Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Portland…
    3. /Wine and Spirits
    4. /Brewery Tours
    5. /Portland Happy Hour Trolley Tour
    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

    Resources

    • Travel Guides
    • Help Center
    [email protected]1-877-GREET-WELL

    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
    Product image 8
    Product image 9
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Portland Happy Hour Trolley Tour

    Sip local flavors and uncover Portland stories aboard a guided trolley

    4.8 stars• 644 reviews
    From$126/ personincl. taxes and fees

    Includes

    Tastings, snacks, chocolate truffle

    Highlights

    Ride through Portland’s craft beverage scene with guided stories, waterfront views, and stops at local favorites. Pair the city’s prohibition-era past with an after-hours tasting experience.

    • Discover prohibition-era stories as you travel by trolley
    • Explore local beverage destinations including Shipyard Brewing Company, Apres, and Batson River Brewing
    • Take in waterfront scenery through the trolley’s open windows
    • Expect stops and menu offerings to change based on availability or private events

    What's Included

    • Guided trolley transportation
    • Curated tastings
    • Shareable snack boards and bar bites
    • Dark & Stormy chocolate truffle

    Know before you go

    • Arrive 30 minutes before departure
    • Ages 21+ only
    • Bring a state-issued photo ID for age verification before boarding
    • Tours run rain or shine
    • Do not bring glass containers, coolers, or outside food and beverages
    • Trolleys are heated but do not have air conditioning

    Cancellation Policy

    All sales are final. This tour may be cancelled if the minimum number of passengers is not met.

    FAQs

    Customer parking is not available at Portland Discovery. Allow extra time for downtown parking; nearby public options include Ocean Gateway Lot, Angelo’s Acre Lot, and Simba Parking Lot, a 7- to 20-minute walk from the ticket booth.

    The trolleys are heated and can stay warm, but they do not have air conditioning. Open windows provide a breeze while the trolley is moving.

    Meeting details

    Portland Discovery, 170 Commercial Street, Portland

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

    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 1-877-GREET-WELL

    Report an issue

    Reference #9EQF7F

    Person | I'm 21+ | Local Libations

    $126.14

    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
    644 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

    My fiancé and I did the food tour with Randy and it was so much fun!! Easily one of our favorite things we did on our trip. We were able to taste a wide variety of what Bar Harbor had to offer us and get a little history with it as well!! Highly recommend Maine Day Ventures food tour!

    Photo of Mabel Zwenger

    Mabel Zwenger

    July 1, 2026

    Review 1 of 1
    5/5

    My fiancé and I did the food tour with Randy and it was so much fun!! Easily one of our favorite things we did on our trip. We were able to taste a wide variety of what Bar Harbor had to offer us and get a little history with it as well!! Highly recommend Maine Day Ventures food tour!

    Photo of Mabel Zwenger

    Mabel Zwenger

    July 1, 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
    Bar and Pub Crawl

    Weird Portland Pub Tour

    $31.80/ person