5 Towns in 14 nights? Too much or to little?

Working from North to South is nearly always a good idea so you have a good start!

I'd suggest going to Florence after Venice since its a much shorter train ride.

This breaks up the long journey to Cinque Terre. Italy doesn't look that wide on a map but its a fair distance. Plus the railways don't have a direct route into the Cinque Terre the way you'd think they would.

You may want to opt to do Cinque Terre OR Sorrento but not both on this trip. Do you prefer remote laid back seaside towns (Cinque Terre) or the many day trip options available in Sorrento - to Pompeii, Naples, Amalfi Coast?

Here's 3 possible itineraries:

Option 1:
3 nights in Venice (Note: you'll lose 1/2 a day due to waiting on customs, getting to your hotel, checking in and getting settled)
Evening train to Florence on the 3rd day (2 hrs)
3 nights in Florence
Morning train to Cinque Terre (3-4 hrs) - This will take a better part of a day since you'll be checking out of one hotel, arriving early to wait on the train, checking into a new hotel etc.
3 nights in Cinque Terre (allowing 1 day for the above train travel)
Morning train to Rome (4+ hours so again allow a full day for checking out, train ride and getting settled in the new hotel)
5 nights in Rome

Option 2
3 nights in Venice
Evening train to Florence on the 3rd day (2 hrs)
3 nights in Florence
Morning train to Rome (4+ hours so again allow a full day for checking out, train ride and getting settled in the new hotel)
3 nights in Rome
4 nights in Sorrento (allowing 1/2 day to get to Sorrento)
Final day train back to Rome for flight home

Option 3
4 nights in Venice
Evening train to Florence
4 nights in Florence
AM train to Rome
5 nights in Rome

Note: For many travelers it would be easy to spend a week each in Venice, Florence and Rome and still not see everything they might wish to see. So examine the guidebooks on these cities very carefully before you decide to add Sorrento or Cinque Terre to the itinerary.

One of the easiest travel mistakes to make is to plan too many cities. :) You always have the option of taking day trips or "adding" another city while on the trip if you've accomplished all you'd hoped to see in one town or if you decide you don't like that town (unlikely!).

Lots of good ideas in the post above. One additional thing to consider - flights home.

If you end in Sorrento, you can fly home from Rome (FCO) or Naples (NAP). While there is a direct bus from Sorrento to NAP, flights from Naples that connect to the US often leave quite early, which may mean a taxi (about €80 or €90).

If you are flying home from FCO, it takes about 3 hours to get there from Sorrento. Unless your flight is quite late in the day and you feel lucky, or you're willing to get up at 4 AM and spend about €300 for a taxi all the way from Sorrento to FCO, you will have to spend your last night in Rome.

When looking at your flight options, take these factors into account. If you are flying out of Rome, one way to order your trip is to go from the CT to Sorrento, then back to Rome for a few days before your flight out.

And for your inbound flight, flights to Milan have recently been much cheaper than flights to Venice. However, you have to add the time, cost, and hassle it will take to get from Milan to Venice.

Good point about the flights, and boy are they expensive!

Hi,

This is a reverse itinerary to what we did on our first trip to Italy, and is "doable".
Recommend:
3 nights in Venezia, train to Firenze
3 nights in Firenze, train to CT
3 nights in the CT- I like Riomaggiore- then long day train from CT to Sorrento- it'll take most of the day for that trip
2 nights in Sorrento, train to Roma
3 nights in Roma- then fly back to reality

The train ride from the CT to Sorrento is a long day, but you'll have a great late afternoon and evening in Sorrento, then a full day, so that is enough time to see Sorrento and have a few limoncellos!

You could also fly into Milano, train to CT, then do Venezia, Firenze, Sorrento, Roma; may be a little cheaper flight wise
Buon viaggio!

If you decide to skip the CT, and are flying out of Rome, go directly from Florence
to Naples so that you are in Rome for your departure. The only way to do it all
would be to add 3 days to your itinerary.
EDIT: Trip from Florence-Napoli 2h51m

Leaving home on 15th August or arriving? The 15th August is a major Italian holiday (Ferragosto) and arriving then will put you on the back foot. This year it falls on a Saturday so the entire weekend may be a touch interesting.

Into Venice, out of where? Rome?

Coming from where? North America? Have either of you flown to Europe before? How are you on jetlag?

If you have a minimum 3 nights in Venice, absolute minimum of 3 nights (3 nights only gives you 2 days in a place), in Florence, 2 nights (only one full day) in the Cinque Terre, only 3 nights in Sorrento, and the minimum 5 nights in Rome, we add up to 16 nights..... oops.

I would include only one or the other of the coastal places, either the Cinque Terre or the Amalfi coast on this trip.

Nigel
{Into Venice, out of where? Rome?} We have not decided and cost will decide this. As far as preferred, we don't care.
(Coming from where? North America?) Chicago and LAX

(Have either of you flown to Europe before?) yes
(How are you on jet lag?) no problem on the way to an exciting location, home is another story, ha.

Seems: The 15th August is a major Italian holiday (Ferragosto) and arriving then will put you on the back foot. This year it falls on a Saturday so the entire weekend may be a touch interesting. So this will make the trip better, right, we love food. Does this effect the whole country?

Ferragosto is celebrated throughout the country.

pndldy,
My wife and I like history and historic places, so it seemed natural that our trip to Italy started in Rome, where the Roman Empire and the past 3,000+ years of Italian history began.
Your itenerary is very similar to ours in 2012, 10 nights, 4 cities.
We began in Rome, 4 nights. Train to Florence, 2 nights. Train to La Spezia, 2 nights. Train to Venice, 2 nights.
In Rome we went to Pompei, took a Vatican tour, but the rest was our on our own. We had tickets to see the Colosseum and Forum on our last day but a strike by workers on that, our last day, closed all attractions and museums. In Florence we took two tours; Uffizi Gallery, and Accademia Gallery. Pisa was a 5 hour side trip on our train from Florence to La Spezia. While in La Spezia we took the morning boat to Monterosso then hiked to Vernazza and trained back to La Spezia while stopping and walking around Corniglia, Manarola, and Riomaggiore. We then trained to Venice for two nights (one half-day walking tour). No flight home as we trained from Venice to Lyon, France.
Good luck and have fun.