Visit Umbria on a Tuscany bike tour
Riders through Italian village on Ride Across Italy bike tour
Ride across Italy on Trek Travel's coast to coast bike tour
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Group of cyclists in Italian countryside on Ride Across Italy bike tour
Visit Umbria on a Italy bike tour
Group ride on the Ride Across Italy bike tour
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21IT - Canva - 1600x670 (2)
Visit Umbria on a Tuscany bike tour Riders through Italian village on Ride Across Italy bike tour Ride across Italy on Trek Travel's coast to coast bike tour 16TCL0612_bjoy_-165 - 1600x670 21IT - Canva - 1600x670 Group of cyclists in Italian countryside on Ride Across Italy bike tour Visit Umbria on a Italy bike tour Group ride on the Ride Across Italy bike tour bar-boutique-hotel-torre-di-cala-piccola-argentario - 1600x670 21IT - Canva - 1600x670 (2)

Italy Coast to Coast Bike Tour

Ride Across Italy from the Adriatic to the Mediterranean Seas

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 »
$3999 Per Person
6 Days & 5 Nights
Rider Level: ?
3 / 4 - Active / Avid
Trip Style: ?
Cross Country
Hotel Level: ?
From $3999 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
Italy Coast to Coast Bike Tour
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.
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Single Occupancy from: +$799
Aug 18 – Aug 23 
$3999 / Person, Double Occupancy Book this date
Aug 25 – Aug 30 
$4099 / Person, Double Occupancy Book this date
Sep 1 – Sep 6 
$3999 / Person, Double Occupancy Book this date
Sep 8 – Sep 13 
$3999 / Person, Double Occupancy Book this date
Sep 12 – Sep 17 
$4099 / Person, Double Occupancy Book this date
Sep 15 – Sep 20 
$3999 / Person, Double Occupancy Book this date
Sep 19 – Sep 24 
$3999 / Person, Double Occupancy Book this date
Sep 22 – Sep 27 
$3999 / Person, Double Occupancy
Date reserved ?
Sep 26 – Oct 1 
$3999 / Person, Double Occupancy Book this date
Sep 29 – Oct 4 
$3999 / Person, Double Occupancy Book this date
Oct 3 – Oct 8 
$3999 / Person, Double Occupancy
Date reserved ?
Oct 6 – Oct 11 
$4099 / Person, Double Occupancy Book this date
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:

  • 10+ Guests Price as advertised*
  • 8-9 Guests +$750 per person to trip price*
  • 6-7 Guests +$1,500 per person to trip price*
  • 4-5 Guests +$2,000 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 town of Pesaro, dubbed the "Cycling City" by the Italian environmentalist association in recognition of its extensive network of bicycle paths and promotion of cycling. Here you'll meet your Trek Travel guides and fellow cyclists, followed by some time to be fit and familiarized with your Trek bicycle. This morning’s ride starts from the Nautilus hotel heading out of Pesaro towards the countryside of Le Marche region. Climb up to enjoy the panoramic views of picturesque farmlands before beginning your final climb toward Urbino. You'll stop for lunch, just as you start to approach the walled city of Urbino high up in the distance, for a traditional meal with a modern spin. After lunch, finish by riding into the beautifully-preserved Renaissance town that has been attracting artists and scholars since the 15th century, from all over Italy and beyond. Tonight, we’ll explore this UNESCO World Heritage Site and dine in a small bistro along winding cobbled streets. It is like a step back in time, where houses and palaces of weathered brick and pantile roofs 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:

Pesaro to Urbino
Approximately 32 mi | 52 km and 3,958 ft | 1,206 m


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 surrounded by magnificent woods and rich in history, beauty and charm. We'll experience the authentic Italian hospitality as we 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 mi | 96 km and 5,665 ft | 1,762 m

Short Option:

Urbino to Monastero di Fonte Avellana, shuttle to Gubbio
Approximately 40 mi | 64 km and 3,470 ft | 1,057 m


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. In the afternoon you have the opportunity to relax, recuperate, and recharge your energy at the hotel's fabulous spa. This evening is yours to find the perfect dinner in town as you admire Spello's well-preserved Roman gates.

Today's Ride:

Gubbio to Spello
Approximately 39 mi | 62 km and 3,330 ft | 1,015 m

Short Option:

Gubbio to Assisi, shuttle to Spello
Approximately 31 mi | 49 km and 2,800 ft | 853 m

Avid Option:

Gubbio to Spello with San Giovanni Climb
Approximately 53 mi | 85 km and 5,000 ft | 1,542 m


La Bastiglia

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 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 by defensive walls and medieval houses made out of the same tufa rock. It's truly astounding. Tonight enjoy a stroll in this enchanting town, before meeting the group for a visit to a 13th-century cellar, complete with a wine tasting and dinner featuring traditional Umbrian fare.

Today's Ride:

Spello to Orvieto
Approximately 59 mi | 94 km and 5,300 ft | 1,650 m

Short Option:

Spello to Todi, shuttle to Orvieto
Approximately 31 mi | 49 km and 2,600 ft | 792 m

Avid Option:

Rocca Ripensena Climb
Approximately 68 mi | 109 km and 6,500 ft | 1,981 m


La Badia di Orvieto

Included Meals:

Breakfast | Dinner

After a freshly baked cornetto and the perfect cappuccino in our hotel’s frescoed refectory, start your day with a climb from Orvieto to Bagnoregio, where you’ll behold the ancient ghost town of Civita di Bagnoregio, perched precariously upon eroding rock and reached only by a causeway bridge. 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 76 mi | 122 km and 4,637 ft | 1,414 m

Short Option:

Orvieto to Farnese shuttle to Porto Santo Stefano
Approximately 40 mi | 64 km and 3,266 ft | 995 m


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. A late check-out time (at 12:00 PM noon) will allow you to 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

Explorer Accommodation | 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

Luxury Accommodation | 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

La Bastiglia

Spello, Italy

Explorer Accommodation | Perched in the highest and most panoramic part of the enchanting medieval village of Spello, this charming hotel combines refinement and modern design. Housed in a magnificent 17th-century building that was a former mill, the hotel features a number of interesting works of art and the rooms boast breathtaking views over the rolling Umbrian hills, also works of art in their own right.
hotel image

La Badia di Orvieto

Orvieto, Italy

Explorer Accommodation | 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

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

Hotel Variation | Hotel Palazzo Piccolomini

Orvieto, Italy

Explorer Accommodation | Set within a renovated medieval building in the heart of Orvieto, Palazzo Piccolomini is a 4-star hotel that once belonged to the Papal family Piccolomini. History, art and architecture are magically forged together in this place, which is rich in charm and culture. Situated just a 5-minute walk from the Cathedral it's in a perfect location to explore town on your guest choice night. You will stay here in place of La Badia di Orvieto on select 2024 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

Experiencing your cycling vacation of a lifetime is not complete without a world-class bike and the Trek Domane is the best way to enjoy the ride. Trek Bikes has launched the all-new Trek Domane and now you can ride it on our trips. It raises the bar to deliver incredible endurance road bike comfort without sacrificing performance and features highly responsive disc brakes and electronic shifting. This new bike is lighter than ever before, and carbon wheels come standard on every bike. The road-smoothing IsoSpeed technology lets you ride as long as you want with less fatigue. The bike you ride on a biking vacation matters. That is why we provide the newest and best bikes in the business. 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 four dinners
  • Two social hours of drinks and hors d'oeuvres
  • Ride a Trek Domane SL 7 disc or Trek Electric-Assist Verve+ (Please note: There is a maximum of 3 Verve+ available per trip date.)
  • Up to three daily route options on riding days
  • Snacks and drinks for each day's ride
  • Trek Travel Santini 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, a flat pack (containing a tube, levers, and a CO2 cartridge with inflator), 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 digital photo album 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 (Please note: There is a maximum of three Verve+ available per trip date.)
  • Trek Travel Santini 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
  • A flat pack containing a tube, levers, and a CO2 cartridge with inflator
  • Garmin Edge 1030 GPS computer
  • Cinch sack day bag to keep
  • 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.


Guide gratuities are customary and at your own discretion, to recognize service, hospitality, and the little extras that surprise and delight. For this trip, we recommend $300-$360 per guest. While local currency is preferred, there are other options to make tipping easier. Most guides accept gratuity via PayPal or our staff can help before or after the trip. Gratuities will be divided among the guide team, so feel free to leave your gratuity with whomever you choose at the end of your trip. 
  • 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?

88 kilometers / 55 miles
435 kilometers / 270 miles
1,400 meters / 4,590 feet
6,990 meters / 22,940 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 Italy Coast to Coast bike 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 Ancona Airport (AOI)
9:00 AM
Hotel Nautilus or Charlie Urban Hotel, Pesaro, Italy

Say Farewell

Rome Fiumicino Airport (FCO)
12:00 PM
Orbetello-Monte Argentario Train Station, Orbetello, Italy


We suggest that you arrive at least one day prior to your Italy Coast to Coast bike 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 (BLQ) or Ancona Airport (AOI).

If you arrive in Bologna (BLQ), take the Marconi Express train, which is direct from BLQ to Bologna Centrale train station. The ride takes just seven minutes and trains depart every 10 minutes. In Bologna Centrale trains depart hourly to Pesaro and the ride takes about 90 minutes. Train tickets can be purchased on www.TrenItalia.com.

If you arrive in Ancona (AOI), take the Raffaello Aerobus to Ancona train station. The ride takes 30 minutes and tickets can be purchased directly on board the bus at a cost of €5.50. In Ancona trains depart frequently to Pesaro and the ride takes about 30 minutes. Train tickets can be purchased on www.TrenItalia.com.

We highly recommend staying at Hotel Nautilus (or Charlie Urban Hotel on select dates) in Pesaro the night before the trip starts, where you will meet on Day 1. The ride starts from there. Please, contact your Trip Consultant for a discount code.

Your Trek Travel guides will meet you in the lobby at Hotel Nautilus (Viale Trieste, 26, 61121 Pesaro PU, Italy) at 9:00 AM on the first day of the Italy Coast to Coast bike tour. On select dates the meeting location will be the Charlie Urban Hotel (Viale Trieste, 281, 61121 Pesaro PU Italy). Please, come to the meeting dressed in your cycling clothes and bring along anything you will need for the day’s ride like personal pedals, saddles, GPS units, etc. At the hotel your guides will spend some time ensuring you have the perfect fit to your Trek Domane. You'll then head out on your bike to begin your bike tour across Italy!

If you will be late for the meeting 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 from Pesaro to the first night’s hotel, Hotel San Domenico in Urbino, for approximately 80 euros. The trip takes 50 minutes.

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. After a challenging week traversing Italy by bike, we recommend enjoying a leisurely morning at the hotel in order to make the most of the hotel’s wellness facilities and infinity pool. We have made special arrangements so that the hotel will allow you to have a late check-out (at 12:00 noon). A 30-minute shuttle ride organized by the hotel will take you the train station in Orbetello-Monte Argentario. From here, trains connect to Rome, Pisa, Florence, and other Italian cities. The first available afternoon train to Roma Termini departs the Orbetello train station just before 2:00 PM. Visit www.TrenItalia.com for specific train information. Please let your guides know your intended departure time to help facilitate the coordination of shuttle times with the hotel.

View our post hotel recommendations

Planning For Your Trip

Packing and Weather

Fall in the heart of Italy is 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: Pesaro, Italy

Pesaro is an attractive seaside resort, a thriving fishing port and an important manufacturing centre overlooking the Adriatic sea in the south of the Marche region. With its 7 km of wide sandy beach, it is an ideal holiday destination for families, offering also more secluded beaches with green hills as a backdrop. Famous for being a UNESCO Creative City of Music, Pesaro is the native city of Gioacchino Rossini, composer of the Barber of Seville and William Tell, some of the gratest masterpieces of the history of opera in the world. The city has recently been named the Italian Capital of Culture for 2024 thanks to its continuous commitment in valorizing a territory rich in historic sites and environmental-landscape treasures. 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:

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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