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

Planning a motorcycle trip that crosses borders, climbs mountain passes, and includes iconic festivals sounds like a dream, right? This 13-day Harley Davidson tour, organized by Dolomitsbyrurales, offers just that — a chance to explore five countries on two wheels, passing through some of Europe’s most breathtaking landscapes. If you’re a Harley enthusiast with at least two years of riding experience, this tour promises a mix of adventure, camaraderie, and picture-perfect scenery.

What makes this experience stand out are two things in particular: the chance to ride on legendary routes like the Stelvio Pass and the opportunity to soak in the festive atmosphere at Oktoberfest in Munich. A potential consideration is the hefty price tag of over $14,000 for two riders, which might seem steep at first glance. But when you consider the comprehensive package — top-tier Harley bikes, boutique hotels, exclusive passes, and guided support — the value becomes clearer, especially for riders craving an all-in-one European adventure.

This trip is best suited for experienced motorcycle lovers who appreciate structured tours with expert guidance and want to combine their passion with cultural highlights. If you’re looking for a lively, scenic, and well-organized journey, this might just be your dream ride.

Key Points

• All-inclusive package with Harley Davidson Road Glide Ultra or Street Glide Ultra motorcycles, hotels, tickets, and support.
• Multi-country route through Italy, Switzerland, France, and Germany, offering diverse landscapes and cultures.
• Iconic stops include Lake Garda, the Stelvio Pass, Mont Blanc, and Neuschwanstein Castle.
• Festivals and scenic drives make this a memorable combination of riding and cultural experiences.
• Guided tour with a passionate, experienced Spanish-speaking guide ensures smooth navigation and local insights.
• Limited group size of only 12 participants fosters camaraderie and personalized attention.

You can check availability for your dates here:

An In-Depth Look at the 13-Day Harley Adventure

Starting Point: Milan and the First Night

The journey begins in Milan, with participants gathering at a hotel near Linate Airport on September 23, 2025. This initial gathering is more than just a check-in — it’s a chance to meet fellow riders, share a few laughs, and briefly get acquainted before hitting the road. The next day, the real adventure kicks off with a ride toward the Dolomites and Swiss Alps.

The choice of a boutique hotel with breakfast included sets a comfortable tone for the trip. This first night also helps mitigate any travel fatigue, giving everyone a chance to prepare for the riding days ahead.

Day 2–3: Lake Garda and the Stelvio Pass

One of the tour’s first highlights is the boat ride on Lake Garda, Italy’s largest lake. We loved the way this adds a touch of leisure and scenic beauty to the adrenaline-filled days of riding. Cruising along the lakeshore in a support van with fellow enthusiasts sharpens the sense of camaraderie.

Next, riders tackle the Stelvio Pass, renowned for its climbs and hairpin turns. This legendary route is a bucket list for motorcyclists worldwide, and the tour ensures plenty of time for stops, photos, and soaking in the views. Expect exhilarating curves, mountain panoramas, and a feeling of accomplishment at the summit.

Day 4–5: Switzerland and the Mont Blanc

The tour’s route continues toward Chamonix, France, where you’ll stand at the highest peak in Europe — Mont Blanc. This area offers stunning vistas and the chance to explore French alpine charm. The ride through mountain tunnels and alongside glaciers demonstrates the diversity of terrain you’ll experience.

More Great Tours Nearby

Day 6–8: Bavaria and Oktoberfest

Next, the ride takes us into Germany’s Bavaria region, culminating in a visit to Munich’s Oktoberfest. The ticket included in the package opens the door to enjoying the world-famous beer halls, lively music, and festive atmosphere. It’s an unexpected but delightful highlight, blending motorcycle adventure with authentic Bavarian celebration.

Day 9–10: Neuschwanstein Castle and the Return Journey

No trip through Bavaria would be complete without a visit to the Neuschwanstein Castle — the fairy-tale fortress that inspired Disney’s Sleeping Beauty Castle. Walking around this picturesque site provides a perfect photo backdrop and a sense of fairy-tale charm.

Day 11–12: The Final Mountain Passes and Return to Milan

The last riding days include a scenic route back through the Alps, with optional cable car rides into the Dolomites, adding a different perspective to the alpine scenery. The tour concludes back in Milan, where you’ll dismount your Harley, return the bike, and reflect on the unforgettable journey.

What Riders Say

Multiple reviews highlight the high quality of the Harley bikes, which are modern, well-maintained, and fitted for touring. One rider noted, “The support van was a real plus, making it easier to enjoy the ride without worry about logistics.” Others appreciated the small group size, which fostered camaraderie and personalized attention.

The guidance of Carlos, a passionate and experienced guide, received praise for his local insights and friendly attitude. Several riders remarked that the organized tickets for activities like cable cars and Oktoberfest saved them time and hassle, allowing for more relaxed sightseeing.

A few reviews mention the price, acknowledging it’s on the higher side but justifiable given the comprehensive nature of the tour, including luxury hotels, exclusive passes, and a curated route through some of Europe’s top motorcycle roads.

Detailed Itinerary Breakdown

Day 1: Arrival in Milan, meet and greet at the hotel near Linate. An evening to relax and prepare for the ride. Having the group arrive in one place helps set a friendly tone.

Day 2: Departure from Milan, heading toward the Dolomites. Expect scenic mountain roads, winding through valleys. The hotel stay near the Milan airport ensures easy logistics and a comfortable base.

Day 3: Lake Garda boat ride. This is a fantastic way to break up the riding and enjoy Italy’s largest lake. The boat cruise offers stunning views and a chance to unwind.

Day 4: Climb the Stelvio Pass — one of the most celebrated motorcycling roads in the world. Expect a full day of exhilarating switchbacks, alpine views, and photo stops. The pass is famous for its scenic curves and the sense of achievement at the top.

Day 5: Cross into Switzerland, heading toward Chamonix. Along the way, riders will enjoy Swiss mountain scenery, forests, and charming villages. The Mont Blanc visit is a highlight, offering panoramic views and photo opportunities.

Day 6: Ride into Bavaria, arriving in Munich well before Oktoberfest kicks into full swing. The included ticket grants you access to the lively beer halls, where you can enjoy traditional German music, beer, and food.

Day 7: Explore Munich or relax, soaking in the festive atmosphere. Some riders may choose to visit local attractions or simply enjoy the lively streets.

Day 8: Head toward Neuschwanstein Castle, passing through picturesque Bavarian countryside. The fairy-tale castle tour is a must-do for its stunning architecture and history.

Day 9: Ride back into the Alps, perhaps taking scenic cable cars into the Dolomites, or enjoying a leisurely scenic drive. The support van accompanies the group, easing logistical worries.

Day 10–11: Return routes through the Alps bring views of glaciers, mountain lakes, and lush valleys. These days are designed to maximize scenic riding and leisure.

Day 12: Final ride back to Milan, ending the adventure with a sense of accomplishment and new friendships.

Is It Worth the Price?

At over $14,000 for two riders, this tour is an investment. But when you consider the all-inclusive nature — top-quality Harley motorcycles, boutique hotels, tickets to major attractions, and guided support — it offers a seamless, stress-free experience rarely found in independent travel. The inclusion of special activities like boat rides, cable cars, and Oktoberfest tickets adds real value, turning this into a comprehensive European riding adventure.

For seasoned riders who enjoy guided tours, the small group size ensures plenty of personal attention and safety. The expert guidance is invaluable on mountain passes and unfamiliar roads, making the experience safer and more enjoyable.

Who Should Consider This Tour?

This adventure is best suited for experienced Harley riders comfortable on touring models like the Road Glide Ultra or Street Glide Ultra. Riders should have at least two years of experience, especially since the itinerary includes challenging mountain passes like Stelvio. If you’re seeking a combination of scenic riding, cultural festivals, and luxury accommodations, this trip hits all those marks.

It’s perfect for those who love structured group tours but still crave authentic landscapes and local flavor. If you’re not keen on riding long days or are hesitant about mountain passes, this might not be the best fit.

The Sum Up

This Harley Davidson tour from Milan offers a world-class blend of scenic riding, cultural highlights, and camaraderie. The route through five countries showcases some of Europe’s most spectacular landscapes, from the towering Alps to historic castles. The inclusion of activities like Oktoberfest, boat rides on Lake Garda, and visits to Mont Blanc ensures the experience appeals to both the rider and the traveler.

While the cost is high, the comprehensive package — quality bikes, boutique hotels, exclusive tickets, and expert guidance — provides significant value for motorcycle enthusiasts with a taste for adventure and comfort. For seasoned riders looking for a well-organized, scenic, and culturally rich European trip, this experience offers a combination you won’t easily find elsewhere.

If you’re a lover of motorcycles, mountain scenery, and European culture, and you’re ready for some serious riding in style, this tour deserves a spot on your bucket list.

FAQs

Do I need to be an experienced rider to join?
Yes, a minimum of two years of Harley touring motorcycle experience is required. The tour includes mountain passes like Stelvio, which demand confident riding skills.

Are the Harley motorcycles comfortable for long rides?
Absolutely. The bikes provided are Touring models like Road Glide Ultra or Street Glide Ultra, designed for comfort during extended rides, with features suited for mountain roads.

What is included in the price?
Your package covers Harley Davidson bikes, boutique hotels with breakfast, activity tickets (boat ride, cable car, Oktoberfest), motorcycle insurance, a support van, helmets, and a surprise dinner.

What’s not included in the price?
Flights, lunches, dinners (beyond one surprise dinner), gasoline, and extra attraction tickets not listed are not included.

What should I bring?
Essential gear includes driver’s license, passport, weather-appropriate clothes, rain gear, gloves, camera, and travel insurance. Also, a long pants, comfortable shoes, and a charged smartphone are recommended.

Can I join if I’ve never been to Europe?
Yes, but you’ll need to arrange your own flights. The tour begins around Milan, so arriving at Milan Linate Airport is easiest.

Is the group small?
Yes, the tour is limited to 12 participants, ensuring personalized attention and a friendly atmosphere.

What about dietary restrictions?
The tour mentions breakfast at hotels but does not specify meal options; it’s advisable to bring or plan for lunches and dinners as they are not included.

This Harley adventure from Milan blends scenic roads, iconic sights, and festive experiences into a memorable two-wheeled journey. Whether you’re seeking a challenge or a cultural escapade, it’s a trip that promises plenty of stories to tell well beyond the last mile.

You can check availability for your dates here: