Tuscany Picnic

This probably isn't what she's wanting, but we took 2 day trips out of Florence with a company called WALKABOUT FLORENCE - a nice bus ride through Tuscany with LUNCH at an amazing vineyard in the countryside. We didn't want to have to rent a car. We did 2 of their tours - THE BEST OF TUSCANY and the CHIANTI WINE & FOOD SAFARI - both VERY VERY good. Check out their webpage.

Rick Steves recommended Tours by Roberto probably has something that will work for you unless you want to be alone

https://www.toursbyroberto.com/

Don't think to picnic in the big cities as Venice and Rome have bylaws for eating on the streets or steps. ;-)
Arezzo is on the train line and in Tuscany, but I don't know the city well enough to determine views. But it could be a place to pick up a rental car and not have to deal with the dreaded no drive zones.
Can you research some agritourismo for a night or two? One willing to shuttle you from a train station? Perhaps one with a vine yard? I am sure they could arrange the picnic part and bound to have some scenic land to Trump to for a picnic. That would be a romantic slow down time to celebrate this special change in your lives.
Alternatively check whether Boboli Gardens in Florence still allow food and drink in the Gardens or consider staying in Fiesole which overlooks Florence. Supposed to be lovely at sunset.

Hi Dr Brinkman, when I think about picnicking in IT, I picture the Villa d’Este in Tivoli that’s a 1h direct train ride away located outside of Rome. You then have to walk from there, but it’s no more than 15-minutes.
While in Rome, I suggest sleeping in Trastevere, it’s very bohemian like and Rome’s most attractive neighborhood.

If I wanted a picnic in Tuscany, I would contact Gianni at Tours Around Tuscany. He's also amazing.

https://www.toursaroundtuscany.com/

Just curious, but what is it she expects from a picnic in Tuscany? The two of you on a hillside overlooking an olive grove as you lift your glasses of Chianti? A quickly assembled selection of treats from a local market? A catered spread of local cheeses and meats? A group experience?

I like the idea of a vineyard lunch, or of having Roberto or another recommended guide arrange something, but you might want to be a bit more specific about what you and she want when you are setting this up.

Note to add: as I reread this, I think it might sound a bit snarky, but I'm not sure how to make my point. I assure you no snark is intended, but I do think you need to be able to describe what you want.

With a car just pick up a bottle of wine, buy some glasses, by a few selections of cheese drive in the country and find yourself a place with a view.

Another option, just outside of Montepulciano is Cugusi a cheese, wine tasting, picnic place, you visit their deli and pick out little things for the two of you, buy a bottle of wine, they supply the picnic basket and everything else, then you go out to their lovely picnic area that looks out over the vineyards and Montepulciano.

https://www.caseificiocugusi.it

https://www.caseificiocugusi.it/pic-nic-in-azienda/

Thanks for all the wonderful suggestions. I guess I was not specific because I was not sure what options were available. I think the picnic idea was more like picking up some local food at the market and finding a nice place to sit and eat and enjoy the view. We are not big foodies or big wine drinkers, so hopping around to all the vineyards is not appealing (unless the birds hang out there).

For picking up victuals, we found Eataly an outstanding place. You could even enjoy your picnic there, indoors, if you didn’t take it to an outdoor setting.

Day trip out of Florence to Lucca (via short train ride). Have a nice "picnic" up on the city wall/strolling the wall.

Take your picnic up to Piazalle Michelangelo at sunset

From one birder to another, I'd pull up a train map, and eBird Hotspots map. See if some are close to train towns. Back it up with google street view for a chance to see it is as idyllic as desired 😊
Edited: At work break, I did as I suggested. eBird is more a North American 'thing', so lots of Europe, though birdy, isn't defined on the hotspot maps. I was going to suggest Montallese train station as a stop, and a walk to the Riserva Naturale Lago di MOntepulciano. A saunter through farm fields to the nature reserve, but it would be at least a 3 hour train ride, when a drive would be just over an hour from Florence.

In Tuscany you could rent a car in Florence, drive along the SR222 road and stop wherever you like.
Since tourists can't drive into the city centers, after the pic-nic you should drop the car at Peretola Airport and take the tramway back to central Florence.

I think your actual itinerary will be Venice -> Cinque Terre -> Florence -> Rome. You could head south from Florence to Rome by car, have your pic-nick along the way, drop the car in a place like Orvieto and get on a train to Rome. Or find an agriturismo on the SR222 where to sleep after your pic-nic.

The Appian Way out of Rome is reserved to bicycles and pedestrians during the week-ends. You could take a walk and have another pic-nic there. Note that Sleeping in Trastevere is an oxymoron, especially after a lock-down.

Every Italian city has numerous little parks where you can picnic to your heart's content. Most have benches and many have tables - just Google a particular site and take your pick.
A particular favorite of ours from an anniversary trip to Florence back in '19 is the Giardino delle Rose - a quiet little place just below Piazzale Michaelangelo that we usually had all to ourselves since everyone else was heading further up the hill. There's an excellent little hole-in-the-wall sandwich shop about a block away called Come Dio Comanda that makes some of the best sandwiches in the city. There are benches in the Giardino, and the views out across the city of Florence are mesmerizing.

Probably one of our favorite picnic spots in the Tuscany area, an hour and a half from Florence by car.

https://saturniahotspring.com

Great spot to idle the day away. Just use GPS and have a good map handy.
Pick a nice sunny day. If you miss the turn, don't panic, it will take you up the road to the overlook where all the pictures of the Casate are taken from. It's on the right hand side just as you come around the curve.
We've visited several times over the last 15 years. The last time was 3 years ago in mid September. One caution, do not wear good gold or silver jewelry, it will end up almost black, and you'll need to find a jeweler to restore it.
Bring water shoes and towels or a bathrobe.
Pack a lunch, and drinks. Including water, to hydrate.
The surrounding towns are fascinating.

In Rome, look up these.

Villa Pamphili above Trastevere, Giardino degli Arancia on the Aventine Hill and Villa
Borghese by the lake.

Florence. https://www.destinationflorence.com/en/details/128-cascine-park

In Venice, take a vaporetto to Certosa. Take a walk and you will find a place to sit and look out over the lagoon. And very few people around.

We have moved off from Tuscany, but the islands around Venice would offer Fall migration opportunities. The Cemetery island could be interesting, but some might find that too morbid for a picnic and birding. A day to Burano and Murano would offer birding, and there is a bridge from Murano adjoining another island with a semi rural, birdy walk. Bound to also offer a picnic spot. If you could make the time, and if willing to drive a rental car with minimal restricted drive zones, Venice is very close to the Po Delta and all its wonderful birding. You could consider a private birding trip there. There is good english documentation for birding that area and it would be an easy drive. I had it in mind, planning to rent a car from the edge of Ferrara heading to Ravenna for Byzantine mosaics, then north along the coast for (at that time, Spring) birding migration. You could return the car to Ravenna, following the Po river inland, and then pick up a train from Ravenna to Venice.

I think the bridge connecting islands referred to in the previous post is actually the bridge connecting Burano and Mazzorbo. If travelling to Burano by vaporetto, get off at the Mazzorbo stop, and it is a pleasant stroll across to Burano.
On Torcello, reachable by vap from Burano, a couple of things to see. Climb the campanile for a great view over the lagoon, it really shows how Venice is all about water.
Take a walk around the left of the Torcello church and keep on walking. A path runs out on a thin strip of land through the lagoon, ending up on another island , at a locked gate, labelled something or other Ashram. You would see water birds from that pathway, white cranes in prticular.

Aussie, you may be correct. I had Burano on my mind but a satellite view the islands, shows Murano offers bridges to other islands as well, which also include greenspaces. Ah, aging memories.

I heartily recommend the small, ancient hill town of Fiesole, located just 5 miles northeast of Florence, about 20-30 minutes away by bus. To reach Fiesole with public transportation, Bus 7 goes from the Florence train station (Santa Maria Novella) straight to Fiesole's main square, stopping near the Duomo and in Piazza San Marco along the way.

Fiesole is absolutely lovely, set high in the hills above Florence, it's much cooler there on a hot day. Keep in mind that some areas are very hilly so wear sensible shoes. In Sept 2001, my husband and I walked through olive groves, along an Etruscan wall & tombs, and up a rather steep hill that eventually leads to Remembrance Park (Parco della Rimembranza; if you reach the convent, you've gone too far - there's a monument that pays tribute to the three brave Carabinieri who, during WWII, gave their lives to save ten innocent citizens of Fiesole held hostage by the Nazi, in retribution for one German soldier killed by the partisans), with magnificent panoramic views of Florence - it's where my husband and I had a lovely picnic right around sunset. Afterwards, you can easily take the bus back to Florence.

Here's a link to a Google Map for reference: https://www.google.com/maps/place/Parco+della+Rimembranza/@43.8074326,11.2902658,771a,13.1y/data=!3m8!1e2!3m6!1sAF1QipMKf7F6hhgKzFw1fSdbF1CxLD2fa-bQPBlnnTyU!2e10!3e12!6shttps:%2F%2Flh5.googleusercontent.com%2Fp%2FAF1QipMKf7F6hhgKzFw1fSdbF1CxLD2fa-bQPBlnnTyU%3Dw129-h86-k-no!7i5472!8i3648!4m8!1m2!2m1!1sremembrance+park,+fiesole!3m4!1s0x132a55ae9bb63349:0x95699610f8fe574e!8m2!3d43.8070996!4d11.2901976?hl=en

Another vote for Fiesole. So different to down town Firenze, and a great day trip.
For what it’s worth, Fiesole township has the highest median income of any town in Italy. Maybe those wealthy Florentine merchants still live in Fiesole.
Or maybe there is a bit of Medici money salted away there.
Worth a visit!

Or maybe those living in Valenza cheat on their taxes...

In 2019 my wife and I had a picnic lunch in Tuscany on the lawn of Abbazia di Sant’Antimo in the countryside. Mentioned in the Trip Report (Part 5) I posted in the RS Forum at the below link. Peaceful and interesting with few visitors. After spending about an hour inside the church buildings we had our picnic lunch on the abbey lawn with a beautiful Tuscan view; we had the lawn all to ourselves. We had a car, but occasional tour buses seem to visit.
https://community.ricksteves.com/travel-forum/trip-reports/italy-2019-sicily-sorrento-amalfi-pompeii-rome-orvieto-tuscany-siena-florence-cinque-terre-milan

The Appian Way out of Rome is reserved to bicycles and pedestrians
during the week-ends. You could take a walk and have another pic-nic
there.

Voting with Dario for this one! The benefit of a place you can walk, bike or take a train or bus (or tour) to is to be able to fully enjoy that bottle of wine. Italy's drink-and-drive laws are very strict so best to imbibe sans a car. Besides, the Appia is a fascinating stretch to explore, and the further out you go, the more you feel like you're in the countryside.

https://www.parcoappiaantica.it

Oh, and picnicking isn't banned everywhere; mostly on the fountains, the monuments (e.g. the Spanish Steps), church steps, etc. It is allowed in most green spaces, such as Villa Borghese in Rome.

Additionally, some posters have spoken very highly about Tours By Roberto (Tuscany area) so he might be able to set you up with a private picnic at a winery, wine, food and driver provided; pickup in Florence. Or join one of his group tours with lunch provided, such as this one, once they're up and running again.

https://www.toursbyroberto.com/daytours/chianti