Enjoy an elegant and relaxing getaway on this seven-day journey to Chicago, Mackinac Island, and the Grand Hotel. From scenic river views and historic architecture in Chicago to the charm of horse-drawn carriage tours and leisure time on the island, each day offers something peaceful and memorable. Guests enjoy premium accommodations, beautiful landscapes, and the timeless experience of the Grand Hotel. It’s a warm and inviting trip ideal for travelers who enjoy history, comfort, and scenic escapes.
• Sept 4 – Sept 10, 2026
• Sept 11 – Sept 17, 2026
• Sept 19 – Sept 25, 2026
Head to the Windy City to enjoy a mix of charm, history, and towering skylines. Overnight in Chicago, IL.
Take a guided Chicago River boat tour, viewing the city’s architecture and skyline from the water. Afternoon travel to Houghton Lake, MI for the night.
Take a morning ferry to Mackinac Island, then check in at the Grand Hotel. Free time to explore the island; lunch is on your own. In the evening, enjoy an elegant dinner in the main dining room at the Grand Hotel.
After breakfast, take a carriage tour around Mackinac Island. Gather for lunch at the Grand Hotel after the tour. Afternoon free to rent a bike, walk, or shop. Dinner is on your own tonight. Second night at the Grand Hotel.
Relax on Mackinac Island in the morning before catching the ferry back to the mainland after lunch. Enjoy a scenic drive across Michigan and spend the night in Lansing, MI.
Day 6 includes visits to several covered bridges in Indiana, alongside scenic countryside. Overnight in Terre Haute, IN. Day 7 concludes the tour with the return trip home.
These cross country trips are designed so that you can see and do a lot of things in a relatively short time. We use custom built full size touring coaches which are designed to accommodate 22 passengers very comfortably with a lot of special amenities. Some of these amenities include card tables for the avid players, a kitchen, wi-fi, 110 volt outlets, and a couch in the back. Just being able to get up and walk around or lie down and take a nap is a great advantage. We also prepare hot lunches on board and carry our own tables and chairs so we can have picnics at some of the most beautiful places in America. The idea is to create a “family” atmosphere which is easy to do with so few people on each tour. These are not ordinary bus trips.
On all the trips, except those with special exclusions, we have vans pick up passengers within 130 travel miles of Rolla and then meet up with the motorcoach to head out toward the destination (see next section for more details). Each day we will typically see or do one thing in the morning and then another in the afternoon. Since there is so much to see and do, we usually depart by 8:00 am and arrive at our destination city around 6:00 pm that evening. Dinner is on your own; however, we will drive to a neighborhood restaurant if there’s not one very near the hotel. On the last day, we arrive back in Missouri in the late afternoon. If we picked you up, we will take you back home, and everyone else will go to Rolla to get their car.
The price of each trip includes the motorcoach, lodging, hotel breakfasts, lunches and the cost of all venues shown. It also includes the shuttle to and from your home if you live within 130 travel miles from Rolla (if there are several people at the same location, this 130 mile criteria will be extended). Everyone living outside the 130 miles receive a $100 discount. If you live inside 130 miles and choose to drive to Rolla, you will receive a $50 discount.
The price is based on two persons per room. If four people share a room, the price will be reduced by the cost of the saved room divided by four. If you would like your own room, please call our office for a quote. To reserve a seat, you must send a $200 deposit per person. The remainder is due 45 days prior to the trip. The price does not include gratuity for the driver and hostess.
If you cancel more than 45 days prior to the beginning of the trip, you will receive back all but a $50 per person processing fee and any credit card fees that may apply. If you cancel between 45 and 15 days prior, you will receive a 50% refund. If we are able to fill the spot you vacated, you will receive back all of your money except credit card and processing fees. If you have to cancel less than 15 days prior or have to leave during the trip, you will receive a refund of any hotel costs and venues we are able to cancel. If you want a cancellation waiver to cover the potential loss if you have to cancel inside of 45 days, the cost is $100 per person (or $75 for the 5/6 day tours). Our cancellation waiver provides no coverage once the trip begins. If you have previously been on 5 or more of our tours, you will receive the cancellation waiver at no cost.
**Itineraries and arranged sightseeing are subject to change at any time due to circumstances beyond our control. Every effort will be made to operate tours as planned, but alterations may occur after the itinerary has been published.**
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