The first from a secluded resort with cottages, pools, and family activities on the water, and the second from a historic, lovingly renovated, in-town house with hilltop views

View One: Spruce Point Inn Resort + Spa
When high school buddies Angelo DiGiulian and Joe Paolillo graduated from college, they headed to Boothbay Harbor to find work in the construction industry. In 1991 they invested with other family members in the Spruce Point Inn, and they have since built their careers and raised their own families around the ever-evolving historic property.

Situated two miles from town on the tip of Spuce Point, the inn was built as a family fishing and hunting lodge in the late 1800s. After many renovations and additions, the inn still manages to retain a timeless aesthetic in its 86 rooms spread across cottages, lodges, townhouses, and the original main building. Three restaurants, saltwater and freshwater pools, clay tennis courts, a children’s game room and playground, a spa, and a network of hiking trails crisscrossing the 57-acre property round out the options.

It’s the kind of place where you immediately settle into the rhythms of summer. My kids alternated between the pool, game room, and playground, and they thoroughly enjoyed lunch at Deck and dinner at Bogie’s before they fell fast asleep in our lodge while the grown-ups enjoyed drinks on the patio. There’s a reason 60 percent of guests return summer after summer. We plan to as well.

Spruce Point Inn Resort + Spa | 88 Grandview Ave. | Boothbay Harbor | 207.633.4152 | sprucepointinn.com

View Two: Topside Inn

In 2001 Ed McDermott and Brian Lamb decided to spend a winter on Southport while looking to buy a bed-and-breakfast somewhere in New England. A year later, they found what they were seeking, right at the top of town. The 1864 sea captain’s house is perched on wide green lawn with white Adirondack chairs that are perfect for taking in the nearly 360-degree views of the inner harbor, outer islands, and Mill Cove. Many rooms in what McDermott calls the “land yacht” have “lying-in-bed views,” and the common areas for breakfast and lounging all look out to the water, as does the wraparound deck.

Newer guesthouses, named Windward and Leeward, bring the room count up to twenty rooms, all decorated in a clean, contemporary style with muted colors and cottage furnishings. Owning a bed-and-breakfast is about division of labor, and Lamb takes care of the “bed” while McDermott manages the “breakfast.” Ours was lemon and wild Maine blueberry pancakes and applewood-smoked bacon. After breakfast, we strolled the 100 feet down to the shops of Townsend Avenue and the piers beyond. We returned to enjoy the hilltop sea breeze and our lying-in-bed view. With a view like that, you really don’t want to be anywhere else.

Topside Inn | 60 McKown St. | Boothbay Harbor | 207.633.5404 | topsideinn.com