Itinerary Suggestions Welcomed

2.5 weeks will not be enough time to handle the needs of all four participants, particularly if sitting and sipping wine is on the agenda.

DS will require stop in Florence - particularly the Duomo Museum and Bargelo Museums (i mention these because of course everyone goes to the Uffizi and Accadmica, but then what?).

Suggestion 1: An agritourismo stay in Tuscany not in a hill town (many include wine tours and cooking classes), but with a car to look around at the nearby hill towns.

Suggestion 2: Although most folks head for Lake Como for hills and lakes, I really like Lugano in the Swiss-Italian canton of Ticino, which is nearby, or Lake Garda farther east...

Suggestion 3: Consider the South Tirol around Bolzano which has great wine. food and hiking in the Dolomite region of the Southern Alps. The DD can taker a selfie of herself looking through the glass window at Otzi the 5,000 year old ice man found a decade ago in the Italian Alps.

I do not mention Rome because that would be the whole trip if you allow it to be, and others on this forum are far more expert there than I.

Chances are very small that there will be flooding in Venice in late May or June. It really is a unique city that I can't imaging not having seen. You don't need a lot of time there, three nights is enough especially if you don't 'need' to see museum interiors. Just wandering around the city - the city itself is a museum. Florence and Rome are on most people's 'must see' list for a reason. While you can spend a week in each of them and not see everything you can also see the 'highlights' in 3 or 4 days. So you could do the 'classic' big three of Venice - Florence - Rome for 4 nights each and still have time for other places. You fly into Venice and out of Rome and train between them. Tuscany would fit well. For that you could rent a car for a few days, you could also do your 'farm stay' (assuming what you mean by that is staying at an agritourismo'. Or you could easily do the CT for a few days. And if you really wanted to move slightly faster you could do Venice - Florence - CT - Tuscan hilltowns - Rome. Personally I would advise to pick either CT or Tuscan hilltowns and not both.

Here are my Italy photos which include all the places mentioned - https://andiamo.zenfolio.com/f739967755

Thanks for the suggestions. I like #1 the best. Rome seriously takes 2+ weeks?

No, Rome doesn't need 2+ weeks......but some people really would love to stay in Rome 2+ weeks, and so recommend others also do so. I was in Rome 5 days, and I was just fine with that and wouldn't have wanted much more.......but I do wish I'd had more than my 5 days in each of Florence and Padua.

So.....different strokes. One size never fits all.

Padua might actually be a good choice for all concerned -- lots of places in the old town to hang out evenings in the piazzas, soaking in some culture and drinking wine, but also some stunning art, history, and maybe even architecture (I thought Florence was better for architecture). It's also just a half hour from Venice by train (very frequent). The old town is where the university is (1222), and universities typically bring a lot of good energy, music, food, and culture, as they do there.

Not that Padua should replace Florence or Rome, but that it might add in some of the extras that you're all looking for, though I'll admit I don't know what qualifies as a "selfie opportunity". I thought that the Scrovegni Chapel left a stronger (positive) experience on me than the Sistine Chapel, and Sant'Antonio basilica there was one of the most beautiful churches (inside) that I saw on my trip (second to St. Peter's).

I don't think you'll have time for a hiking/biking/country trip, but you'll still find lots of time for sitting in piazzas with a glass of wine (albeit old city piazzas), wandering neighbourhoods with a gellato, and seeing lots of beauty and history.

@isabel — those photos are incredible! Thank you for sharing them.

How many nights will you have? kind of need to narrow that down first.
What are your best flight options? In to where, out of where? I see from a previous post you are in Oakland- is that still true? (I grew up in Oakland)

For a first trip to Italy I think Sicily might be too intense.

You cannot go wrong with the big 3-
Venice- architecture, history and selfies galore
Florence- art, architecture, history, food, wine
Rome- all of the above, too much to list

If you want to incorporate a bike ride/small town stay- consider Lucca? I’ve not been there, but know you can bike around the walls, easily visit other hill towns, etc.
Or an agriturismo that has bikes, I think Marciano does- you can ride into Siena.
You’ll do enough hiking just in the hill towns.

Fly into Venice- 3 nights
Train to Florence- 3 nights
Pick up car-
hilltown of choice/agriturismo- 6 nights or split 2/4
drop car
5 Rome

Hi, Christine. We’re flexible on days. We live in SF and flew Norwegian out of Oakland for our last trip. We haven’t looked into flights yet. Thank you for the recommended itinerary. It’s very helpful.

I was born in SF

Use Google flights to check your flight options, book with the actual airline.
If you can get “open jaw” in to Venice, out of Rome- that is always the best. If you cannot then I think Rome RT next best. Avoid out of Venice.

Booking. com for lodgings and you should probably get on that soon for best availability
Research/filter on booking.com, book with actual hotel or with booking, whichever works

I use rome2rio.com to figure out transpo options
You can purchase fast train tix in advance for nice discounts- trenatalia.com
We always use AutoEurope.com for our car rentals in Europe.

I only know what I know from our 2 trips to Italy
First trip was 17 nights
Venice 3, Florence 3, got car > Siena 2, Montepulciano 2, Assisi 2, drop car < Rome 5
We felt that was practically perfect. We enjoy smaller towns most in the morning and evening, thus the 2 night stays. Day trips were easy.

Rome, Florence, Venice and other towns will have art, architecture, experiences and quiet areas to explore and drink wine and tons of selfie ops. What I would consider is splitting up for several hours on several days (like gals together and guys together) to do different things, meeting for lunch or dinner.

In Venice, the 4 of you could take a gondola rowing lesson (rowvenice.com). You'd probably be in the quiet, charming parts of Venice, and what could be better than a selfie on a gondola? Even Florence, which is chock full of art and architecture, has quiet neighborhoods to explore, gardens,

“DS is into architecture and art.” Does this just mean that old buildings are of interest, or does it mean how architecture drives social behaviour and vice versa, which is really what architecture is about.

If it is the latter, then it would be worth investigating the Architecture Biennale in Venice, starts mid May 2020.

Flooding in Venice at that time of year is a non-event.

My favorite hill town, Montepulciano, great medieval feel, amazing views, coffee bar at the top of the main hills have seating balcony panoramas over the Tuscan countryside.
My favorite CT town, Manarola, beautiful marina
My favorite visit, Island of Capri
Favorite meal, Matricianella in Rome
Worst place we visited, no where (okay, maybe the rental car line in Florence, that sucked)

Thank you, everyone, for the helpful suggestions. Is there an advantage in going from north (Milan/Venice) to south (Rome) as opposed to from south (Rome) to north (Venice/Milan)?

It is decidedly easier to ARRIVE in Venice than it is to leave from Venice unless you can get a departure flight past noon of which there are very few going to US

We lucked out this past May and had an 11am departure that was still a bit of hassle to get there on time but we’d been to Venice before and knew the drill.

I do think Venice is the better “arrival to Italy” choice, great place to get over jet lag.
Rome is much more intense

hey hey eliz
i'm from the bay area too. heard norweigian will be leaving out of SFO now, not oakland anymore. also keep an eye out for airitalia. will be new airline outta SFO coming soon in may i think. do a multi-city (open jaw) into one city out of another SFO-VENICE-ROME-SFO, so no backtracking and shouldn't be that much more, considering price of train tickets. easier to fly into venice and out of rome. the flights are usually at dark thirty (6am) out of venice which means up, pack, find your way to airport at that ungodly hour. it's a nice place to get over jetlag, walk the back canals, take a gondola ride (find one in back canals and they do cross the grand canal. the grand canal is like a busy hiway with all types of boats traveling up or down it. travel to islands, i love burano away from the daytime crowds until late afternoons and early mornings. don't worry about flooding, the high tides which is natural doesn't last that long, been there done that. i would spend about 3 nights there enjoying the scenery, getting lost in he alleyways, it's an adventure of zigging instead of zagging.
alessandro does a cichetti walking tour of wine (optional), appetizers and history of venice schezzini.it
camarana.com a place to design your own venetian masks
streaty.com does food/market or food/wine tours
we stayed in an apartment near the train station, la levantina, on booking.com or check cross-pollinate.com
look at arrival and departure times, if early checkin and if they have storage for luggage until check in.
i'll private message you later on other places to stay in italy that may interest you.
aloha
GO NINERS!

Rome is a big city, lots of noise, traffic, and crowds and major sights. Venice (away from the two pretty small tourist areas - St. Mark's and Rialto Bridge) is quiet, no crowds, and with no major sights. So it's much easier to get over jetlag in Venice while you soak up the atmosphere and then appreciate Rome's grandeur after you are well acclimated to the time change and just being in Italy.

Hi Elizabeth, I agree with the previous response about Montepulciano. It is a fantastic town full of great restaurants and shops. There is always something going on and much to do. It's also close to so many other towns that makes adventuring easy. As previously mentioned, you will definitely need a car to explore the area fully. Some of our best adventures was getting lost on purpose! There are countless wineries and lots of hiking opportunities to explore.

2 great places to stay are Fonte Martino (www.fontemartino.com) and Charming Homes (www.charminghomesmontepulciano.com). Fonte Martino is an amazing bed and breakfast just outside of town. Awesome views and awesome hosts from the US - we stayed there this past summer. Charming Homes has great apartments located in the historic center of town and a really nice Italian host.

One of our other favorites is Siena. If you haven't been, put it on your list. The town is larger than Montepulciano and offers a wonderful piazza to people watch. If you go, be sure to buy a ticket to see the main duomo - it is awe inspiring! You can easily take a day trip to Siena from Montepulciano (only about a 50 min drive) or split the trip up and stay a few days there. A great B&B is Aia Mattonata (www.aiamattonata.it). The hosts are really nice and the b&b is about 10-15 minute drive from Siena.

Have a great trip and feel free to contact me with any other questions!

Thank you, everyone. I’m having a hard time finding a reasonably priced flight into Venice. There’s one option on Norwegian to Barcelona and then Vueling to Venice. There’s a 2 hour layover in Barcelona, which I’m worried is too short. Otherwise, I’m looking at over $900 per ticket. I can get a Norwegian flight from Venice that leaves at 9:40 to Oslo and then SFO if we do Venice last. If we do Venice first, there is a nonstop flight to Milan that is moderately priced. We could take the train from Milan to Venice. There are also good deals with round trips to Milan ($650 round trip) that would make it cheaper to take the train from Rome to Milan at the end of the trip.

I think I 'd go with the RT Milan. I don't like connecting flights TO Europe, don't mind on return so much but prefer not.

You could train to Venice on arrival
3 nights Venice
Then head to Rome- # nights?
Then Florence/Tuscany last- you are closer to Milan from here
You will want to be IN Milan the night before your departure flight, so last night is Milan- see The Last Supper?

hey hey eliz
that's sounds like a good deal going R/T milan. just put your feelers and alerts out, when good fare suits your budget, book it and don't look back. it'll drive you nuts/crazy and grow more gray hair!!
kayak.com, goggle flights. check if charge for luggage and seats within the classes airlines gives for prices. (economy, economy plus, economy premium)
give it a couple weeks, prices may come down middle january, after holidays are over.
alitalia.com will start flying to italy from SFO june 1
look at arrival and departure times. i agree with christine, if early into milan take a train to venice, maybe 3 hours. or spend one night in milan then train to venice.
when you see what you like and want, come back and ask more questions. the posters on this forum are great, give you advise and options, good bad and ugly, everyone has their own ideas. it's your vacation to enjoy and not stress out. just know you can't see everything, maybe your kids can give input. have a list of musts sees, if time to see. let them pick one adventure for a day and all of you have to compromise to their day. it's a challenge to plan things but in the long run it pays off for researching. enjoy
aloha
GO NINERS!!

@princess pupule - that was some game tonight!

hey hey eliz
yippee kai yea!!!! loved it, sat on the edge of my seat squeezing.
got niner fans eating deep fried hawk tonite!
aloha

I know you're getting bombarded with ideas :) but here's a little food for thought. I adore Rome (studied abroad there 16 years ago and took my family back for 10 days last spring). There really is SO MUCH you can do/see there--but even I would say a lot of the "must see" kind of sights are no fun in the hot, crushing crowds of high tourist season. So---if I were you, I would "major in the minors," so to speak. If you devoted a few days to Rome, know that you can condense your itinerary, save money and probably have a much better time if you avoid a few traditional crowd-magnets (I'm talking about you, Sistine Chapel!) Give yourself permission to skip doing what everybody else does and instead go just a little off the beaten path. MOST of the "must see" sites are accessible just by walking the city; but instead of paying a bunch of money and spending a lot of time (much of it in line) say, to tour the inside of the Colosseum (which, honestly, isn't that different than the outside!), just keep walking---YOU CANNOT HELP but stumble upon a REAL Roman neighborhood, where you'll discover the sweetest little cafe--or bakery--or diner--or something that will enchant you. Last spring, we accidentally found a tiny jewel of a park on the Palatine Hill (where only locals were teaching kids to ride bikes and walking dogs) and a lovely (donation-only) museum in the Borghese Park dedicated to the memory and work of some sculptor I'd never heard of; and I remember those quirky little places so much more vividly than many of the things on the "must do" list.