The Dirty Double-Crossing Tour! 6-days, 5 nights from Milwaukee 2025

Milwaukee, WI, USA

Bike Tour Vacations LLC
  • Email address verified
23 reviews
Jun 22 - 27, 2025
Group size: 6 - 50
The Dirty Double-Crossing Tour! 6-days, 5 nights from Milwaukee 2025
Milwaukee, WI, USA

Bike Tour Vacations LLC
  • Email address verified
23 reviews

Jun 22 - 27, 2025
Group size: 6 - 50

About this trip

We've got something with the Dirty Double Crossing Tour, a 200-mile, six day tour with two ferry crossings of Lake Michigan and some great riding in Michigan and Wisconsin! 


Pick the starting point which fits you best. Coming from Chicago and points to the west? Start in Milwaukee!


The Milwaukee start is one day and one night shorter vs. our guests who start and end in Muskegon

What’s included

  • Lodging
    5 nights of good hotel lodging
  • Tour Dinners
    Enjoy tour dinners on Sunday, Tuesday and Thursday nights!
  • Sag lunch
    Our Sag wagon has water, ice, sweet & salty snacks, plus a basic sag lunch every day!

What’s not included

  • Bike Rental
    Optional on all tours (based on local vendor availability)

Available Packages

Double Crossing, 2 guests shared room
Deposit:$0
Available until June 1, 2025

Milwaukee departure, Register here for 2 guests in a shared room. Choose between one person registering 2 guests for $3,798.00, or each guest registering separately and each paying $1,899.00. 

$1,899
Deposit:$0
Double Crossing, solo guest private room
Deposit:$0
Available until June 2, 2025

Milwaukee departure, Solo travelers in a private room please register at this link. 

$2,259
Deposit:$0


Itinerary

Noon arrival Milwaukee
Dirty Double Crossing

We depart Milwaukee about noon on the paved rail trail after loading your luggage in our sag wagon and meeting the other guests who started in Muskegon. Our route today heads out through the downtown area, and passes Estabrook Beer Garden, a great place for lunch. Destination tonight, Port Washington.

Your Organizer


BT
Bike Tour Vacations LLC
23 reviews
Joined in September 2023
See profile

Reviews

A good trip with 2 guides who went out of their to support the group. Nearly 2 full days of riding was along Wisconsin highway 35. This was both boring (miles of unchanging scenery, no turns) and unnerving (trucks and cars moving at high speed). The first and fourth days featured riding on bike paths that were very enjoyable. Three hotels were just ok. The Charmont Hotel in La Crosse was superb. I would rate it 3 stars because of Highway 35.
By Robert T for Biker Boys River Towns on the Mississippi Road Tour on Sep 23, 2024
I had a great time! Jordan and Trent were fun and helpful. The accommodations were acceptable with the last 2 stops being my favorites. The room was extremely small in The Terrace Inn and the room did not have a refrigerator. The meals provided were fabulous and our sag stops were plentiful. I have food allergies and my issues were dealt with completely! I would highly recommend this trip!
By Pamela W for Northern Trails Tour August 4-9 departure on Aug 18, 2024
SV
This trip was a great value for the price. Efforts were made to accommodate our particular group, most especially in terms of diet restrictions. Our guides were very helpful and personable. I did feel that they were not familiar with our route and had they been so, bike travel would have gone more smoothly. I would definitely recommend this company for future bike travel.
By Susan V for Northern Trails Tour August 4-9 departure on Aug 13, 2024
Excellent itinerary, accommodations were as good as you get in the U.P. without being overly expensive. Tour leaders were knowledgeable and friendly.
By rebecca w for Ride to Pictured Rocks on Aug 12, 2024
Overall, I thought the tour was average. The staff was good as were the accommodations (specifically, the rooms). It was nice having a day off to do something else and to have a break from biking. The ride to the Big Spring was nice in that it included a destination and an interesting one at that. The ride from Munising to Grand Marais was scenic and it had a couple of nice sights off the route worth visiting. I only visited one, as it was a long bike ride without the detours, and one detour was enough for me. Other than that, the other bike rides were just okay, and the whole point of the rides just seemed to be to get from point A to point B. For the most part, there was nothing to really stop and see or do along the way. Overall, the lodging was okay. What was lacking was staying at places that offered a decent breakfast (other than the lodging in Curtis) and had decent lobbies. This was the first tour I had been on where breakfast was not provided at the hotel (I have not forgotten about the restaurant in Manistique). Also, the places, for the most part, did not provide a decent place for the group to gather together after the ride and before dinner for a "happy hour." That was something I enjoyed on the River Towns tour. We did have one in Munising, but that was really the only one. What is nice about having such a gathering after a ride is that it gives the opportunity for solo travelers to make dinner plans with others on those nights when we are on our own for dinner. I think it would have been nice to have had a group meeting and dinner on Day 1 (something that occurred on the River Towns tour). For solo travelers like myself, it provides an opportunity to meet the other riders and to not have to eat alone. For the above reasons, I only give the tour three stars and frankly would not recommend the tour to others. I did not have a bad time and the staff did not do a poor job at all, but I have been on other tours and in comparison, this particular tour just was not as good.
By Eric D for Ride to Pictured Rocks on Aug 06, 2024
Thanks Eric, I appreciate your candor. Please help me understand your concern over dinner/happy hour, especially as it relates to two nights in Manistique. If we were to swap the Sunday dinner on the beach to Saturday, and have Sunday as on-your-own dinner, would this have made a difference? Also, thinking about Grand Marais where all the guests were at one location and staff was elsewhere due to the number of available rooms, where would you have held the happy hour, and what time? Regarding breakfasts in general, we prefer hotels which offer a hot breakfast. Unfortunately the lasting effects of Covid have made many of our hotel and restaurant partners rethink their strategy regarding breakfast and also on which days they're open. This effect is especially apparent in the U.P., along with a continual permanent shortage of staff. I'll send this message in an email, and I'd like your response. Thanks! JP
By Bike Tour Vacations LLC on Aug 06, 2024
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