exceptionally plump, hand raised Bangs Island mussels, grown sustainably in Casco Bay. Other favorites are the black garlic & blue cheese crusted filet mignon and the bouillabaisse, which overflows with the fish of the day, mussels, shrimp, cod, salmon, scallops, and lobster, as well, if you like. Or add a side of lobster garlic smashed potatoes. If the weather allows, dinner is also served on the deck or on the lawn.

To learn more about the area’s history, visit the Ft. McKinley Museum, generally open June-September 11-2. It is staffed by volunteers from the Diamond Cove Homeowner’s Association.

The Portland by Land and by Sea Package is offered until Friday, September 21st and is subject to availability.  Rates start at $1,375 based on three nights double occupancy and include a $100 dinner and $30 breakfast credit at Bluefin; $120 dinner credit at the Inn at Diamond Cove; $150 dinner credit at Diamond’s Edge; complimentary town car service to ferry and three nights free parking at Portland Harbor Hotel. Package must be booked in its entirety. No substitutions or refunds allowed on dining or transportation credits. For more information call 207-805-9836 or visit or 

Portland is a 90-minute drive from Boston. It is 5 minutes from the Downeaster Rail Terminal, and 10 minutes from Portland Jetport. Valet parking at the Portland Harbor Hotel is included throughout the stay.

Roger Fasteson

A sample of Halibut with kelp noodles, plankton butter and pulverized uni (sea urchin) at the BlueFin Restaurant at the Portland Harbor Hotel, part of a six-course tasting menu

Roger Fasteson

One of the fabulous desserts at The BlueFin Restaurant at the Portland Harbor Hotel

Roger Fasteson

Some of the award-winning rye whiskey, bourbon, gin, and rum at New England Distilling, Portland, Maine

Roger Fasteson

Portland Observatory, Portland, Maine

Roger Fasteson

Spring Point Ledge Lighthouse with Portland Head Lighthouse and Cape Elizabeth in the background, Casco Bay.

Roger Fasteson

Lobby of the Inn at Diamond Cove, Great Diamond Island

Roger Fasteson

Casco Bay Island Ferry at Great Diamond Island

Roger Fasteson

Lobster omelet at the Inn at Diamond Cove, Great Diamond Island

Roger Fasteson

Moon Garden Punch at the Inn at Diamond Cove, Great Diamond Island

Roger Fasteson

Phoenix, the symbol of Portland, at the Inn at Diamond Cove, Great Diamond Island

Roger Fasteson

Bouillabaisse, Diamond's Edge Restaurant & Marins, Great Diamond Island

Roger Fasteson

Halibut special at Diamond's Edge Restaurant & Marina, Great Diamond Island

Roger Fasteson

Private residences at the former Fort McKinley, Great Diamond Island

Roger Fasteson

Pleasant Cove Beach, known as Sea Glass Beach for the abundance of fragments that wash up, Great Diamond Island 

Linda Fasteson

Linda Fasteson is an award-winning food and travel writer whose favorite travel souvenirs are foods and wines shared with friends and family. Her cultural and culinary adventures have taken her down through the cobwebs of medieval passageways to little-known wine cellars and up to palatial alpine banquets. She shops local markets, travels country roads, and goes behind the scenes with food produce...(Read More)

Around the web