Thanks to all the folks that helped with advice in planning our long awaited trip to Italy. I am far overdue in reporting back but got sucked into a whirlwind of work upon our return, but as they say, better late than never, so here goes! We had a fantastic time over 2 weeks, starting with 2 nights in Venice, 2 nights in Rome, 4 nights in Sorrento, 4 nights in Montalcino and a night in Florence. People warned against the whirlwind but we loved it. Venice was an amazing place to start and one of our favorite stops, and Tuscany blew us away and definitely was the right place to finish. Sorrento, eh, and Rome and Florence we definitely had to see where the tourists were headed and turn the other direction, but everywhere we went we found wonderful spots that we fell in love with - and we can't WAIT to go back to Italy!!! Here are a few of the spots we loved that I'd highly recommend to others:
Al Prosecco in Campo S. Giacomo da L'Orio - this was a great spot we'd have never found if it weren't for the help of online reviewers. What a great lunch in Venice to really feel like we'd found our little piece of Italian paradise. We sat in a quiet little beautiful square and had this amazing platter, the Insalata de Pesce, with all kinds of little seafood treats. With a glass of prosecco and some crostini, this is a perfect lunch.
We enjoyed gelato from Alaska gelateria - the banana was wonderful - and dinners at Vini da Gigio and Do Farai, both of which were good but not the highlights of the trip. The can't miss would be Al Prosecco. We went before and after dinner each night to a great bar on the water but around the corner from the St. Mark's crowd and off the beaten path where they made perfect negronis and provided blankets at night. We stayed at Ca' Angeli which I'd recommend - for the price the service and quality and location were all quite good. The water bus is really convenient - no need for a water taxi. St. Mark’s and Rialto are absolute madness but we liked the Doge's Palace.
We found a fantastic wine bar by the Pantheon called Spiriti that we really loved, the quintessential Roman setting. Would love to go back there someday. We also had one of our favorite meals of the trip here, at Etabli. The veal was phenomenal, veal slices "Roman style" with crispy ham on parmesan and sage fondue. The spaghetti with pepper was also delicious as was the grilled calamari. Great cocktails and vino, and setting and service. Highly recommended.
I loved the lemon gelato from Alberto Pico - we actually had some sandwiches and beer there too outside with the locals, not a bad low-key spot. Il Matriciano by the Vatican where we intended to have lunch was closed, but looked fancier than we were in the mood for anyway. We also had a wonderful experience getting a panini and coffees at a bar near the Vatican, which proved that you really can't stick to your lists when you wander, the little holes in the wall can be the best finds. We also had a great coffee at Tazza d'Oro, great cocktails at the Stravinsky Bar Hotel de Russie (super pricey but a delightful setting worth the splurge for a nightcap) and a good dinner at La Taverna dei Fori Imperiali (not a must visit but was near our hotel and a nice neighborhood spot). The Hotel de Russie - if you have some cash, what a place this would be to stay! Not so touristy and the epitome of luxury, and the ideal location at the Spanish Steps' best shopping off the beaten track of the crowds. We stayed at Nicolas Inn which was a great location for a quick tourist trip - right by the Coloseum - and good price. You get a voucher for breakfast at a classic Roman coffee bar instead of breakfast at the hotel. We loved the Coloseum and the Vatican but otherwise we just enjoyed walking around and exploring. Lunch our first day at Cavour 313 was good but not a must visit. Very convenient to Nicolas Inn though.
We squeezed in a quick pizza and beer lunch between our train ride and ferry. Not for the faint of heart if you're dragging all your luggage and not street savvy but if you're used to cities and can avoid pick pockets and live for food, definitely do it! Da Michele had fantastic pizza and was such a cool spot to check out. Tourists and locals alike crowded in for goodness.
Got these directions from someone on tripadvisor:
Da Michele - 10 minute walk from train station across the piazza and past all the buses. Walk straight away from the station by all the buses, bearing towards the far left corner of the piazza. Walk down Corso Umberto to Via Cesare Sersale, make a right and walk to number 1/3.
We didn't find the street name and almost missed the sign but a guy at a smoothie shop helped - they're used to directing tourists here so you'll get there if you're not afraid to ask! :-)
Not our best meals of the trip, but we did find, when in doubt, go to a place with Lanterna in the name. Lanterna, Lanterna Due, and there was a third one too - all guaranteed good service, a nice setting and quality pastas. I think my favorite was the fresh pasta with asparagus and calamari at Lanterna Due. We also had a lovely lunch at a wine shop and wine bar that had a nice garden terrace, where we had a fantastic lemon cake with lemon and orange sauce. Once we lowered our expectation of having food as good as we'd had in Venice and Rome we had some nice meals and a good time - and had the fantastic food of Tuscany to look forward to - but would have been tough to end the trip here! Loved the coconut gelato from Davide. (Yes, we ate a lot of gelato. I had chocolate cake for breakfast one day at the hotel at Sorrento! When in Italy...) Great hotel in Sorrento, Grand Hotel la Favorita. Great rooftop pool overlooking the coast. Most modern hotel we stayed in with the most comfortable beds of the trip, and a huge bath. At all costs avoid the Marina Grande for dinner. Worst experience of the trip. We'd also planned to go to Inn Bufalito but walked right out, it looked like touristy awfulness. The limoncello shops were also not a chowhound scene at all. The weather was rough when we went to Positano so we missed out on the Da Adolfo experience but had a nice wine filled lunch at one of the touristy spots on the beach. The bus to and from Positano looked painful - we ferried both way. We loved ducking in all of the little churches in this area - tiny and quiet.
The Hotel Vecchia Oliviera in Montalcino is a great place to base yourself for exploring this area. The service was phenomenal, the price and location were great, nice breakfast, great back patio for drinking wine in the sun, really recommended for this price range. Day trips from here to Montepulciano, Pienza, S Quirico, Siena, etc were all extremely easy. We started off with lunch at Enoteca Osteria Osticcio, what a way to start! A fantastic, unbelievable view of the valley, wonderful wonderful brunello, and really great food. We loved everything we ate, best of all the anchovy crostini. Made it back for a drink but would have had another lunch here had we more time. We had 2 of our best dinners in Montalcino, Taverna del Grappolo Blu, where our favorites were the tagliatelle with porcini and truffle and the orechiette with peas, proscuitto and chili; and Il Giglio, where our favorites were the truffle gnocchi and the chianini beef. Both meals were phenomenal with great wine and service and both are highly recommended. If I had to choose it would be down to whether you're in the mood for a more refined evening (Il Giglio) or a more classic Tuscan (Taverna del Grappolo Blu). It's definitely hard to stumble across a bad meal in Tuscany - we went off plan a bit and could never go wrong. Latte de Luna was closed the day we went to Pienza and we ended up at a wonderful little spot on a beautiful sunny courtyard - hard to complain! The first night we had to cancel our reservation at Osteria di Porta al Cassero due to our family arriving late and had a great experience at the one restaurant in town that could seat us so late - about 9:30 if I recall! So definitely don't think you can do the late dining you do in the Italian cities. We had a good dinner at Il Leccio but found we liked going to lunches in other areas and walking to dinner at night in Montalcino. We adored Sienna, this is a must visit if you're in the area - we preferred to Florence! Hard to find a place to eat that you can sit in the sun that isn't touristy, so just give in and sit in the Campo and enjoy the people watching. We had a wonderful porcini, speck and truffle pizza and big cold beers, tough to beat! Great gelato at Perche No, my favorite was the Bounty. We had a wonderful tour at Poggio Antico and bought some unbelievable Brunello to ship back. We hit another winery in the area as well but it didn't hold a candle to Poggio Antico. Our hotel was fantastic setting up winery visits with tours, dinner reservations, you name it. In fact, I emailed a lot of hotels for reservations before we came out soI didn't have to call places long distance since most don't do email, and most hotels were quite helpful. But our hotel in Montalcino was most helpful. We also loved the little town of S Quirico d'Orcia and bought some wonderful picnic items at a little shop there to enjoy in our back patio with some vino before heading down to hear the monks sing. Of course with all the vino and having finally said to hell with my files we missed the monks singing but that made for quite a laugh with the group! Le Logge was a good spot for drinks. We didn't buy any of the driving books everyone says you need
We stayed at Residenza Giotto. Location was convenient but really Florence is small so you don't have to worry about being close to the Duomo. The worst breakfasts of the trip for sure. Florence had WONDERFUL shopping, try not be be done spending when you get there, and leave some luggage space! Our best purchases of the trip clothing wise! Our lunch here was pretty average, can't even remember the name of the place, but had great shops nearby. We had walked over to Alla Vecchia Bettola but weren't feeling the area and decided to head back to the area we wanted to hang out. We had an amazing dinner in Florence, one of our favorites from the trip, the reviews aren't wrong, definitely recommend La Giostra. Come HUNGRY. Champagne, complimentary starters, filet topped with foie gras, we ate and ate and ate and loved it all. Great setting and service, definitely tourist geared but really great. Got to hear some crazy street band performing for the crowds in the streets, which was wonderful, and then had a nightcap at the Brunelleschi Hotel, which would also be a great place to stay with some cash, great location and very understated, worth checking out. We ended our trip with beers and sandwiches in the alley, at I Fratellini - Via dei Cimatori 38/r, 2 blocks from Piazza della Signoria, off Via Calzaiuoli, Near the Duomo. Great classic Italy experience. Not the best panini you'll ever have but good fun to go and sit with the Italians in the street.
We trained from Venice to Rome and then from Rome to Sorrento and then drove to Tuscany and then drove to Florence and flew out of Florence. The trains were great and the drive from Sorrento to Tuscany was great as well, beautiful. Definitely wouldn't do Tuscany without a car and definitely wouldn't have wanted a car elsewhere.
All in all a phenomenal first trip to Italy with lots of places we'd happily recommend. Not 100% thorough but hopefully my notes provide enough support to help others going over as all my online research helped us! Thanks again to those that helped me prepare!!!
For those looking for great research - Dean on SlowTrav had some really wonderful write-ups to get you started in Tuscany. Highly recommend starting there.
Ciao! And happy travels!