Two week Itinerary help - any advice appreciated !

Exactly how many days (and nights) do you really have to work with? It's helpful if you post actual dates of your trip, including arrival/departure dates (rather than "the last two weeks of May" which is a bit vague and subject to interpretation), so folks can advise on whether your planned pace is breezy and easy, or hard and brutal.

It's worth noting that (IMHO) most first-time travelers wildly under-estimate the time it takes to get around and complete basic every day life tasks, and wildly over-estimate what can be reasonably accomplish in their trip. So, begin by being honest with yourself about how many real, full, usable days on the ground you will have. If you fail to take a sober look at that (as many travelers fail to do), your plan can turn into a nightmarish, grim death-march, rather than the trip of your dreams.

Thanks for that tip!

We will be flying out May 14th, arriving in Venice May 15th at 10am, with the jet lag and only half a day I am mostly writing off this day/night

Venice - 2 full days (will also see burnao or murano)
Cinque Terre - 2.5 days
Pisa - 0.5 day
Florence - 2 full days (this is where we are unsure if we would rather have one and a half days and spend the additional time elsewhere)
Sienna/Surrounding Countryside - 1 day trip from Florence
Rome - 2.5 days (potential to add an additional day here instead of staying in Florence)

May 28th afternoon flight from Rome to Canada

Thank you!

OK, good start. So, if I'm reading that right, you have 12 full, usable days on the ground in Italy. Yes, after a redeye from North America, it's best to pretty much write-off your arrival day, since you're gonna be pretty wiped out (I'll share that, from personal experience, some of us START our trips exhausted, stressed out and short on sleep from excitement and all the pre-trip tasks...then add an overnight in a cramped tube, and well, you know). You're also wise to fly in to one place and depart from another (which is usually more efficient). Also wise to go in May, rather than say August. Good.

Couple other things...

You need to account for the time it takes to pick up and move yourself from one location to another. While we all have romantic visions of European trains as efficient and easy (and that's generally true), it still takes time. You wake up, eat, etc., assemble your possessions, check out, get to the train station, get on your train...upon arrival, you need some time to get oriented, figure out how to get to your accommodation, maybe you get lost a couple times on the way, check in, get settled, wander your new neighborhood, eat something, etc... Point being: you will consume half a day at best every time you move locations (it'll take longer if conditions aren't perfect). You need to account for this time, it comes out of your "X days in Y city" planning.

As a general rule, if you start saying "I have X days there" in fact you have X-1 days there, plus maybe an evening or late afternoon. Until we invent a way to instantly teleport ourselves from place to place, don't forget this.

All that said, I think you have plenty of locations already on your list so do not add any more! And I think you may have one or two too many locations already - it depends if you want to be hurried or relaxed. With 12 full days, most folks would suggest you pick 3 or 4 locations maximum. You have 6 (although one or two that are day-trip-ish). Hmmm.

If you had to drop one, which would that be? How about if you needed to drop two? Start thinking about that.

Sarah, your path would be more efficient if you did this.

Venice>Florence>CT>Rome.

That 51/2 hour trip from Venice-CT in all reality will consume around 7 hours. Crisscrossing the country takes an immense amount of time.

Venice...unless you're on a dead run, there's not a way to visit the city and 2 of its islands in one day. Doing this is why people Don't enjoy the city.

Venice ( Venezia S. Lucia)>Florence (Firenze SMN ) 2H05m

Florence...Even if you don't hit a single Museum, just walking around this beautiful city is engaging.
2 days is barely enough.

You'll need a full day for Siena, doing it as a combo with a winery tour short changes both.

Florence SMN>La Spezia Centrale 2H4m.
From this station You would change at the Firenze C. Marte station. Then switch trains to reach either CT 6-28 min. or a ferry/bus to Portovenere. 30 min. Keep in mind, Portovenere can be very expensive.

La Spezia>Rome Termini. 3H49m.

To utilize your time wisely, make sure you book your must see sites as soon as possible. Vacation time is not enjoyable standing in lines

Hope this is of some help. Whatever you decide, you'll have a great time.

At 20something, you have more resilence than at 40 or 60, so I am not going to say 'cut back'.....you can always use this as an exploratory trip for longer, more intensive trips later. I love Florence, but if you are only going to one museum, I suggest spending the extra day in Rome. You can take a day to bike the Appian Way, visit the Aqueduct park or go to gladiator school....all a little outside the city.
Just be sure to book your Florence museum beforehand and remember museums are often closed on Mondays.

Since you want to do a tour with Siena and a winery, I suggest this tour:
https://walkaboutflorence.com/tours/best-tuscany-tour

The tour starts in Florence and goes to Siena, then a winery for lunch (free wine!). From there, the bus goes to San Gimignano and finally Pisa. The return bus ride to Florence is just long enough for a good nap so you can be ready to go to dinner. It's a long day (12 hours) but you see a lot. If you do this tour, you can skip your 0.5 day in Pisa and spend it in Florence. Have you already purchased train tickets? If not, you may want to go ahead and book those for savings on ticket prices.

https://www.trenitalia.com/tcom-en

Here is a possible itinerary for you to consider:
May 15 - Arrive Venice, check into lodging and set out
May 16 - Venice/Burano/Murano
May 17 - Venice/Burano/Murano
May 18 - Morning train to CT (5-6 hours), afternoon in CT
May 19 - CT
May 20 - CT
May 21 - Morning Train to Florence (2.5-3 hours), afternoon in Florence (Duomo?)
May 22 - Florence
May 23 - Day trip
May 24 - AM in Florence, Afternoon/evening train to Rome (90 minutes)
May 25 - Rome
May 26 - Rome
May 27 - Rome
May 28 - AM in Rome, PM fly home

Ok, after seeing your allotted time, it's much better than I thought initially.

You have plenty of time in Venice. For a very good overview, try this "free" tour. Do tip the guide. http://www.venicefreetours.com

Book your skip the line reservation for St.Marks Basilica here. https://www.venetoinside.com

In Florence you have the time to do your own day trip to Siena. The bus takes 1H15m and drops you very near the Campo.

This 1/2 day wine tour may fit in if you do get bored 😐 https://www.getyourguide.com/florence-l32/chianti-wine-tasting-half-day-tour-from-florence-t4433/?referrer_view_id=c50fc3fc1def90f0bf66acbd3c30d724&referrer_view_position=11

Rome is a city to wander,there's plenty to see, many Piazzas to visit, and wonderful cafes for great wine and people watching. If you do want to visit a site, book tickets. We can help with the places to do this. Just let us know which sites.

Florence is a beautiful city, and a great place to just walk and enjoy the architecture. But it is one of the most crowded cities in Italy, which takes away from the enjoyment for many of us. Why not add an extra day to one of your other cities?

Thank you all for the advice I think you are right in that it will seem like less time with all the travelling.

In regards to changing the order and visiting Florence second instead of Cinque Terre I had originally considered it but it seems although that first travel day will be shorter in the end the total travel time will be close to equal as this will mean a longer travel time into Rome. If there is any specific reason to switch or ease of transportation I’m curious to hear it. The only logic I cane up with is that often Sunday/Monday some sites are closed so I figured being in cinque terre for these days when we are mostly outside and the closures would impact us least could be best ?

Sarah, yes, total travel times are almost equal. Travel from Venice to CT uses almost a whole day traveling, while going to Florence first gives you useable sight seeing time. The only variable to me would be cruise ship arrivals impacting the towns of the CT on the dates you are there.

Edit: ships in port. Check La Spezia and Genoa ports for your possible dates.

http://crew-center.com/italy-ports-cruise-ships-schedules-2019

If you use Gerri's plan, you could leave Florence early, store your luggage at the Pisa Centrale train station, spend 3-4 hours seeing the Leaning Tower and the rest of the beautiful campus, and then continue on to the CT. Look at the train schedules on trenitalia.com. There is at least one train a day from the CT to Rome that doesn't require a train change. And you wouldn't have a train change between Venice and Florence either.

You can day-trip to Siena by bus from Florence.

Hmm by changing the orders the 2 days i'm there both have boats docked, the original dates only have boats in La Spezia 1 of the 2 days. Will I notice this difference ?
I have not bought train tickets yet and have been using Trenitalia which I believe is the easiest site. I am happy to book online to save a few Euro but do you think I need to book already or I can wait until just the month before ?

Thanks,

Having one or 2 boats docked should not make that big of an impact. As long as they're not the mega ships.

If you wait to buy your train tickets the month before, odds are you'll have little choice other than "Base fare". Look at the schedule now, click on the arrow on the right side to see all available fares. If standard are out of super economy and economy, check premium to see if any of their fares are less than standard base.

why would you go to florence without being into art?

florence is an art city...the birthplace of the renaissance

it is like going to naples and not having pizza