Chebeague Island Inn Centennial: A Three-Night VIP Experience
Celebrate 100 years of Chebeague Island Inn with a curated weekend of coastal charm. Enjoy boat transportation, island accommodations, signature events, and optional enhancements—from beach setups to gala tickets—all designed to make your stay unforgettable.
Step 1 - Select Your Accommodations
Choose your accommodations for the Centennial Weekend. Each reservation is part of a curated three-night experience that includes private ferry transportation, exclusive island programming, and access to signature Centennial events.
Accommodations must be reserved before customizing your experience package.
Step 2 - Customize Your Experience Package
Your VIP package is designed to immerse you in a weekend of island celebration, coastal beauty, and timeless hospitality. It includes round-trip boat transportation from Portland, accommodations at Chebeague Island Inn, a porchside welcome dinner, daily breakfast, and access to the Chebeague Chebang.
Optional enhancements—such as golf cart rentals, beach day setups, a round of golf, chef-prepared picnic lunches, tennis access, and tickets to the Centennial Gala—are available to personalize your stay.
Packages starting at $400 per person
Itinerary
arrival - August 29
Your weekend begins with a scenic, hour-long boat ride from Fore Points Marina in Portland to Chebeague Island, passing by the storied shores of House Island along the way.
After settling in, join us on the porch for a relaxed three-course welcome dinner, set against sweeping coastal views. It's the perfect way to ease into island life and connect with fellow guests.
Leisure & gala - August 30
Spend the day your way—whether you're playing a round at the Great Chebeague Island Golf Club, relaxing on the beach, exploring by golf cart, enjoying a picnic, or playing a game of tennis.
As evening falls, gather for the weekend’s signature event: the Centennial Gala. Celebrate 100 years of Chebeague Island Inn with a beautifully prepared multi-course dinner, live music, and dancing under the stars. (ticket required)
chebang - August 31
The festivities continue with the Chebeague Chebang—a lively, all-day celebration of local music, island flavors, and community spirit. Settle in, soak it up, and enjoy the energy of this once-in-a-century weekend.
departure - September 1
Enjoy a final breakfast on the island before boarding the return boat back to Portland, closing out a weekend of timeless island charm.