20th anniversary trip--first time to Italy

Late June.
Rethink Cinque Terre. Plenty of people will say the opposite, but the villages are just too crowded. If you are a hiker, you understand the point is to commune with nature. Italy has a wealth of national parks where you can enjoy nature without a zillion other tourists. Some make a car rental more necessary, but driving in rural areas is not difficult, and if you choose "Tuscany" you will likely be doing so.
With 10 days, you can definitely visit Venice and parts of Tuscany, with a little nature thrown in--but I think an open-jaw flight is optimal. Just don't overdo it. Start reading, and take it from there, enjoy!

First off, you better save Rome for a separate trip---it's that good. And I can almost guarantee you'll be back to Italy after this trip.

But with only 9 nights (count nights, not days) you can't run around that much anyway. I've never been but they say Venice is a good place to start a trip and combat jet lag as well, so maybe fly in there, stay 3 nights. Then train down to Florence. This is where you make your base, either in town or on the outskirts, or even a villa in Tuscany. I'd stay in one place--sleeping-wise--once there. If you're in the countryside, you can visit Florence for the day, or vice versa.

So fly into Venice, out of Florence. Cinque Terre would be too much in the time allotted. And late June or July doesn't really matter--it's going to be crowded no matter what.

Enjoy your planning!

Since Siena and Florence are in Tuscany, Tuscany wins! Venice is special and so unique, add it too. Also consider Umbria or a mix of Tuscany and Umbria as Umbria is the much less crowded of the two. Enjoy whatever places you choose.

You'll have a better idea after reading the RS book and looking at various options on-line. Venice immediately came to mind for an anniversary. Our 2nd trip's itinerary to Italy might appeal to you: Venice, Verona, Moena, Bologna and fly back from Venice.

About the time you were celebrating your 2nd anniversary, we had a week in Italy (first time there together), and split it between the Cinque Terre and Venice. The 5 Terre wasn't a national Park back then, and the trail between Riomaggiore and Manerola was closed for construction/repairs, so we didn't do any of the trails. We managed to just show up without reservations and get the last available room in Riomaggiore. Lunches and dinners were particularly good! Haven't made it back since that first time (yet).

We took a train to reach Venice, connecting thru the Milan train station, which had to have been the HOTTEST place in the world that June.

We arrived in Venice on the night of the Summer Solstice, where Venice (nd much of the rest of Europe) has live music on just about every street corner at night. It truly is a magical place, and we returned again in 2005, but I understand now that huge cruise ships unload tons of visitors there these days.

We visited Florence last November, and I'm going back this December, but even in the fall there were lots of people. All the tourists at the Piazza della Signoria with protruding selfie sticks presented a real tripping hazard, and make sure they don;t swing one into your head! Seriously. But it's also a fabulous place , which is why so many people go there. If you could pick between June and July, I'd go with June, to have fewer crowds.

Happy Anniversary in advance, and have a great trip, wherever you wind up going!

Thanks for your thoughts! You all have already inspired me... I always get a little overwhelmed at the beginning of trip planning and this helps a lot. We can just put Cinque Terre on a list for another time-- it's hard to appreciate a place when it's totally overrun by crowds, especially smaller towns.

I love the idea of combining Venice with Siena/Tuscany. It might be just the right mix for us!

I've already looked into open-jaw flights, flying into Venice and out of Florence. I'm guessing that's what we would have to do-- fly out of Florence if we end up our trip in Siena or elsewhere in Tuscany?

Yep, though Pisa occasionally works. I search on kayak and buy from the airlines.
This site/book may be of interest:
http://www.50hikesoftuscany.com/

I'm flying in and out of Florence this December -- first time using that airport, then connecting thru London -- but if you get a better price or better connection timing, taking a train to Rome or Milan for their airport might be worth considering.

Elizabeth, are you committed to late June or July? I always choose to travel to Southern Europe in either April/May or September/October. June, July and August can get very hot and very crowded with tourists, including cruise passengers on day trips in popular cities and towns. In terms of places to visit, I think you are on the right track for a first visit to Italy: Fly into Venice for three nights, and take one day to visit the islands in the lagoon, especially Burano and Torcello; then 3 nights at a nice Tuscan agritourismo, to commune with nature and excellent homemade cuisine and wine, probably with a rental car to explore the countryside and Tuscan towns, including Siena; then 3 nights in beautiful Florence, and fly out of Florence airport. I don’t know where you are located, but you likely can book the open jaws routing with a connection, maybe in Frankfurt or Munich, or various other major European airports. Happy Anniversary! If you need a driver or someone to carry your bags, just send me my air ticket and a list of where you’ve booked our rooms!

If you need a driver or someone to carry your bags, just send me my air ticket and a list of where you’ve booked our rooms!

I like that--- will work for travel!!

are you committed to late June or July? I always choose to travel to Southern Europe in either April/May or September/October.

I have three reasons for you-- and they are 7, 12, and 14 right now! Spring and Fall are great times to travel to Europe I know.... Cheaper, cooler, less crowded... But with three very active kids with multiple sports/recitals/etc. that group heavily in spring and fall, it would, sadly, be a logistical nightmare... Also, I have to be aware of my babysitters' age and stamina --my parents' and in-laws...

Elizabeth, if you haven't already, learn to FaceTime with the kids and their babysitters. Works quite well on both sides to quash the separation anxieties. Maybe they'll want to accompany you next time (or NOT!).

One more thing--wherever you stay, make sure there is A/C, which is not a guarantee like the U.S. The heat is not like here. It can knock the stuffing outta you, and if you have a cool oasis to return to at the end of the day, it's like the carrot on the stick!

I see you are in Pittsburgh, Elizabeth. Not from Pittsburgh, but I see American Airlines has a daily, overnight, non-stop flight from Philadelphia to Venice.

QElizabeth, I do want to offer you an opposing viewpoint. While the towns of the CT can be crowded, the trails (except for the easiest) are not overly crowded. The trail from Corniglia to Manarola goes up into the hills and back down to sea level. There were other people on this trail, but it was not crowded and plenty of time that we did not see other people. The trail from Riomaggiore to Portovenere was a real “back road”. The views after the first climb was the best in the CT. There were 30-45 min stretches that we saw no one. We connected with a few locals and only saw Italians on this trail. Portovenere has European tourists but not many Americans. This was 6 hours of hiking and was the most incredible of all my hikes in CT. There are additional trails up on the hills by Telegrapho. We were there in early July.
The cycling that goes from Impuneta to Greve down to Siena is amazing cycling. The scenery is unbelievable.
There is a 30K race in Postoia at the end of June. All of these activities that I have described are not easy but incredible experiences.
I would spend a few days in the CT and then get a rental in Tuscany between Florence and Siena.
Venice is also a great place for a honeymoon. You have plenty of options and they are all good. Your description of yourselves sounds a lot like my wife and I, so I wanted to provide a different option than has been presented.
You can’t go wrong with Venice, but I believe that you have other posters discussing that wonderful city.
Congrats on 20 years.

A 10 day trip would most likely mean 8 nights on the ground in Italy. Milan offers direct flight departures as it’s a major Italian gateway. Florence on the other hand has minimal flights.

Day
1. Arrive Venice (3)
2. Venice
3. Venice
4. Early train to Florence (3)
5. Florence
6. Day to Siena
7. Train to Cinque Terre (1)
8. Train to Milan (1)
9. Depart Milan

Congrats on 20 years !!

Here's another thought . . . leave Tuscany for your next trip and combine it with Rome. For this one, stay in the north. Venice, Verona, and fly out of Bologna (or Milan). Verona is one of my favorite Italian cities and you can visit by leaving Venice in the morning and storing your bags at the train station for the day, then taking a late train to Bologna - which saves the time and hassle of a one-night stay. Bologna is a good base to just relax or to take day trips (you can decide on the spur of the moment) to see lovely, less crowded places - Ravenna, Ferrara, Modena, Padua, even check out Florence for a day. Bologna's airport is larger so it may be easier to get a flight out from there. Also consider that it's only a 1-hour train ride to Milan and you might get a better price and/or itinerary using that as your departure airport. If you have an early flight, spend the night in Milan, otherwise go to the airport from Bologna.

Bologna is not a big tourist destination because it doesn't have the top-tier sights of other towns. It's a lovely city with great train connections and lots of restaurants which promote its reputation as the gastronomic center of the country. You could probably find a cooking class there.

It sounds like you are on the path to a relaxing, celebratory trip. I would stay in a maximum of two locations if you want to make that a reality. The natural beauty is amazing.

Venezia is lovely but I would never go in July. Nor would I go to the Cinque Terre in summer. While another poster is correct, that the trails are not (at least have not been so far) terribly crowded, the towns are too crazy to enjoy and the trains look like the Tokyo subway at rush hour.

Here's an idea: Fly directly into Florence if you can arrange it and spend 3 or 4 nights. Arrange a day trip to Chianti with Tours by Roberto. Then take a train to Bolzano and on to the Val Gardena by bus or taxi (PM me if you need details) for at least 4 nights. Here you will find a paradise of hiking and biking in the mountains that never feels overwhelmed. (Do NOT stay in Castlerotto nor Bolzano or you will miss the best the area has to offer.) You can take lifts all over the valley to fabulous hiking, rent bikes, etc., and in the evening spend your time in cute villages with great Italian food and regional wines.

You may need to reserve a final night in the city you fly out of, probably Milan.

learn to FaceTime with the kids and their babysitters. Works quite well on both sides to quash the separation anxieties. Maybe they'll want to accompany you next time (or NOT!).

Oh, we aren't worried about staying in touch-- the kids love staying on their grandparents' farm and won't miss us so terribly... And of course they want to accompany us! We took a first-time family trip to England and Scotland this past July and they can't wait to go back to Europe... Our seven-year-old is particularly mad we aren't taking him to Italy.

"but the pasta..." he keeps saying....

Venezia is lovely but I would never go in July.

Out of curiosity--why? Heat or crowds? Temps in Venice (well, at least the chart with the daily averages in the back of the RS book) sound much better than, say, Rome in late June, which is when we will probably go vs. July...

Venezia suffers from cruise ships and day trippers. It is oppressively hot and to me, somehow worse than Roma. The tiny calle become impossible with the sweaty crowds. The humidity is terrible being right on the sea. Yes, you can "escape" to some degree by getting away from Rialto and San Marco, but even staying in a sestiere like Dorsoduro or Castello, you have to pass through the busy areas to see the sights.

In Firenze and Roma it seems easier to escape the oppressiveness. Wider streets, parks, etc.

BTW we love Venezia and just finished our 10th stay there. We prefer October-December.

I would avoid Venice in July at all costs. We spent two nights there a few years ago and I unfortunately have no desire to return...so extremely hot and humid and very crowded. I would recommend time spent in Verona and Ravenna.

As I said upthread, I've never been to Venice for many of the reasons stated above--cruise ship gridlock mainly--but others love it. I do want to see Venice but not stay there, however, so our next trip--prob spring 2019--will include a stay in Verona, which will allow an easy 70-minute train ride to Venice for daytrip purposes, as well as a less-than-an-hour ride in the other direction another day to all the little villages on Lake Garda.

Verona might be a better base for you for 2-3 nights, see some water, than move on to Tuscany & Florence.

Nice that we're planning your trip for you, Elizabeth? Ha!

Elizabeth,
It's possible to combine relaxing at an agriturismo and sightseeing, but you'll have to concentrate on one area. I suggest you find a nice agriturismo in the hear of Tuscany and use it as your base for day trips. We stayed near Greve, just south of Florence, but staying near Siena would also be a viable alternative. Using our Greve agriturismo as a base, we were able to visit Florence, Siena, San Gimignano, Volterra and the Abbazia di Monte Oliveto Maggiore monastery near Montepulciano.

This will necessitate a car rental. Ignore the horror stories regarding driving in Italy. If you are a careful, defensive driver, can obey the speed limits and are smart enough to study the web and figure out what a ZTL sign looks like, you'll have no problems. There's really no better way to enjoy Tuscany than by car. My wife and I discovered out of the way jewels not serviced by train or bus. Speaking of the bus, if you plan on visiting Florence, I suggest you find an agriturismo near a bus line that will take you there. We didn't have a problem in Siena, but after advice from the staff at the agriturismo, who actually live in Florence, we opted to take the bus. Once we got to the outskirts of town, I understood why they recommended it.

There's a wide variety of agriturismos available at different price levels, from economical to luxury. Some have pools, some are part of working wineries.

Doug, we took a cooking class/winery tour a few years back at Montagliari Winery in Greve-in-Chianti, which was fabulous. Did you visit there or stay nearby?