This unique charter service was launched so that many more people can take advantage of beguiling Casco Bay, and all the charms it has to offer. Captain Willard has worked toward this goal for decades, but several harbor businesses are partnering with the Captain and Portland Harbor Fleet to introduce Maine natives and visitors alike to the magnetism of the bay and the spectacular City of Portland.

Portland Harbor Hotel
Setting the luxury standard for hotels in Portland, the Portland Harbor Hotel is located in the heart of Portland’s seafaring Old Port District. With spectacular rooms, sumptuous dining options and first-class amenities, a stay here is not to be forgotten! For more information, visit

Inn at Diamond Cove
What better way to accentuate an exhilarating excursion on the Joseph S. Kennedy than with a splendidly traditional Maine lobster bake, seaside, at Portland’s new deluxe island getaway, the Inn at Diamond Cove. This brand new property is hidden away in a tranquil private island community, and exudes the creativity, authenticity and craft that one associates with the coast of Maine. For more, visit

Shipyard Brewing Company
One of the harbor businesses most excited about “ a new day for chartered inter-island transportation” is Shipyard Brewing Company, which has crafted a new specialty brew to honor the UB85. The Shipyard brand is the most famous collection of craft beers brewed in Maine, distributed in nearly 50 of these United States. For more, visit

Diamond’s Edge Restaurant & Marina
Island dining at its finest. If you’ve not yet gazed over the delicious visual feast of “Cocktail Cove” as the locals call it, just wait until your eyes take in this unmatched visual feast. Here you’ll find yourself literally in another world, totally removed from the hustle and bustle of Portland’s Old Port district. A favorite among locals and visitors alike, Diamond’s Edge Restaurant is the perfect spot for a relaxing lunch or dinner featuring local seafood, New England favorites and amazing views. You MUST visit them:

Colleagues & Collaborators

Casco Bay Lines
Truly the lifeline for the hearty people who live in Casco Bay and call it home, Casco Bay Lines operates passenger, vehicle and freight service year-round. Every year its ferries transport nearly one million passengers, 30,000 vehicles and 5,300 tons of freight. It also offers a wide range of scenic cruises and charter trips for celebrations, meetings and sightseeing. If you haven’t yet been on a Casco Bay Lines ferry, you don’t what you’ve been missing! Visit

Portland Discovery Land & Sea Tours
These fine folks have been offering narrated trolley tours and narrated harbor cruises on Casco Bay for two decades, offering a variety of group tours, charters and private lobster bakes. More info at:

Call (207) 775-9090 to book your charter.