I am reliving the best of my travels across Italy in 2015 and 2019 by organising a majestic mid-summer trip of top Cultural and Outdoor activities. For 7 days immerse yourself in breath taking countryside, charming old cities and the very best of Italian culture. With plenty of activities including walking, cycling, and visits to Florence, the Mediterranean and Lake Trasimeno – a memorable trip awaits. Beginning with an early morning train journey from Rome to Certaldo via Florence. Certlado in the Tuscan wine region will be our base for the first 3 nights.

Tuscany premiers with it’s beautiful rolling countryside, and numerous charming towns with centuries of heritage and story. Umbria the Green Heart of Italy also boasts many medieval towns, and endless delights. Soak up the peace around Assisi and refresh at the sandy shores of Lake Trasimeno. Ramble through the countryside of golden sunflowers, oak groves and olive trees. My photos from 2015 give a sample of the many highlights across Umbria and Tuscany – an exciting feast of Culture, Fiesta and Outdoors awaits!
The June 9 tour is full, and the next tour begins on Saturday September 16. Departure from Roma Termini station at 8am to Florence and later then to our accommodation in Certaldo.
The Itinerary is almost the same as June, with the addition of a local festival close to Assisi in the evening – Palio San Michele! A festival where an entire city becomes a theatre, and catering taverns around the city serve up Umbria’s best cuisine prepared with passion by the locals! On Friday September 22 we return to Rome in the afternoon. https://www.paliodesanmichele.it/
Itinerary
- Sat: Train travel to Florence sights, and light evening walk. Train to Certaldo
- Sun: Walking Trail from Certaldo to ancient city of towers – San Giminango (12k)
- Mon: Train travel to Pisa, and Viareggio by the sea
- Tue: Morning local walk. Afternoon departure to Umbria. Arrival in Assisi for 3 nights. Evening walk in the foothills to Rocca Maggiore castle
- Wed: Local Greenway cycle, Best Greenway in Italy 2015! Evening at Palio festival
- Thurs: Train hop to Lake Trasimeno region for local Trekking
- Fri: Train to Rome
- All walks are moderate, the walk to San Giminango is the most demanding.

Accomodation and Flights
Flights : See skyscanner.com or any Airlines for flights. People can meet up in Rome on Friday night September 15 at Alessandro Palace hostel(link below) near the train station. I can also meet people at the train station arriving from Rome Airport. The outgoing train route is Rome-Florence-Certaldo, and the return route is Assisi-Rome. Perhaps book a Saturday flight home.
On Saturday September 16, we plan to depart by train out of Rome at 8am.
*I would advice Rome is the best hub for returning home coming from Assisi(Umbria).
Accommodation, Certaldo 3 nights: We stay in a couple of apartment and guesthouse options
Assisi 3 Nights : Similarly a lot of the group can stay at a Guesthouse in Assisi with twin rooms. Assisi is a beautiful picturesque city on a hillside leaning against Monte Subasio. It has some beautiful old town options

https://Skyscanner.ie
https://alessandropalace.com/en/home-alessandro-palace/ (Rome Hostel)
https://www.italiarail.com
Train travel is reasonably priced – take a look at Italiarail.com. The six train journeys are currently priced at €126.
Mini bus taxi will be used for part of trip, about €10.
We will have an organised group meal every day, lunch or dinner.
A Group meetup will be arranged before departure – a walk followed by pizza in April!!
Book those flights and have 7 fabulous days across Italy!
Please Email with any queries or feedback: Mrk.smyth@gmail.com














