How would you spend your time if you had seven weeks to travel in Italy? My husband and I had that opportunity before we moved from Milan to the USA, and because I get the “what should I see in Italy” question so often, I thought I’d share what we decided to see on that particular trip, and why we chose each place.
If it had been our first trip to Italy, I would have started with a standard two week Italy itinerary. But after 5 years in Italy – including having worked as a tour leader – I’d done Rome, Florence, Venice and much more, so we were looking for Italy off the beaten track, and our itinerary became a mix of places neither of us had been (Dolomites, Isola della Maddalena, and Ischia), mixed with places I’d been but my husband hadn’t.
We started at the end of June, and spent a week hiking in the Val Gardena in the Dolomite mountains. Why we chose it: We both love hiking, and July is the perfect month to visit the Dolomites, because it’s warm and not as crowded as August. Some of the most incredible hikes I’ve ever done were on this trip – and I grew up hiking in the Rocky Mountains.
Tuscany is not the first place people think of when they think about Italy off the beaten track but there are so many wonderful small towns, and just exploring the countryside is fabulous. I’d spent a lot of time in Tuscany, guiding week-long biking tours in a few different corners of the region, and I wanted to introduce my husband to this part of the country.
We rented a car and spent 10 days in Tuscany exploring the countryside. We also hit the less off the beaten path stops of Siena, San Gimignano, Monteriggioni, Montepulciano and Pienza. Why we chose it: It was partly a wandering-the-hills-of-Tuscany trip for photography, looking for fields of sunflowers and just taking our time exploring and discovering.
We started with 5 days in gritty, authentic Naples, then hit the archaeological ruins of Pompeii and spent 4 days on the island of Ischia. Since it was high season, we chose Ischia over the island of Capri because there were fewer crowds. We rented motorinos on Ischia to get around, and loved Ischia’s natural hot springs. Why we chose it: I like the balance of putting Naples, Pompeii and Ischia together, because you start with a big vibrant city, then visit an incredible must-see attraction (but with lots of tourists), and then end with island beach time.
We spent 4 days on the Amalfi Coast after driving on impossibly narrow and twisting roads over the mountain from Naples — which I would not recommend for any couple. We didn’t miss the main tourist towns of Positano and Ravello of course, but we also visited lots of smaller towns along the coast. Why we chose it: I had been, and wanted to go back with my husband because it’s such a romantic spot (or became romantic after we made up post mountain-crossing!)
We flew to Sardinia and then took a boat to Isola Maddalena and spent a week exploring the island, lying on the beach, going for bike rides, and SCUBA diving (I got my certification there). Why we chose it: With only a week, we didn’t have nearly enough time to visit the huge island of Sardinia, so we chose 1 spot, saw it well, and relaxed.
We spent 2 weeks on the island of Sicily, which I wrote about in detail. Why we chose it: I had been to Sicily before and wanted to go back. Sicily is another great place for a balanced vacation. We climbed a volcano, lay on the beach, walked through Greek ruins, spent time in large bustling cities, saw incredible art, and ate and drank well.
So that adds up to a little more than 7 weeks believe it or not! (We actually had more time off, and also took a week to go up to Switzerland and see the Montreux Jazz Festival, on at the end of July every year.) And after all that, was I satisfied? Well, yes. But my still-to-visit list in Italy is long, because when you go to Italy with a list of things to see, you don’t come home with everything checked off. You come home with a longer list.
Photos: me hiking in the Dolomites, detail from the Nile Scene mosaic at the archaeological museum in Naples, view from Isola Maddalena of the bridge to Caprera. All photos by Sanjay.
"We had a wonderful trip! We did so many amazing things and experienced many wonderful places yet never felt like..."
"We thank you so much for all you gave us, guided us to, arranged for, and detailed for us. Not..."
"We are in love with Venice and the Dolomites. The ski adventure was amazing and beyond anything we could have..."
"Absolutely everything that you planned went off without a hitch. Every tour, every restaurant, every train and activity came through..."
"Thank you again from all three of us for your help in planning such a delightful trip. I know that..."
"Madeline carefully planned a fabulous, personalized 19 day itinerary (Lake Garda, Dolomites, N/S Tuscany, Rome) that enabled us to be..."
Join our mailing list to get the free Driving In Italy eBook
Check out the Travel Expert Network where you’ll find Certified Travel Experts™ like us ready to plan custom bucket trips for you all over the world!
Visit the Travel Expert Network →
+1 773 621-3024
Contact San Francisco
+39 320 028 6827
+39 331 222 2349
Subscribe to our newsletter.