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Fall Italy Trip Planning Questions

My husband and I are planning our first trip to Italy - a bit of a dream trip! - and I'm feeling overwhelmed. I've been researching online for months and taking notes and reading books and asking friends for advice now it's time to get some flights and hotels booked and I want to make sure I'm on the right page. A bit about us - definitely not an unlimited budget but willing to pay to do it right where it matters (figure we won't spend much time in our hotels so location matters most but also want ideally comfortable beds and air conditioning!), foodies, don't want to cram too much in to ruin a trip...our favorite parts of a recent Paris trip were sitting outside on hidden alleyways with Parisians enjoying wine or coffee and just experiencing the city. Hope that helps! Oh - also - we'd rather eat authentic Italian cuisine at hole-in-the-wall Mom and Pop joints than Michelin star type places - we've learned this the hard way living in SF - but we don't mind if tourists like a place if it's worth visiting. :-)

SO - we've got about 2 weeks. We're more interested in spending time in small towns than big cities to really experience local culture, but obviously have to fly in and out of major cities so might as well see them. Here's what I'm thinking:
Fly into Florence
1-2 nights in Florence
Pick up rental car when leaving Florence
Head to Tuscany – Chianti region – stay in hilltop town – spend ½ our days here
Head to Amalfi Coast – 2-3 days?
One day take boat over to Capri for lunch
Drive to Rome
Drop off rental car
1-2 nights in Rome
Fly out of Rome

Hotels:

Florence - Hotel Perseo - figure we want to be quite local, this is just off Piazza Duomo

Rome - Hotel Navona - a few steps from the Piazza Navona

Tuscany - torn between Villa Cicolina in Montepulciano and Vecchia Oliviera in Montalcino, not sure which is a better place for exploring the Chianti region but also having a pretty local area to enjoy?

Positano - Hotel Marincanto

Restaurants:

Rome - based on where we're thinking of staying I'm thinking the best options are Il bacaro, Santa Lucia, Ristorante Fiammetta and Trattoria Monti. I am also interested in Ditirambo and Colline Emiliane but not sure if they are too far from where we're staying? Also obviously need to narrow this list down - what would be the best choice if I can only pick 1-3?

Florence - based on location thinking Il Latini, Osteria Delle belle, Cibreino, and Buca Lapi. Other options I like but not sure if they're hard location based on hotel - Coco Lezzone, Trattoria Sostanza, Da Sergio, Trattoria Mario, and Da Ruggero, and again, obviously need to narrow down to 1-3.

Tuscany - thinking at night we'd eat near our hotel, but try to have lunch in a different town each day? So I've narrowed down based on location. Are these the best in each area? Any towns we should skip over others, as we obviously won't be able to get to them all?
Montepulciano - Osteria dell' Acquacheta - also any other recommendations here in case we stay here?
Greve in Chianti - torn between Taverna del Guerrino and La Cantinetta di Rignana
Pienza - Latte de Luna
Panzano in Chianti - Solociccia (is this worth doing or better to just check out Dario's butcher shop?), also Ristorante Oltre Il Giardino would be an option
Castellina - Osteria alla Piazza
Radda - Le Vigne or Chiasso dei Portici
Monticchiello - Osteria la Porta
Strada - Ristorante da Padellina
Siena - Ristorante Conte Matto in Trequanda
Any great recommendations for restaurants in Montalcino, in case we stay there?

Also in Tuscany interested in hitting some wineries that we don't need to reserve tastings at. So far have only figured out Caparzo in Montalcino.

Other must dos in Tuscany outside of restaurants? Read that it's great to listen to the singing of the monks at the Abbey of Sant'Antimo outside Montalcino.

Positano - Lo Guarracino, Da Adolfo (lunch), Ristorante al Palazzo, La Tagliata, Da Costantino
Capri - La Fontelina (is this an easy one to do if we boat over from Positano?)

I know it's a lot to read through and give recommendations on and I know there have been an unheard of number of posts on this sort of topic. I can assure you I've read them! Just trying to get some input on my agenda as I get it finalized - any advice is greatly appreciated!!! Thanks in advance for your help!

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  1. wow. that's ambitious.
    deb and i like italy. we usually rent an apartment in march (rome, via giulia this year) and pretty much live on the economy.
    ditirambo is a decent restaurant off the campo de' fiori. try the cacio e pepe. make friends with the guys who run the place. you have time. rome isn't going anywhere.

    1. Regarding your Florence visit, the city is relatively small and you can walk to a lot of places or use the electic bus routes to get around more quickly. So for restaurant choices, you should focus on quality not distance from your hotel. That being said, I Latini is not very far from Sostanza, so you would be better off going to Sostanza for the bistecca forentina and you must try their pollo in burro (2 chicken breasts in a butter sauce which you will find exquisite). I Latini is a noisy free-for-all with lots of tourists (English is the main language you hear from the clientele) and the food is not all that great (nor is the price). Cibréo has 3 different rooms to choose from: Cibréo Ristorante (elegant, excellent, but pricey), Trattoria Cibréo (small intimate restaurant serving many of the dishes available at the ristorante but at much lower prices), and Teatro Del Sale for an experience unlike anything you will find in Florence or elsewhere. I did a write-up in December on this board (FLORENCE REPORT DECEMBER 2007 - LONG, BUT ...) I recommend you read it to get a feel for Teatro del Sale (at lunch - dinner includes live performances after the meal). It is the best dining experience we have ever had in Florence or Rome in our last 7 trips to those cities. There are other recommendations in that post which may be useful to you as well.

      As for Rome, I recommend you get away from concern about restaurants being near your hotel, as that will needlessly lessen your potential choices. Rome has a good bus system which you can use to get all around the city (monuments, restaurants, hotels) and the buses run into late evening hours (11 PM or later). The system is easy to figure out and your hotel concierge can assist you with route numbers or how to read the bus stops. If you are staying in Piazza Navona, Ditirambo is very close by and they have good home-made pasta but it is not an extraordinary place to dine. Trattoria Monti, however, is quite far from there and you would need the bus or taxi. I'm not fond of Trattoria Monti, as we had difficulty on 3 separate Rome visits finding them open for dinner (the restarurant was quite close to our hotel). So we finally got there for lunch and found it far from worthwhile and a bit pricey for what we had (roast stuffed pigeon done to dryness and the stuffing was too dense). For best value and good mean in Rome, we always go to Vladimoro/Marcello in the Via Veneto area. They serve a great fixed price menu which includes multiple vegetable appetizers (all you wish to eat), a platter of 3 different pastas, each in a different sauce, and a main course of roast veal with potatoes. Price is about 35-40 Euros per person if you drink their house wines.

      1 Reply
      1. re: CJT

        Thanks so much for your thorough response CJT, this is super helpful! :-)

      2. I agree with the above post regarding Il Latini. It was recommended to us by the proprietors of the hotel (the Belletini, which we liked a lot and very convenient), but it seemed touristy to us (forgettable food, communal tables, loud).

        You do not mention Lucca on your Tuscany tour. I think it would be a shame to miss it. It is close to Pisa, which we found totally forgettable, but Lucca is a beautifully preserved medieval city and the restaurant to go to is Buca di San Antonio. We had lunch there on 2 different trips and it was wonderful both times. Very popular with locals. If you can, I would try to spend some time in Umbria after Tuscany. Gubbio has a wonderful restaurant, Taverna del Lupo. Towns to visit include Gubbio, Assisi, Todi, Spoleto and Orvieto (plus many smaller hill towns). The scenery is magnificent, more beautiful and green than Tuscany, and many great restaurants (if you decide to spend time there, post again and I will recommend some). For the Amalfi coast I think Sorrento may be a better base than Positano. I can recommend some restaurants there as well. We did a day trip to Capri from Sorrento, and had a wonderful lunch at La Capannina. You should also be aware that one of only a few Michelin 3-star restaurants in Italy is Don Alfonso in Sant' Agata a few miles from Sorrento. We had a nice lunch in Positano but I cannot remember the name of the restaurant, only that it was right on the water. over to the left when you come down the main street. Elegant with simple fresh fish. Overall I really like your itinerary. We do similar trips, no more than 3 days in any one place, so we find the places we like best and then plan future trips to go back to those.

        3 Replies
        1. re: rrems

          rrems, what restaurants do you recommend in Sorrento? (We'll be a family of four with 13 year old boy/girl twins.) Also, is it easy to get a cab from Sorrento to Sant'Agata?

          1. re: pkdof

            The best is Caruso, pricey but well worth it. I particularly remember the spaghetti with bottarga. Antica Trattoria is also very good and moderate in price. I don't think you would have any difficulty getting a taxi to Sant'Agata. We also had a really nice lunch in Marina Grande at a restaurant whose name I can't recall, but it was on a pier with windows all around, right in the center of the village. The food was simple and superb. I had a pile of baby clams for the appetizer that were wonderful. O Parrucchiano was not as good as the others but nonetheless decent and reasonable. The hotel where we stayed, La Tonnarella, has a nice restaurant with a huge menu. The food is very good, not exceptional, but we ate there twice because it was very good value, and the view is amazing. Nice hotel, too, though I see they have raised the prices and it is no longer the bargain it once was.

            1. re: rrems

              When we went to Don Alfonso from Sorrento, we took a bus there (which was fairly easy), and then had the restaurant call us a taxi for the return.

        2. Could I suggest going back to the drawing board and planning a MUCH less ambitious trip? Unless you think it's going to be your last trip to Italy, I'd concentrate either on Tuscany or on the Bay of Naples/Amalfi coast, depending on your interests. Tuscany is "easier". Both are highly touristed destinations. As for skiipping the cities, first, you're underestimating the logisitcs of getting places, being tired, finding your way around, etc., which will cut deeply into useful time on a short trip. Second, Florence and Rome are not just "cities" but two of the most important, beautiful, interesting, etc., etc., places in the universe. They deserve more, or at least one of them does, with a promise of seeing the other soon. I doubt I will change your mind, but I think most people would agree at least that the more time you spend in one place, the more fun you will have.

          As for your restaurant choices, in Florence Cibreo (any) and Ruggero would be my choices. In Rome, Monti is very good but not the be-all and end-all many posts make it sound like. Likewise Colline Emiliane is very good, but might as well be in Bologna for all it has to do with Rome. We go there, but we live in Rome and go out for a change. CJT is right that you needn't worry about eating near your hotel if there's a place you like the sound of elsewhere. The rest of your list leaves me cold, though I would go to Fiammetta if it was convenient, which it would be if you're staying near Piazza Navona. It's a modest neighborhood place (though I confess I haven't been there in eons). Paris, in Trastevere, would be my choice for a classic Roman dinner for beginners, including the Jewish fritti. Don't forget that many restaurants are closed on Sunday, or sometimes Sunday evening and all day Monday.

          1. As I stated in another post, just having a restaurant itinerary for Rome is very important I found. Rome has so many tourists (many of whom who have a limited sense of what is good Italian food) that many, many restaurants really don't need to do much to make a killing. Therefore, eating on the fly in Rome can be problematic I found. I found this to be not as true in other major cities.