RS Venice, Florence and Rome

You will deal with jet lag on your arrival day so do not visit museums, rather go for a walk in the fresh air, easy to do in Venice. You will be fine the next morning.
I would spend your extra days in Rome itself as you have such a short time there included in your tour. Walk through the neighborhoods, visit Travesterre, Appian Way and catacombs , take a food walking tour; explore Ostia Antica near FCO if you want an excursion right outside of Rome.
For only ten to 12 days you do not need to pack much. Lightweight, hamdwashable clothing is best. A few tops for daytime and a few more for night, two pants or skirt and pants, sweater, rain jacket, nightgowns, underwear, shoes-one you waer on plane, add one more pair. Flip flops to wear as slippers.
Laundry kits, toiletries in 3oz carry on bag.
If you haven’t booked your flights, I would add more time on each end of your tour. It sounds very rushed.

Also, if anyone has tips on packing a carry on for 14 days I will so appreciate any information. I have Rick Steves packing list, but I don't seem to be able to pack like him!

LAUNDRY--- you wash a wear your clothes again. You do not need a new/different wardrobe for everyday of the trip.

If you have only 2 'extra' days for touring, use them at the end of the trip. Arrive the day before the tour begins.

I agree you should arrive a day before your tour to get over jet lag. Use the arrival day and the morning/afternoon of the next day to see some sights in Venice before meeting your tour group late afternoon. That would have been enough free time for us in Venice, though we had an additional day before. I wish we would have put that extra day on the end of the trip. We spent one extra day in Rome, but wished we'd had more time.

donnab, you can do whatever you want before or after the tour, as long as you show up for the meeting on the first afternoon. We went three days early, flying into Milan, and stayed in Varenna and Milan before taking the train to Venice. Arriving early is highly recommended. We had people who showed up at the first meeting just off the plane, who were nodding off into their dinners from exhaustion and jet lag.

Packing light requires a change in normal mind set. You have to accept the idea of wearing clothes more than once, doing some laundry, and not worrying about how you look. If you just can't do it, its not a crime to check a bag, it just makes moving around to & from hotels more cumbersome. We always take an extra empty duffle bag for souvenirs, anyway.

As to packing for 14 days, yes, it takes some thinking but easily doable. Don't think it terms of outfits, think in terms of tops and bottoms. I do better if everything I have matches everything else.

Here's a link to a thread I did April 2017 when several of us had been discussing capsule wardrobes. Different location, different time of year but it's still mostly the same things I would take to Italy. It IS the same list I took to UK in September of 2017 (3 weeks) and to UK in May/June of 2018 (5 weeks). I have swapped out the black jeans for the Costco travel pants and this May I added in a pr of capris.

https://community.ricksteves.com/travel-forum/packing/capsule-wardrobe-paris-and-western-france-april-may

The best advice I've ever gotten on this forum regarding packing was to pack on paper first. I'd also do a trial pack soon including your 3-1-1/toiletries so you are not scrambling at the last minute.

I'd also agree I'd not do a day trip on your day ahead of the tour -if it's your arrival day, just walk outside and see sights!

I agree that you should arrive a day early, wander through Venice. It is beautiful city just to explore. This will allow you to adjust to the new time zone (don’t know if you get over jet lag that fast, but for me it takes a few days), you will be more comfortable on the first day of your tour. I would also add time at the end of the trip and spend more time in Rome.

As for packing, you will be thankful at the end of your trip for packing light. The key is to take separates and make sure that every top works with every bottom. Also, I try to take clothing that doesn’t really show stains (and take a stain remover pen). Look at items that add bulk and adjust. In October, you may need a light jacket and a travel umbrella, but the rest of your clothing can be very lightweight. Rather than bringing a lot of connectors, just bring a hub for charging (saves on bulk and space). I get buy with only 2 pairs of shoes, my walking shoes and sandals, resist the urge to take more shoes, you won’t need them and if you do, Italy is a fabulous place to buy shoes.

Do a trial packing a week before, carry and lift, to see if the weight is comfortable for you. Everytime I travel, there is always something that I look back and say that I didn’t wear or use it enough to justify.

Have a great trip,
Sandy