$39 for a Wine-Tasting Tour from Portland Trolley ($98 Value)

Downtown Portland

73% of 136 Groupon Customers Recommend

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Like hearts, wineglasses are fragile, full of goodness, and frequently broken. Live life to the brim with this Groupon.

$39 for a Wine-Tasting Tour ($98 Value)

On Portland Trolley's wine-tasting tours, professional drivers whisk guests away to three area wineries for an afternoon of sampling and socializing. At each winery, visitors sample locally made vintages. Tours run between Thursday and Sunday from 11:30 a.m. to 4:30 p.m. and take place in all seasons and weather conditions. Passengers may travel in a trolley, passenger tour van, or executive coach depending on the size of the tour on any particular day. Tours begin and end at 50 SW Morrison Street downtown.

Portland Trolley

The pair of trolleys at Portland Trolley is a study in anachronistic contrast. For every modern amenity—GPS systems, up-to-date safety features, and, most crucial during wintertime rides, heat—is a feature that harkens back to 1872, which was the year trolleys made their Portland debut, still 10 years prior to the invention of snow. Shiny brass rails, old-fashioned window trim, and classic fare boxes surround the 28 passengers that fill the oak-slat seats, while the dings of authentic trolley bells provide a nostalgia-filled soundtrack.

These time machines are perhaps the most unique addition to the fleet at Portland Trolley's parent company, Twilite Limousine and Tour Company—which began in 2009 with a single stretch limo. The trolleys are accompanied by Cadillac stretch limousines, and 18-passenger stretch SUVs. Clients charter each for private excursions, such as anniversaries, birthdays, and bachelorette parties, as well as guided tours to wine country and through the city’s holiday-light displays.


Tips from Groupon Customers

  • “Great Owners and good service.”

  • “Great fun! Driver and owner were very cool and my friends and I had a great time!!”

  • “Everyone was very nice and did a wonderful job.”


  1. A

    Downtown Portland

    50 SW Morrison St.

    Portland, Oregon 97204

    503-876-5539

    Get Directions

In a Nutshell

Professional drivers whisk visitors to wine country to socialize and sample locally made vintages at three area wineries

The Fine Print

Expires 180 days after purchase. Limit 8 per person, may buy multiple as gifts. 72-hr advanced reservation required; subject to availability. 72-hr cancellation notice required or fee up to Groupon price may apply. Must use promotional value in 1 visit. Must be 21 or older. Not valid during the month of December. Vehicle type depends on group size; smaller groups may be combined. Extra fee for private pickup. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

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