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16 Mar 2025Updated last time
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Portland Maine Itinerary

Portland, Maine Highlights Itinerary Overview

Discover the charming and historic city of Portland, Maine with this specially curated itinerary. Begin your journey in the iconic Old Port, where cobblestone streets and 19th-century brick buildings create a nostalgic atmosphere. This vibrant waterfront district is renowned for its eclectic mix of shops, restaurants, and bars, making it perfect for a leisurely stroll, unique shopping experiences, and sampling exquisite local cuisine.

Next, make your way to the renowned Portland Head Light, one of the most photographed lighthouses in the United States. Located in Fort Williams Park, this historic site offers stunning coastal views, picturesque walking trails, and insightful exhibits about its storied past. It's a must-visit for photography enthusiasts and history buffs alike.

Continue your adventure at the Eastern Promenade, a scenic park providing panoramic views of Casco Bay. With its lush green spaces and recreational facilities, it's an ideal spot for picnicking, walking, or simply soaking in the natural beauty of Portland's waterfront.

Your itinerary wouldn't be complete without a visit to the Maine Narrow Gauge Railroad Museum. This unique museum offers a fascinating glimpse into the history of narrow gauge railroads in Maine. Enjoy a scenic train ride along the waterfront and delve into the historical exhibits that bring this piece of living history to life.

Lastly, step back in time at the Victoria Mansion, an extraordinary example of pre-Civil War architecture and interior design. Marvel at the opulent furnishings, intricate woodwork, and exquisite artwork that adorn this historic landmark, offering an unparalleled glimpse into 19th-century elegance.

This diverse and engaging itinerary will provide a comprehensive experience of Portland's rich history, stunning landscapes, and vibrant local culture.


Recommended Activities

  • Old Port is a historic district featuring cobblestone streets, 19th-century brick buildings, and a vibrant waterfront with shops, restaurants, and bars. It's perfect for a leisurely stroll, unique shopping, and sampling local cuisine.
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  • Trip Point Pin2

    Portland Head Light

    Portland Head Light is one of the most photographed lighthouses in the United States, offering stunning coastal views, historic exhibits, and picturesque walking trails in Fort Williams Park. It's a must-visit for photography enthusiasts and history buffs.
    Open Google Maps Button
  • Trip Point Pin3

    Eastern Promenade

    Eastern Promenade is a scenic park with panoramic views of Casco Bay, lush green spaces, and recreational facilities. It's ideal for picnicking, walking, and enjoying the scenic beauty of Portland's waterfront.
    Open Google Maps Button
  • Trip Point Pin4

    Maine Narrow Gauge Railroad Museum

    The Maine Narrow Gauge Railroad Museum offers a unique glimpse into the history of narrow gauge railroads in Maine. Visitors can enjoy a scenic train ride along the waterfront, explore historical exhibits, and experience a piece of living history.
    Open Google Maps Button
  • Trip Point Pin5

    Victoria Mansion

    Victoria Mansion is an exceptional example of pre-Civil War architecture and interior design. Visitors can marvel at the opulent furnishings, intricate woodwork, and exquisite artwork inside this historic landmark, offering an unparalleled glimpse into 19th-century elegance.
    Open Google Maps Button

Restaurants

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    Duckfat, Portland, ME

    Duckfat, Portland, ME

    Known for its exceptional Belgian-style fries cooked in duck fat, this cozy spot offers a unique and delicious twist on comfort food.
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    Eventide Oyster Co.

    4.6
    $$$$

    Eventide Oyster Co.

    A modern take on the classic oyster bar, Eventide is famous for its fresh local seafood and inventive dishes.
    4.6
    $$$$
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    The Honey Paw

    4.4
    $$$$

    The Honey Paw

    Offering an intriguing mix of Asian-inspired dishes, this restaurant is known for its creative and flavorful menu.
    4.4
    $$$$
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    Boda

    4.6
    $$$$

    Boda

    An upscale Thai restaurant, Boda is celebrated for its authentic street food cuisine and unique cocktail selection.
    4.6
    $$$$
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    Central Provisions - Portland, ME

    Central Provisions - Portland, ME

    This tapas-style eatery features a dynamic menu of small plates made with locally sourced ingredients, making it a must-visit for foodies.
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Hotels

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    The Press Hotel, Maine

    4.7

    The Press Hotel, Maine

    Housed in the former headquarters of the Portland Press Herald, this hotel offers a unique blend of historic charm and modern luxury, with newspaper-themed decor and artwork.
    4.7
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  • The Francis

    Located in a beautifully restored historic mansion, The Francis offers boutique accommodations with a focus on local art and design, providing a unique and intimate experience.
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    The Danforth Inn

    4.5

    The Danforth Inn

    This elegant inn combines historic charm with modern amenities, featuring beautifully designed rooms, a cozy lounge, and a secret speakeasy bar for a unique stay.
    4.5
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    Blind Tiger Guest House

    4.5

    Blind Tiger Guest House

    Set in a historic townhouse, this guest house offers eclectic decor and a relaxed atmosphere, making it a charming and unconventional lodging choice.
    4.5
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    Inn by the Sea

    Inn by the Sea

    Located just outside of Portland, this eco-friendly luxury resort offers stunning ocean views, beautiful gardens, and a spa, providing a serene and unique escape.
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Local Events & Happenings

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    TAUK

    TAUK

    The event will take place at Portland House of Music and Events in Portland.
    Map IconPortland House of Music and Events in Portland (0.79 mi)
    Calendar Icon1 Feb 2026
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    Xtreme Motorsports Ice Racing Pre-Party - Starts at 12:00 PM

    Xtreme Motorsports Ice Racing Pre-Party - Starts at 12:00 PM

    Party with us before the races! The Pre-Party takes place at the Cross Insurance Arena from 12:00 PM - 1:00 PM and includes food, soft drinks, and a special appearance from select riders. Cash bar is available for 21+. No re-entry.
    Map IconCross Insurance Arena in Portland (0.83 mi)
    Calendar Icon10 Jan 2026
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    The Harlem Globetrotters 100 Year Tour

    The Harlem Globetrotters 100 Year Tour

    THE HARLEM GLOBETROTTERS 100 YEAR TOUR This is a once-in-a-century celebration of 100 Years of Jaw-Dropping No Way! moves, 100 Years of Wow! and 100 Years of Heart-Pounding Thrills! The Harlem Globetrotters are coming to your city with their most LEG...
    Map IconCross Insurance Arena in Portland (0.83 mi)
    Calendar Icon13 Feb 2026
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    The Harlem Globetrotters 100 Year Tour Souvenir Ticket

    The Harlem Globetrotters 100 Year Tour Souvenir Ticket

    THIS WILL NOT BE YOUR TICKET TO THE EVENT AND IS NOT VALID FOR ENTRY. This limited-edition Harlem Globetrotters 100 Year Tour Souvenir Ticket is your chance to capture the legacy of the Globetrotters with your very own, 3-D printed ticket with black ...
    Map IconCross Insurance Arena in Portland (0.83 mi)
    Calendar Icon13 Feb 2026
    Picture for The Harlem Globetrotters 100 Year Tour Souvenir Ticket
  • Event Icon

    Limited Edition 100 Year Golden Replica Game Ball by Spalding®

    Limited Edition 100 Year Golden Replica Game Ball by Spalding®

    THIS IS AN OPTIONAL UPGRADE. TICKET TO THE MAIN EVENT IS ALSO REQUIRED. How to Redeem Your Limited Edition 100 Year Golden Replica Game Ball by Spalding® To pick up your exclusive game ball, visit the Harlem Globetrotters Merchandise Stand located in...
    Map IconCross Insurance Arena in Portland (0.83 mi)
    Calendar Icon13 Feb 2026
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  • Event Icon

    Jeff Dunham Artificial Intelligence

    Jeff Dunham Artificial Intelligence

    All guests age 2 & older are required to have a ticket.
    Map IconCross Insurance Arena in Portland (0.83 mi)
    Calendar Icon14 Feb 2026
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    Jim Gaffigan: Everything is Wonderful!

    Jim Gaffigan: Everything is Wonderful!

    There is an eight (8) ticket limit per person.
    Map IconCross Insurance Arena in Portland (0.83 mi)
    Calendar Icon12 Mar 2026
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Travel Gems from Reddit


Music for Your Journey

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    Eagles - Take It Easy - 2013 Remaster

    Eagles - Take It Easy - 2013 Remaster

    This classic Eagles song is perfect for a relaxed drive, setting the tone for a stress-free trip.
    Listen on Spotify
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    Willie Nelson - On The Road Again - Live

    Willie Nelson - On The Road Again - Live

    Willie Nelson’s upbeat track captures the excitement and freedom of being on a road trip.
    Listen on Spotify
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    Rascal Flatts - Life is a Highway

    Rascal Flatts - Life is a Highway

    Tom Cochrane’s energetic anthem embodies the spirit of adventure and exploration.
    Listen on Spotify
    Picture for Rascal Flatts - Life is a Highway
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    Katrina & The Waves - Walking On Sunshine

    Katrina & The Waves - Walking On Sunshine

    Katrina and the Waves' hit is an instant mood lifter, ideal for sunny days and scenic routes.
    Listen on Spotify
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    The Beatles - Here Comes The Sun - Remastered 2009

    The Beatles - Here Comes The Sun - Remastered 2009

    The Beatles’ classic brings a sense of optimism and calm, making it perfect for your travel playlist.
    Listen on Spotify
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  • Music Icon

    Edith Whiskers - Home

    Edith Whiskers - Home

    Phillip Phillips’ comforting tune is great for reminding you of the joys of both travel and returning home.
    Listen on Spotify
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    Rusted Root - Send Me on My Way

    Rusted Root - Send Me on My Way

    Rusted Root’s feel-good song adds a touch of whimsy and joy to your journey.
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  • Music Icon

    Lynyrd Skynyrd - Sweet Home Alabama

    Lynyrd Skynyrd - Sweet Home Alabama

    Lynyrd Skynyrd’s iconic track adds a classic rock vibe to your trip, perfect for long drives.
    Listen on Spotify
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  • Music Icon

    Tom Petty - Runnin' Down A Dream

    Tom Petty - Runnin' Down A Dream

    Tom Petty’s driving rhythm and hopeful lyrics are great for keeping energy levels high on the road.
    Listen on Spotify
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  • Music Icon

    Weezer - Island In The Sun

    Weezer - Island In The Sun

    Weezer’s laid-back tune is perfect for relaxing moments and enjoying the beautiful scenery.
    Listen on Spotify
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