My Way Italy vs. Best of Venice, Florence & Rome

The ideal minimum number of nights is:
Venice + Murano and Burano islands: 3 nights (2 full days)
Florence: 3 nights (2 full days). One of the two days could be used for a day trip somewhere in Tuscany if too much art overwhelms you.
Tuscany towns/countryside: Add 2 nights to Florence for each full day you want to add to Tuscany, depending on how many towns you want to visit. Use Florence as a base for Tuscany.
Rome + Ostia Antica or Tivoli: 4 nights (3 full days).
Gulf of Naples area (Naples, Sorrento, Amalfi Coast, Pompeii, Capri, Procida, Ischia etc.): 4 nights (3 full days)
Cinque Terre: 2 nights (one full day). If you want to add them, should be added after Florence/Tuscany. Then from the Cinque Terre you would go to Rome.
Remember the above are minimums numbers of nights.

If you organize your own trip, it is best to put the Gulf of Naples area before Rome, then back track to Rome at the end. Since Rome is likely your airport from which you will depart back to North America, it makes sense to leave Rome for last.

If you go on an organized tour, then you are stuck with their schedule. I don't like organized tours, I prefer to do my own thing. Organizing my own trip is half of the fun of travel. There is certainly value in having a guide who explains the art to you in a museum. But you can sign up a guide just for that, for the museum part. Also many large organized tours, due to the large number of passengers, have to use large hotels that are often located outside of historical centers. When I travel to a city like Rome or Florence, I like to stay in the middle of it all, not at the EUR district in Rome or on the Lungarno Colombo or worse, Novoli, in Florence. I have never been on a Rick Steves' tour, but I know that Rick Steves' tours are better since they are smaller groups.

Roberto,
One of the big advantages of Rick Steves tours is that they stay in the historical centers.

I haven't taken a RS tour, so I don't have any direct experience on that. I plan all the details of our trips to Europe, and I would likewise prefer the "My Way" type of tour, rather than stick with a guided tour group. Regarding Florence... we stayed in Siena for four nights on one trip, and just visited Florence as one day-trip. I know there is plenty more to see, but we did see Ponte Vecchio, the Duomo, Uffizi Gallery (tickets ordered in advance!), and a good, full day of walking around and absorbing the atmosphere of Florence. So, I think 1.5 days will be fine -- do Academia on your extra 0.5 day if you want another big attraction. And, you can go back again some day if you want more. But, I have to say... Cinque Terre is my favorite place on the planet and it's totally different from the big cities that you're planning to visit. If you and your family enjoy hiking, spectacular views, great food, some time on the beach, and the tranquility of small isolated villages, then you should go to Cinque Terre. I'm not sure how crowded it is in July, I've only there in May a couple of times and it was fine then.

The real treasure and in my opinion, the point of the RS tours are the guides. So far they have all been simply amazing to me. We went to the "test drive a tour guide" earlier this month and met dozens more guides that I would love to spend a tour with. So for me, I would either take the guided tour, or plan the trip on my own. We did a RS tour last year and this year I am planning Italy on our own.

atsemer The great thing about a RS tour is that your head will hurt less, because they handle all the difficult stuff. I have been on the VFR tour and loved it. Not having been to any of those places before, I found the tour was a more efficient use of time since they know the short cuts, have all the tickets ready, and if you don't want to do the planned day of activities, they don't force you to go - you do have plenty of free time. But the best thing was that the guided tour provided more than logistics: the guides provided an educational experience we would never had on our own, and we had a great time with our fellow travelers.

Either of those tours would be excellent however given the specifics of your group, my suggestion would be to consider the My Way Italy tour. A few thoughts.....

• The V/F/R tour will include a number of local walking and museum tours, not all of which may be of interest to your group. The My Way tour would allow you to tailor the sightseeing more to the preferences of your group and tour at your own schedule.
• If you choose the My Way tour, you'll have to plan your touring well in advance and pre-book reservations for things like the Uffizi and Accademia in Florence, Borghese Gallery in Rome, etc. (if you were planning to visit those).
• The My Way tour will allow you to see a wider part of Italy rather than just "the big three" cities, which I believe you'll really enjoy. Although you're not interested in seeing Lago di Como (Varenna) or Assisi, you may find that you enjoy having a look at those places.
• If you plan your touring carefully in Florence, 1.5 days should be adequate to allow you to see the highlights.
• YES, the Cinque Terre is absolutely "worth it" (IMO). You'll have the benefit of being there in peak season, but not having to worry about finding accommodations. I believe the My Way tour uses Monterosso as the home base, which is one of my favourite places in Italy. It will be busy in July, but certainly worth seeing. Your girls might enjoy some beach time, and Monterosso has the best beaches of the five towns.
• The tour escort will be available on the My Way tour to help you sort the details. By the end of the trip, you should be quite comfortable doing things on your own.

I'd suggest arriving in Venice a day or two prior to the tour, both to allow you to recover from jet lag as well as provide a bit more sightseeing time. At the end of the tour, stay a few days extra in Rome to visit more sights. Try to book the same hotels used by the tour in Venice and Rome.

Good luck with your decision!

I know I could plan it all myself but just the though of it makes my head hurt!

You have two teens. Get them involved. Let them do the planning. A fellow I knew planned his family (5 people) trip to Italy when he was 12 and 15 years later he remembered everywhere they went, everything they did.

With two kids, if they can do it together, excellent. If not, each one could sketch out a plan, then decide on a rough itinerary as a family. After that, each kid could plan 1 week in detail.

Thanks for all the replies. It was very helpful. I'm thinking that I can plan this myself. I can look at other people's suggestions for hotels - that was the daunting part to me, w/o having to research all the options. However, I'm thinking of buying plane tickets to coincide w/ a My Way tour in case it just becomes too much and I can sign up for the tour and not stress over it.
In reviewing all the wonderful advice - here's my tentative plan:
Venice - 3 nights - fly in
Florence - 3 nights
Cinque Terre - 3 nights
Naples area - Sorrento, Pompei, Positano - 4 nights since I'm thinking day trip to Pompei, day for Sorrento and we'll probably be on the train all day from CT.
Rome - 4 nights - fly home

Any reason why I couldn't fly home from Naples - is it more expensive? We're flying out of Newark.

That's 17 days but depending on prices, I was planning on tweaking it up or down. Would you consider this plan to be the minimum, therefore, go up rather than down? Excluding time in Naples area, this is about the same # of days of My Way tour. Do you think I could do it for < $12,000 ( this is what the My Way tour would cost for hotel & bus)?

I think you can manage the hotel + flights for <$12,000. I'm figuring $5000 max for the four of you for the flights, and two double-rooms per night for up to $200 per room per night = $6800. If you can manage B&Bs or hotel rooms less expensive than that, go for it. And maybe you can get cheaper flights as well. I just recently booked a vacation for a family group of 6 (3 couples) and those are the costs that I ended up with. Rooms were typically 100-140 euros per night. I got 70 euros per room in Pisa, 100 to 140 euros per room/apt in Vernazza, about 580 euros total (a bargain!) for a 3 bedroom apt for 5 nights in a villa/agriturismo in Tuscany, and 125 euros per room for a great B&B in Venice. You should definitely check out the fight prices on Expedia or whatever for a return flight vs flying in to one city and departing from another -- sometimes the price differences are minimal. Of course, if you rent a car there will be a drop-off fee if you don't return it to the same place, but you will save time and money otherwise spent by going back to the same place.

I just finished planning a 4 week trip to Italy in May. My hotel/b&b cost average is 98 euro per night. All rooms are double with ensuite bath, located in the historic area and are well rated on both TripAdvisor and Booking.com.

atesmer,

Regarding hotels there are lots of good hotel listings in the RS Italy Guidebook. I'd highly recommend that you buy a copy of that straight away, as there's an enormous amount of information there! It will also help with transportation, sightseeing (ie: how to beat the queues), etc.

As you're now planning to do this on your own, I'd suggest that you start looking for accommodations especially in the Cinque Terre ASAP. I typically start booking in February for travel in September, but as you'll be there in peak season you'll have to get that sorted fairly quickly. That's one advantage of taking one of the tours - no worries about finding a room.

There are some potentially expensive "caveats" to be aware of when using public transit in Italy, but you should be able to easily get to all of your stops using well planned rail or bus trips. As you won't have a tour escort / guide during the trip, you'll have to do some homework on how to use transit there.

You should certainly be able to find a return flight from Naples. I'm not familiar with flights from EWR but I'm sure one of the others will be able to provide information on that.

A budget of $12,000 should be more than adequate for a 17-day trip.

Good luck with your planning!