Self-guided: Umbria – Cycling the Green Heart of Italy

Self Guided Tour in Umbria
  • Length 8 days
  • From USD$2175
  • Style/Level Self-Guided 3.0
  • Countries Italy
  • Begin/End Perugia / Orvieto
Umbria is the birthplace of St. Francis, the heart of Roman Italy and home to some of Italy’s best-preserved medieval towns. Bicycle past vineyards, chestnut and oak forests and across rolling hills to monasteries, castles, and hilltop villages unchanged since the Middle Ages. Start in Perugia, the ancient and modern capital of Umbria, continue to Assisi, the home of Saint Francis, and on through enchanting hilltop towns such as Spello, Spoleto, Todi and Orvieto.

Highlights

  • Perugia, artistic center of Italy

  • Assisi – the town of Saint Francis

  • Deruta ceramics

  • Roman ruins in Spello

  • The Roman Via Flaminia, Trevi, and Montefalco

  • Spoleto

  • Piazza del Popolo in Todi

  • Civita di Bagnoregio

  • Orvieto

    Extra meals & activities: (please inquire for price and availability)

  • Dinner at the hotel in Perugia

  • Guided visit of Assisi

  • Olive oil tasting in Bevagna

  • Dinner at the hotel in Spoleto

  • Dinner at the hotel in Todi

  • Guided visit of Orvieto

Includes

  • 7 nights in 3- and 4-star lodging

  • All breakfasts

  • Bike fitting and briefing in English by our professional staff at tour start

  • GPS device

  • Luggage transfers

  • All Self-Guided tour inclusions

Keep in mind

We work hard to maintain consistency across all of our tours, but some trips have unique differences. Here are some things to keep in mind about this tour.

  • The final itinerary, including hotels and/or activities described here, are subject to change according to availability.
  • City hotel taxes are not included.

The tour starts easy then it gets hilly, but distances are moderate so take your time! For an easy option you can end in Spoleto.

  • PRICING: Based on double occupancy. $500 per-person deposit. Departures for solo travelers will incur supplemental fees.
  • START DAYS: This tour departs any Monday between March 1 and October 31. Other start days of the weeks may be available on request, for USD $300. Please note that changing the start day could make some cultural visits and activities impossible.
  • REQUEST YOUR DATE: Click the blue “Request a date” button to submit a tour inquiry.

Date Price Private room fee Note
May 1-Jun 15, 2025 USD$2295 USD$455 High season pricing
Jun 16-Aug 31, 2025 USD$2175 USD$455  Low season pricing
Sep 1-Oct 15, 2025 USD$2295 USD$455 High season pricing
Oct 16-31, 2025 USD$2175 USD$455   Low season pricing 
DateMay 1-Jun 15, 2025
PriceUSD$2295
Private room feeUSD$455
NoteHigh season pricing
DateJun 16-Aug 31, 2025
PriceUSD$2175
Private room feeUSD$455
Note Low season pricing
DateSep 1-Oct 15, 2025
PriceUSD$2295
Private room feeUSD$455
NoteHigh season pricing
DateOct 16-31, 2025
PriceUSD$2175
Private room feeUSD$455
Note  Low season pricing 

Download Itinerary

We’ll send you a link to a full day by day tour itinerary that can be downloaded and printed so you can review all the details online and offline. This packet also includes details about what to expect on tour and arrival and departure details.
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Open all days
  • Total distance 270 km (168 miles)
  • Average daily distance 45 km (28 miles)
  • Tour style Self-Guided
  • Tour level 3.0

Highlights: The well-known artistic centre of Italy: Perugia

Arrive in Perugia today, the ancient and modern capital of Umbria. Perugia is famous for Perugina chocolate and its vibrant old town! Take time to explore it today or tomorrow morning. We’ll meet you for bike fitting and briefing in the afternoon.

Daily distance: 0-12 km (0-7.5 miles)

Accommodation: Hotel La Rosetta, or similar. Upgrades available – please inquire for details

Highlights: Assisi, the town of Saint Francis

Leave Perugia to enter the Umbrian Basin and arrive to Assisi. You’ll want to explore the church of Saint Francis, the second most important pilgrimage destination in Italy after St. Peter’s in Rome. If you arrive early you might enjoy an extra ride to the hermitage just outside the village where Francis often retreated for meditation.

Long option: 38 km (23.5 miles), with + 721 m (2365 ft) elevation gain.
Short option: 31 km (19 miles), with + 394 m (1292 ft) elevation gain.
Extra ride from Assisi to the hermitage: 14 km (9 miles), with + 515m (1690 ft) elevation gain.

Accommodation: Hotel Giotto, or similar. Upgrades available – please inquire for details

Meals : Breakfast

Highlights: Roman ruins in Spello, medieval wall and Renaissance buildings

You leave Assisi behind you this morning and head south to Spello, a puzzle made of Roman, Medieval and Renaissance pieces. 13th century town walls connect Roman gateways dating to the 1st century BC and AD. Take time to explore and you’ll find the 13th century town hall dominating the Renaissance town square. From Spello you pedal to Foligno, another Roman town but with fewer Roman ruins. Enjoy lunch in the square and then head across the Umbria valley to Bevagna. Bevagna is the picture of a well-preserved Medieval village. It, too, dates from Roman times and is centered on the 13th century square and town hall. Unlike most Medieval towns, Bevagna is located on the plains of the Umbrian Basin.

Daily distance: 35 km (22 miles)
Elevation gain: +324 m (1063 ft)

Accommodation: Hotel Resort Porta Guelfa, or similar. Upgrades not available

Meals : Breakfast

Highlights: The preserved town of Spoleto, its fortress, the Roman aqueduct

Your ride todays takes you to the well-preserved medieval town of Spoleto, famous throughout the world for the Festival dei due Mondi, a three week dance, music and opera festival. Arrive early to discover the hidden corners of this fabulous town that dates back to Roman times. Don’t miss the Cathedral and a walk to the fortress Fortezza Albornoz on top of Colle Sant’ Elia.

Daily distance: 34 km (21 miles)
Elevation gain: + 211 m (692 ft)
Extra ride to Monteluco available: 17 km (11 miles), with + 509m (1670 ft) elevation gain

Accommodation: Hotel dei Duchi, or similar. Upgrades available – please inquire for details

Meals : Breakfast

Highlights: Off the beaten track to medieval Todi

You’re route today takes you away from the busy heartland of Umbria to the beautiful hilltop town of Todi. Todi’s history is one of the region’s oldest: three thousand years of continual inhabitance by Umbrians, Etruscans, and Romans. Today its main square “Piazza del Popolo” is often described as the most perfect medieval piazza in Italy. Discover why.

Daily distance: 57 km (35 miles)
Elevation gain: +787 m (2582 ft)

Accommodation: Hotel Fonte Cesia, or similar. Upgrades available – please inquire for details

Meals : Breakfast

Highlights: Orvieto and its Duomo

A quiet ride along the shoulders of the Tiber Valley takes you to the spectacular Renaissance city of Orvieto. Perched on the remnant of a volcanic plateau, Orvieto is one of the most beautiful cities in Umbria. Its cathedral, a transition style between Romanesque and Gothic architecture, is richly decorated with a variety of colored marble and bright mosaics. Orvieto is also famous for its white wine.

Daily distance: 48 km (30 miles)
Elevation gain: +944 m (3097 ft)

Accommodation: Hotel Palazzo Piccolomini, or similar. Upgrades available – please inquire for details

Meals : Breakfast

Highlights: “Ghost town” of Civita di Bagnoregio and Bolsena Volcanic Lake

We suggest a loop ride today to one of several volcanic lakes in this part of Italy, the Lago di Bolsena. Before getting to the lake the ride will take you to the “ghost town” of Civita di Bagnoregio. Take time to explore this interesting village.

Daily distance: 66 km (41 miles)
Elevation gain: +1292 m (4238 ft)

Accommodation: Hotel Palazzo Piccolomini, or similar.

Meals : Breakfast

After breakfast your cycling experience in Umbria ends. We hope you have enjoyed cycling with us! Orvieto is conveniently located on the main rail line to Florence or to Rome. It is also beautiful enough to warrant a relaxing rest day if you are so inclined.

PLEASE NOTE: The final itinerary, including hotels and/or activities described here, are subject to changes according to availability. City hotel taxes are not included.

Meals : Breakfast

Visit our Tour Level page to learn more about terrain levels and how we determine day and tour levels.

  • 2025 premium gravel bike

    Premium road bike

    Frame : Titanium with Carbon Fork built by Van Nicholas, or similar
    Type : Premium Road

  • Titanium hybrid road bike with flat handle bars and rear rack

    Premium hybrid bike

    Frame : Titanium with Carbon Fork
    Type : Premium Hybrid

  • Titanium hybrid with step-through frame

    Premium mixte step-through hybrid

    Frame : Titanium with Carbon Fork
    Type : Premium Hybrid Mixte

  • Co-Motion or Cannondale tandem

    Frame : Steel / Aluminum
    Type : Tandem

  • E-hybrid bike

    Surcharge: $250 for 6-8 days; $300 for 9-15 days; $500 16+ days
    Frame : Aluminum frame with front suspension
    Type : E-Hybrid

  • e-gravel bike

    E-road bike

    Surcharge: $300 for 6-8 days; $375 for 9-15 days; $600 for 16+ days
    Frame : Carbon frame with carbon fork
    Type : E-Road

Pre-trip planning checklist

Italy travel planning page

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