Where to spend an extra day? Florence vs Cinque Terre

You have too many stops, 2 nights only a single full day. The CT is the weak link.

Give Florence 3 nights.

Have been to both, Florence several times. Florence for sure for the extra time. My opinion, you don't need to visit all five "terres". I would skip Riomaggiore and the one that's up on the hill above the water if you are pressed for time. I know hiking to them all is the goal for some, but is time consuming. Taking the boat between villages was easy, fun and not expensive. Hike some, boat some, train some. Florence just has so much more going on, IMO. We were there in 2012, but I doubt much has changed re "what to see and do".

Of course, only you can judge what your family will likely enjoy the most.

Make a list of what you want to see in Florence. If you are just including it because you feel you should, then free yourself! If you think your kids will benefit from some time hiking along the coast in between some fairly intensive sightseeing, why not?!?
I’d consider adding night to Venice though.
I am reading “hiking family” and taking it quite seriously. Florence will still be there when they do their college trips, or when you do a couple trip and visit wineries.

Sorry to tag along, between which villages is it better to take a boat to add on to experience instead of a train?

On my first trip to Italy, which included Rome, Florence, and Venice plus the Cinque Terre...the highlight for ME was the Cinque Terre. I was awed by its beauty, and I'm just not a big museum buff. Florence just seemed touristy and really didn't ring my bell.
Don't get me wrong, Venice was amazing and I've since been back several times. The Roman ruins were everything I was hoping for. (Rome the city was not.) But...I love the ocean, and I loved the hikes I did in the Cinque Terre were memorable and amazing.

There is more to see in the Italian Riviera besides the Cinque Terre. There are some beautiful towns to the north like Camogli, Rapallo, Santa Margherita Ligure. All are easy to get to by train for easy day trips. There are hiking opportunities up that way too. If you want a rugged hike (with few other people on the trail), try hiking from Camogli up the steps up, up, up to San Rocco...then from there hike to the abbey at San Fruttuoso and perhaps on to Portofino (there's also a ferry that runs between Camogli, San Fruttuoso, Santa Margherita Ligure, and Rapallo, but check the schedule for April. Here's a good blog describing this itinerary. Note that they chose the easier, inland trail from San Rocco to San Fruttuoso. I chose the harder one via Batterie which had perhaps better views but it was a bit scary, as I am NOT an expert hiker! I had to scale some parts of that trail by holding onto chains in the rocks. Expert hikers would have no problem with this, I guess, and I survived, but I wasn't prepared for that. Avid outdoor enthusiasts might really enjoy this hike - it sure was memorable for me. Very different from the mostly crowded hikes I've done in the Cinque Terre.

https://www.neverendingvoyage.com/hike-camogli-to-san-fruttuoso/

If your teenagers love art, churches and museums keep Florence. If they would prefer hiking I I would add a night to CT and add one to Venice. Venice is a much more one of a kind place that might make a bigger impression on them. I would suggest that you talk to them and have them help you make some decisions. Point out to them that 2 nights does not equal 2 days because of travel checking in, checking out when leaving, travel and checking in.

If you are arriving in Venice you must take into consideration Jet Lag! Some in your family may do better than others but you just don"t know. Add a night and day to Venice!

Have a Great Trip!

I'd say Florence, for sure. So much to see there! But as Mimi said, if your family is into the outdoors/hiking and not so much into what Florence has to offer, then spend the extra in the CT. It's all about individual interests.

confusedtraveler, the OP's question isn't about getting around the CT so it would be best to start a new thread with your question. Just FYI, the ferries only stop in 4 of the 5 villages: Corniglia doesn't have a harbor.

Andrew, I’m cracking up — I had pretty much the same experience at Portofino park! I was just telling my spouse I would not do that hike now, but I’m so glad we did back then. Not that anyone should take risks they are not prepared for, mind you.
I’m usually talking people out of going to Cinque Terre—those who try to squeeze in a day trip, usually, but also in seeking to spread the love to Italy’s other parks and coasts—but sometimes it really works best for a plan, and no one should feel like they have to see only the big deal sights.

If you want an additional one-night stopover, consider Lucca, pretty close by train, after your Pisa couple of hours. Lucca’s fairly compact within its Renaissance-era walls. There’s a path atop the entire ring of walls encircling the city, great for walking or cycling (or rent a four-person, four-or-five-wheeled “bicycle rickshaw” contraption), and the family can stroll or pedal its way around. There are cannons and fortifications turned into little parks along the walls, if the kids want to frolic, or to peer down to the city below, on either side of the tall, thick walls. There are a couple of museums, but the outside parts of town are the real attraction. Lucca is the birthplace of Puccini, so there are opera opportunities, if some cultural pursuits are any interest. What had been the ancient Roman amphitheater 2,000 years ago has been surrounded by residential buildings, and the amphitheater is gone, but the oval open space remains, encircled by the surrounding buildings. You can stand in the middle of the Piazza dell’Anfiteatro, as if you’re in the center of a Coliseum, although you won’t be in Rome, and you’ll be the imaginary gladiators.

If it’s absolutely just either Florence or Cinque Terre, then Florence, no question. Both get big crowds nowadays, but Florence can handle them better. The trails and outdoor spaces in and among the 5 small villages were just inundated by the crowds when we stayed in the CT in 2021, and the magic of the CT when we visited on a previous trip wasn’t there so much on that trip 2 years ago.

It's still possible to enjoy the Cinque Terre despite the crowds. You just need a strategy to avoid them. First of all, don't to hike the popular trails between towns during the day (maybe very early or very late might work - but not a few hours before or after mid-day). And second, don't try to explore the towns during these times. If you are staying in the area, you can explore the towns at night or in the mornings. Then find a way to be elsewhere during the day. On my last visit in 2019, I hiked from Levanto to Monterosso (very few hikers). On another day, I took the ferry on to Porto Venere. The ferry was pretty crowded but the town was not. Later that same day I returned by ferry to Manarola and dodged the crowds through the town and hiked from there to Corniglia via Volastra. There were more hikers than the trail from Levanto but still not nearly as many as the popular trails below. This hike was also very rewarding - the best views of any hike I've ever done in the region. It was a very steep climb up a zillion steps to Volastra, though! I took it easy and had no trouble though.

I haven’t been to CT since 2006. At that time we were on a tour of Tuscany & Umbria & CT wasn’t inundated with crowds. Our tour began in Florence & ended in Rome. If we were to return to the area we would consider staying in the commune of Levanto. Located on the coast it has a beautiful town center, and a lovely beach. It would make a great base for a couple nights. We did a day trip and enjoyed a wonderful dinner at Zita’s. A nice hike up to the restaurant and a magficient view of the valley. Levanto could tick your boxes. Hikers love the surrounding hills, gorgeously covered in pine and olive trees.

I'm going to throw out a very unpopular idea. Skip Florence. Stay Lucca instead, and either day trip in to Florence, or stop on your way to Lucca. Then have 3 nights in CT to enjoy. I would even consider doing just 1 in Lucca on way to CT from Venice and adding another night to Venice.

Hiking Family- If you want outdoor activities, I suggest extra time at Cinque Terre. Florence is a lovely city, but by the time I arrived there, I was pretty much at my limit of museums. I imagine your teenagers might have a similar response unless they are really into Art or history.

The good news is that whatever you choose, you can have a great time.