Cruise Port Guide · 152 cruises visit Portland →
The bucket-list things to do — and the private, expert-led way to do each.
Here’s the bucket list for your day ashore: the most extraordinary thing to do at each stop, and the private, small-group, or expert-led way to make it yours — your own pace, real access, none of the crowd.
Sail past iconic New England lighthouses on a narrated cruise through Casco Bay, culminating at the legendary Portland Head Light — Maine's oldest and most photographed lighthouse, set dramatically on Fort Williams Park's rocky shore.
Taste your way through Portland's celebrated Old Port dining scene — raw oysters plucked from Maine's cold waters, lobster rolls at legendary shacks, artisan cheesemakers, and locally crafted ales — guided by a passionate local food expert.
Ascend the 1807 Portland Observatory — the last surviving maritime signal tower in the US — for a sweeping panorama of Casco Bay, the White Mountains, and the city below, guided by a specialist historian.
Hop the Casco Bay ferry to car-free Peaks Island — just 3 miles offshore — and spend the day cycling past Victorian cottages, tide pools, and ocean-facing bluffs on one of New England's most enchanting island escapes.
Step inside the Victoria Mansion — considered the finest surviving example of pre-Civil War interior decoration in America — for a private guided exploration of its jaw-dropping frescoed ceilings, carved mahogany, and gilded opulence.
Join a working Maine lobsterman aboard his traditional wooden boat, haul traps in the wild waters of Casco Bay, and learn the centuries-old art and culture of lobstering — the most authentic ocean experience in New England.
⚓ Your bucket-list concierge
Tell us your sailing and we'll send the bucket list for every port — the most extraordinary thing to do at each, and the private, expert-led way to make it yours.
No spam. The honest plan, even when it says skip the ship’s tour.