Two Seas Trail: Crossing Italy's Hidden Gems
Itinerary
Pedal from coast to coast on a cycling journey that dives deep into the heart of Italy, from the Adriatic to the Mediterranean, through hidden roads and landscapes untouched by time.
This isn’t just a ride; it’s a living, breathing passage through four regions, each with its own rhythm, flavors, and stories. Along the way, you’ll pass through hilltop towns, quiet valleys, and ancient paths that echo with history and tradition.
Every turn brings a new layer of Italy’s soul, from rustic trattorias and Renaissance piazzas to rolling hills and timeless views. It's an odyssey through authenticity, where the scenery shifts as naturally as the dialects, and every moment feels like a personal discovery.
If you're looking to ride deeper into culture, into history, into beauty, this is the journey.
Highlights
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Pedal from the Adriatic to the Mediterranean Sea
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Climb to Hilltop Towns and Renaissance Piazzas
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Ride Through Quiet Valleys and Ancient Pilgrim Paths
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Savor Rustic Trattorias and Local Flavors
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Discover Timeless Landscapes and Rolling Hills
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Experience the Changing Dialects and Traditions of Four Regions
Day 1 - Pesaro Warm Up Ride
As the Adriatic waves lap the shores of Pesaro, our coast-to-coast Italian adventure begins. From this eastern gateway, we head toward the Tyrrhenian Sea, ready to cross a landscape rich in history, culture, and natural beauty. A scenic ride introduces us to the rhythm of the road, while a traditional aperitivo and dinner in Pesaro set the tone cycling, culture, and cuisine woven into every mile ahead.
Hotel Charlie in Pesaro
Level 1 - Very easy
30Km
Activity
BikingDay 2 - Pesaro to Urbino
At sunrise, we begin our coast-to-coast cycling journey with a symbolic dip of the wheels in the Adriatic Sea. Leaving Pesaro behind, we follow a peaceful riverside path into the rolling hills of the Marche region. Along the way, we pass historical sites like the Gothic Line and charming hilltop villages such as Colbordolo and Monte Fabbri.
The route offers sweeping views, blending natural beauty with touches of modern art. By afternoon, we arrive in Urbino, a Renaissance gem, where we explore its rich heritage and enjoy a well-earned dinner. From sea to summit, it's a day of history, culture, and scenic discovery.
Albergo San Domenico
Level 2 - Easy
50Km
Activity
Biking
Day 3 - Urbino to Gubbio
At dawn in Urbino, we begin a scenic journey from the Renaissance heart of the Marche region into the green landscapes of Umbria. Riding through peaceful countryside and historic towns, we experience a blend of natural beauty, cultural heritage, and quiet reflection. The route takes us through dramatic gorges and gentle valleys, culminating in a rewarding climb before descending into Gubbio, a perfectly preserved medieval town. It’s a day marked by changing regions, shifting landscapes, and a deep sense of Italy’s timeless spirit.
Relais Ducale
Level 3 - Moderate
75Km
Activity
BikingDay 4 - Gubbio to Montefalco
As the mist clears over Gubbio, we begin a day filled with scenic beauty and historical depth. Riding through quiet valleys and hilltop villages, we take in the rich tapestry of Umbria’s countryside and past. A stop in Assisi offers a powerful moment of reflection in a city shaped by faith and art. The journey then continues through ancient riverlands and medieval towns, each echoing centuries of culture. We end the day in Montefalco, surrounded by vineyards and views, where wine, history, and art come together. From sacred sites to timeless landscapes, it’s a ride through the spiritual and cultural heart of Italy.
La Rocca Guest House & SPA
Level 4 - Challenging
79Km
Activity
Biking
Day 5 - Montefalco to Orvieto
As dawn rises over Montefalco, we begin a new day of our journey through Umbria’s timeless landscapes. Descending from the vineyards, we follow ancient roads through rolling hills and villages steeped in history, including a stop in a town with a curious past along the Via Flaminia. The ride unfolds through fields, olive groves, and river valleys, leading us to the banks of the historic Tiber. After a peaceful pause in a hilltop hamlet, we take on the day’s final challenge—a climb to the striking city of Orvieto, perched high on a volcanic plateau. From Roman roads to Etruscan heights, today’s ride offers a powerful mix of natural beauty, deep history, and dramatic geography, culminating in one of Italy’s most unforgettable hilltop towns.
Hotel Palazzo Piccolomini
Level 4 - Challenging
86Km
Activity
BikingDay 6 - Orvieto to Manciano
As the sun rises over Orvieto, the journey begins with a descent from its volcanic cliffs into a day of striking landscapes and rich history. Winding through quiet roads and countryside, the route leads to Civita di Bagnoregio, a dramatic hilltop village slowly eroding with time yet full of timeless charm. Crossing into Lazio, the vast Lake Bolsena appears, born from ancient volcanic activity and tied to a famous medieval miracle that inspired the Corpus Christi feast. Entering Tuscany, the route reaches Pitigliano, a town known for its dramatic setting and historic Jewish heritage, followed by Sovana, a small village with deep Etruscan and medieval roots. The day ends in Manciano, perched above the Maremma’s wild hills, offering panoramic views and echoes of a storied, often turbulent past. As the sun sets, the journey leaves behind a vivid impression of Italy’s natural beauty and layered history.
Agriturismo il Poggio di Teo
Level 5 - Very challenging
91Km
Activity
Biking
Day 7 - Manciano to Porto Santo Stefano
As dawn breaks over Manciano, the final leg of a coast-to-coast journey begins with excitement and anticipation. The route descends into the wild Maremma, weaving through the legendary Valle d'Arna, once a haven for brigands, now a landscape of raw Tuscan beauty. Approaching Capalbio, the scent of the sea signals the nearing end, and the view of Monte Argentario confirms the journey’s coastal destination.
Pedaling across one of the tomboli connecting Argentario to the mainland, riders pass through pine forests and fragrant coastal vegetation, eventually reaching Porto Santo Stefano.
As the sun sets over the Tyrrhenian Sea, the full sweep of the adventure becomes clear, a crossing of Italy through four diverse regions, from the Adriatic to the western coast. The day ends in reflection and celebration, honoring not only the miles covered but the depth of experience and discovery along the way.
Baia D'Argento
Level 3 - Moderate
59Km
Activity
BikingDay 8 - Celebrating the Journey
Our wheels may have stopped turning, but the spirit of the trail rolls on. From coast to coast, every view, laugh, and shared meal has become part of a story we’ll keep reliving, until the next adventure calls.
Level 1 - Very easy
0Km
Activity
Relax & Discover
Two Seas, One Soul
The journey begins with the salty breeze of Pesaro and ends as the Tyrrhenian Sea sparkles below Monte Argentario’s cliffs. But between these two coasts lies a deeper story: one of changing dialects, evolving landscapes, and the rhythm of Italy unfolding mile by mile. This ride is a moving tapestry of coastlines, countryside, and connection that lingers long after the final descent.
Roads Less Ridden
This isn't the Italy of postcards, it's the Italy of whispered legends and weathered farmhouses tucked between olive groves and wildflower fields. Here, the roads curve through vineyards, crest sleepy hills, and lead to towns where life moves at the rhythm of tradition. These quiet paths reveal an intimate, unfiltered side of Italy no highway could ever show.
Flavors of the Land
From the seafood feasts of Marche’s coast to the hearty mountain fare of Umbria, and the earthy elegance of Tuscan trattorias, every meal along the way is a revelation. Each dish is rooted in local history, passed through generations and served with pride. This is not just nourishment, it’s culture you can taste, paired perfectly with regional wines and warm conversations.
Etruscan Whispers
Every turn of the pedal brings you closer to the remnants of a world long vanished. In places like Sovana and Pitigliano, carved into the tufa rock, the presence of the Etruscans still stirs the air. Tombs, temples, and silent alleyways speak volumes to those who pass by slowly enough to listen. This is history not behind glass, but alive beneath your tires.
hotels
Please note that accommodations may vary based on availability.
Hotel Charlie in Pesaro
Located directly on the seafront of Pesaro, just a short walk from the historic city center, Charlie Hotel offers stunning panoramic sea views and free WiFi throughout the property. Pesaro Train Station is approximately 2 km away, making the hotel easily accessible for both leisure and business travelers.
The hotel features modern, comfortable rooms equipped with air conditioning, satellite TV, and en-suite bathrooms. Each room includes a safe and minibar, while most offer beautiful sea views and private balconies.
Guests can enjoy a rich breakfast selection of sweet and savory products, including pastries, cakes, croissants, and cold cuts, served on a scenic terrace overlooking the Adriatic Sea. Room service is also available upon request.
Charlie Hotel provides a range of business and leisure facilities, including conference rooms and co-working spaces with advanced technology. For cycling enthusiasts, the hotel offers secure bike storage, making it an ideal choice for bike travelers exploring the Adriatic coast.
Hotel level
Premium
Plus
Pool, Restaurant, Parking, Gym, Free WiFi
Albergo San Domenico
Located in a historic Renaissance convent, Hotel San Domenico enjoys a prestigious setting right in front of the Ducal Palace, between the Monastery of Santa Chiara and the University. The building has preserved its refined and elegant original architecture, offering a unique atmosphere that blends history with comfort.
Guests can enjoy breakfast in the beautiful cloister, set among arched loggias that enhance the charm of the historic structure. The property also features a private parking area for added convenience.
All rooms are equipped with air conditioning, satellite TV, minibar, telephone, bathroom scales, and a hairdryer, ensuring a comfortable and well-appointed stay.
A highlight of the hotel is its impressive monumental courtyard, featuring a renowned rose garden and sculptures by prominent contemporary artists, creating a distinctive cultural and artistic setting.
Hotel level
Premium
Plus
Parking
Relais Ducale
Located in the heart of the medieval town of Gubbio, overlooking the stunning Piazza Grande, Relais Ducale is a charming 4-star hotel set in a historic 14th-century residence, once part of the Ducal Palace. Its exceptional central location places guests within walking distance of the city’s main landmarks, including the Palazzo dei Consoli, the Cathedral, and numerous historic churches and museums.
The hotel offers around 30 elegant rooms, combining antique furnishings with modern comforts such as air conditioning, minibar, satellite TV, and free WiFi. Many rooms enjoy views over the historic center, the surrounding hills, or internal gardens, creating a peaceful atmosphere in the heart of the city.
Guests can relax in the panoramic terrace, roof garden, and quiet internal garden areas, while a rich breakfast is served daily. Additional services include a bar, 24-hour reception, room service, and concierge services.
For cycling travelers, the hotel can accommodate bike storage upon request, making it a good base for exploring the Umbrian countryside and the surrounding hills of Gubbio.
Hotel level
Premium
Plus
Parking, Free WiFi, Bar
La Rocca Guest House & SPA
Located within the medieval walls of Montefalco, La Rocca Guest House & Spa is a charming boutique property set in the heart of the historic center, just a short walk from the main square and key attractions such as the San Francesco Museum. Its central location makes it an excellent base for exploring Umbria.
The property features elegant and tastefully furnished rooms equipped with air conditioning, flat-screen TV, private bathroom, and free WiFi. Many rooms offer beautiful views over the Umbrian countryside or the historic village, combining modern comfort with the charm of a traditional setting.
Guests can enjoy a rich breakfast with both sweet and savory options, while the on-site wellness area (available on request) includes a Turkish bath, sauna, hot tub, and massage services, ideal for relaxation after a day of exploring.
For cycling travelers, the hotel offers convenient bike storage options on request, making it a great starting point for discovering the scenic hills, vineyards, and quiet roads of the Montefalco area.
Hotel level
Quality
Plus
SPA, Parking
Hotel Palazzo Piccolomini
Located in the heart of the medieval center of Orvieto, Hotel Palazzo Piccolomini is a charming 4-star boutique hotel set within two historic buildings. The hotel blends Renaissance architecture with modern comfort, offering a unique atmosphere rich in history, art, and elegance.
Thanks to its central location, guests can easily explore Orvieto on foot, with key landmarks such as Piazza della Repubblica, the Duomo, and Torre del Moro just a few minutes away. The hotel is also easily accessible by car, with parking facilities available, and the nearest train station is approximately 2 km away.
The property offers a wide range of accommodation options, including double rooms, junior suites, a family room, a studio, and a spacious deluxe suite. All rooms are equipped with air conditioning, satellite TV with Sky channels, minibar, safe, and private bathroom, combining classic style with modern amenities.
Guests can enjoy a variety of facilities, including a breakfast room, bar, reading and TV lounges, meeting and conference spaces, and a wellness area with fitness facilities and massage services. Free WiFi is available throughout the hotel, along with secure parking.
For cycling travelers, the hotel offers bike storage solutions, and its location makes it an excellent base for exploring the scenic Umbrian countryside and surrounding routes around Orvieto.
Hotel level
Premium
Plus
Parking, Gym, Free WiFi, Bar
Agriturismo il Poggio di Teo
Located in the heart of the Tuscan Maremma countryside, Il Poggio di Teo is a charming agriturismo, its peaceful rural setting, between rolling hills and the Argentario coast, makes it an ideal base for exploring southern Tuscany while enjoying nature and relaxation.
The property offers a small number of recently renovated rooms and one apartment, all tastefully furnished and equipped with air conditioning, WiFi, TV, minibar, and private bathrooms. Each accommodation has independent access and direct connection to the surrounding garden, ensuring privacy and a relaxing atmosphere.
Guests can enjoy a renowned on-site restaurant focused on fresh, locally sourced ingredients, including vegetables produced on the estate, with breakfast and meals served in a bright glass room immersed in greenery. The property also features indoor and outdoor pools, wellness facilities with sauna and spa services, and large outdoor areas ideal for walking and enjoying the natural surroundings.
Additional amenities include free parking, gardens, and easy access to scenic routes across the Maremma countryside. For cycling travelers, the quiet roads and rolling landscapes make it a perfect destination, and bike storage can be arranged on request, making it well suited for bike-friendly stays.
Hotel level
Quality
Plus
SPA, Pool, Parking, Free WiFi
Baia D'Argento
A 4-star seaside hotel in Argentario Bay offering a private beach, free parking, and complimentary summer beach services. It features air-conditioned rooms with Sky TV, free Wi-Fi, Mediterranean dining with a panoramic terrace, and a daily buffet breakfast.
Hotel level
Quality
Plus
Restaurant, ParkingImportant info
- 2 expert guides
- 1 assistance van
- 7 nights accommodation in charming hotels or guesthouses (double occupancy)
- 7 breakfasts, 7 lunches and 5 dinners featuring local cuisine
- Coffeè stops, fruits and snacks, powerbar and gels for everyday use.
- Welcome cocktail, guided tour of Palazzo Ducale in Urbino, Sant'Ubaldo cable car tickets, wine tasting in Montefalco area.
- Road bike rental with helmet and pedals included for the entire tour (E-Bikes available with an extra cost)
- Daily luggage transfer between accommodations with the van
- Living Roads Kit: cycling jersey, cap and water bottle
- Detailed GPS routes
- Welcome briefing and orientation withe the guides
- Secure bike storage at each overnight location
- Access to the Ride with GPS navigation app
- Single room supplement
- E-Bikes supplement
- Additional gears
- Travel insurance (highly recommended). See our protection plan here.
- Airfare or transportation to/from the tour start and end locations
- Lunches and dinners not specified in the inclusions
- Personal expenses (e.g., souvenirs, drinks, snacks)
- Optional activities or excursions not mentioned in the itinerary
- Gratuities for drivers or hotel staff
- Additional nights of accommodation before or after the tour dates
Included
- 2 expert guides
- 1 assistance van
- 7 nights accommodation in charming hotels or guesthouses (double occupancy)
- 7 breakfasts, 7 lunches and 5 dinners featuring local cuisine
- Coffeè stops, fruits and snacks, powerbar and gels for everyday use.
- Welcome cocktail, guided tour of Palazzo Ducale in Urbino, Sant'Ubaldo cable car tickets, wine tasting in Montefalco area.
- Road bike rental with helmet and pedals included for the entire tour (E-Bikes available with an extra cost)
- Daily luggage transfer between accommodations with the van
- Living Roads Kit: cycling jersey, cap and water bottle
- Detailed GPS routes
- Welcome briefing and orientation withe the guides
- Secure bike storage at each overnight location
- Access to the Ride with GPS navigation app
Not included
- Single room supplement
- E-Bikes supplement
- Additional gears
- Travel insurance (highly recommended). See our protection plan here.
- Airfare or transportation to/from the tour start and end locations
- Lunches and dinners not specified in the inclusions
- Personal expenses (e.g., souvenirs, drinks, snacks)
- Optional activities or excursions not mentioned in the itinerary
- Gratuities for drivers or hotel staff
- Additional nights of accommodation before or after the tour dates
Tours come with an experienced guide, and on-road assistance, ideal for those preferring a more immersive group experience.
Trips can be booked exclusively by contacting our team directly. We’re happy to assist you via email or phone and will guide you through every step of the booking process.
Yes, we’re here to help! We can assist you with flights, extra nights before or after the trip and any additional travel needs you may have.
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Why Living Roads?
OUR LOCAL TOUCH
As locals, we create journeys inspired by the way we live. Enjoy the best of Italian Roads and Hospitality with our expertise of more than 50 years as a tour operator.
FOR EVERYONE
Our tours are open to everyone, with different levels of difficulty. They’re never meant to be a race, but rather a chance to embrace the slow joy of discovery.
Culture you can taste
Cycling means earning every view and every bite. Our tours include regional wine tastings, cooking class, countryside dinners, and food experiences you’ll remember forever.
CURATED ACCOMODATIONS
Our selection of hotels is guided by the desire to promote local businesses and historic palaces or buildings, creating the perfect blend of authenticity and charm.
ASSISTANCE
You’ll never be alone on the road. You can always count on our remote support during the Self-Guided tours, or on the expertise of our local guides during the guided or joinable tours.
Meaningful miles
We ride slow and smart: our tours are designed to support local communities and reduce environmental impact for a way of traveling that feels as good as it looks.