BobJoy-IMG_6777-1600x670 16TCL0612_bjoy_-165 - 1600x670 Ride across Italy on Trek Travel's coast to coast bike tour 21IT - Canva - 1600x670 16TCL0612_bjoy_-125 - 1600x670 Italy-BobJoy-DSC03547-1600x670 chianti-coast-05-1600x670 chianti-coast-02-1600x670 bar-boutique-hotel-torre-di-cala-piccola-argentario - 1600x670 21IT - Canva - 1600x670 (2)

Ride Across Italy Bike Tour

Italy Coast to Coast

Discover the essence of the heartland of Italy. Ride across Italy with us as we dip our toes in the Adriatic sea and traverse the enchanting regions of Le Marche, Umbria, Lazio, and Tuscany to the Mediterranean coast. Along the way, you'll indulge in sumptuous cuisines, world renowned wines, and charming medieval towns. You'll ride across the rugged, misty Apennine mountain range, roll through vine-covered landscapes, and climb up to the towering tufa mesas of Umbria before you celebrate your journey's end on the stunning Orbetello peninsula in Tuscany with a sunset cocktail. This is truly the once-in-a-lifetime experience for lovers of all things Italian! Book your trip with confidence »
$3899 Per Person
6 Days & 5 Nights
Rider Type: ?
3 / 4 - Active / Avid
Hotel Style: ?
From $3899 per person View All Details
Trip Wows
Ride across the rugged, misty Apennine mountains, which form the spine of Italy
Ride over 280 miles and climb over 24,000 feet as you go from coast to coast in five short days
Wander the twisting alleyways of the medieval town of Gubbio, beautifully set on the lower slopes of Mt. Ingino
Savour fresh green olives and the crisp, dry, white wines of Orvieto
Enjoy a spontaneous gelato and the allegria of Italian hospitality
I found the guides that supported our trip to be exceptional and knowledge of the geography we were riding each day but just as important to me they were intelligent and very likable.
-Robert, Trek Travel Guest

Dates & Prices

The Earlier You Book, The Greater The Rewards

We reward our guests with lower pricing and more dates to choose from the earlier you book. Rest assured, once you book, your price is guaranteed.
to run
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Single Occupancy from: +$700
Oct 3 – Oct 8 
Limited Availability
$3899 / Person, Double Occupancy Book this date
Oct 10 – Oct 15 
Limited Availability
$3899 / Person, Double Occupancy Book this date
Oct 17 – Oct 22 
Limited Availability
$3899 / Person, Double Occupancy / Hotel Variation: Castello di Petroia Book this date
Would you like to get early access to next year’s dates?
Please contact us to join our exclusive waitlist for first notice about new dates.
Don't see your ideal travel date? 
Call us at (866) 464-8735 for custom date availability
Looking for a one of a kind, once in a lifetime experience?
Look no further. Choose your trip date, get your group together and we will do the rest. Private trip pricing is as follows:
2020 - June 1, 2021 Departures:
  • 6+ Guests    Price as advertised*
  • 4-5 Guests +$500 per person to trip price*
  • 2-3 Guests +$2,500 per person to trip price*
  • 1 Guest        Call us for pricing*

2021 Departures After June 1, 2021:
  • 10+ Guests Price as advertised*
  • 8-9 Guests +$500 per person to trip price*
  • 6-7 Guests +$1,000 per person to trip price*
  • 4-5 Guests +$1,500 per person to trip price*
  • 2-3 Guests +$3,000 per person to trip price*
  • 1 Guest        Call us for pricing*

Traveling with a small group? Consider semi-private trips.
For groups of up to six people, semi-private trips offer unique flexibility within a larger Trek Travel guided trip. Learn more »

*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Private pricing is not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Looking for a date that you don’t see?
Look no further. Simply tell us your preferred travel dates and we’ll work together to deliver the same great trip on your custom schedule.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom dates are not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Want to customize this trip?
We've got you covered. We’ll work with you to build your perfect vacation from scratch, including your choice of riding, accommodations and dining options. With the help of our trip designers and travel experts, the world is available like never before.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom trips are not available on Ride Camp, Race, Special Edition or Cross Country style trips.

We start our coast to coast journey in the beach resort town of Rimini, where you'll meet your Trek Travel guides and fellow cyclists. A short shuttle brings you to the medieval cliff-hanging village of Verrucchio, where you’ll be fit and familiarized with your Trek bicycle and where you'll enjoy a fresh local lunch. This afternoon’s ride passes through the Republic of San Marino and picturesque farmlands before climbing into Urbino. This beautifully-preserved Renaissance town has been attracting artists and scholars from all over Italy and beyond since the 15th century. Tonight, we’ll explore this UNESCO World Heritage Site and dine in a small bistro along winding cobbled streets. It is almost a step back in time, where houses and palaces of weathered brick and pantiles cluster around steep narrow streets, with misty mountains stretching mysteriously beyond, like the background of a Rafael portrait. It's only the beginning of our odyssey, but one you won't soon forget.

Today's Ride:

Verrucchio to Urbino
Approximately 34 miles with 4,300 feet of climbing


Hotel San Domenico

Included Meals:

Lunch | Social Hour | Dinner

Today’s ride takes you into Umbria and the Parco del Monte Cucco before tackling Passo Madonna della Cima, our first pass in the Apennine mountains. We'll stop for lunch at an 11th-century monastery where you can refuel with a fresh pasta of the region or "Torta al testo," a typical Umbrian flatbread. This afternoon's ride winds through the jagged cliffs of the Monte Cucco and to our luxurious hotel, which is situated just a few kilometers from the beautiful medieval town of Gubbio. Enjoy views of the mountains and Mount Ingino from the hotel terrace before joining the group for a traditional and delicious Umbrian dinner at our hotel’s acclaimed Nicolao restaurant.

Today's Ride:

Urbino to Gubbio
Approximately 60 miles with 5,665 feet of climbing

Short Option:

Urbino to Monastero di Fonte Avellana, shuttle to Gubbio
Approximately 40 miles with 3,470 feet of climbing


Park Hotel ai Cappuccini or Castelo di Petroia

Included Meals:

Breakfast | Lunch | Dinner

Enjoy an active recovery day today. The ride starts with a gentle warm up and then climbs along forgotten roads through tiny Umbrian villages. Experience the tranquility of the woods mixed with views of rugged farmland and olive groves, then savor a relaxing descent as you inhale the views of Assisi from above. This stunning medieval village is best known as the birthplace of Saint Francis, Italy’s patron saint, and it is your lunch destination for this afternoon. Choose your own lunch at one of Assisi’s many trattorias and take some time to explore its Roman ruins and sacred shrines. After lunch, it’s a short descent to the quiet hillside town of Spello, our home for the evening. Admire its well-preserved Roman gates as you seek out traditional Umbrian fare featuring salami, wild asparagus, or strangozzi (a local ribbon pasta) with black truffles for dinner this evening.

Today's Ride:

Gubbio to Spello
Approximately 39 miles with 3,280 feet of climbing

Short Option:

Gubbio to Assisi, shuttle to Spello
Approximately 31 miles with 2.800 feet of climbing

Avid Option:

Gubbio to Spello with San Giovanni Climb
Approximately 53 miles 5,000 feet of climbing


Palazzo Bocci

Included Meals:


Our ride begins with an easy 20 kilometer cruise through the fertile valley below Mount Subasio before the climbing begins. Remember your camera today as there is no shortage of views, including hilltop towns and hidden fortresses, as we ride through the very heart of Umbria. Take a break when you reach the Todi, an elegant medieval village overlooking the Valtiberina (the Tiber River Valley), and refuel with lunch at a restaurant of your choice. Leaving Todi, we will descend to the Tiber River and then work our way back up to the picturesque ridge that delivers us to Orvieto. Built on Etruscan ruins, this town rises 1500 feet from the floor of the Paglia River Valley, and sits atop almost vertical faces of tufa cliffs. It's surrounded with defensive walls and medieval houses made out of the same tufa rock. It's truly astounding. Tonight enjoy a stroll in this enchanting town, where you're free to explore the local flavors for dinner.

Today's Ride:

Spello to Orvieto
Approximately 59 miles with 5,300 feet of climbing

Short Option:

Spello to Todi, shuttle to Orvieto
Approximately 31 miles with 2,600 feet of climbing

Avid Option:

Rocca Ripensena Climb
Approximately 68 miles with 6,500 feet of climbing


La Badia di Orvieto

Included Meals:


After a warm cornetto and the perfect cappuccino in our hotel’s frescoed refectory, start your day with a climb from Orvieto to Bagnoreggio, where we’ll behold the ancient ghost town of Civita di Bagnoreggio. Your ride continues with a few rolling climbs until you descend to the serene shore of Lago di Bolsena, the largest volcanic lake in Europe. Enjoy a quiet break here before lunch at an agriturismo and your final climb into the region of Tuscany through the forested slopes up to Manciano. Finish your epic journey on the stunning Orbetello peninsula. It's time to dip a toe into the Mediterranean and celebrate in style with a sunset cocktail and toast to a week-long coast to coast Italian cycling adventure!

Today's Ride:

Orvieto to Porto Santo Stefano
Approximately 82 miles with 4,950 feet of climbing

Short Option:

Orvieto to Farnese shuttle to Porto Santo Stefano
Approximately 40 miles with 3,300 feet of climbing


Torre di Cala Piccola

Included Meals:

Breakfast | Lunch | Social Hour | Dinner

This morning, linger over a second cappuccino with fresh fruit and soak in the gorgeous views from the breakfast patio. Lounge by the infinity pool overlooking the Mediterranean Sea or wander down to the Grotto. Before you bid your farewells, stroll through the grounds of the hotel one last time and savor the picturesque, peaceful landscape of Italy and the Orbetello peninsula. We're sure you'll never forget your bike trip across Italy!

Included Meals:



hotel image

Hotel San Domenico

Urbino, Italy

Standing in the main square of the small village of Urbino, this hotel is a careful restoration of a 16th-century religious complex, offering an excellent combination of modern with long-standing traditions. Its mix of modern luxury and rich history is sure to enchant you.
hotel image

Park Hotel ai Cappuccini

Gubbio, Italy

Lying on the outskirts of Gubbio, in the heart of the Umbrian countryside, is the Park Hotel ai Cappuccini, a carefully restored Capuchin monastery from the 17th century. The hotel captures an incredible mix of ancient and new for your comfort and rejuvenation.
hotel image

Palazzo Bocci

Spello, Italy

Just south of Assisi, in the charming medieval town of Spello, this beautifully refurbished 17th-century palace is now elegantly restored into a refined 4-star hotel. Be sure to explore the hanging garden with two century-old palm trees and its spectacular Hall of Frescoes before enjoying an aperitif on the garden terrace.
hotel image

La Badia di Orvieto

Orvieto, Italy

This elegant and discreetly luxurious 5-star hotel is suspended between the sky and sea. With fragrant gardens, a soothing spa, and spectacular views of the Tyrrhenian sea, you are sure to have an unforgettable stay.
hotel image

Torre di cala Piccola

Porto Santo Stefano, Italy

This elegant and discreetly luxurious 4-star hotel is suspended just 100 meters above the Mediterranean Sea. With spectacular 360 degree views of the Argentario peninsula, a private swimming cove and, gourmet restaurant, you are sure to be enchanted by this beautiful property.
hotel image

Hotel Variation | Castello di Petroia

Gubbio, Italy

Castello di Petroia is a 12th-century medieval fortress. It is settled on a hilltop, surrounded only by woods and green. You can lose yourself admiring the endless landscapes, walking along the trails, and feeling the quietness of nature. You will stay here in place of Park Hotel ai Cappuccini on select 2021 dates.

What's Included

For us, the details matter most

Every moment of a Trek Travel bike trip has more than you could have ever dreamed. More romance. More scenery. More choice. It's the little additions to every Trek Travel cycling vacation that make it truly special. And that's how we help you create more memories.


Trek Domane SL 7 Disc

It isn’t the cycling vacation of a lifetime unless you have the industry’s best bike to match. In 2019, we upgraded our fleet to feature the award-winning Domane SL 7 with Shimano Ultegra Disc brakes. Because when you combine the lightweight stability and comfort of the Domane with the superior safety and stopping power of disc brakes, you get a match made in cycling heaven. And the best part? It’s included in the trip price. Ride confidently, comfortably and longer in the most beautiful destinations around the world with the new Domane SL 7. Learn More


Trek Electric-Assist Verve+

With its Low-Step frame design, hopping on and off the Trek Verve+ is super easy. The front suspension will take the edge off any bumps in the road and the Bosch system will keep you smiling from ear to ear. The integrated battery keeps this bike looking sleek as you pedal through amazing terrain. Learn More


  • Five nights of accommodation at handpicked hotels
  • Two experienced guides to provide local knowledge, support, and camaraderie
  • Daily route support with both guides and our support van
  • Daily breakfast, three lunches, and three dinners
  • Two social hours of drinks and hors d'oeuvres
  • Ride a Trek Domane SL 7 disc or Trek Electric-Assist Verve+
  • Up to three daily route options on riding days
  • Snacks and drinks for each day's ride
  • Trek Travel Bontrager cycling jersey to keep
  • Trek Travel water bottles to keep
  • Cinch sack day bag to keep
  • Each bike is equipped with a Garmin Edge 1030 GPS computer, flat pack, front and rear Bontrager Flare R lights, a Bontrager saddle, and pedals (Shimano clipless road pedals, Shimano clipless mountain pedals, caged, or flat pedals)
  • Bontrager WaveCel helmets
  • All gratuities for drivers, local experts, and hospitality staff
  • All luggage transfers and transportation during your trip
  • A personalized digital photobook of your trip
  • Entrance fees for all activities, private tours, and events


  • Trek Domane SL 7 disc carbon road bike with Shimano Di2 electronic shifting or Trek Electric-Assist Verve+, available in a limited quantity
  • Upgrade your bike to a Trek Electric-Assist Domane+ LT carbon road bike with Shimano Di2 electronic shifting
  • Trek Travel Bontrager cycling jersey to keep
  • Trek Travel water bottles to keep
  • Shimano clipless road pedals, Shimano clipless mountain pedals, caged, or flat pedals
  • Bontrager WaveCel helmet
  • Bontrager men's and women's specific saddles
  • Bontrager front and rear Flare R lights and a flat pack
  • Garmin Edge 1030 GPS computer
  • Cinch sack day bag to keep
  • Upgrade your bike to include carbon wheels (+$200)
  • Coupon valued up to $500 off a new Trek Bicycle. Your coupon will be delivered via email prior to your trip.
  • For the most comfortable ride, you may choose to bring your own pedals, saddle, and helmet on the trip. Your guides will install your gear on the first day during your bike fit.


Gratuities for your Trek Travel guides are not included in your trip price. We recommend tipping 7.5-10% of your trip price for the guide team. Local currency is preferred and unless you want to tip separately, guides will divide tips amongst themselves. Please tip your guides at your discretion, based on their level of professionalism, guest care, and service.
  • Airfare and transportation to and from the trip pick-up/drop-off locations
  • Lodging before and after the trip
  • Personal items purchased during the trip
  • Optional activities not scheduled by Trek Travel
  • On select trips some meals are not included. On these trips, Trek Travel invites you to explore the local cuisine at your leisure.

More Information

Rider Level: 3/4 - Active, Avid?

55 miles
276 miles
4,595 feet
22,975 feet
The terrain is consistently hilly, with quiet, narrow and winding roads. Many towns sit atop hills and ascents and descents can be steep. Our Bike Across Italy tour is best suited for our Type 3 and Type 4 Riders. Our Trek Travel guides can also easily accommodate Type 3 Riders, who seek less mileage or fewer uphills, with a boost in the van. Those who wish to ride every mile but are concerned about their physical ability may want to try our electric bike option—you still get a workout but can climb alongside even the strongest rider.
Our Italy coast to coast cycling tour is best suited to guests who want to ride every day. Because of the terrain and/or remoteness of the hotels and riding routes, there are few, if any, non-riding options available. If a non-rider wants to accompany a rider guest on this trip, they would need to spend many hours in the van and/or at the hotels on the trip. Due to this, we strongly discourage non-riders from this destination. As an alternative, call a Trek Travel Trip Consultant at 866-464-8735 for trip suggestions where more non-rider activities are available, such as:
  • Tuscany
  • Puglia
  • Costa Brava

See itinerary for specific daily ride distances and elevation options. On all of our vacations, Trek Travel seeks to find quiet, paved secondary roads or bike paths to experience a region; busy roads are avoided as much as possible. Our itineraries are an approximation of our trips. Trek Travel strives to offer every guest a vacation of a lifetime on every trip. At times routes, hotels, activities, etc. listed here may change at the discretion of the trip designer or guides to improve the trip experience.

Averages and totals are calculated from our Today’s Ride/Avid Ride options.

Travel Details

How to Get There

Bologna Airport in Bologna (BLQ) or Rimini Airport (RMI).
10:30 AM
Grand Hotel Rimini, Rimini, Italy

Say Farewell

Rome Fiumicino Airport (FCO)
9:30 AM
Orbetello-Monte Argentario Train Station, Orbetello, Italy


We suggest that you arrive at least one day prior to the Bike Across Italy tour, which will enable you to adjust to the time zone and minimize the risk of missing the trip start due to flight-related delays. We recommend that you fly into Bologna Airport in Bologna (BLQ) or Rimini airport (RMI).

Once you have arrived in Bologna, there is a direct shuttle bus to Rimini train station that leaves every two hours. Alternatively, you can take a shuttle bus to Bologna Centrale train station and catch a train to Rimini, which leaves every 30 minutes. From Rimini, airport taxi’s are readily available for a short transfer in to the city center.

Your Trek Travel guides will meet you at the Grand Hotel Rimini (Parco Federico Fellini - 47921 Rimini, Italy) at 10:30 AM on the first day of the Bike Across Italy tour. After a 30-minute shuttle, your guides will spend the morning ensuring you have the perfect fit to your Trek Domane. You'll then enjoy a light lunch before our first ride of the week. Please have your first day’s riding gear handy and separate from your other luggage to facilitate the bike fitting and ride.

If you will be late for the pick-up or are going to miss it altogether, please inform your guides. You will receive an email a week before the trip start with their names and contact details. If you cannot reach them, please call our first hotel, Hotel San Domenico (+39 0722 2626), and leave a message with your expected arrival time and contact details. You may take a taxi to the first night’s hotel, Hotel San Domenico in Urbino, for approximately 70 euros. The trip takes 60 minutes from the center of Rimini.

View our pre hotel recommendations


You will say farewell to your guides at 9:00 AM at Hotel Torre di Cala Piccola, Porto Santo Stefano. You’ll depart by private shuttle for the train station in Orbetello-Monte Argentario, arriving close to 9:30 AM. From here, trains connect to Rome, Pisa, Florence, and other Italian cities. Trek Travel will also provide a second shuttle to the train station to accommodate later departures. Please let your Trip Consultant know your intended departure time to help facilitate the coordination of shuttle times. Please do not book train tickets before 10:30 AM. Visit www.TrenItalia.com for train information.

View our post hotel recommendations

Planning For Your Trip

Packing and Weather

Spring and fall in the heart of Italy are usually clear and sunny, with warm daytime temperatures (65F-75F) and evening temperatures 10-15 degrees cooler. A jacket or wrap will be useful in the evening. Rain is always a possibility, however, so be prepared with wet-weather gear as we bike across Italy. Packing List

Before and After Your Trip


Before: Rimini, Italy

Dating back 2000 years, Rimini boasts long sandy beaches on the Adriatic Sea and a historic center with Roman ruins and a beautiful Renaissance cathedral. The town now attracts a mostly Italian crowd and was home to the famous film director Federico Fellini. We recommend the following accommodations for your pre-trip hotel:


After: Rome, Italy

Rome is a powerhouse of stunning architecture and ancient history, beautifully told through its ruins and buildings. It seems that every street you walk down provides another unexpected glimpse of ancient times, yet modern bustle and energy abound as well. The Coliseum, the Forum, Vatican City, and the Pantheon are some of the must-see attractions. Be sure to linger on the Spanish Steps one afternoon and take advantage of great shopping and fantastic cuisine. We recommend the following accommodations for your post-trip hotel:

Customer Reviews

Why Trek Travel

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the ultra-smooth Trek Domane SL 7 to the Trek Electric-Assist Verve+, you deserve the best ride on your vacation. Plus, we offer a range upgrade options to take you the extra mile.

Our Guides

Our guides are trained to make your trip magical. They aren't just experts in riding; they're trained in delivering uncompromising service in ways you won't believe. We know that it's the unexpected surprises that make a trip magical. That's why our guides pride themselves on anticipating your needs before you ask.

Your Day. You Decide.

Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.

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