Chebeague Island Inn: Your Perfect Escape to Recharge

Readers often seek suggestions for destinations that offer a peaceful retreat from the demands of daily life. They desire a place that is not too rustic or overly remote but still provides an opportunity for couples to reconnect or for individuals to reflect and heal. Therefore, they search for a safe, welcoming haven where tranquility reigns supreme, allowing the pace of life to be determined by spontaneity.

After spending a single night on a picturesque island in Maine, we discovered that the Chebeague Island Inn offers just the kind of respite one seeks while also providing the perfect backdrop for a memorable getaway filled with outdoor activities.

Initially, we felt a bit anxious about the journey to Maine, which involved driving, taking a ferry, and exploring an island on our own. However, the ferry ride proved to be delightful, and the welcoming, attentive staff at Chebeague Island Inn made us feel completely at home. Riding a bike turned out to be an enjoyable experience, reminiscent of childhood adventures.

After an afternoon of ocean swimming, biking to a clam shack, and wandering through charming streets to a quiet cove, we savored delicious lobster corn dogs and warm mint chocolate chip cookies while watching one of the most stunning sunsets over New England. We fell into a deep sleep, revitalized not by rest from stressful tasks but through exhilarating experiences, waking up refreshed and ready to embrace a new day.

1. Getting to Chebeague Island

Chebeague Island (pronounced shuh-Beeg) is the largest of approximately 200 islands in Casco Bay, famous for being home to Portland, Maine’s largest city. Three main methods exist to reach Chebeague Island:

• The island-hopping Casco Bay Lines ferry, running on a limited schedule from Portland and taking roughly 45-90 minutes due to various stops;
• A water taxi from Portland, with options like Portland Express Water Taxi or Island Water Taxi, although this can be costly;
• The more popular Chebeague Transportation Company’s Chebeague Island Ferry, departing from Yarmouth, which is the preferred choice for locals and visitors alike.

A bonus: The ferry service used most frequently by islanders allows you to overhear genuine conversations in Maine accents and gain insights into island life as you cross Casco Bay.

The drive from Boston to the Chebeague Island Ferry parking lot takes about two hours, while it’s approximately three hours and 45 minutes from Hartford, Connecticut.

2. An Inn with a History

The Chebeague Island Inn has roots dating back to 1920, following the reconstruction of the original Hillcrest Hotel after a fire devastated the site in the 1880s. This charming three-story inn, built in a classic Greek Revival style, boasts a sunlit yellow exterior that melds both charm and character.

Among the few century-old grand hotels in New England, the Chebeague Island Inn has successfully preserved its character while undergoing renovations, thanks to the dedicated stewardship of mother-son hoteliers, Gerry and Casey Prentice, since 2010.

3. A Place to Unplug

While internet and cell service are available throughout the property, visitors can enjoy a plethora of classic board games, original Nancy Drew mysteries, and outdoor activities like croquet on the seaside lawn. The restaurant emphasizes fresh, local ingredients, showcasing the best of Atlantic seafood.

The inn retains a vintage charm that many travelers appreciate, though it is important to note that it lacks an elevator. Therefore, guests will need to navigate at least one flight of stairs to access their rooms. Additionally, while air conditioning is typically unnecessary due to the coastal breeze, adventurers may find their accommodations warm during heat waves.

4. Rooms at the Chebeague Island Inn

I arrived at the Chebeague Island Inn slightly ahead of the 3 p.m. check-in time, and fortunately, my ocean-view room with a private bath was ready. After electing to walk from the ferry dock to the inn under the hot sun, I was relieved to find my room was prepared for my arrival.

During my stay, I faced a brief service hiccup when my luggage was stored instead of delivered to my room. Lacking a phone in the room, I had to descend two flights of stairs to retrieve my bags. Nevertheless, the 21 rooms in the inn exuded charm with their elegant color schemes and unique antique decor, paired with Maine-inspired artworks. TVs are not present in the rooms, promoting a true getaway experience.

The inn operates seasonally from mid-May through early October, offering six room configurations to suit various needs. Prices range from $147 to $430 per night, including a full breakfast. Notably, there’s no minimum stay requirement, making it an appealing choice for travelers with limited time. However, it is essential to be aware of the inn’s cancellation policy, which may be less flexible.

With ocean breezes flowing through my windows and the soothing hum of an antique fan, I experienced restful sleep despite the warm night. Waking around 5:30 a.m., I realized there was no clock in my room, leaving me delightfully unsure of the time. This natural wake-up felt revitalizing, prompting me to reconsider my own sleep habits and prioritizing an earlier bedtime.

5. Getting Around Chebeague Island

As you explore Chebeague Island, you will not use a car. Instead, you’ll rely on your own power to navigate the island. The nearest public beach, Hamilton Beach, is about a 10-minute walk from the Chebeague Island Inn, while a leisurely 15-minute bike ride will take you to Calder’s Clam Shack.

After not biking for a decade, the experience was refreshing, and all motorists on Chebeague Island are extremely respectful of cyclists and pedestrians. With only about 400 permanent residents, the island’s population swells tenfold in the summer, resulting in a friendly, welcoming atmosphere.

The inn provides a fleet of bicycles, and I learned that new L.L. Bean Cruiser bikes are on the way to replace the older ones. Alternatively, if you wish to bring your own bike, there is a nominal fee of $3 each way on the Chebeague Transportation Company’s ferry.

Moreover, guests of the Chebeague Island Inn also have access to a complimentary van service to any destinations on the island they’d like to explore.

6. Things To Do on Chebeague Island

Chebeague Island, measuring just five miles long by three miles wide, is ideal for exploring, ensuring visitors can experience many of its highlights in a short time.

One of the finest activities on Chebeague is unwinding at one of its six public beaches. The inn provides beach chairs and towels for guests to enjoy the beauty and tranquility of Indian Point beach. Although I had only requested a short stay, I quickly regretted my decision to ask for the shuttle driver to return too soon.

After swimming in the chilly ocean, I bicycled toward Calder’s Clam Shack, stopping briefly to peek into the Museum of Chebeague History, located in an 1871 schoolhouse. Even though the museum was closed, they kindly let me take a quick look at the fascinating displays, illustrating the island’s late 19th-century evolution into a tourist destination.

As I reached Calder’s, I contemplated my meal choices and finally opted for enormous fried clams—while they were not the best, the locale spoke to a classic Maine experience. Late in the afternoon, many patrons at neighboring picnic tables indulged in delicious Maine-made ice cream.

After returning my bike, I continued my exploration, strolling past picturesque island homes toward Hamilton Beach. The following morning, just before heading back to the mainland, the inn’s shuttle took me to another island must-visit: The Niblic, Chebeague Island’s general store. Here, I found an array of items, from local crafts to food staples, and picked up a note card and unique lobster earrings crafted by an island artist.

For guests at Chebeague Island Inn, several recreational options await, including access to the 9-hole course at the Great Chebeague Golf Club, established in 1920, and the clay tennis courts at the island’s Recreation Center. Available fishing poles invite guests to cast from the inn’s docks, while island outfitters offer kayak and boat rentals.

If you run out of activities on Chebeague, you can take a water taxi or ferry to neighboring islands like Great Diamond, where dining options await at destinations like Diamond’s Edge Restaurant.

7. Dining at the Chebeague Island Inn

All you need for a delightful dining experience can be found at the Chebeague Island Inn, where the restaurant serves breakfast, lunch, dinner, and Sunday brunch. The culinary offerings attract not only overnight guests but also visitors journeying across Casco Bay for a standout meal. Executive Chef Justin Rowe frequently adjusts menus featuring fresh, local choices, specializing in seafood.

I chose to skip dinner due to a late snack of fried clams earlier in the day; however, the inn presented an excellent alternative option for lighter fare. The Sunset Landing menu, available on the inn’s waterside porch from 2:30 to 9 p.m., offers tasty snacks perfect for pairing with a cocktail, beer, or wine.

Tempted by the Artisan Cheese and Charcuterie Plate, I couldn’t resist the Lobster Corn Dogs instead—massive, tender bites encased in sweet batter paired with a zesty sun-dried tomato aioli. I decided to indulge further by ordering warm mint chocolate chip cookies straight from the oven while attempting to engage some boys playing croquet nearby in a sharing moment.

The next morning, I settled onto the screened porch amidst a flowing fog that enveloped the island. I enjoyed a filling breakfast plate of eggs, sweet Apple Wood smoked bacon, and Maine maple grits, delighting in the quiet atmosphere of a Monday morning with only a few occupied rooms.

8. Chebeague Island Memories

During my brief stay at the Chebeague Island Inn, I was fortunate enough to create precious memories and photograph stunning moments. However, one of my fondest recollections occurred while I savored cookies and admired the vibrant sunset. A lively celebration in the dining area featured a three-generation family recognizing a 50th wedding anniversary. Their heartfelt recitation of a poem honoring the couple was poignant, evoking strong emotions.

After the touching moment, the atmosphere was lightened by jokes, including one that quipped about the timing of their celebration. Such spontaneity and warmth underscored the community spirit of the island, leaving an indelible mark on my heart.

Chebeague Island may not offer highways, nightlife, or sophisticated amenities. Meanwhile, the Chebeague Island Inn’s absence of a spa, television, or modern conveniences invites guests into a realm of relaxation, where they can reconnect with what truly matters in life. A stay—however brief—can serve as a powerful reminder to embrace serenity, nurture intuition, and treasure experiences felt with both heart and mind for a lasting impact even far from this intoxicating island.

For bookings or dining inquiries, please visit the Chebeague Island Inn website or call 207-846-5155.

As is common in the travel industry, the writer was provided with complimentary lodging and breakfast for the purpose of reviewing this property. While it has not influenced this review, iBestTravel believes in full disclosure of potential conflicts of interest. Ethics Policy