Free Concierge Service
    Text or call (650) 414-7338
    Ask AIAI
    Ask AIAI
    1. Local experiences/
    2. Things to do in Portland…/
    3. Cultural Tours/
    4. Historical Tours/
    5. Old Port Walking Tour with Local Historian
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Concierge Support

    • Help Center
    [email protected](650) 414-7338

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 3
    Product image 4
    Product image 5
    Product image 6
    Product image 7
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Old Port Walking Tour with Local Historian

    Uncover 300 years of maritime and cultural heritage with a guided stroll through the Old Port.

    4.8 stars• 641 reviews
    From$44/ personincl. taxes and fees

    Duration

    2 hrs

    Includes

    Guided walking tour, Bakery treat

    Highlights

    Stroll Portland’s working waterfront and cobblestoned Old Port with a guide who weaves 300 years of stories into every stop. Feel the salt air, admire Victorian architecture and finish with a bakery treat.

    • Discover lobstermen in action on the bustling wharves
    • Hear tales of fires, railroads and revolutionary battles
    • Admire ornate Victorian buildings and iconic City Hall phoenix
    • Walk sections of the Portland Freedom Trail and Civil War sites
    • Enjoy a James Beard–nominated sweet treat at tour's end

    What's Included

    • Guided walking tour
    • Sweet bakery treat

    Wear comfortable walking shoes, dress for changeable Maine weather, and arrive at least 10 minutes early.

    Things to know

    Due to preservation efforts the route includes uneven surfaces and steps, making it unsuitable for some mobility devices.

    Cancellation Policy

    Tickets without tour insurance are non-refundable and tours run rain, snow, or shine. Tour insurance must be purchased during initial booking and cannot be added later.

    FAQs

    Portland's historic streets limit full accessibility for wheelchairs or walkers.

    Use a parking garage or lot; Custom House Square at 25 Pearl Street is the nearest.

    Well-behaved dogs are welcome with advance notice noted in your booking.

    Meeting details

    Andy's Old Port Pub, 94 Commercial Street, Portland, ME 04101.

    Experience provided by Maine Foodie Tours
    Experience provided by Maine Foodie Tours

    Related locations

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

    Report an issue

    Reference #YU447D

    Adult

    $44.51

    0

    Senior 65+

    $39.21

    0

    Active Military / First Responders / Veterans

    $39.21

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.8
    Excellent
    641 reviews•Google Maps
    585
    27
    11
    7
    11

    The guides here really make or break the experience, and fortunately most travelers rave about their personalities and expertise. Tyler brings Portland's history to life on walking tours, while AJ wins people over with her humor and local recommendations. Ray and Timothy both get praise for their knowledge and storytelling abilities, though opinions vary on pacing. The oyster and bubbles boat tour sounds particularly special, with a master shucker guiding you through Portland's oyster scene. Tours cover both Portland and Bar Harbor locations, with options ranging from history walks to culinary experiences. Food portions generally satisfy guests, with most leaving pleasantly full from stops featuring lobster rolls, chowder, and other Maine staples. A few travelers felt the tours spent too much time on guide monologues rather than diving into building histories or meeting restaurant owners. The occasional complaint surfaces about pacing or wanting more variety in stops. Overall though, visitors appreciate getting a solid introduction to Portland's food scene and Old Port area, especially from guides who clearly love their city and know where locals actually eat.

    What people are saying

    Review 1 of 5
    5/5

    Marlene was wonderful and truly felt like we had the best food at each restaurant along the way! Would recommend for anyone + girls trips!

    Photo of Emma Horath

    Emma Horath

    May 20, 2026

    Review 1 of 1
    5/5

    Marlene was wonderful and truly felt like we had the best food at each restaurant along the way! Would recommend for anyone + girls trips!

    Photo of Emma Horath

    Emma Horath

    May 20, 2026

    Nearby activities

    Thumbnail
    Waterfalls

    4-Hour Columbia River Gorge Waterfalls Guided Tour

    $95.23/ person
    Thumbnail
    Beach Tours

    Explore the Oregon Coast on a Full-Day Guided Tour

    $159.43/ person
    Thumbnail
    City Tours

    Explore Portland on a 3-Hour City Tour & Tram Ride

    $84.53/ person
    Thumbnail
    Waterfalls

    Explore Columbia River Gorge & Mt. Hood Full-Day Tour

    $159.43/ person
    Thumbnail
    Wine Tours

    Willamette Valley Guided Wine Tasting Tour From Portland

    $159.43/ person
    Thumbnail
    Ghost and Haunted

    Haunted Pub Walking Tour in Portland

    From$37/ person