One week each in Florence and Venice

Just an answer to your first question: If you get an open jaw flight, it is easier to fly into Venice and home from Florence. Venice is also a gentler beginning....Also, the dock is just steps from the Venice airport and it's a beautiful and easy ride into the city.

I would suggest flying into Venice and out of Florence. Venice would be a quieter, easier city in which to get over jet leg, and it's much easier to fly home from Florence than to try to make a very early morning flight home in Venice.

I usually visit in the second half of September through early October, and I've had good luck with the weather at that time – Though it's never absolutely predictable. I would be prepared for some rain.

You don't mention how mobile everyone is, and that could be an important factor in choosing where to stay in Venice. No matter where you stay in Venice, you're going to be walking from the dock to your hotel, with your luggage. Pack light! I would suggest finding a hotel relatively near a vaporetto stop. Also, if someone has mobility issues, look carefully at how many bridges you're going to cross between the dock and your hotel. Some of the bridges are a little steep, and some are stepped – dragging luggage over the bridges can be challenging. Definitely stay within Venice itself, not in Maestre (sp?). Any of the districts will do, although I stay on the quiet side canal near San Marco or in Dosadoro.

I've used in Context Travel extensively in both Florence and Venice for walking tours, and I believe they also do airport transfers. Their customer service is really good, and I've always found them to be reliable.

Good day trips from Venice are the other islands (Murano, Burano, Torcello, and some really interesting smaller islands), Padua, and Verona. Many people like the cemetery Island of San Michele, although I saw some really disrespectful tourist behavior when I visited and consequently didn't stay long. I did however enjoy a visit to the monastery church on that island.

There are also a number of day trips from Florence, but I've never been able to drag myself away from the city to do those day trips. Instead, I've done them as overnight stays on a subsequent visit to Italy. I particularly enjoy Ravenna, with amazing Byzantine-style mosaics, and Assisi.

To add to Venice day trip ideas: Vicenza, if architecture interests you. I second the suggestion of Torcello. The mosaics in the church are beautiful and very old. And speaking of mosaics, Ravenna would also be a top choice for a day trip.

Thanks so much for your replies. To clarify somewhat, we are very mobile, no restrictions.

I agree with the other poster about flying into Venice and out of Florence. There are hundreds of apartments in both cities and much more comfortable and usually less expensive than hotels.
I'm spending a week in each city this October. I actually prefer October because it's cooler. The one trip I made in the latter part of September was very hot.
To find apartments, you can just search for "vacation rentals venice Italy". I have used VRBO and Homeaway a number of times with good results. I am mid sixties and prefer ground floor apartments or those accessed by elevator. I find I climb many more stairs when traveling without having to climb stairs to my apartments. I also ask the owner of the apartments I rent how many bridges between the Vaporetto stop and the apartment.
Cannaregio and Dorsoduro are great areas in which to stay. Cannaregio still has quite a few actual Venetians who live there. I really enjoyed watching the children on their scooters in the Ghetto.
I don't think you need someone to meet you at the airport. Transport into Venice is easy and you have a number of options. I've used the Alilaguna in the past trips but will be taking the bus and Vaporetto this year.

I would start in Venice. I like the Canarregio area, quiet but close to everything. Get the vaporetto pass.

Daytrips from Venice: be sure to visit Burano and Torcello. then Padova, Verona, Ferrara, Ravenna are all possibilities.

Florence: I like the Duomo area but the Oltrarno is a great place to get away from the madding crowds. Daytrips to Siena, Assisi, Cortona, Montepulciano or Montalcino, San Gimignano, Fiesole is a short bus ride away for a morning or afternoon, Pisa, Lucca.

In Florence, take a cab to your hotel, taxi queue is outside the station. I recently stayed at Hotel Paris, equally distant from the Duomo and the train station - no apartment experience.

In Venice we loved this apartment with three bedrooms with baths, washer, good location. Alvise will meet you at the vaporetto dock and guide you in.

I like October better. Not as warm, fewer people.

We stayed 4. Nights in Venice and 5 in Florence. We flew into Venice ( gorgeous aerial view from plane). Personally, we found that 4 nights was one night too many for Venice. So, you may want to day trip from Venice. Alternatively, maybe cut 1-2 days off of Venice/Florence and add 1-2 nights in Siena. It's really easy to get to Siena from Florence. I was glad we had 5 nights in Florence. There was a lot to see and do there. I liked hotel Pendini in Florence. Request a quiet room. Great location and lovely, recently renovated rooms. Easy to walk to most sites.

One more note - Venice transportation. Venice Marco Polo Airport. Once you leave baggage claim area ( just follow the crowd through the doors), you will be in a lobby area. On the left side of the doors, there is a ticket counter. Here, you can buy a combo. bus/vaporetto pass. Then just outside the lobby, you will see buses. Hop on the bus and validate your ticket by scanning it into the machine. The bus takes you to Venice. (Piazzale Roma). At Piazzale Roma, you catch the vaporetto to the appropriate stop. It may sound a bit overwhelming, but it's a good system and works rather smoothly even for first time visitors. Marco Polo is a small airport and easy to walk through. You can get bus/vaporetto details later after booking your flight and hotels. It's good to know which type of pass you will buy before arriving in Venice.

You should get Rick Steves Florence and Rick Steves Venice. These are a great introduction to each city, particularly about logistics (how to get from the airport to the city, how to get around, which museums are closed on which days, which attractions need advance reservations, etc). He also has details on the most popular daytrips (from Venice: Verona, Vicenza, and Padova; from Florence: Siena, Lucca, Pisa, and San Gimignano).

But since you're planning to stay a week in each place, you should supplement Rick's books with other ones that will have more detail on sights beyond the "first tier," as well as more daytrip possibilities.

I will make it unanimous: start with Venice first. Be sure to fly "open jaws," into Venice and out of Florence. To find these flights, use the "multi city" option on Kayak, Matrix ITA, etc. Don't book two one-way flights, as that's much more expensive.

As for being met at the airport: I'm sure you can arrange that if you need or want to. But for Venice, you can take a water taxi right from the airport to your hotel's (or apartment's) dock, as long as you can afford it (something like €100 or €120 total cost for the three of you). There are several other ways to get in from the airport; none are difficult, but they take longer and/or involve changing from a bus or land taxi to a boat. All are detailed in Rick's book.

To get from your hotel or apartment to Venice's train station (called Venezia Santa Lucia), you can take a vaporetto (water bus, relatively inexpensive) or a water taxi (not inexpensive, but certainly easy). By this point you will have been in Venice a week, so you will know how to get around. And you'll certainly want to get a one week vaporetto pass, and if it's still valid on your last day, your trip the train station on the vaporetto will be covered.

For Florence, the train station is right at the edge of the city center, so you can walk or take an inexpensive taxi. And the airport is not far from the city center, so a taxi is something like €25 or €30 for all of you.

I think I'd be bored with an entire week in Venice, but that's me. I like Venice, but am happy with three nights. Florence, I could live there. Also Rome.

In Florence I've rented a beautiful 2 bed 2 bath apartment several times. Perfect for two couples. VRBO 68776. The owner is Christina and she's a lovely woman. There's even a washing machine, which is nice to have on the second week of a trip. This apartment is in a residential area in the Santa Croce neighborhood, and its within easy walking distance to the center of town. There's also a nice little garden, since the apartment is on the "first floor" meaning up about 5 steps (that's European.) The address is 9 via Ghibbolina. You can google map it. From Florence you can take any number of day trips, Siena, San Gimigano (sp) even a day long wine trip. Don't wait too long to book this apartment, as it's pretty popular.

Any chance you'd like to spend a few days in Rome (rather than the whole week in Venice, or have you been there before?

I love Venice, but I agree that 6 days is a long time if you stay in Venice Proper. I suggest you visit Murano, Burano, and the Lido.

This summer I was on Burano for the first time and IMO it beats both Murano and the Lido.

Also I love walking around the eastern part of Venice around the Castello - leaving the day tourists behind :-)

Arrival: The bus and Vaporetto solution is the cheaper and faster, but I love taking the boat (not watertaxi - that's too expensive for me) from the airport and arriving directly on Piazza San Marco.

We used Airbnb for our stays in Venice and Florence and had a great experience. Our Venice host provided us with pretty clear instructions on getting from the airport on the bus and then catching a vaporetto once we were on the island. And then she even provided a map on how to walk from the vaporetto stop to her place in the Dorsoduro area (which I would highly recommend -- convenient to most attractions but without the crowds).

In Florence, our place was near the Palazzo Vecchio, which turned out to be perfect an centrally located. We walked everywhere. We didn't stay in fancy places, but they were clean and we were able to get a great location for a much cheaper price than a hotel.

Odd woman out, here. I've done a Venice/Florence trip, in that order, and I prefer it the other way. My reason is because Venice (to me) was a more laid-back, quiet place, while Florence had a very hectic city vibe, and I enjoy ending my vacations on a more quiet note. Everyone's got their own preferences.

Happy travels!

We were recently in Venice and took the Allilaguna boat from dock near the airport. The walk from ap to dock was about a half mile. Took boat to San Zaccaria stop which was the nearest to our hotel and we had checked carefully on bridges we would have to cross with luggage ( just one in our case). We were pleasantly surprised to find porters near bridges throughout Venice. This was our third visit to Venice and I don't remember porters on past trips. The charge for handling luggage was very reasonable. On previous trips we stayed in the Dorsoduro area in a hotel right at the Zattere stop--La Calcina Pensione--but it was fully booked on last trip. They do have an apartment so you may want to take a look at it.

Check out the Quattro Leoni apartment in Florence on airbnb.com. Stayed there last Oct with 4 other friends. It had 3 bedrooms, 2 baths and a washer. It's in the Oltrarno about 5 min walk to Ponte Vecchio on a quiet little piazza with a great restaurant, gelateria and cafe. It was about a 12 euro cab ride from the train station. We loved the quiet locations and the narrow little streets around where you can see artisans working on their crafts. PM me if u have questions