Italy trip with 5 other ladies (all over 60) in late august early september 2026

Florence to Cinque Terre is a loooong time on the train, so if you were going to split the locations, that is one I would consider--and who doesn't love a stay by the sea? However, I would also strongly consider staying in Venice instead of taking a day trip. I'd mull over those decisions before choosing.
Are flights purchased yet?
Lucca, San Gimignano, and Siena are relatively easy day trips from Florence. I would swap Orvieto for something else because of travel time.

Don’t take the train from Florence to Lucca because none are direct. Instead, take a direct bus (1h 15m). Take the bus to Siena too because the train takes longer and drops you off further from the old town.
Hire a driver for your day trip to San Gimignano.
Take a direct train from Florence (Firenze SM Novella station) to Venice (Venezia S Lucia station which is the end of line). Get an early start.
You can also take a direct train from SM Novella station to Orvieto (2h 15m). You want to get up early on this day too.
The Cinque Terre is not a day trip from Florence.

Venice and Cinque Terre are not worthwhile day trips from Florence. As mentioned above, don't overlook buses. Many times that is the better choice.

Regarding VRBO or similar. Wherever you book, you want AC. Late August/early September will be HOT.

Also, with 6 of you, book early if needing 3 bedrooms and 2 sets of bathroom facilities. They are scarce. You may decide to hotels will work out better.

As much as we like Florence I would not want to spend 10 nights there
Consider splitting your time between Venice and Florence
Both have many easy and worthwhile day trips
Fly IN to Venice, much easier than flying out of

As far as apartment type rentals-make sure you have at least 2 bathrooms and make sure all the beds are actual beds-not futons or pull outs
AC is a must

So I'm really curios why if you're all over 60 are you going in the hottest time of the year? Also Florence sits in a bowl at the foot of mountains so super hot in summer and super cold and windy in winter. J

I really appreciate the feedback! In answering the question as to why we are going in August when its so hot is because its the only time all 6 of us can go due to other commitments with families, wedding in Oct. etc. I was also thinking maybe spending half the time (VRBO) in Florence and half in Sorrento. What are your thoughts on that? Or does it makes sense for the places we want to visit?

Sorrento is a great base if you are interested in Pompeii Naples Capri Amalfi
It’s a fun town with great views , food and shopping
But it’s a bit of a hassle to get to and transportation in the region is chaotic to say the least!
August will be extremely hot and very crowded

You’ll want to fly out of Naples and will likely need to stay in Naples night before departure

Repeating from above-Venice is not a day trip from Florence so if that’s a high priority you need to stay there

There are dozens of threads here about Sorrento
Spend some time reading thru before you make a decision

Margie, Sorrento doesn't really make sense as a base for day-tripping any of the locations you listed. It's much too far south and only makes sense for Naples, Capri, Pompeii, Amalfi coast, etc. although that's also a very busy destination in high season.

Of your wish list, Venice is the one I would plan a 2-3 night stay for so you could explore the main city and some of the islands. Yes, I'd fly into that one and move on from there. The CT is a long day trip from Florence, is no fun in wet weather, and tends to be overrun during high season; another choice I wouldn't personally make in late summer. That said, if one is to do it it's best to stay at least one night there due to the distance from Florence and that it calms down a bit in the evenings when the day-tripping mob departs.

To exchange Florence nights for the CT and more time in Venice you'd obviously need to drop a couple of day trips, and I'd start with Orvieto due to the distance. Florence itself is a marvelous city if you're interested in Renaissance art and architecture - + it's VERY walkable - so I sure wouldn't shortchange that one. Managing the late summer heat will be easier as well if you're not trying to sightsee the many treasures at a dead run. :O)

Editing to add: have the 6 of you ever traveled together before? If not, it may become even more important not to overload the schedule. Let's just say that if you're dealing with a mix of night owls and early birds plus trying to get everyone in and out of shared bathrooms, fed and off to trains stations and whatnot, you'll only move as quickly as the slowest friend. Love 'em dearly but as much as we'd like to travel with some of ours, too many of them don't get going until late morning when a hefty chunk of our sightseeing day is already history! Just something to think about?

Margie, just my 2¢. Traveling to Italy during the hottest time of the year, I would not go further south unless I never plan to return to Italy.

Assuming you spend half your stay in Florence sightseeing, shopping, taking a day trip. Florence will be busy, crowded and hot and you'll be on the go.

How do you all envision the next 5 days when you're not seeing the sights?

• relaxing by a pool in Tuscany
• sitting on a terrace overlooking a glistening lake surrounded by mountains
• town hopping between the villages of Cinque Terre
• strolling the canals of Venice after the daytrippers have left

What's your Italian vision?

hey hey margiebiebel
welcome aboard. understand about your travel dates and why. you all know about the heat so just go for it and look for A/C. where are you flying in from? i have couple ideas to get you starting your research, nothing written in stone, it's your vacation.
visit 2 areas, 10 days is short but you can do things. do a multi-city flight (into one city and out from another) not 2 one ways. you do not want to be backtracking, spend last days in city you fly home from. check-in is 2-4pm and check-out is 10-11am, check your flight arrivals & departures, not waiting hours with luggage. if flight is early we have double booked for night before and let them know so you have a place ready for you.
ChristineH: sounds good. fly into venice "VCE", easier to get over jet lag, flying out is a pain usually 6am flights out! beautiful place with things to do, train for day trip to the lagoon islands, padua, treviso, vicenza, prosecco region tour. renting two rooms/apts will give you more availabilty. book room/apt early since august/september are busy months with high season plus harvest time.
take the train to florence with many sights to see & activities to do, very walkable with the heat again, bus to siena or train to lucca and spend a few days. there is the florence airport or pisa airport to chose from.
you could also stay in northern italy, training from venice to stresa on lake maggiore or perscheria del garda on lake garda. small towns nearby and fly home from milan.
so many different ways to see italy. the towns you listed will be busy, since they are always mentioned here, go out of the bubble with smaller towns and less crowding.
booking.com
search city, dates, # of people, on left are filters (click apts with other amenities you hope)
beb.it/ ca' badoer venezia
we stayed here several years ago in san polo area near frari chuch. they are a lovely couple and will help you, we were able to leave our bags, small elevator, small washer & we just hung clothes to dry within our place.
we loved it. there are a few different apartments, we stayed west studio. rent two apts for bathrooms and bedrooms, look at bed sizes (don't want a sofa bed) may be too early to reserve online. contact "[email protected]"
just a few of my own opinions, take it with a grain of salt. happy to see you are starting early. get your airfare and hotels/apts situated then you can decide what activities you want to do. keep asking questions, forum here to help you with good bad and ugly, discuss with your traveling ladies. have a great time, you'll enjoy it with stressing, researching/planning is part of the fun.
aloha

I was also thinking maybe spending half the time (VRBO) in Florence and half in Sorrento.

and

10 nights in Florence but do day trips by train to Siena, Cinque Terre, Lucca, San Gimignano, Orvieto, Venice.

Are essentially mutually exclusive.

If Venice is important then spend 2-3 nights there. As noted already, that would be a good place to start your trip and then move on to Florence to fit in as many of the other places on you wish list that is practical, based on just what you want to do at each.

If Sorrento is a priority, then Venice becomes 'to far afield' and the Florence area based wish list needs some pruning.

No right or wrong answer, but trying to do ALL of it in 10 days becomes more like competing in a Decathlon than being on vacation.

Happy planning and travels

( Would love to be a fly on the wall as the 6 of you discuss this) :-)

We will be flying in from Kansas City, MO. To answer one of the questions on if us ladies have traveled together before and the answer is yes, we have gone many girl trips together. We are very much on the same page with just about everything! Great friends! I’m really interested now in flying into Venice after reading some of your comments and probably flying out of Florence. I’m not sure which of the places we want to see would be better from Venice?

None of the places you’ve listed above are reachable from Venice as day trips

From Venice-Padua, Vicenza, Verona, Bologna
Venice itself deserves at least 3 nights and be sure to stay IN Venice ( not Mestre)

Sounds like a great group of friends. I am going to ask, “Since you are committed to this time period, are you equally committed to Italy as the location?”

I think that going further north, Germany, Austria, Switzerland could be another great location.

Half in Florence and half in Sorrento makes good sense to me. One big city per trip is enough for me and Sorrento is more of a town than a city. (End of August is the perfect time for Switzerland). Been to Italy around 12 times and I could still do 5 nights in either of those places. Have a wonderful trip. J

From Venice-Padua, Vicenza, Verona, Bologna

This is a really nice option.

From Florence we used tour company Walk About Florence for an all day Tour which included Sienna and San Gimignano and Pisa. It was a long day but very fun. If you want to visit some wineries I reccomend tour company Prestige Rent, small group, beautiful wineries

You all are so wonderful to give such great suggestions!
1. I’m really interested in your ideas of flying into Venice and staying for a couple of nights and then train to Florence.
2. From Florence day trips to Lucca, Siena, Tuscany, San Gimignano. Rethinking about not going Cinque Terre.
3. Or, second option is to stay half time in Florence and other half in Sorrento, or close do we can explore Sorrento. I would like your opinions on this trip and maybe visit Capri and Amalfi coast. Or should we stay in Naples and fly out of Naples? What are your suggestions as to where we should fly into on this plan?
I really appreciate all of you! Thanks

Only you can decide along with your travel partners.

All locations will be heaving with tourists and very hot.

Are you interested at all in any of the great day trips from Venice? Padua, Verona, Vicenza...
If so- spend half your time in Venice and fly IN to Venice. If you don't care about those day trips then spend at least 3 nights in Venice- IN Venice, not outside (like Mestre)

Florence is in Tuscany as are all of the days trips you list above. If you mean to visit a different Tuscan hill town then you will have to decide which one and figure out transportation as almost all will require a car.
There are lots of organized bus tours from Florence that will take you to several in one day (such as Walk About mentioned above).

If Sorrento, Pompeii, Capri, Amalfi coast towns interest you then stay in Sorrento. Sorrento itself doesn't really have much to "explore"- it is full of great restaurants, fun shopping, fantastic views though. Not a beach but sort of a beach/resort feel.
it is the transportation hub for the area. If you fly out of Naples (as you should if you are in Sorrento) you will need to spend night before departure IN Naples- that 1 night in Naples might be enough for your group..
There are dozens of threads here about visiting Sorrento, AC, etc and all the pros and cons. Please take the time to do some searches here and read thru all the info
Transportation is a big issue there-it is chaotic, slow, super crowded. Hiring a driver for an Amalfi day might work but with 6 you will need a van. Of course there is also the ferry option.
Another good option is to sign up for a shared tour with RS recommended Mondo Guides
www.sharedtours.com

Perhaps you all should start watching some YouTube videos of the places you think you want to visit- there are literally hundreds.
Get all the guidebooks you can get your hands on- either purchase them or check out of library, study some maps so you get a handle on distance between locations.