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CONVENTION + VISITORS BUREAU /
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City Fun, Island HOPPING
No visit to Portland is complete without venturing out to one of the nearby Casco Bay Islands. Dine at a
fine Portland restaurant, stay in a comfortable hotel, then get out onto the sparkling waters in a number
of fun and affordable ways.
Photo: Tim Greenway
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The Casco Bay Lines ferry offers daily trips
to seven of the nearby populated islands as
well as sunset and moonlight cruises, and a
sunrise cruise for early risers.
Peaks Island, a commuter neighborhood
of Maine’s largest city, is only 15 minutes
away but feels like a world apart. Rent
bicycles or kayaks, or simply take a
leisurely stroll through the lovely town
streets lined with gift shops, cafes, and
ancient elm trees, which survived the
blight due to their secluded island location.
Visit the Fifth Maine Regiment Museum,
built in 1888 as a memorial and reunion
hall for veterans of the 5th Maine Regi-
ment, and now maintained as a Civil War
and local history museum. Top off the day
with drinks or dinner at the Inn on Peaks
Island, a stone’s throw from the ferry back
to Portland.
Chebeague, the largest of the Casco Bay
islands, can be reached by a leisurely 1 ½
hour ferry ride from Portland or a 15
minute jaunt from nearby Yarmouth. The
island contains many Greek Revival homes
that were built by the “stone sloopers,” men
whose ships carried granite for many of
the nation’s most spectacular monuments
and churches. Play a round of golf on the
nine-hole golf course and have lunch at the
Chebeague Island Inn, which offers great
food and a spectacular panoramic porch
view of the ocean.
Looking for an authentic old-fashioned
schooner sailing experience? You can
enjoy sunset cruises on the bay provided
by Maine Sailing Adventures and Portland
Schooner Company, both located next
to the ferry terminal. For a tasty and
educational evening, join sommelier
Erica Archer of Wine Wise who offers
fine-wine experiences as part of some of
the evening schooner excursions. Or take
the ferry to Great Diamond Island for a
romantic dinner at Diamond’s Edge.
And for a great family excursion, head up
to South Freeport for a trip with Captain
Tom Ring on Atlantic Seal Cruises, bound
for nearby Eagle Island. Eagle Island was
the summer home of Admiral Robert E.
Peary, the first man to reach the North
Pole. The magnificent home has ocean
views on all sides, lovely indigenous
flower gardens, and is filled with Peary’s
belongings. Captain Tom will show you
seals playing on nearby rock outcroppings
and even pull a lobster trap or two on the
way back.
No matter which adventure you choose
(and we suggest trying them all!), once
back from the islands there is so much
to do in Portland, including a visit to the
Portland Museum of Art, which has
assembled some of the best paintings
frommany of Maine’s museums into one
fabulous summer-long show.
See article
on pg. 23