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    1. Local experiences
    2. /Things to do in Wisconsin Dells…
    3. /Wine and Spirits
    4. /Wine Tours
    5. /Historic Trolley Winery Tour & Lunch near Wisconsin Dells
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    Historic Trolley Winery Tour & Lunch near Wisconsin Dells

    Ride a trolley to 3 wineries with tastings and lunch included

    4.2 stars• 320 reviews

    Duration

    5.5 Hours

    Includes

    Lunch, winery tastings, trolley

    Highlights

    Tour Wisconsin wine country on a climate-controlled trolley with tastings at three winery stops and a complimentary lunch. Enjoy scenic woods views, music, and time to shop for bottles and cases along the way.

    • Ride a chauffeured trolley through the Wisconsin Woods
    • Taste wine at 3 local wineries or tasting rooms
    • Enjoy a complimentary lunch with a non-alcoholic beverage
    • Bring non-alcoholic drinks and snacks on board
    • Purchase wine at stops and drink it on the trolley
    • Store bottles and cases on board with plenty of space

    What's Included

    • Chauffeured trolley transportation
    • Wine tastings at each winery stop
    • Lunch
    • Non-alcoholic beverage with lunch (coffee, soda, or water)

    Things to know

    Ages 21+ with valid government-issued ID required. Gratuity is not included; suggested gratuity: driver $5 per person, wine taster $1–$2 per person, restaurant staff $2–$5. The meal is sometimes first, and tours may run longer or return early due to external factors.

    Cancellation Policy

    No refunds or date changes. No transfers. The operator may substitute a bus if unforeseen circumstances occur or weather conditions won't allow for a trolley. If the tour does not meet the minimum number of people, the operator will notify in advance.

    Product ID: 7BUCK3

    FAQs

    Bring snacks and non-alcoholic beverages on board. Do not bring outside alcohol; you may buy wine at the tour stops (or Bobber's Island Grill) and drink it on the trolley.

    Dress comfortably and for the weather. The trolley seats are wooden, so you may want to bring a small cushion.

    Board at the curb by the outdoor bar where the white Dells Trolley sign is. Do not wait by the trolley parked in the back of the lot; park near the restaurant and the trolley will pull up to the curb.

    Meeting details

    Bobbers island grille. 750 wisconsin dells parkway south.

    Experience provided by Wisconsin Dells Trolley Service

    Related locations

    Prairie Hawk Winery

    Admission included

    Tucked into the rolling landscape outside Wisconsin Dells, Prairie Hawk Winery invites you to slow down and savor something local. The tasting room is unhurried and approachable, where pours come with easy conversation and genuine hospitality. Prairie Hawk Winery draws on Wisconsin-grown fruit and grapes to craft wines that reflect the region's agricultural character rather than chasing trends.

    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

    Adult

    $114.21

    21+ w/ Valid ID

    0

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    Review summary

    4.2
    Very Good
    320 reviews•Google Maps
    245
    9
    7
    6
    39

    The trolley tours here get high marks for their guides, particularly Brian, who shows up repeatedly in glowing reviews across different tour types. People rave about his knowledge of local history, friendly personality, and ability to make everything from ghost tours to wine tours memorable. Michael also gets a shoutout for bringing great energy. The variety of tours, from haunted experiences to scenic history rides to wine and bar hopping, seems to offer something for everyone, and guests appreciate learning lesser-known facts about the Dells area. The main frustration centers on communication and booking issues. Several reviewers describe difficulty getting responses to calls and emails, with some having to take their business elsewhere after multiple attempts to reach someone. There's also an alarming mention of an inappropriate text message from staff about tipping. One reviewer notes tours getting cancelled for low attendance, though they were offered alternatives. If you can get past the booking hurdles, the actual tour experience tends to deliver, especially if Brian's your guide. Just plan ahead and be persistent with your initial contact.

    What people are saying

    Review 1 of 4
    1/5

    We used a another platform. At most places, you make a reservation, present the another platform and you're good to go. Not here. You need to email your another platform to someone. We still weren't able to get a reservation. We did not get to go on the trolley at all. Horrible.

    Photo of Shana Morrisette

    Shana Morrisette

    August 22, 2026

    Review 1 of 1
    1/5

    We used a another platform. At most places, you make a reservation, present the another platform and you're good to go. Not here. You need to email your another platform to someone. We still weren't able to get a reservation. We did not get to go on the trolley at all. Horrible.

    Photo of Shana Morrisette

    Shana Morrisette

    August 22, 2026

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