Rhine & Wine Tour: Exploring Hidden Vineyards, Charming Villages, Medieval Castles

Boosenburg Castle and Vineyards, Rudesheim, Germany

What to expect on this itinerary

Old-world mystique cascades across the Middle Rhine as vineyards roll beneath fabulous castles, and half-timbered taverns reveal medieval charms. Germany's most scenic region is also its most sensual, a realm of sublime aesthetics and subtle smells, captivating in its revelation of bygone centuries. This 8-day tour follows the great river, unraveling the vineyards and the surprises.

Countries Visited

Germany

Places Visited

Frankfurt, Rüdesheim, Worms, Heidelberg

Suggested Duration

8 Days

Customizable Itinerary

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Day 1

Frankfurt – Culinary Welcome

Frankfurt's culinary heritage is far more complicated than the simple sausage it gave its name to. While Frankfurters are easily found from the street hawkers, the city reveals a gourmet indulgence far beyond a sausage and a bread roll. This city has been a cultural hotbed for 2,000 years, and its legacy prevails amidst the towering skyscrapers of its future. You'll be greeted at the airport and transferred to a five-star hotel in the city's heart, where the atmosphere is distinctly old-world. Relax. Refresh. Admire the skyline. Then head out in the evening for a fantastic restaurant experience.

Housed in a fabulous country residence, this fabled restaurant has two Michelin stars and an outdoor terrace of pure indulgence. After an outdoor drink, step inside to a dining room that's as kitsch as it is chic, a style that reflects the royal tastes of a bygone era. The food is innovative and sophisticated, delicate flavors in bold and daring creations, an ode to creation that reflects the bounty and style of the Rhine. It's an ideal introduction to the tastes of this region, one that's rooted in regal history and pioneering in every dish.

What's Included:

Accommodation
Transfer
Day 2

Frankfurt – Exploring an Intriguing City

Day 3

Rudesheim – Discovering the Wine of the Rhine

Day 4

Rudesheim – The Medieval City of Winegrowers

Day 5

Worms – Cruising Along the Rhine and More Sensual Wine

Day 6

Heidelberg – Walking Through a Pre-Roman City

Day 7

Heidelberg – The History of Heidelberg

Day 8

Heidelberg – Departure

Trip Highlights

  • Explore the delightful wine of the Rhine River, one of Europe's unknown and unexpectedly sensual regions
  • Lose yourself in the medieval city of winegrowers with two nights in Rüdesheim
  • Cruise along the Rhine River by boat, stopping to find chateaus and vineyards that delight in their rurality
  • Start the luxury tour in Frankfurt, where the juxtaposition of styles begins to unravel the historical wonders of Germany
  • Spend a day exploring the local Rheinhessen wine that's been cultivated for centuries
  • Step back into a distant century and spend two nights in Heidelberg, where castle ruins symbolize the impression of a fairytale world
  • Spend evenings in cozy, traditional wine taverns found in half-timbered houses, historical buildings that retain their old-world atmosphere

Detailed Description

The old-world atmosphere feels untouched along the banks of the River Rhine. Crumbling castles stand above terraced vineyards; towns reveal streets of cobblestone and intrigue, and the image of yesteryear infiltrates every angle. The Middle Rhine is Germany's most scenic area, a sublime landscape carved along the shores of a river steeped in history. Along this water, you find the medieval and Roman remains of Germany, symbolized by fairytale castles, or fine old cities of half-timbered houses, or baroque cathedrals dominating quaint stone squares. 

Elevating the ambiance is the fabled produce of the Rhine and the wines and gourmet treats nurtured for centuries. This is Germany's exquisite wine growing region, an area that values quality over quantity and always provides a delightfully unique place to try it all. Sip wine in castle ruins, spend evenings in medieval wine taverns and watch the river softly ripple as you wander through the vines. Wine tasting is integral to the itinerary, and you spend two full days exploring the various styles of the Rhine, including the Liebfraumilch, and the historic home of Germany's winegrowers.

This private luxury tour starts in Frankfurt, a city that juxtaposes a modern financial center with a beguiling cultural legacy. Roman remains blur into the relics of first millennia emperors, all beneath a backdrop of glass-fronted skyscrapers. You will travel along the Rhine, wine tasting along the banks and cruising past 1000-year-old castles. Stop in the spa town of Wiesbaden, taste in a medieval ruin, and continue to Rüdesheim, the famous city of winegrowers. Several nights here allow you to soak up the atmosphere of historic wine taverns and medieval streets.

Cross the Rhine to Bingen, for a series of tastings focused on Rheinhessen wine. With the river glimmering below, you're in Germany's rural heartland, an area of elegance and continual panoramas. Worms is where Liebfraumilch wine originated, and the town's prosperity from the high Middle Ages is discovered. Then move on to Heidelberg, an ancient town that responds to its legendary reputation and provides nights of atmospheric bliss to complete this luxury tour. Private guides and wine experts offer the narrative throughout while a selection of stellar hotels exudes the old-world charm. 

Starting Price

$4,000 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

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Zicasso's travel specialist crafted an unforgettable journey through Germany for us in September 2025. He truly listened to our interests and designed a phenomenal itinerary that showcased the very best the country has to offer—from small, charming medieval villages and breathtaking Rhine wine country to magnificent castles, dynamic modern cities, and the majestic Bavarian Alps. We also appreciated the thoughtful inclusion of sites tied to WWII and Cold War history, providing a meaningful and reflective perspective on Germany’s past.

Members of our group have personal family connections to Nazi forced labor and concentration camps, as well as life behind the Iron Curtain in post-war East Germany. Our incredible guides handled these sensitive topics with knowledge and compassion, helping us dive deeper and even find answers to lingering questions.

Every guide we met along the way was exceptional—knowledgeable, personable, and fluent in English—which brought each experience to life and deepened our appreciation for the places we visited. The trip was full and fast-paced, yet perfectly balanced for what we were looking for.

The variety of experiences—from somber memorials to the grand pageantry of palaces and the pure joy of Oktoberfest—made the trip incredibly rich and memorable. Throughout it all, our travel specialist kept close communication and ensured everything ran smoothly, giving us complete peace of mind.

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

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