First time to Italy, tips on organizing our itinerary

Travel, Wine Tourism, and Restaurants Forum
1

Hi all,

My wife and I plan to go Italy this fall for our 10th wedding anniversary trip. Likely going to spend 10 days there and want to include some combination of the following:

Barolo & Barbaresco (1-2 days for wine tasting)
Milan
Venice
Florence
Cinque Terre

For those who have been before, are there particular cities that can be seen in just a day and others where it’s worth spending longer? We were thinking of spending a couple nights in Cinque Terre in particular (any tips on hotels would be great).

2

Baglioni hotel in Florence was pretty great in the Santa Croce neighborhood, quiet, but walkable to anything you could want

1 Like
3

Milan has a great church (Duomo. Walk to the roof to get up-close views. Do this in the morning before the roof gets hot!), and of course The Last Supper fresco. The glass-covered shopping area you may have seen is right next to the Duomo; sort of neat once but … meh. Milan is considered boring by Italians that live elsewhere, but it’s a reasonably nice city. It’s just not as cool as the others on your list. I have spent a total of two months in Milan on business trips, in all seasons. Milan is to Italy (fashion, risotto) as Frankfurt is to Germany (finance, apfelwein), I guess I would summarize. Milan has a fortress in town (Sforza Castle) which has some permanent art exhibited and often some special exhibits (if you have a day to kill for flights or whatever).

Venice is funky: getting around is weird because everything that seems like it should be a street is a canal. Some have walkways next to the canal; most don’t. With GPS on a smartphone, life is easier. But it’s still pretty disorienting. There are less-touristy areas of Venice with great restaurants; I liked those best by far. The city is depopulated and it’s obvious when you take a canal boat around the city how many buildings are empty and falling apart inside. We stayed at a hotel in Venice itself. There are a ton of hotels outside the city, which I don’t think have the right ‘vibe’.

Florence - pretty epic overall. I have spent 7 days there (over two trips) and still feel I have only scratched the surface. The city exudes its history. Perhaps my favorite of what you are considering to visit. Churches are epic, the bridge over the river is surprisingly nice and pretty, food is overall best of the places you list (especially if during truffle season; you didn’t say when you are visiting and I don’t recall your wedding day!), David is worthwhile, Uffizi is epic (crowds are also epic), and there is a ton of 2nd and 3rd tier sorts of things to see, too. Lovely city. Be cautious if you’re driving in/out of Florence as they restrict access; I found that confusing because I didn’t have the details on my map.

Cinque Terre is fun; mornings are best before the other tourists wake up (and before the heat of the day!). I stayed in Vernazza but was so long ago I can’t find the hotel. The town just to the north, Monterosso, has cars, big hotels, sandy beach, and completely not the same vibe as the rest of Cinque Terre. The towns to the south are fun and smaller than Vernazza. Vernazza has just enough restaurants for different dinner location each night. I spent 2 nights there myself which was just barely enough to get to each town for lunch, take train between them afterwards, and suchlike. The fresh anchovies are spectacular; I ate two (uncooked) anchovy appetizers myself one night and then had a main course.

4

Tough question about how long to spend. I can only personally speak to Venice, Florence and Cinque Terre. The short answer - I don’t feel that a day is sufficient for any of those cities.

There’s always a balance for me between a ‘survey trip’ (brief stays in multiple cities) vs how I and my family prefer to travel (settle in for 3-4 nights minimum - preferably longer). I will say that while the Cinque Terre was spectacular, two nights there was enough for me. Perhaps this was due to visiting at the end of the summer and peak tourist/packed with people. It just wasn’t a very good fit for me or my family.

My advice would be to spend at least two nights in each place, even for a ‘survey trip’.

Florence - lots of great info on the board. We stayed at Hotel Degli Orafi, recommend by @Nathan_V and @Andrew_Gelb. Andrew specifically had some great write-ups about Florence and Venice. Hotel Degli Orafi was a stellar location, solid breakfast, and literally adjacent to the best sandwich shop in Florence - 'Ino. My daughter tonight spontaneously brought this place up tonight out of nowhere at dinner! We also loved Enoteca Pitti Gola and their Osteria - solid food with great wines available. Also liked l’Ortone, slightly out of the center. I think a 3 night minimum for Florence would be wise. More to see and do? For sure.

Venice - Osteria Testiere was terrific. Go twice or three times. Didn’t love our other meals there. Stayed at Ca Pisani and really enjoyed it, but ownership has changed since, so not sure about current status. Could spend 2-3 nights and feel like you’ve seen Venice. Would there be more to see? Absolutely. But 2-3 nights would be a solid feel.

Have a great time!! Feel free to PM with any specific questions.

5

Rome, Florence, Venice, and Naples are full of history. Always book a private guide for the popular museums in Rome and Florence (skip the lines). - well worth it. Don’t miss the Peggy Guggenheim museum in Venice if you like that style of painting. I’ve been a couple of times but recent trip was for my 60th. In Florence, we stayed at the Palazzo Niccolini right behind the Duomo - gorgeous. I woke up to the fresco below. In Venice, we stayed Ca ‘Nigra Lagoon on the grand canal near the train station. All four cities are worth several days each. We used a driver sometimes and took the trains other times (super easy). Ton of great restaurants.

2017-04-13_18-44-43_078
2017-04-13_18-44-43_0783264×2448 1.97 MB

6

I’ll start on a positive - that time of year can be a superb time to go. Weather often very good, but warm rather than hot, and that’s great if you’re actively visiting places. In addition, it can be superb for food, with good porcini & other mushrooms (finferli also good for instance), leading into white truffle season (which might lead you to extend the Langhe section if it’s late enough you plan to be there.

The rest may come across as being critical of your initial thoughts, and I’m sorry for that. We’ve spent countless holidays in Italy and very much have grown to love it. Away from the mass tourist trail we’ve encountered incredible hospitality, but the times we’ve ventured close to mass tourism, we’ve seen how that corrupts the attitude in locals (making it anything but the ‘real Italy’). We’ve also seen people disappointed by trying to cram too many tourist sights in, rather than really enjoying the places they visit.

Too many locations for 10 days - this isn’t one of those organised tours where you are bussed to their pre-determined view of what’s ‘best’ (most touristy) in Italy, but your planned holiday, with you handling the logistics.

For starters I’d say ditch Venice. It’s out of the way of your other locations, it being in the north-east, whilst your other locations are north west. Whilst it’s famous, it is blighted by tourism, and unless you carefully plot routes away from the mass tourist trail, can be a huge disappointment.

Cinque Terre can be lovely, but it too has suffered tourist blight, ironically as a direct result of Rick Steves trying to tempt US tourists away from the ‘big 3’ of Rome, Venice & Florence. The conveyor belt feel of English speaking tourists on the coastal paths (typically saying ‘buongiorno’ to each other, despite looking obviously like English speaking tourists) is not the experience it would have been before such exposure. The villages remain interesting (for now) and it’s easy enough to escape the crowds, plus the efforts at recycling and wider conservation by the locals are superb. Personally I’d drop this for some wonderful walks through the vineyards of the Langhe, almost all ‘free to roam’ due to splintered inheritance resulting in the need to have open access to the small parcels of land. The tourist office in Alba (Langhe, Roero and Monferrato tourist office) is exceptionally good, and their website also good, including for booking accommodation and winery visits. They have a superb cheap walking map (probably ~€15 these days) that makes planning walks through the vineyards simple.

Milan. If fashion appeals, then it’s an option, and one with choices of arrival airport and good transport links. If fashion isn’t a reason to go, then I personally found it disappointing, rather superficial and aloof.

Florence. It may make sense to have one of the ‘big 3’ tourist locations, and Florence has much you can see on foot. Lucca could be a day trip, or indeed the base, and if later in Autumn, San Miniato has a truffle festival (not as enjoyable or big as the one in Alba, but worth a visit if nearby). Lucca is a lovely small walled city, great to explore even on a wet day, and also has the superb Enoteca Vanni, with it’s back room cellar of older wines.

So my suggestion would be splitting the 10 days over just 2 bases, one in the Langhe, the other in / near Florence or Lucca. There will be plenty to see and do there, and the time you save not incessantly packing/unpacking, checking in/out, and travelling between bases, will be time that gets more productively spent enjoying your holiday. Look for either flights in/out of Pisa, or into Milan Malpensa and out of Florence (or vice-versa). You’ll want a hire car for the Langhe, but that may not be desirable for Florence/Lucca, but can be made to work if you find a nice place in the countryside that gives you options to easily drive to a car park in Florence etc. or even more ideally, be on a local bus / coach (aka pullman) route into the city, with the added appeal that buses usually drop you right in the centre, unlike the trains for much of Tuscany. Driving in the Langhe is enjoyable.

I hope this helps

6 Likes
7

The fall is a great time to be there, you’ll have a great time! I’d start off by joining others and saying that 5 locations in 10 days is ambitious, when I did a trip to Northern Italy we took 18 days to do Turin, Barolo, Milan and Venice, and then left feeling like we had barely scratched the surface in some places. That aside, I can’t speak to Florence and Cinque Terre but here are my suggestions for the other spots you’re visiting:
Barolo - It’s worth staying in one of the larger villages, I loved Monforte. Our favorite restaurants were Faula, Iride, and Alessandro Mecca at the Castello di Grinzane Cavour.
Milan - If I had to pick any of your locations to do faster I would suggest Milan, I loved the museums and shopping there but you can probably see a good number of the main attractions in one day. I stayed in San Marco and found the city super walkable. Our favorite restaurants were Trattoria Trippa, Ratana, l’Alchimia, and the Trattoria del Nuovo Macello.
Venice - There are a ton of tourist traps as others have mentioned here but I think it is definitely worth a visit! I would stay in Cannaregio which is pretty well removed from the worst crowds. I’d try a mix of restaurants and cichetti bars, our favorites were Vini da Gigio, Sepa, Vino Vero, La Sete, and Osteria alle Testiere.

8

I agree with cutting Venice, disagree about Cinque Terra. Still though, you’d be stretched thin over 10 days. Italy is just so goddamn dense (in a good way) when it comes to traveling there!

If Milan is a gateway in or out, 2 nights will give you the feel, but as Ian says, it’s not the Italian experience many imagine. Still, I’m more impressed each time I go back there.

Also, you have to factor in how you’re getting around. You’re not going to want to drive to Cinque Terra or from Milan to Florence.

If I had to plan your trip (I’m based in Chicago):
Day 1 - Fly into Florence, arrive AM (3 nights), 1 day into Chianti Classico
Day 4 - Afternoon train to Cinque Terra (3 nights)
Day 7 - Early train to Genoa, pick up car, drive to Barolo/Barbaresco (2 nights)
Day 9 - Drive to Milan, drop car (1 night)
Day 10 - Fly out of Milan

The issue is that you’re in St. Louis, so Florence will be a three-leg flight. Milan would be two.

If I had to cut one thing, it probably would be Cinque Terra due to travel times, but it might be something your other half really wants.

9

The best thing about Italy is La Dolce Vita which is gotten by slowing down to enjoy life. Looking for places you can see in one day and switching hotels every other day is the opposite of La Dolce vita. Avoid each day being a checklist,

In general, I’d just follow what Ian says.

If Venice is the most important (it often is for us), then a great time is possible- but it requires more local knowledge to get into the Dolce Vita zone. Ian is giving you tips with logistics in mind. Always underestimated by the first time visitor,

3 Likes
10

As others have said, 10 days isn’t nearly long enough to cover all those areas considering all the travel days you’d lose bouncing around the entire country. Pick your favorite 2 or 3 spots and leave the rest for another trip.

3 Likes
11

Milan is the best place to enter Italy from the US in my opinion because you can essentially arrive in two legs from almost anywhere in the country and you can fly emirates first on the jfk/mxp fifth freedom route on the 787 which makes any red eye 10000x better, I personally liked.Milan but agree you don’t need to spend that many days there. That said, it’s not a bad place to get over jet lag for a day or two.

I personally liked spending time in Sicily much more than spending time in Mainland Italy, it feels much more like Italy before the tourist invasion.

1 Like
12

White Lotus theme intensifies

13

We’re not planning to go that far south LOL

Thanks for the tips all. In terms of our “priorities”, I think Barolo (for me, she doesn’t drink much red so might keep this leg of the trip short), Florence, and Cinque Terre are probably at the top of our list. We’d be fine skipping Milan. I realize Venice is far out of the way from the other sites but is a day trip there feasible? How long would a high-speed rail from Florence take?

Any other cities we should be thinking of in the part of the country where we’ll be?

14

Frecciarossa will get you there in 2 1/4hrs from Florence. Doable, but certainly not ideal. Better would be Bologna, which is only 40min, but still Florence and the surrounding area can easily fill those days. Lucca or Siena are other good day trips.

I was wrong about flights. I didn’t realize there is a Lufthansa flight from STL to FRA. Because of that you can fly to Turin 1-stop, rent a car and hit up Barolo country, and drop it Genoa. Then take the train to Cinque Terra and onto Florence. Fly out of Florence.

Day 1 - Fly into Turin, rent car and down to Barolo (3 nights since you’ll be getting in later)
Day 4 - Drop car in Genoa in the morning, train to Cinque Terra (2 nights), plan for one whole day to hike the five towns
Day 6 - Midday train to Florence (4 nights)
Day 10 - Fly out of Florence

4 Likes
15

One thought that might be contrary to the majority here. Venice is sinking and it has other issues. It might not even be a viable place to visit down the road. Who knows when you will get back to Italy. I’d prioritize that over Milan any day.

1 Like
16

Feasible? Yes. Desirable? IMO no.
Here’s a good option for the outward journey (from the excellent trenitalia site)

image
image1462×327 31 KB

I’ve not checked return journey

So what you get is getting up earlier on holiday, than you’d do for work (meaning an early night the night before), be on your feet all day, and arrive back in Florence over-tired, to the extent the following day may be compromised). You’d probably want to pre-book a taxi with enough leeway to avoid missing the train, skipping breakfast, so getting a brioche + coffee at the station. Arrival at 9:34, with a fairly large swathe of similar daytrippers. IIRC there is now a day trip tax. You’ll be pretty tired, but probably balanced by excitement of being in Venice. You’ll probably want to see the ‘big sights’, so that means following the morass of day trippers following the same route, with the tourist tat that has built up along such routes, that will form a strong impression of what Venice (and Italy) is like. It’s a horrible perspective of the country. Instead perhaps tap into the experience of someone whose been multiple times (Barry?) to plot a route in advance that’s more circuitous, but gets a less tourist tat perspective of the city.

With all that said, I’d actually recommend at some point taking a fast train in Italy, as we find these enjoyable. If booked in advance (as we tourists find easy to do) the prices can be very appealing, and so much so that we aim to go 1st class to make a (cheap) event of it. Keep an eye out for regular offers and prices ~3 months out can be very keen. This little map gives a basic summary of Frecciarossa routes, suggesting Perugia (Chocolate) and Bologna (Food/history) as good options from Firenze. Note however Bologna has a c.30 min walk from train station to centre (or often crowded buses), so factor that in.
image

17

Or you could just walk the 15 minutes from the centrally located hotel you’ll be staying at.

Everything else: yes.

1 Like
18

Invariably yes, and what I tend to do when organising holidays in Italy, is to start off with a very rough plan of arrival & departure airports and logistically easy locations connecting them. From there we’ll typically settle on bases that appeal, offering variety, and where the connections are fast/easy. Transfer days are invariably badly compromised, with the hassles of packing / unpacking, checking out/in, travelling and the stress involved with all of that. Never a complete write-off of a day, but often severely compromised. The simpler the better.

I’ve got a book recommendation, but ironically not for its primary goal. Italy for the gourmet traveller (Fred Plotkin) is ostensibly a book to guide tourists to good places to eat and shops to buy food. In this it’s not great, with few suggestions, some resting on laurels, too many in obvious locations. The annual ‘golosario’ Italian language publication is massively more useful in that respect. However Plotkin has a wonderful writing style, conveying his great love of the country, traditions and culture, and this comes across fantastically in his precis of the cities and other locations in the book. It’s a super way to find places that feel like they might be ‘just right’ for your interests.

Once you’ve settled on 2-3 base locations, it will be easier for us to suggest possible day trips that deliver you with minimum stress to a place of interest, plus of course ideas for those locations you choose.

19

Piling on what @Ian_Sutton and @J_Patrick_Lynch are saying - anything more than two destinations and you’re subjecting yourself to a tour de force. Yes Italy is small, but getting around is not always a breeze. There are so many beautiful day trips around Florence (Chianti, Montalcino, Siena, San Gimignano, etc.) that you could easily spend 10 days in Tuscany alone. Day trips will require a car, though, so perhaps if you want to be anywhere other than in the city of Florence you may want to get a country home and drive into Florence once or twice. Alternatively you could split your Tuscan stay between two nights in Florence and 2-3 at a villa outside the city. And if you slow down in the Langhe you can seek out more meaningful experiences like truffle hunting that are more time consuming but also more meaningful.

Having said that, if it’s just you and your wife, you probably could add one more stop if it works out with travel/logistics. I have a soft spot for Venice, especially if you go outside of the tourist season, but it would not be as easy to work in to your itinerary as Milano. In Milano, one night would be plenty but you’d get a great sense of the city and there are plenty of restaurant recommendations already on the board. I find Cinque Terre a bit overrated but that’s just me.

3 Likes
20

Super info, and I smiled when I saw we’d both mentioned Bologna as a day trip option.

Torino a good airport to fly into or out of, as it’s not too busy. The hire car desks are diagonally to your right as you exit the arrivals hall after clearing bag collection/passport control, and they park them across the road in the multi-story car park. I’d recommend using google street view to familiarise with which turning you need as you hit the hit the junction at the end of this airport road. Once on the autostrada, the driving to the Langhe is generally easy, sometimes hitting heavier traffic for 2-3 junctions around Torino (especially near rush hour), but otherwise cool until you reach the outskirts of Alba. That’s the other junction I’d advise a sneak preview on google streetview, as it’s a slightly funky junction with the flyover, that is a lot less stressful if you know where you’re going (visually). From there into the Langhe itself is fine, and you’ll appreciate the shift from long straight autostrada to country roads over rolling hills (and a lot less traffic).