ITALY SELF-GUIDED TOURS

Below are sample Self Guided Cycling Tours. You will have a detailed route map, daily luggage transfers and great lodging waiting for you each evening. These tours are perfect for couples, families and small groups of friends. You choose the dates and tour location, and we will take care of all the details to make your tour a most memorable bicycling adventure. We can easily customize these itineraries for longer or shorter number of days and distances.

Tour accommodations are in a splendid assortment of villas and charming country inns that will provide a sense of history and a taste of the local warmth and hospitality. You can look forward to gourmet meals that are characteristic of this region and made with the freshest local ingredients seasoned with tasty olive oil and herbs. You will be able to sample some of Italy's most famous cheeses and wines from vineyards along our route.

Tuscany l Umbria l Sicily l Piedmont l Veneto

Day 1: Arrival in Poggibonsi: You will be met by a representative of our Italian representative who will drive you to your accommodations for the night,Villa Lecchi. This is a beautiful villa near Castellina in Chianti and is also known for excellent food.

Day 2: Monteriggioni/Colle Vald'Elsa/San Gimignano - 35 Km: Your first day of cycling takes you to Monteriggioni, a perfect fortress town built in the 13th century and totally encircled by high walls with 14 heavily fortified watchtowers. Continue to Colle de Val d'Elsa, take time to visit some of the glass-blowing workshops. Then it's on to San Gimignano, the "city of beautiful towers" and one of the best-preserved medieval towns in Italy before you head back to Villa Lecchi.

Day 3: Villa Lecchi/Castellina in Chianti/Siena - 60 Km: Follow winding roads through the Chianti countryside, past lush vineyards and superb wineries, to Siena, one of the most beautiful cities in Italy. Stroll through the famous Piazza del Campo, enjoy a gelato, and find a charming trattoria for dinner. (Dinner on your own tonight.)

Day 4: Siena/Buonconvento - 35 Km: Winding on the Chianti country roads is quite dramatic as the landscape changes from the lush vineyards to the more linear cypress-crested hills of the "Crete" near Buonconvento. Here shepherds tend the sheep whose milk is used to make pecorino cheese. You will pass through the tiny borgo of Murlo, the oldest settlement in the area, before arriving at today's destination, a delightful agriturismo just 3 km from Buonconvento.

Day 5: Buonconvento/Montalcino - 46 Km: After a steep climb, pedal through the spectacular eroded hills of "Crete" and then through thick cypresses and olive groves as you approach the 14th-century Benedictine monastery of Monte Oliveto Maggiore. Contemplate the cloister with its magnificent fresco cycle on the life of St. Benedict. Then continue to Montalcino, a classic Tuscan hilltown renowned for its ruby-red Brunello wines, considered by some to be the finest in Italy.

Day 6: Montalcino/Sant'Antimo/Montalcino (your choice of mileage for the day as you will not be changing hotels tonight): Stroll around the town before following the trail to the abbey of Sant'Antimo, 10 km away. Few of the monastic buildings remain, but the 12th-century church is well preserved and is an outstanding example of the Italian Romanesque. With luck, you'll visit at a time when the monks celebrate mass and the church echoes with Gregorian chants. Then return to Montalcino where you spend a second night. (Dinner is on your own tonight and you might choose a gourmet dinner and wine tasting at the Fattoria dei Barbi.)

Day 7: Montalcino/Montepulciano - 46 Km: You pass through many wonderful places today. Pause at the hot sulfurous pool in the piazza at Bagno Vignoni, then continue to Pienza, a Renaissance jewel and birthplace of Aeneas Sylvius Piccolomini who completely redesigned its center after he became Pope Pius II. Relax over a cappuccino in Montichello, a tiny walled village, and then head for beautiful Montepulciano, one of Tuscany's highest hilltop towns and famous for its red Vino Nobile wines.

Day 8: Stroll around Montepulciano before departure. Today you will be transferred to the Chiusi train station that has access to Rome, Florence or Milan.

DATES: MID-MARCH THROUGH MID-NOVEMBER

TRIP COST: €1,200 Euros/pp (double occupancy) Single supplement: €250 Euros.

TRIP COST INCLUDES: 8 days/7 nights, 7 nights hotel, 7 breakfasts, 4 dinners, luggage transfer, trip information package that includes maps, route descriptions, suggested sights to visit, emergency phone numbers for our Italian staff support (shorter itineraries available)

TRIP COST DOES NOT INCLUDE: Bike rentals (you may choose to bring your own bike or rent one for €140 Euros), lunches, 3 dinners.

Umbira is often called "the green heart of Italy." Pedal through olive groves and past vineyards, wonder at Etruscan burial chambers, Roman ruins and splendid churches. Pause in medieval villages perched on the hillside and lose yourself in the tales that ancient stones tell. Italy's "green heart" offers you food for body and soul. Medieval villages perch on hillsides cloaked with dark forests hiding truffle secrets. Nourish your soul with a splendid history of painters and saints. Begin in Cortona, Lake Trasimeno. Continue to magnificent Perugia, rich and dense like the Perugino Bachi chocolates. Pass the ceramic workshops of Deruta, then arrive in Assisi and let the spirit of St. Francis fill you. Savour the beautifully preserved towns of Spello, Bevagna, Spoleto and Todi. Let the great colored cathedral of Orvieto be your beacon across vineyards producing a winning white wine. Umbria offers broad valleys lined by rolling hills, and is not as demanding as Tuscany.

Day 1: Arrive in Cortona, the setting for Francis Maye's best seller, Under the Tuscan Sun

Day 2: Enter Umbria and cruise by Lake Trasimeno, whose shores shelter bamboo, migratory birds and lovely villages surrounded by olive groves. Take a boat to Isola Maggiore where old ladies weave lace and fisherman mend their nets. Today's destination is a country B&B near Solomeo or a lovely inn in Solomeo. (45m/28 miles)

Day 3: Enjoy the day's ride into Perugia, the lively capital city of Umbria. Stroll along Corso Vannucci to watch the parade of Umbria's style-makers and style-followers. Visit the Palazzo dei Priori, which houses the Galleria Nazionale di Umbria and its many treasures. (32 km/20 miles)

Day 4: As you cycle through the heart of Umbria, pause to visit Deruta, famous for its ceramics, and Torgiano, home of Umbria's finest wines, produced by Giorgi Lungarotti. Visit their wine museum, which also includes medieval machinery. Settle in for two nights in Bevagna. (35 km/21 miles)

Day 5: Enjoy the day ride into Assisi and tour the city's artistic highlights. (The Basilica of St. Francis is still being repaired and only the upper part will be open to visitors.) Take the time to immerse yourself in its life as you explore the winding streets of the pink city. Continue on an easy ride along the Subasio slopes to the small town of Spello, a perfectly preserved town still encircled by Roman walls. (20km/12 miles to 50km/31 miles possible today)

Day 6: Cycle into the heart of the wine country to Montefalco, nicknamed "the balcony of Umbria" because of its spectacular views. It's also famous for its wine. Don't miss the dazzling Renaissance frescoes painted by Benozzo Gozzoli in the 15th century in the huge church of San Francesco. Then ride along lovely riverbanks before arriving in Spoleto, a city of endless architectural treasures, known for its world-famous music festival held in late June and early July. (43 km/26miles)

Day 7: Continue through the Umbrian hills to the hilltop town of Todi. Visit the impressive Piazza del Popolo, one of the most striking squares in Italy, designed so that narrow exits at each corner could be closed off and the square defended. Be sure to see the Palazzo as well, one of the oldest surviving public buildings in Italy. (42 km/26 miles)

Day 8: Wind through the rugged, beautiful landscape. Pause to enjoy the views over Lake Corbara before reaching the Etruscan town of Orvieto, perched atop reddish-brown cliffs of soft, volcanic tufa stone. Visit the Duomo, considered the finest cathedral of its period in Italy and home of some amazing frescoes by Signorelli. (38 km/23 miles)

Day 9: Catch a train from Orvieto to your next destination

DATES: MID-MARCH THROUGH MID-NOVEMBER

TRIP COST: €1,300 Euros/pp (double occupancy) Single supplement: €275 Euros

TRIP COST INCLUDES: 9 days/8 nights, 8 nights hotel, 8 breakfasts, 6 dinners, luggage transfer, trip information package that includes maps, route descriptions, suggested sights to visit, emergency phone numbers for our Italian staff support (shorter itineraries available)

TRIP COST DOES NOT INCLUDE: Bike rentals (you may choose to bring your own bike or rent one for €150 Euros), lunches, 2 dinners.

Day 1: Arrival in Palermo, transfer on your own to hotel accommodations in Palermo.

Day 2: Morning transfer from Palermo, Sicily to Segesta where you will start biking. Our Italian representative will pick you up at your hotel in Palermo after breakfast and drive you to the start of the day's biking in Segesta. They will go over all of the trip logistics and fit you with a rental bike at that time. In Segesta, there is no way of describing the beauty of the place: the golden stone of the temple shining in the sun and the peacefulness of the lanscape of soft hills rolling toward a sea as blue as saffire. After visiting the archeological site you will start biking to Scopello, (30km) a tiny village on the seaside in the Castellamare gulf at the entrance of the Zingaro park. This village is comprised of a charming little hotel and a few cafes in the enclosed courtyard of a " Baglio" a fortified farmhouse that is now transformed into private residences.

Day 3: Scopello /Erice - (62 km) Your cycling destination today is Erice, a small medieval town on top of Mount San Giuliano that overlooks the Mediterranean. Erice is the only Sicilian town that has been inhabited since prehistoric times. You ’ll have plenty of time to enjoy its winding cobblestone streets, castle walls and picturesque squares in the historical part of town. Make sure to try some of the pastry shops! Hotel in Erice.

Day 4: Erice/Marsala - (60km ) You begin your downhill trip toward the sea. You'll make your way to the Salt Road on the west coast of Sicily. Here you will find numerous salt mills and endless views of seaside life in Sicily. Your destination is Marsala, a city rich in Carthaginian, Roman, Norman and Arab history. Spend the night in the old center of Marsala enjoying a meal of the freshest fish.

Day 5: Marsala/ Selinunte - (70km). You are off and riding to the temples of Selinunte. Founded by the Greeks in the 7th century BC, Selinunte is one of the most intriguing archaeological sites in the Mediterranean area. From the massive acropolis you’ll have a panoramic view of distant hillsides dotted with temples that stretch to the sea. Hotel near Selinunte.

Day 6: Selinunte/Contessa Entellina - (65 km) - Today you’ll pedal to the Ruins of Poggioreale. The route that leads to Poggioreale, one of the towns of the Belice Valley struck by the earthquake in 1968. Tonight's accomodation is in a B & B and though a bit simple, this is always a favorite with our guests.

Day 7: Contessa Entellina/Piana degli Albanesi - (64km) - Today you'll pedal through a vast agricultural region of vineyards and olive groves. This is also the area where Pecorino, a flavorful typical Italian cheese, is produced. Your evening lodging is in the countryside in a luxurious farmhouse.

Day 8: Piana degli Albanesi/Monreale - (50km ) - Almost entirely descending, you return to civilisation. The superb Monreale cathedral of pure shining gold will be the best ending to the day and the Baglio Conca d'Oro a welcome night's accommodation. Monreale is world-renowned for its Cathedral called Santa Maria la Nuova, a dazzling mixture of Arab, Byzantine and Norman artistic styles framed by traditional Romanesque architecture, all combined in a perfect blend of the best that both the Christian and Muslim worlds of the 12th century had to offer. Hotel in Monreale.

Day 9: Monreale /Palermo - In the morning you will be transferred to Palermo. (You could also choose to spend your final night 8 in Palermo rather than Monreale.)

DATES: March through October

TRIP COST: €1,400 Euros/pp (double occupancy) Single supplement: €275 Euros

TRIP COST INCLUDES: 9 days/8 nights, 8 nights hotel, 8 breakfasts, 4 dinners, luggage transfer, trip information package that includes maps, route descriptions, suggested sights to visit, emergency phone numbers for our Italian staff support (shorter itineraries available).

TRIP COST DOES NOT INCLUDE: Bike rentals (you may choose to bring your own bike or rent one for €150), lunches, 4 dinners.

The Piedmont is the Undiscovered Cyclist’s Paradise! Nestled between France, Switzerland and the Mediterranean, the Piedmont is a rich agricultural province most famous for its exceptional cuisine and superb wines, but the hidden gem is the remarkable bicycling. You will be riding on quiet roads that wind through vineyard covered hillsides dotted with quaint medieval villages and regal castles. The visuals are truly astounding!  Your nightly accommodations are a wonderful mix of old-world style inns and country houses to give you a good feel for the history and charm of this unique area.

Day 1: Transfer from the train station in Alba to your first lodging. You'll have a bike fitting in the early afternoon and then take an easy introductory ride
A wine tasting is scheduled and you will overnight for 2 nights in Barolo. 20 km Hotel di Barolo

Day 2: Today's ride has a few climbs and is well worth the effort. In the historical town of Monforte there is a patrician residence built on the walls of an old castle, a 13th century bell  tower and a parish church dating to the 10th century. You return to Barolo for the evening. Hotel di Barolo

Day 3: You will visit the lovely town of Alba, known as the City of 100 Towers. In the city center are impressive medieval towers and Roman walls, and many refer to Alba as the truffle capital of the Piedmont. 60 km and then ride to Torre Bormida. You will cycle to Dogliani, the capital of southwest Langhe, where you find the much admired Dolcetto wine. 60 km Farmhouse La Costa, dinner included

Day 4: You will ride to the fascinating city of Monastero Bormida, famous for its main square and castle, and finish in Acqui Terme, your home for 2 nights. 45 km
dinner on you own in the first evening.

Day 5: From Acqui Terme, you will ride through a sparsely populated region into the Appennino Hills, one of the most beautiful places in the Piedmont. 60 km, dinner tonight is a special experience in the home of a local Italian family

Day 6: After leaving Acqui Terme, you'll cross the boundary between the Dolcetto and Barbera vineyards on route to Noche di Vinchio. 60 km Farmhouse San Michele, dinner included

Day 7: A visit to Canelli and Cantina Fratelli Gancia loop ride from Noche. Wine tasting at one of the most important cellars of the Piedmont, Moscato Spumante (spumante = sparkling white wine) Farmhouse San Michele, dinner included.

Day 8: Morning transfer to train station in Asti.

DATES: April through October.

TRIP COST: €1,100/pp (double occupancy) Single supplement: €300

TRIP COST INCLUDES: 8 days/7 nights, 8 nights hotel, 8 breakfasts, 4 dinners, luggage transfer, trip information package that includes maps, route descriptions, suggested sights to visit, emergency phone numbers for our Italian staff support (shorter & longer itineraries available)

TRIP COST DOES NOT INCLUDE: Bike rentals (you may choose to bring your own bike or rent one for €100)lunches and 3 dinners

Veneto is an enchanting province in northeastern Italy situated between the deep blue of the Adriatic Sea and the brilliant white of the Dolomite Mountains. This easy-paced cycling tour is a visually stunning journey through an area rich in art, culture, history and natural beauty. The Veneto region combines the maritime feeling of the canals of Holland with the stunning architecture and vineyards of France’s Loire Valley to make a wonderful vacation destination for riders of all abilities.The route uses uncrowded country roads that wind past extensive vineyards, near two of Italy’s largest rivers and along a network of canals that lead to picturesque small towns. The tour spends two nights in Venice, amid the historical splendor of its churches, the lace like elegance of its palaces and the romance of its canals.

Day 1: Arrival in Vicenza. The town of Andrea Palladio, famous architect of the 17th century who influenced the architecture to the 19th century. Discover its palaces, churches and little streets. Between the small lanes one can still find the domicile of Pigafettas, the seafarer and the companion of Magellan. You will be have a 6 pm meeting with our Italian representative who will give you your maps and spend time with you going over all of your trip logistics as well as delivering your rental bike.

Day 2: Vicenza - Bassano del Grappa (40 km.) From Vicenza you pass along the venetian fields heading to Sandrigo, home of the "Baccalà alla Vicentina". Then along the walls, the castle and the Square of the Human Chess Game“ of Marostica, scene of the famous chess-game that dates back to 1454 when Marostica belonged to the Venetian Republic. Finally, you reach Bassano del Grappa, a charming town in the valley of the mountains, famous for its old wooden bridge and the grappa!

Day 3: Bassano del Grappa - Treviso (55 km.) Passing gentle hills you get to Asolo, a magical village that Robert Browning called the "Jewel of Italy". Enjoy strolling down the town's narrow streets and romantic cobblestone plazas. You will cycle along the back roads between the wine-fields of the prosecco to Maser where you can see the most splendourous villa of Palladio: Villa Barbaro. The ride ends in Treviso, a lovely city surrounded by water and known for the creation of the famous Italian dessert, tiramasu. This region is also known for its cultivation of grapes and ancient vines.

Day 4: Treviso - Venice (45 km.) Leaving Treviso, you follow the silent course of the river Sile to Casale. This is a most impressive stretch of the tour. Small villages reflect on the water, which, in the past, was an important tradeway. Take a look at the cimitero dei Burci (cemetery of the Burcis). The burcis are old barges, which now lay semi-sunken where you can see a variety of different waterfowl. At the end of this stage, Venice awaits you with an evening between little lanes and canals.

Day 5: Venice - Today you are free to explore Venice, the most romantic and beautiful city in Italy!

Day 6: Venice - Chioggia (25 km.) Take the ferry along the canal Giudecca and reach Lido. Cycling alongside picturesque houses and fishing boats you take a boat to the island of Pellestrina, a narrow eleven kilometre-long barrier suspended between sea and lagoon. A third ferry ride takes you to Chioggia, a miniature replica of Venice, complete with a vast cathedral, fine plaza and numerous canals. The only thing missing here are the tourists! You will spend the night in a on the waterfront near the ferry.

Day 7: Chioggia - Padua (60 km.) Cycling through countryside, along country lanes and beside two rivers that, along with the Sile, were the main trade routes in this Venetian region. Alongside ancient working canals and locks until you arrive at Stra at the beginning of the Riviera del Brenta which is famous for its garden and maze. Once you arrive in Padova, the home of Italy’s second oldest university, which was built in 1222, you can take a stroll through this renaissance city, following the footsteps of Galileo.Shakespeare called Padua “the Nursery of the Arts.” Do not miss a visit to the dazzling Scrovegni Chapel with the frescoes of the life of Christ by Giotto. Also worth a visit is the huge Basilica del Santo, the historical café Pedrocchi, the Prato della Valle, and the astronomical clock.

Day 8: Padua - Vicenza (45 km.) Today you cycle alongside the river Bacchiglione to arrive in Costozza, a small village at the foot of the Berici hills, where you can admire the beautiful gardens of the Villa da Schio. Visit the old Ice cave of the Villa now a very unique wine bar. The cyclepath takes you past the Villa Rotonda, the most famous villa of Palladio. Before arriving into Vicenza, you have the opportunity to visit the villa Valmarana ai Nani, so called because of the statues decorating the property. In the inside one can admire the frescoes of Tiepolo.

Day 9: Vicenza. Your tour ends after breakfast.

PLease Note: If you prefer a shorter tour, you can easily eliminate the last night in Vicenza and/or the second night in Venice. Tour costs will be adjusted for the shorter tours.

DATES: MID-MARCH THROUGH OCTOBER. Trips begin in Vicenza on Saturdays. Other departure days may be arranged for an additional cost.

TRIP COST: €1,000/pp (double occupancy) Single supplement: €300

TRIP COST INCLUDES: 9 days/8 nights, 8 nights hotel, 8 breakfasts, luggage transfer, trip information package that includes maps, route descriptions, suggested sights to visit, emergency phone numbers for our Italian staff support (shorter itineraries available), hybrid bike rentals.

TRIP COST DOES NOT INCLUDE: lunches and dinners, train and ferry transfers.

Check out our Guided Italy Tours:

Tuscany & Umbria Cycling l Sardinia & Sicily Cycling l Piedmont Cycling