Tuscany, Umbria and Cinque Terre in October ~ October 5th - 17th, 2025

We spent 5 nights in Tuscany, at the beautiful, Hotel Borgo Di Cortefreda, 3 nights in Assisi at the historic and lovely Hotel Giotto Assisi, and 3 nights in the Cinque Terre area of Rapallo at the perfectly placed Hotel Tigullio Royal. All the hotels were excellent, had a nice breakfast, great settings and nice amenities.

Our time in Tuscany was comprised of a variety of wine tastings at numerous lovely wineries, a really fun cooking class, day trips to the historic towns of Pisa, Siena, Lucca, San Gimignano and a day in Florence which included seeing the famous David by Michelangelo. The wine tastings were at a variety of vineyards, all different, extremely nice and many included a meal and additional wine. We definitely had plenty of great wine on this trip! Our Tuscanm hotel had a beautiful outdoor area with a pool where you could relax and watch the sunset. This portion of the trip was pretty jam packed and busy but there were moments to breathe and relax and many definitely enjoyed that sunset view.

The next stop was Umbria and the amazing town of Assisi! We enjoyed a day trip and tour to Perugia and tour of the town of Assisi and the incredible St. Frances of Assisi Basilica. While in Assisi the group was able to enjoy a bit more free time on their own. The Basilica is huge and the town is very walkable and provides a good cardio workout as much of it is uphill (but then you do get to go down!) There was a “March for Peace” an annual event where the participants walk from Perugia to Assisi (25 km). Although it did provide a bit of an afternoon crowd it was interesting to see. We also got to see a Polish contingency who had made a pilgrimage to Assisi. Their beautiful outfits were striking and they sang on the steps of a local church, much to our delight. It was really unique to see that.

Our last stop was the lovely city of Rapallo and we had a very nice stay at the Hotel Tigullio Royal which was right on the water, rooftop bar that many enjoyed and there was a very nice walking path along the water that went for many miles in either direction. From there we trained to the Cinque Terre region, first stop was Manarolo, then on to Riomaggiore and Monterosso. They are just beautiful towns situated on the edge of hills, reaching down to the Mediterranean. Transportation that day included both trains and ferries, and to be able to enjoy the site of the towns from the water is spectacular. Our last day we ferried the Gulf of Tigullo to Portofino and Santa Margherita- just beautiful!

All the travelers enjoyed the trip immensely! It was a bit faster paced in the beginning then slowed a bit and people were able to spend more time on their own and relax a bit. There was quite a bit of walking up and down hills and steps but everyone was encouraged to go at their own pace and take a break if needed. We saw so much on this trip and many people expressed how fun it would be to rent a place in Tuscany and spend more time exploring that area. There is so much to see and do in these areas. The trip definitely provided a wonderful taste of all three areas.

Unfortunately there were a few flight issues but everyone did manage to arrive on October 6th. On the return, 12 travelers spent an evening at a hotel in Paris and 2 remained in Florence for a night, but everyone (and eventually, their luggage) made it home with everything intact.

Group Travel Simplicity (GTS) provided us with a wonderful guide, Ilenia Sala. She assisted any traveler with whatever they needed and she made the trip a lot more enjoyable, and definitely easier for me as a trip leader. I would highly recommend using a tour guide on a trip like this. GTS put together an excellent trip; the hotels were all lovely and well situated, the wineries and wine tastings were excellent, the local guides were all very good, and we had the added benefit of being on the second trip and being able to gets tips Debbie who led the first trip. 

I believe all the travelers truly enjoyed the trip and I definitely did!

Ellen Parda

Trip Leader, October, 2025