29 days in Italy Itinerary

29 days in Italy Itinerary

Created using Inspirock Marche trip itinerary planner

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Route & dates

29 days in Italy Itinerary

Start: Ancona
1
Ancona
— 12 nights
Drive:  30​min
2
Sirolo
— 3 nights
Drive:  15​min
3
Loreto
— 2 nights
Drive:  1​h 15​min
4
Fabriano
— 3 nights
Drive:  1​h
5
Terre Roveresche
— 1 day
Drive:  45​min
6
Urbino
— 2 nights
Drive:  1​h
7
Gabicce Mare
— 2 nights
Drive:  15​min
8
Gradara
— 2 nights
train:  45​min
9
Senigallia
— 2 nights
train:  30​min
End: Ancona

12
nights
Ancona

Ancona ©
Ancona is a city and a seaport in the Marche region in central Italy, with a population of around 101,997. Do some cultural sightseeing at Cattedrale San Ciriaco and Azienda Agricola Lanari. Let the collections at Museo della Rocca and Museo della Liberazione di Ancona capture your imagination. Change things up with these side-trips from Ancona: Chiaravalle (Casa Natale di Maria Montessori & Abbazia Santa Maria in Castagnola) and Riserva Naturale Ripa Bianca (in Jesi). There's much more to do: enjoy the sand and surf at Baia di Portonovo, identify plant and animal life at Orto Botanico Selva di Gallignano, head outdoors with Mezzavalle, and contemplate in the serene atmosphere at Chiesa Santa Maria della Piazza.

To find where to stay, ratings, reviews, and more tourist information, you can read our Ancona trip itinerary planner.

If you are flying in from Thailand, the closest major airports are Ancona Falconara Airport, Federico Fellini International Airport and Perugia San Francesco d'Assisi – Umbria International Airport. Expect a daytime high around 30°C in June, and nighttime lows around 19°C. Wrap up your sightseeing on the 19th (Wed) to allow time to drive to Sirolo.

Things to do in Ancona

Parks Historic Sites Museums

Side Trips

Offagna, Chiaravalle, Chiesa del SS. Sacramento, Parco Zoo Falconara, Riserva Naturale Ripa Bianca
Find places to stay Jun 7 — 19:
Highlights from your plan
Baia di Portonovo ©
Baia di Portonovo
Cattedrale San Ciriaco ©
Cattedrale San Ciriaco
Rocca Medievale Di Offagna ©
Rocca Medievale Di Offagna

3
nights
Sirolo

Sirolo ©
Sirolo is a comune (municipality) in the Province of Ancona in the Italian region of Marche. On the 20th (Thu), delve into the distant past at Grotte di Camerano - Citta Sotterranea di Camerano, examine the collection at Antiquarium Statale, and then kick back and relax at Riviera del Conero e Colli dell'Infinito. On the next day, stroll through Beach of the Two Sisters and then kick back and relax at Spiaggia dei Sassi Neri.

To find more things to do, traveler tips, reviews, and tourist information, refer to the Sirolo driving holiday planner.

Sirolo is just a stone's throw from Ancona. In June, plan for daily highs up to 30°C, and evening lows to 19°C. Wrap up your sightseeing by early afternoon on the 22nd (Sat) to allow enough time to drive to Loreto.

Things to do in Sirolo

Outdoors Beaches Parks

Side Trips

Filottrano, Grotte di Camerano - Citta Sotterranea di Camerano, Antiquarium Statale
Find places to stay Jun 19 — 22:
Highlights from your plan
Museo Del Biroccio ©
Museo Del Biroccio
Antiquarium Statale ©
Antiquarium Statale

2
nights
Loreto

Loreto ©
Loreto, a hill town, is a comune of the Italian province of Ancona, in the Marche and most commonly known as the seat of the Basilica della Santa Casa, a popular Catholic pilgrimage site.LocationLoreto is located 127m above sea level on the right bank of the Musone river and 22km by rail south-southeast of Ancona; like many places in the Marche, it provides good views from the Apennines to the Adriatic.Main sightsThe city's main monuments occupy the four sides of the piazza: the college of the Jesuits; the Palazzo Comunale (formerly the Palazzo Apostolico), designed by Bramante, that houses an art gallery with works of Lorenzo Lotto, Vouet and Annibale Carracci as well as a collection of maiolica, and the Shrine of the Holy House (Santuario della Santa Casa). Kick off your visit on the 22nd (Sat): explore the world behind art at Museo Cinema a Pennello and then examine the collection at Casa Leopardi. Here are some ideas for day two: take in the spiritual surroundings of Santuario Della Santa Casa, enjoy the sand and surf at Porto Potenza Picena - Spiaggia Libera, then examine the collection at Museo della Carrozza, and finally contemplate in the serene atmosphere at Abbazia Cistercense Santa Maria di Chiaravalle di Fiastra.

For reviews, other places to visit, more things to do, and tourist information, use the Loreto vacation site .

Loreto is very close to Sirolo. In June, daytime highs in Loreto are 30°C, while nighttime lows are 19°C. Wrap up your sightseeing by early afternoon on the 24th (Mon) to allow enough time to drive to Fabriano.

Things to do in Loreto

Historic Sites Museums Outdoors

Side Trips

Casa Leopardi, Lungomare di Porto Sant'Elpidio, Abbazia Cistercense Santa Maria di Chiaravalle di Fiastra, Porto Potenza Picena - Spiaggia Libera, Piazza del Popolo
Find places to stay Jun 22 — 24:
Highlights from your plan
Museo Cinema a Pennello ©
Museo Cinema a Pennello
Casa Leopardi ©
Casa Leopardi
Santuario Della Santa Casa ©
Santuario Della Santa Casa

3
nights
Fabriano

Fabriano ©
Fabriano is a town and comune of Ancona province in the Italian region of the Marche, at 325m above sea level. Start off your visit on the 24th (Mon): learn about winemaking at Belisario and then see the interesting displays at Museo del Pianoforte Storico e del Suono. Here are some ideas for day two: learn about winemaking at Foyer Verdicchio di Matelica, look for all kinds of wild species at Gole dell’Infernaccio, and then see the interesting displays at Paper and Watermark Museum Fabriano.

For where to stay, maps, photos, and other tourist information, read Fabriano trip itinerary tool .

You can drive from Loreto to Fabriano in 1.5 hours. Another option is to take a train. June in Fabriano sees daily highs of 30°C and lows of 19°C at night. On the 27th (Thu), you'll travel to Terre Roveresche.

Things to do in Fabriano

Wildlife Parks Museums

Side Trips

Gubbio, Matelica, Gole dell’Infernaccio, Parco Naturale Regionale della Gola della Rossa e di Frasassi
Find places to stay Jun 24 — 27:
Highlights from your plan
Gole dell’Infernaccio ©
Gole dell’Infernaccio
Paper and Watermark Museum Fabriano ©
Palazzo dei Consoli and Museo Civico ©

1
day
Terre Roveresche

Terre Roveresche ©
Start off your visit on the 27th (Thu): explore the historical opulence of Rocca Roveresca, then don't miss a visit to Walls, then take in the architecture and atmosphere at Santuario Diocesano di Santa Maria Goretti, and finally experience rural life at Azienda Agraria Guerrieri.

Find out how to plan Terre Roveresche trip without stress by asking Inspirock to help create an itinerary.

Traveling by car from Fabriano to Terre Roveresche takes an hour. In June, daytime highs in Terre Roveresche are 30°C, while nighttime lows are 19°C. Wrap up your sightseeing on the 27th (Thu) early enough to drive to Urbino.

Things to do in Terre Roveresche

Historic Sites Wineries

Side Trips

Corinaldo, Rocca Roveresca
Find places to stay Jun 27 — 28:
Highlights from your plan
Azienda Agraria Guerrieri ©
Azienda Agraria Guerrieri
Walls ©
Walls

2
nights
Urbino

Urbino ©
Urbino is a walled city in the Marche region of Italy, south-west of Pesaro, a World Heritage Site notable for a remarkable historical legacy of independent Renaissance culture, especially under the patronage of Federico da Montefeltro, duke of Urbino from 1444 to 1482. On the 28th (Fri), steep yourself in history at Casa Natale di Raffaello, explore the world behind art at Oratorio di San Giuseppe, take in the spiritual surroundings of Oratorio di San Giovanni Battista, then contemplate in the serene atmosphere at Cathedral, then admire the striking features of Galleria Nazionale delle Marche, and finally admire the masterpieces at Palazzo Ducale di Urbino. Keep things going the next day: explore the activities along Parco Naturale del Sasso Simone e Simoncello.

To see other places to visit, reviews, and other tourist information, refer to the Urbino trip itinerary planner.

Traveling by car from Terre Roveresche to Urbino takes an hour. In June in Urbino, expect temperatures between 30°C during the day and 19°C at night. Finish up your sightseeing early on the 29th (Sat) so you can go by car to Gabicce Mare.

Things to do in Urbino

Outdoors Wildlife Nature

Side Trip

Parco Naturale del Sasso Simone e Simoncello
Find places to stay Jun 27 — 29:
Highlights from your plan
Palazzo Ducale di Urbino ©
Palazzo Ducale di Urbino
Galleria Nazionale delle Marche ©
Galleria Nazionale delle Marche
Oratorio di San Giovanni Battista ©
Oratorio di San Giovanni Battista

2
nights
Gabicce Mare

Gabicce Mare ©
Kick off your visit on the 30th (Sun): enjoy the sand and surf at Lido delle Sirene, kick back and relax at La Spiaggia Malu 90 93, and then admire the local landmark of Fontana Delle Sirene. Here are some ideas for day two: kick back and relax at I Delfini Beach Village, enjoy the sand and surf at Altamarea Beach Village, and then contemplate in the serene atmosphere at Chiesa di Maria SS. Immacolata.

To find where to stay, reviews, and tourist information, read our Gabicce Mare trip builder site .

You can drive from Urbino to Gabicce Mare in an hour. In June, daytime highs in Gabicce Mare are 30°C, while nighttime lows are 20°C. Finish up your sightseeing early on the 1st (Mon) so you can travel to Gradara.

Things to do in Gabicce Mare

Beaches Outdoors Parks

Side Trip

Cattolica
Find places to stay Jun 29 — Jul 1:
Highlights from your plan
Altamarea Beach Village ©
Altamarea Beach Village
I Delfini Beach Village ©
I Delfini Beach Village
Chiesa di Maria SS. Immacolata ©
Chiesa di Maria SS. Immacolata

2
nights
Gradara

Gradara ©
Gradara is a town and comune in the Province of Pesaro e Urbino (PU), in the region of Marche in central Italy. Start off your visit on the 2nd (Tue): don't miss a visit to Chiesa San Giovanni Battista in Gradara, see the interesting displays at Museo Storico di Gradara, look for all kinds of wild species at Il Teatro dell'Aria, then step into the grandiose world of Castello di Gradara, and finally don't miss a visit to Camminamenti di Ronda. On the next day, explore the different monuments and memorials at Cimitero di Guerra del Commonwealth, enjoy breathtaking views from Torre del Girone, don't miss a visit to Gothic Line Q204 Memorial, then stroll the grounds of Montecchio War Cemetery, then contemplate in the serene atmosphere at Abbadia di San Tommaso in Foglia, and finally look for gifts at vr46 Store.

For ratings, maps, reviews, and more tourist information, go to the Gradara day trip website .

Gradara is just a stone's throw from Gabicce Mare. In July, daytime highs in Gradara are 34°C, while nighttime lows are 23°C. Wrap up your sightseeing on the 3rd (Wed) to allow time to take a train to Senigallia.

Things to do in Gradara

Historic Sites Wildlife Parks

Side Trips

Tavullia, Montelabbate, Torre del Girone
Find places to stay Jul 1 — 3:
Highlights from your plan
Castello di Gradara ©
Castello di Gradara
Il Teatro dell'Aria ©
Il Teatro dell'Aria
Cimitero di Guerra del Commonwealth ©

2
nights
Senigallia

Senigallia ©
Senigallia is a comune and port town of the province of Ancona on Italy's Adriatic coast, in the Marche region. Start off your visit on the 4th (Thu): see the interesting displays at Museo del Telefono, then explore the galleries of Palazzo Pianetti, and then kick back and relax at Baia Canaria. Get ready for a full day of sightseeing on the 5th (Fri): step into the grandiose world of Rocca Roveresca di Senigallia and then tour the pleasant surroundings at Bagni 77.

To see more things to do, ratings, where to stay, and tourist information, you can read our Senigallia online vacation builder .

Getting from Gradara to Senigallia by train takes about an hour. Other options: drive; or do a combination of bus and train. July in Senigallia sees daily highs of 34°C and lows of 22°C at night. Finish up your sightseeing early on the 5th (Fri) so you can catch the train back home.

Things to do in Senigallia

Outdoors Beaches Parks

Side Trips

Museo del Telefono, Palazzo Pianetti
Find places to stay Jul 3 — 5:
Highlights from your plan
Baia Canaria ©
Baia Canaria
Museo del Telefono ©
Museo del Telefono
Palazzo Pianetti ©
Palazzo Pianetti
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