Restaurants & Bars 66

Fall Italy Trip Planning Questions

mrsricho | Feb 10, 200803:10 PM

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


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


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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