From Milan: Harley Davidson motorcycle tour in 5 countries unique experience!

From Milan: Harley Davidson Motorcycle Tour in 5 Countries – A Unique Adventure

This 13-day Harley Davidson motorcycle tour promises a journey through some of Europe’s most breathtaking landscapes, spanning five countries from Italy to France, Germany, and beyond. It’s designed for motorcycle enthusiasts looking for more than just a ride — it’s an immersive experience filled with spectacular scenery, iconic destinations, and plenty of authentic local flavor.

What makes this tour stand out? First, the carefully curated route through the Alps and the Dolomites offers unforgettable views that will leave you breathless. Second, the use of high-end Harley models like the Road Glide Ultra or Street Glide Ultra ensures that the ride itself is as comfortable as it is exhilarating. Lastly, the expert tour guide, with years of experience riding these routes, provides insights and support that make the adventure both smooth and enriching.

That said, a potential hiccup is the cost — at $13,642 for the group, it’s a significant investment. However, for those who value quality, authentic experiences, and the thrill of riding through some of Europe’s most scenic spots, it could well be worth every penny. This tour is best suited for seasoned riders who are comfortable on Harley touring bikes and eager to explore in the company of other motorcycle enthusiasts.

Who will love this? If you’re passionate about motorcycling, enjoy structured guided trips, and want to combine adventure with scenic sightseeing, this 13-day journey will likely be a highlight of your riding life. It’s perfect for those who seek a mix of adrenaline, scenic beauty, and cultural richness.

Good To Know

• Comprehensive 13-day itinerary through five countries featuring iconic destinations.
• Luxury Harley Davidson bikes included for the entire trip, ensuring comfort and style.
• Rich cultural stops, such as Oktoberfest in Munich and the visit to Mont Blanc.
• Support and safety are prioritized with a dedicated van, insurance, and experienced guides.
• Authentic local experiences like boat rides on Lake Garda and cable car trips in the Dolomites.
• Limited group size (up to 12 riders) for a personalized and intimate experience.

You can check if your dates are available here:

A Closer Look at the Route and Highlights

Starting Point: Milan and the First Night

The adventure kicks off near Milan at a boutique hotel close to Linate Airport. After a meet-and-greet on September 23, 2025, you’ll get acquainted with your fellow riders and the guide, Carlos Santillan — a Mexican rider with a decade of experience and a passion for these routes. Staying at a comfortable hotel ensures you’re rested before the riding begins, and it’s also a chance to get your gear sorted.

Day 1-2: The Dolomites and Swiss Alps

Riding from Milan, you’ll head toward the spectacular Dolomites, crossing into the Swiss Alps. The itinerary includes a cable car ticket for the Dolomites, letting you soak in the views from a higher perspective. Expect winding roads, sharp curves, and jaw-dropping vistas that are perfect for the Harley’s handling.

One rider notes, “We loved the way the guide kept the pace perfect for all skill levels and made sure we didn’t miss any photo opportunities.” The scenery here is a perfect blend of rugged mountains and lush valleys, ideal for motorcycle photography.

Lake Garda and the Boat Ride

A highlight early in the trip is a boat ride on Lake Garda, Italy’s largest lake, which offers a relaxing reprieve after days of riding. The serene waters and surrounding villages provide an ideal backdrop for photos and a chance to enjoy Italy’s beautiful coastline.

More Great Thing To Do Nearby

The Stelvio Pass: A Motorcyclist’s Dream

One of the trip’s crown jewels is the Stelvio Pass, famous worldwide among motorcycle lovers. Its hairpin turns, elevation changes, and breathtaking views make it a must-ride. The rider reviews indicate that “climbing Stelvio was challenging but incredibly rewarding,” with many mentioning the thrill of conquering such an iconic route.

Germany’s Oktoberfest Experience

Arriving in Munich, the tour hits the Oktoberfest festival, where you can experience the lively halls, traditional music, and famous beer tents. The ticket included in the package grants access to the festival, making your visit seamless. It’s a vibrant cultural stop that adds a festive flavor to the ride, with some riders describing it as “a fun, lively break in the journey.”

France’s Mont Blanc and Chamonix

Crossing into France, you reach Chamonix to see Mont Blanc, the highest peak in Europe. The panoramic views from here are spectacular, and the ride offers a mix of alpine roads and charming mountain villages. Riders appreciated the balance of riding and sightseeing, with one commenting, “The vistas of Mont Blanc truly are unforgettable.”

Germany’s Neuschwanstein Castle and Bavarian Charm

In Germany, the Neuschwanstein Castle provides a fairy-tale backdrop for photos and exploration. The castle’s fairy-tale image is as iconic as ever, and riding nearby offers that perfect blend of history and scenery.

Return to Milan

After 13 days traveling through five countries, your journey concludes back near Milan, where you’ll leave your Harley with a sense of accomplishment and a wealth of memories.

The Motorcycle and Support

The Harley Davidson models, either Road Glide Ultra or Street Glide Ultra, are designed for long-distance touring, with comfortable seats and ample storage. Riders are expected to have a minimum of two years of experience riding Harley Touring models to ensure safety and comfort.

Throughout the trip, support is provided by a support van ready to assist with any mechanical issues, luggage, or emergencies. Helmets are included, and gas is on the rider, with the first tank filled. This support setup ensures peace of mind, especially in remote mountain areas.

Accommodation and Inclusions

Staying in 3- and 4-star boutique hotels, the tour guarantees comfortable lodging with breakfast included. Additional inclusions like a surprise dinner, motorcycle insurance, and tickets for various attractions (Dolomites cable car, boat ride, Oktoberfest) add value, making this a well-rounded experience.

What’s Not Included?

Travelers should consider that flights, lunches, dinners outside the included surprise meal, gasoline, and entrance tickets to other attractions are not covered. This allows flexibility in how you spend your time and money during free moments.

Practical Aspects and Preparation

The trip requires good preparation — riders are advised to take a training course beforehand and bring appropriate gear, including weather-appropriate clothing, gloves, rain gear, and a valid international driver’s license. The group size is small, limited to 12 participants, fostering a personal and attentive atmosphere.

Meeting points are well-organized, with pickup at Milan Linate Airport or the hotel reception for those arriving early. The tour ends back at the starting point, simplifying logistics.

Rider Experience and Group Dynamics

Most reviews mention that the tour guide, Carlos Santillan, is passionate and attentive, ensuring everyone’s safety and enjoyment. The group size and the shared love for riding make for a convivial atmosphere, perfect for forging new friendships.

Is This Tour Worth the Price?

At $13,642 for two, this tour isn’t cheap, but it offers a comprehensive package: high-quality bikes, hotel stays, unique excursions, and expert guidance. The value lies in the convenience and the curated experience — exploring five countries with a seasoned guide in a safe, well-supported environment.

For seasoned motorcyclists, especially Harley enthusiasts, the experience of riding through iconic European landscapes with like-minded people is priceless. Plus, the memories of conquering Stelvio or celebrating Oktoberfest are bound to last a lifetime.

Who Should Consider This Tour?

This adventure is ideal for experienced Harley riders who are comfortable handling large touring bikes for long hours. It’s perfect for those craving adventure, scenic beauty, and a cultural journey in one package. If you love combining thrill with sightseeing and don’t mind the investment, this trip could be a highlight.

However, it’s not suited for children, unlicensed riders, or those with health or mobility issues that prevent long rides or altitude exposure.

Final Thoughts

This Harley Davidson tour offers a rare chance to combine motorcycling, stunning scenery, and cultural highlights across five European countries in just over two weeks. From the winding roads of Stelvio to the lively halls of Oktoberfest, every day promises new adventures and incredible views. The inclusion of high-end bikes, quality accommodations, and well-planned logistics makes it a compelling choice for serious motorcycle fans.

While the price tag is steep, the experience’s depth, variety, and quality justifies the cost for those looking for a premium, all-inclusive motorcycle journey through Europe’s most spectacular landscapes.

FAQs

Is this tour suitable for riders with less experience?
No, a minimum of two years of experience on Harley Touring motorcycles is required to handle the mountain roads and long distances safely.

Are helmets provided?
Yes, helmets are included as part of the tour package, ensuring safety and convenience.

What is the group size?
The tour is limited to 12 participants, providing a more personal and attentive experience.

What should I bring?
Prepare with passport, driver’s license, weather-appropriate clothing, gloves, rain gear, camera, and a charged smartphone. Long pants, comfortable shoes, and waterproof gear are recommended.

Are meals included?
No, lunches and dinners (except one surprise dinner) are not included, giving you flexibility in dining choices.

What if I have to cancel?
You can cancel up to 24 hours in advance for a full refund, providing some peace of mind if your plans change.

Is this tour family-friendly?
No, it’s designed for adults with sufficient riding experience and is not suitable for children or those with mobility or health issues.

In summary, this Harley Davidson motorcycle tour offers an exhilarating way to see Europe from a rider’s saddle, combining scenic drives, cultural stops, and camaraderie among fellow enthusiasts. It’s a well-rounded, carefully organized adventure that promises unforgettable memories for those ready to hit the road.

You can check if your dates are available here: