Portland, Maine in summer
Portland, ME · July 2026
4 days · 2 adults · relaxed pace · $$
Day 1
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08:00
Standard Baking Co.
“Get there before the morning buns go, which is before 9.”
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09:30
Eastern Promenade walk
“The whole loop with the water on your right. An hour.”
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12:00
Lunch at Eventide Oyster Co.
“The brown butter lobster roll. Do not debate it, just order it.”
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14:00
Portland Museum of Art
“Two hours. The Winslow Homer rooms are the reason.”
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17:00
Drinks at Novare Res
“Down an alley, in a courtyard. Enormous beer list.”
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19:30
Dinner at Fore Street
“Book, or queue at five for a bar seat. The wood oven does everything.”
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The Press Hotel
“Old newspaper building. The typewriter wall is a bit much and the rooms are great.”
Day 2
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08:30
Coffee at Tandem
“In an old garage on Congress. The best coffee in town.”
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10:00
Casco Bay Lines mail boat
“Three hours around the islands. The best thing we did all week.”
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14:00
Lunch at Duckfat
“Belgian fries in duck fat. Expect a wait, put your name down first.”
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16:00
Walk the Old Port
“Cobbles, bookshops, not too precious about itself.”
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19:00
Dinner at Central Provisions
“No reservations. Name down, walk, come back.”
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The Press Hotel
Day 3
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09:00
Portland Head Light
“Twenty minutes out. Go early, the car park fills by ten.”
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11:00
Fort Williams Park
“Walk the cliff path from the lighthouse.”
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13:00
Lunch at Bite Into Maine
“The food truck at the park. Lobster roll, Connecticut style, warm butter.”
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16:00
Nap
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19:30
Dinner at Scales
“On the wharf. Whole fish and a view of the boats.”
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The Press Hotel
Day 4
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09:00
Standard Baking Co.
“One more time.”
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10:30
Peaks Island ferry
“Twenty minutes each way. Rent a bike and ride the loop in an hour.”
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14:00
Lunch at Eventide
Going to Portland?
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