First trip and don't want to feel rushed

Welcome to the Forum!
Just some initial thoughts-
Do you have air booked yet?
You may be late for finding lodging in Lake Como. Varenna fills up quickly, but Bellagio is larger and may have more options. The area is beautiful, and the mornings and evening so peaceful.
If you're flying into and out of Milan, I'd recommend a few nights in magical Venice. Or-flying into Venice, which is easier than flying out of Venice.
iMHO, train travel is the least stressful mode.
Italian beaches aren't as beautiful as US beaches, for the most part.
What are the teens interested in?
Make sure your lodging has air conditioning for June. Florence gets quite hot.
W wedding in Italy sounds dreamy.
Wishing you a memorable family trip!

My question is mostly about the best day trips or activities and tours in Florence that would be worth doing

On this page https://www.ricksteves.com/watch-read-listen/read/articles click on Italy and scroll down to find articles on Florence and Tuscany. Arm yourself with a good guidebook (like the one Rick writes) and read the sections on the areas that interest you most. Maybe have your kids read it too so they can have input.

I really like Rick’s books because he helps with the logistics, points out what sites are excellent and what’s skippable. Sometimes people try to plan just from things they’ve heard from friends or seen in a short magazine or online article. Having a book helps you see the things you don’t know that you don’t know.

WOW! Your family is in for an amazing shared adventure! My suggestion first of all is make sure the teens are involved in the planning. The RS books are very good places to start. Over dinner, pasta of course, share your first thought about wants and not-wants. History? Art? Architecture? Music? Relaxation? Hiking? Hotel or apartment? All together or separate excursions? Make it part of the fun, part of the planning, part of the enthusiasm.

From Florence, it is easy to get to Lucca, Pisa and Siena. Got to Siena by bus, not train - it's easier to get into the medieval city from the bus stop. All three could each fill a long day. Verona is beautiful. If you are there on the 13th or 14th, why not experience opera in an ancient Roman colisseum? Arena.it for information.

Venice offers an experience unlike any place I've ever been. After over a dozen annual visits, the city still takes my breath away. Padova is a short train ride away. It's a university city so there will be plenty of young people your teens might enjoy meeting.

The best part of the trip, I feel fairly confident in saying, is the time you'll spend with your family sitting on a piazza with two or three scoops of gelato. You can sit quietly. You can reflect on the day's adventures. You can just enjoy being a family on a very special adventure. BTW, don't let the Jubilee stop you. Italy in June is always crowded, hot and humid. Timed reservations at places of interest (museums etc.) . Will take some of the pressure off you. Also, dinner reservations at places that look most interesting (and very local!!). You might make those reservations the day before - again for a specific time (after 8 o'clock and seated outside would be my suggestion). And to really experience the Italian culture, plan on dinner lasting 2 or 3 hours. Don't worry, the waiters are not in a hurry to get you out!

Keep checking this forum - you'll find a lot of us love sharing experiences and suggestions!

10 days are not enough.
Fly into BLQ and spend 5 days in Bologna.
Day trip to Modena and the Ferrari museum.
Train to Milano. 5 days.
Day trip to Varenna and Bellagio.
Fly out of LIN.

hey hey azduemers
welcome to the forum. so many decisions to make but research does wonders and help from the forum will give you ideas. it's your vacation with options to check out. what's best for you may not be what's best for us, what we like you may not. being your first international trip with your gang have them search.
where is your wedding at in tuscany, likes and dislikes for the group? any planned activities with the wedding group?
if you rent a car, make sure to get an IDP from AAA.com/IDP (international driving permit) for each driver, good for a year.
you are traveling during high season (summer) and will crowded. florence is always crowded since doesn't seem to be low season anymore with so many traveling all year long.
are you staying in florence and have rooms booked? booking.com to see what's available on your days, what amenities you need, any mobility issues, rooms for 4 people, cancellation policies, budget in euros, how many beds (if sofa bed how big/long), bathrooms, A/C, email hotel for better rate if possible.
what attractions/sites you want to see and book ahead of time, some are date/time stamped, skip the line does not mean skip security (everyone needs to go thru), many like to see museums, art, statues, history which i've been there done that, i like looking for fun things especially your kids may enjoy.
popular restaurants may have long waits (make reservations), goes down small alley/calle for small mom&pop's place that aren't crowded, waiters hanging out front luring you in, stay away.
eatingeurope.com/florence
mercatocentrale.com
scroll to artisans, click what they offer. we loved this place just roaming around, stopped to have a glass of wine, looked at local homemade gifts, outside market
florencesidecartour,com
look at tours and if something you & tribe like
vinoevinci.com
sip and painting class in florence, it was fun
thevintagenews.com
renaissance - era "wine windows" in florence
educated-traveller.com
wine windows of florence, read history and they remodeled and some open for service now. pedi-cab tour driver we hailed off street, he was studying opera and sang to us, took us by there few years ago. he took us across ponte vecchio to santo spirito piazza and dropped us off at osteria santa spirito for a meal. was good and fun. before careful for days/times many restaurants are open, many close afternoons and open up later afternoons. on our walk back we stopped at gelato shops, tasting different flavors to see which had the best to our liking.
vivoli.it
handcrafted ice cream & pastry shop.
another lake to check out lago de garda (lake garda) since many people want to see lake como which gets very crowded. we drove from venice years back to bardolino for their annual wine festival late september. it's absolutely gorgeous with all the mountain views, the towns & villages, ferries rides on the lake. many places and things to see and do.
rossiwrites.com/ best towns to visit
visitgarda.com
look at the towns and villages and what they offer. hope yoy can find something that suits you & the gang to enjoy your trip and adventure
campingspiaggiadoro.com
in lasize on lake garda. a camping resort with accomodations, water park, beach, entertainment, supermarket, restaurant/food & bar, lounge to watch the sunset on the lake. relaxation and kids loving it. depending on flight time departure can catch train to milan airport from pescheira del garda or desenzano main hubs for transportation
make your own decision about milan. lots to see and do and a train ride to airport. always remember check-in time is usually 2-4pm
and check-out time is 10-11am. give yourself time in morning to pack up, shower and get ready with time to train station. it's nice to have late morning/afternoon flight back. pack a picnic or pick up at airport a meal/sandwich to take on your flight. good luck and have fun
aloha

If Florence and Tuscany is your focus then fly to Florence (FLR). There are no direct flights from FLR to Paris (CDG) with Air France, Frankfurt (FRA) and Munich (MUC) with Lufthansa, Zurich (ZRH) with Swiss, Amsterdam (AMS) with KLM, and other European gateways as well, such as Madrid (MAD), London (LHR), Lisbon (LIS), Rome-Fiumicino (FCO). Note that Delta is a partner with Air France-KLM, United is a partner with Lufthansa-Swiss. American is partner with Iberia, Vueling, and British Airways. ITA Airways (Italy’s main airline) is currently partner with Delta but since Lufthansa might buy it soon, it might become partner with United.

There are plenty of day trips you can take from Florence, even without a car.

If this is your first trip to Italy, and Rome is not in your plans, then you might want to consider 3 nights in Venice. Since Venice airport is one of the major airports in Italy after Rome and Milan, you might consider flying there and return from Florence.

If Lake Como is in your plans flying to Milan (and return from Florence) is an option. Varenna, Bellagio, Menaggio are the preferable towns in the lake Como mid lake area because all,are served by the frequent midlake ferries. Varenna is the smallest and is very popular so finding accommodations there is more challenging but the other two are just minutes away by ferry.

We just got back from a trip that included a couple days in Tuscany. I think Pisa is a nice day trip if you’re staying in Florence - the tower, church and related sites are all close together. We also went to Livorno, which is on the coast. There’s no actual beach in town but there are swimming clubs right on the waterfront with pools fed by ocean water and steps for climbing into the ocean. There were all closed of course in January but if the weather’s nice your kids might enjoy it.

One thing about cars and Florence - the hotels you’d likely stay at are probably inside the “ZTL” zones where you’re not allowed to drive. So if the hotel offers parking, make sure they can arrange for a permit that allows you to drive in that zone and study the map for how to get to and from. Each zone requires you to enter and leave via specific streets - only emergency vehicles can use other entrances. We drove from Pisa and parked at the big parking lot right off the A1 and took Tram 1 into town - I highly recommend that approach if driving into Florence from somewhere else.

Good luck with the trip!

Thank you for the fantastic input! I appreciate the enthusiasm and have now ordered a Rick Steve's book for a family assignment :)

I guess I should clarify a few points: We will arrive May 26 and depart June 5 or 6. The wedding takes place in Radda in Chianti. If anyone has recommendations of a place to stay near there, please let me know!