5-7 days this July, connecting anywhere from Milan, where to?

Any of those would be five to seven day stays for me, easy. If the lake wins, a few days there and the remainder in Milan.

One take on this would be to head down to Genoa after the festival, which might be less than an hour and a half. This would allow some de-compression after the teaching and give your wife some varied waterfront opportunities. From there it would be less than a three hour train ride to Florence, which could be the arts and culture stop (plus the food, oh the food) for you. I haven't personally been to Genoa, so can't comment on the food, but I think all over Italy if you read the reviews and the menus posted on the door, you can find great food.

July heat is likely to be brutal in Rome and Florence. (Florence will be worse than Rome, probably.) I think some time on a lake (though hotel reservations on lakes in mid-summer may be challenging at this point) followed by some time in Milan or Turin would give you a better shot at not sweltering every minute of every day. The only way to be virtually certain of avoiding heat would be to head up high in the mountains. Milan puts you quite close to Switzerland.

Here are the day-by-day temperatures in Milan and Florence for last July. As you can see, it was pretty doggone miserable even in Milan.

Milan weather July 2025

Florence weather July 2025

Weather can vary a lot from year to year, so I encourage you to check some additional recent years via the pull-down box just above the graph a the right.

Use the Search box for data on other locations you want to consider.

All of those possibilities have potential for hot and miserable weather. And crowds, given the time of year. Even so, if it were me, I'd take the train to Venice as it ticks the arts/culture/water/food/walking boxes. Plus it's sinking so best to see it sooner than later and it's magical in the late afternoon/evening when the cruise people leave. Then back to Milan and a few days split between the city and Lake Como. I'd suggest flying back from Venice but many US bound flights leave at an unholy early hour (but check to see if maybe you'd get lucky).

hey hey benjaminordaz007
is it just you & your wife? it's very very high high season and will be HOT. the places you mentioned will be crowded and busy, you're late in the game for accomodations with hotel rates skyrocketing for a while now. i would stay near milan, you days are too short and spending too much times on trains and not sitting to relax and see the town/city.
as nancycantravel mentions
GENOA: a train ride/ferry south ( industrial along the ligurian coast. look at the small towns/villages, camogli is mention here several times. beach for your wife, food/cafes/ shops along the pedestrian platform, eat some focaccia bread, seafood. san fruttuoso bay cave and abbey monument using the ferry. beautiful portofino. spend couple days to enjoy drinks, water views and food.
wanderingitaly.com
genoa chiaroscuro and the soul of a port city
discovernorthernitaly.com
scroll down to see what small towns on italian rivera you can visit and stay at. another thing to think about. genoa is a cruise ship stop, lots in summertime.
cruisemapper.com (left side click unselect all, click ports, type genoa, click july 2026), check dates that ships are in port, some have 1 and then again some have 4 which adds to all the thousands of cruisers are in the town
back to milan and you decide where
TURIN: italyreview.com
click from top to bottom about what to see and do. known for chocolate (do a tour) sightseeing city tour, history of fiat car museum (museoauto.it), museum and palace tours
eatwith.com (torino or milan)
dinners/lunch in a residents home, or other tours/classes offered.
MILAN or ???:
other places you can check out are the lakes (friends tried to book lake como and was outrageous$$$, slim to none and was sooooooo crowded, to me ruined by social media, instagram, tiktok
LAKE GARDA: (lakegardatravel.net)
this lake was gorgeous, lake and mountain views. we stayed in bardolino for the annual wine festival "festa dell'uva. many small towns/villages around the lake/ pescheira del garda is transportation hub, bus service around lake also taxis. busy and crowded with summer time, some towns have nice beaches (some smooth and some rocky pebbles). click the towns to read about (sirmione is very tourisy and crowdwd with day trippers on many tours, wineries, olive oil, weekly markets. we enjoyed just walking around
LAKE MAGGIORE:

discovernorthernitaly.com 10 most beautiful towns on lake maggiore to visit
stresa is mentioned a lot here to stay on the lake. read up about if it suits your fancy.
check-in times 3-4pm check-out times 10-11am. what time is flight back, where ever you are spend night before at airport area. some flights can be early early "dark thirty" and 3 hour s before flights. just ask questions, people on forum will give you good bad and ugly. it's you decision what suits your fancy, enjoy and have a great time
aloha