The Riverboat Twilight
September 2-4, 2026
Dubuque, IA
Enjoy a captivating 3-day Mississippi River getaway blending history, elegance, and nature. Stay at the historic Four Mounds Estate in Dubuque, enjoy a private Dubuque Trolley Tour, and take a full-day Riverboat Twilight cruise with meals and entertainment.
Step back in time and unwind in elegance on this unique small-group journey along the mighty Mississippi. The Riverboat Twilight Getaway is a 3-day escape that blends the tranquil beauty of river life, rich historical exploration, and warm, welcoming hospitality. From scenic bus travel to the breathtaking vistas at Four Mounds Estate and a full-day riverboat cruise with gourmet meals and live entertainment, this thoughtfully curated trip offers an unforgettable taste of the past with the comforts of today.
For more information or to sign up for the trip, and payment, call Lori at (414) 477-0155.
As seen on PBS:
Historic Buildings of Iowa: Dubuque
John McGivern's Main Streets - Dubuque, Iowa
Inclusions:
2 nights lodging at the historic Four Mounds Estate
Riverboat Twilight full-day cruise
2 breakfasts, 2 snacks, 2 lunches, and 2 dinners
Guided tours of Dubuque and Four Mounds
Small group size for a relaxed and personal experience
Pricing:
$1,299 Person Double Occupancy
$1,499 Per Person Single Occupancy
$400 Deposit Will Hold Your Place.
Balance Due August 2, 2026
No refunds after August 2, 2026
Additional Information:
- Be prepared to register for trip insurance at the time of the trip sign-up. You will be asked
your date of birth. Trip insurance is available only at the time you book the trip. - There are no elevators at Four Mounds. You will have to walk up to the second floor to get to your room. We will do our best to accommodate.
- There is an above average amount of walking and stair climbing.
- The boat does not have an elevator. You can access the first floor and deck on the first floor
- If you have a hard time with stairs. You must be able to board the boat walking a deck and
ramp.
For more information or to sign up for the trip, and payment, call Lori at (414) 477-0155.
September 2:
- 10:00 AM (Time subject to change) – Depart from Watertown Plank Park & Ride, with an
additional pickup at Pewaukee’s Golf Road Park & Ride. - We enjoy a light picnic lunch (I) on the way to Dubuque. Upon arrival in Dubuque, we check into the historic Four Mounds estate, a hidden gem perched high above the Mississippi River.
- This remarkable 60-acre property—once a 20th-century gentleman’s farm—is known for its Craftsman and Colonial Revival architecture, sweeping views, and curated landscapes including gardens, prairies, and rare oak savanna.
- Settle into your unique room (note: rooms are upstairs and some have shared hall baths).
- Enjoy a delicious dinner at the Grey House (I), followed by a private Trolley Tour of Dubuque, offering a fascinating look at the city’s storied past.
- Return to Four Mounds for a restful night surrounded by nature and history.
September 3:
- Continental breakfast, snacks, and lunch (all included)
- Expert narration about the river’s history and landmarks
- Opportunities to spot bald eagles, river wildlife, and historic sites
- Live entertainment and time to relax in classic riverboat style
- Return to Four Mounds and enjoy cookout dinner (I) on the estate grounds—an idyllic end to a memorable day on the water.
September 4:
- 9:30 AM – Enjoy brunch (I) served in the Grey House.
- Take a guided historical tour of the Four Mounds estate, gaining deeper insights into its architecture, original family history, and preservation.
- Board the bus for the return trip to Pewaukee and Watertown Plank.
- A quick stop will be made for a grab-and-go bite (NI) before arriving back home filled with memories of Mississippi charm.
