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Roamly

Portland, Maine in summer

Portland, ME · July 2026

4 days · 2 adults · relaxed pace · $$

Nora B. Example trip · written by Roamly to show the format

Day 1

  • 08:00

    Standard Baking Co.

    “Get there before the morning buns go, which is before 9.”

  • 09:30

    Eastern Promenade walk

    “The whole loop with the water on your right. An hour.”

  • 12:00

    Lunch at Eventide Oyster Co.

    “The brown butter lobster roll. Do not debate it, just order it.”

  • 14:00

    Portland Museum of Art

    “Two hours. The Winslow Homer rooms are the reason.”

  • 17:00

    Drinks at Novare Res

    “Down an alley, in a courtyard. Enormous beer list.”

  • 19:30

    Dinner at Fore Street

    “Book, or queue at five for a bar seat. The wood oven does everything.”

  • The Press Hotel

    “Old newspaper building. The typewriter wall is a bit much and the rooms are great.”

Day 2

  • 08:30

    Coffee at Tandem

    “In an old garage on Congress. The best coffee in town.”

  • 10:00

    Casco Bay Lines mail boat

    “Three hours around the islands. The best thing we did all week.”

  • 14:00

    Lunch at Duckfat

    “Belgian fries in duck fat. Expect a wait, put your name down first.”

  • 16:00

    Walk the Old Port

    “Cobbles, bookshops, not too precious about itself.”

  • 19:00

    Dinner at Central Provisions

    “No reservations. Name down, walk, come back.”

  • The Press Hotel

Day 3

  • 09:00

    Portland Head Light

    “Twenty minutes out. Go early, the car park fills by ten.”

  • 11:00

    Fort Williams Park

    “Walk the cliff path from the lighthouse.”

  • 13:00

    Lunch at Bite Into Maine

    “The food truck at the park. Lobster roll, Connecticut style, warm butter.”

  • 16:00

    Nap

  • 19:30

    Dinner at Scales

    “On the wharf. Whole fish and a view of the boats.”

  • The Press Hotel

Day 4

  • 09:00

    Standard Baking Co.

    “One more time.”

  • 10:30

    Peaks Island ferry

    “Twenty minutes each way. Rent a bike and ride the loop in an hour.”

  • 14:00

    Lunch at Eventide

Going to Portland?

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