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3 Days of Family Fun in Portland, Maine Itinerary

Last updated: 2024 Jun 14

Exploring Portland's History and Cuisine

Morning

Start your day with a delicious breakfast at Becky's Diner, a classic spot known for its hearty meals and family-friendly atmosphere. After breakfast, head to Portland Trolley City Tour with Portland Head Light Stop. This guided tour is perfect for families as it combines the excitement of a trolley ride with the opportunity to see one of Maine's most iconic lighthouses.

Afternoon

For lunch, enjoy some fresh seafood at J's Oyster, a highly-rated restaurant offering a variety of seafood dishes that will delight both kids and adults. After lunch, take part in the Portland Old Port Culinary Walking Tour. This tour is not only educational but also fun as it allows you to taste some of the best local foods while learning about Portland's rich history.

Evening

End your day with dinner at DiMillo's On the Water, an iconic floating restaurant that offers stunning views and a diverse menu. The unique setting will surely be a hit with the whole family.

Bedtime

Find amazing hotels in Portland, Maine.

4.82
Portland Trolley City Tour with Portland Head Light Stop
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4.81
Portland Old Port Culinary Walking Tour
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Lighthouses and Local Flavors

Morning

Begin your day with breakfast at Hot Suppa, known for its Southern-inspired dishes and cozy atmosphere. Following breakfast, embark on the Portland Best of Maine Lighthouse Scenic Cruise. This scenic cruise offers breathtaking views of multiple lighthouses along the coast and is an enjoyable experience for all ages.

Afternoon

For lunch, head to The Honey Paw, where you can enjoy innovative Asian-inspired dishes in a casual setting. Post-lunch, explore more of Portland’s culinary scene with the Portland Old Port Seafood Lovers Tour. This tour is perfect for families who love seafood and want to learn more about Portland’s maritime heritage.

Evening

Conclude your day with dinner at Fore Street, one of Portland’s top-rated restaurants known for its farm-to-table cuisine. The sophisticated yet welcoming environment makes it suitable for families looking to enjoy a special meal together.

Bedtime

Find amazing hotels in Portland, Maine.

4.86
Portland Best of Maine Lighthouse Scenic Cruise
Book Now

4.71
Portland Old Port Seafood Lovers Tour
Book Now

Cruises and Cultural Tours

Morning

Kick off your morning with breakfast at Central Provisions, offering a variety of small plates perfect for sharing among family members. Afterward, set sail on the Portland Schooner Tall Ship Cruise on Casco Bay, where you can experience sailing on an authentic schooner while taking in beautiful coastal views.

Afternoon

For lunch, visit Duckfat, famous for its Belgian fries and sandwiches that are sure to please everyone in the family. In the afternoon, delve into Portland’s past with the engaging Portland Hidden Histories Guided Walking Tour. This tour reveals fascinating stories about Portland’s history that both kids and adults will find intriguing.

Evening

Wrap up your trip with dinner at Flatbread Company Portland Maine, known for its wood-fired pizzas made from organic ingredients. The relaxed atmosphere is ideal for families looking to unwind after an exciting day.

Bedtime

Find amazing hotels in Portland, Maine.