1st trip to Italy October 2020

Is 3 hours enough in Pompeii?

Just barely--- better than not going, but not ideal.

CT from Florence could be done; an on the spot decision based on weather and other activities you may want to do. Since you are going to Positano, not getting to CT is not a critical loss.

4 nights Florence with a day trip to Cinque Terra

Some people do a day trip to Cinque Terre, it does make for a long day. It can be done, but you will arrive when all the other tourist do and your hike among the popular ones will be crowded. Most people prefer to spend a night, or 2, or 3. Start your hike early AM. Enjoy Cinque Terre in the PM. All villages are about 5-10 minutes apart by train.

Or, easier day trips would be to Siena or Pisa/Lucca.

4 nights Positano with a stop in Pompeii for 3 hours from Naples

Not sure I understand this. Are you traveling from Positano to Naples and want to see Pompeii on the way? Pompeii can take most of a day to visit.

A day trip from Florence to Cinque Terre is doable, albeit a long day, and the weather should be decent in early October. I would consider taking the 7:28am Freccia train from the Campo di Marte station (not SMN station) that arrives at La Spezia Centrale at 9:11am, one of the fastest trains of the day. The Campo di Marte station is a short and fairly inexpensive taxi ride from central Florence.

Imo 3 hours at Pompeii is too little time. You could march through it in 3 hours, but I would try to budget more time.

Ferries should still be running from Positano to Capri in mid-October. They usually stop running at the end of October. No clue what the hike of the gods is, so I can't comment on that.

Thanks!

To clarify some questions:
We would go from Naples Train Station to Pompeii and than onto Positano. And we are spending 4 nights in Positano.

As with CT what Villages do you recommend? I was thinking of starting in Vernazza and hike to Cornigilia. And Than hit manarola and finish at Riomaggorie.

Oct 2 or 3 would be good days for a Cinque Terre day trip, as there are no cruise ships in port. You would ideally want to take the train to the village of your choice from Campo d Marte at 7:28AM, changing to the local train in La Spezia [see the 5 villages plus Levanto]:

https://www.e656.net/orario/treno/21182.html

Return would be to SM Novella. For a maximum of 6 hours in the villages you will spend at least 7 hours on trains and going to and from stations.

As to Pompeii and Positano you will no doubt be taking the commuter train to Sorrento, downstairs at Napoli Centrale, getting off at Pompeii Scavi [where there is a luggage drop]:

https://www.sorrentoinsider.com/en/naples-to-sorrento-train-schedule

Then back on the train to Sorrento, possibly a driver [Sorrentocars or other company]. A ferry from the port, requiring a taxi, would be the other option:

https://www.sorrentoinsider.com/en/ferry-schedule

I saved this excellent Positano report:

https://www.tripadvisor.com/ShowTopic-g194863-i286-k12875639-Positano_Trip_Report-Positano_Amalfi_Coast_Province_of_Salerno_Campania.html

I also think 4-5 hours would be better for Pompeii. We spent similar amounts of time as you in Barcelona, Positano, and Venice, but longer (7 nights) in Rome. While I would have loved another day in each, it allows a good sample of what is available in each location. With our 3 full days in Positano, we did make a full day trip to Capri and enjoyed it. We also spent one day in Ravello and part of another day in Amalfi.

I'm worried about your trip to Pompeii Scavi, then onward to Positano as there is not a train to Positano.
Pompeii Scavi is accessed by the commuter train the Circumvesuvian. There is luggage storage at the entrance to the site for free, or if you prefer, there's a left luggage facility downstairs in the station with a small fee.
To continue on to Positano you would take this same train to Sorrento, then travel the rest of the way by either taxi $$$, bus or ferry. Which will both be running in October unless the seas are to rough to use the ferry.

If you have an early AM flight, (anything before noon) Naples-Barcelona, I would highly recommend spending your last night in Naples. Positano is too far to reach the airport without a private driver.

For our Leg from Naples, Pompeii, Positano. We hired a private car from Sorrento 1st choice. They are picking us up from Naples train station. And having a 3 hour stop in Pompeii and than into Positano. And they are picking us up on our departure day from Pasitano and taking us to the Airport in Naples

Driver, excellent idea. Answers to your ferry question all month]:

travelmar.it/downloads/orari_travelmar.pdf

Sunset's around 6.15 in Sorrento then. To get to Pompeii from Naples, take the Circumvesuviana (about 30-40 minutes) which runs about every half hour. To get from Pompeii to Positano, the best is arrange a private transfer either from Sorrento or Pompeii. Second best is Circumvesuviana train to Sorrento, then bus to Positano. The train runs about every half hour (but usually not on schedule and often late). It is likely to be crowded with lots of folks returning from Pompeii. The ride is at least half an hour. The bus to Positano leaves from the train station. The bus takes close to an hour. Right now only the winter schedule is available. Buses are about once an hour. In October they could be more frequent, but expect to wait up to half an hour. If you want to take a ferry, you would have to get from the train station down to the pier - either by slow bus, expensive taxi, or longish steep downhill walk with lots of stairs.

Now that you've clarified that you've already hired a private driver who will stop at Pompeii for 3 hours in transit from Naples train station to Positano, the answer is: your visit will be rushed. With a 3 hour stop, you'll probably have no more than 2.5 hours to actually visit the sight. You'll need to be selective about what you plan to see as Pompeii is fairly large and you won't be able to see all of it in that short amount of time. That said, a short visit is still better than not visiting at all.

I’d suggest the hike from Monterosso to Vernazza, then on to Corniglia and complete in Manarola. This way, you’ll get the “money shot” photo of Vernazza. Corniglia is worth passing thru and Manarola is picturesque too.
Good luck and hope it’s great!

With all due respect to the previous poster, I'd use this site for Amalfi/Sorrentine Coast ferries as Travelmar doesn't go to Capri. Use the dropdowns to view different departure/arrival posts. It's currently showing the winter schedules when the ferries don't serve many locations along the coast:

https://www.capri.net/en/ferry-schedule?from=sorrento&to=#

Also when in Positano would a day trip to Capri be ok?

Yes. Positano is really small so 4 nights would have been much too long for us. That said, day-tripping Capri will put you onto the island with the rest of the day-tripping mob so it may be very busy during peak hours. I would take the first ferry out in the AM and the next-to-last or last one out in the evening: whatever you do, don't miss that last one!

I'm pretty much in the camp of only doing the CT only if you can stay overnight due to day-tripping putting you there squarely during the most overrun hours, same as day-tripping Capri. Early mornings and the evenings are the best time to experience that area before the mob arrives and after they depart. That said, if you decide to do it in a day from Florence, pick a dry one as it's no fun in the rain, and foul weather usually results in closed trails anyway. As mentioned, I'd choose to hike Monterosso> Vernazza for that "money shot" of Vernazza from above but be aware that if it's a nice day, if you can't get started until mid-to-later morning, segments of the Sentiero Azzurro reported to be open next year (Monterosso>Vernazza>Corniglia) will likely be very busy.

Thanks for all the replies this really helps. Also wanted to know what you use for booking tours? Right now I’ve been saving tours on viator.com but is there another site you would recommend other than Viator?

I use Viator or Trip Advisor for research purposes, and then directly book tours with the specific company on their website.

I’ve been saving tours on viator.com but is there another site you
would recommend other than Viator?

What attractions do you want tours for? If willing to do a little reading or use audioguides, not all of them really need a tour, and Viator isn't the best resource for guided tours depending on the attraction.

Tours I’ve been looking at on viator are:

Venice- St Marks and Doges

Florence- Duomo Sky Walk/ Uffizi

Rome- Early access Vatican and underground/ arena floor Coliseum

Are there some that you have done or wish you did? I don’t want it to be a tour vacation because I like to wonder and explore but also don’t want to miss the major stuff!

I'm not sure whether you were considering hiring a private guide for your visit to Pompeii, but keep in mind that the standard private tour lasts about 2 hours which would leave you virtually no time to explore on your own. Personally I would explore on my own using an audio or guidebook tour for reference, but you could fit in a private tour of the standard highlights if your prefer.

OK, I'll leave Venice to someone who has been there more recently than I have but for the Rome and Florence attractions you've listed, these are the resources I'd use:

Florence:
Duomo Sky Walk (essentially the dome/terraces). This is the tour offered by the official website for the Duomo complex:

https://grandemuseodelduomo.waf.it/en/little-peek-on-florence-tour-tickets

Note that it's VERY nicely priced compared to 3rd-party tours, and does include entry (self-guided) to the other parts of the complex (bell tower, museum, baptistry, crypt). Read the details carefully: the ticket is good for 72 hours AFTER the time of your terraces visit so you may visit those other structures anytime they are open within those 72 hours.

Uffizi:
If willing to tour the museum on your own, this is the official ticketing site:
https://www.uffizi.it/en/the-uffizi

Audioguides are available in English for 6.00 €. at the entrance. Rick Steves also provides an audioguide tour which can be downloaded free to your own devices:

https://www.ricksteves.com/watch-read-listen/audio/audio-tours/italy

Note as well that if you are interested and will be in Florence long enough to take advantage, a combo ticket (PassePartout 3 Days) is available that includes the Uffizi, Pitti Palace, Boboli Gardens and National Archaeological Museum. While you must choose a day/time for the Uffizi, the others can be visited at any time they are open during the 3-day life of the ticket. https://www.uffizi.it/en/pages/combined-ticket

You didn't mention it but if wanting to visit the Accademia (same ticketing vendor as for the Uffizi):
https://webshop.b-ticket.com/webshop/webticket/eventlist?production=4

For a guided Uffizi tour (you don't really need a human guide for the Accademia) these companies get high marks from RS posters whom have used them:

Walks of Italy:
https://www.walksofitaly.com/florence-tours/

Context:
https://www.contexttravel.com/cities/florence

Others of the forum folks might have additional recommendations for guides. And onto Rome.... :O)

Rome:
Early access to the Vatican Museums + St Peter's Basilica: I'd choose a tour which includes the church so that you get direct access into it from the Sistine. That saves a long walk between the two, and standing in a long security queue for St Pete's. These companies are oft-mentioned and come highly rated from RS posters who've used them, Walks of Italy's "Pristine Sistine" probably being the most popular:

https://www.walksofitaly.com/vatican-tours/pristine-sistine-chapel-tour/
https://www.contexttravel.com/cities/rome/tours/early-entry-vatican-tour
https://www.througheternity.com/en/vatican-tours/early-morning-vatican-tour.html
https://theromanguy.com/tours/italy/vatican/sistine-chapel-vatican-tour?layout=layout2

Colosseum Underground (guided tours are mandatory for this section):
All sorts of of options here. The companies mentioned above for the Vatican will also work for this critter, and the arena has its own tour besides. That one is sort of a bugger to get tickets for as it's so inexpensive - they sell out within hours of becoming available - but you could give it a shot. It's much too early for booking tours for next fall so keep an eye on the site. I'll warn you in advance that it's a complicated thing with a LOT of text that won't apply to you. Ticketing also appears to be down this morning - my browser can't find the URL - so I'll check it later:

https://www.coopculture.it/en/colosseo-e-shop.cfm

IMHO, the jury is sort of out on the Underground. Tours really do not spend all THAT much time down there, and you can see down into that area from above (where guided tours are not required) so whether to spend the extra $ is a personal thing. What I would spend the $ on is a guided tour which includes the Colosseum, Forum and Palatine; all of these are in the same vicinity. The Forum and Palatine are complex sites which can benefit greatly from an experienced guide, and are really quite interesting! These tours last about 3 to 3.5 hours - see the companies I listed above - so won't shoot an entire day.

Ah, the coopculture site is back up now. This is the page specifically for Colosseum entry tickets and/or tours:

https://ecm.coopculture.it/index.php?option=com_snapp&view=products&catalogid=A4CC149C-BEE1-5773-5E59-01675F3EA81C&snappTemplate=template3&lang=en

Tickets which include the underground tours are released on a schedule that is usually published under the "NEWS" section on the righthand column of this page....

https://www.coopculture.it/en/the-colosseum.cfm
Click the [++] at the end of the column of text to reveal ALL the text and schedules.

....and will not be available for Sept for quite some time. As this site saw a LOT of changes this past year, you need to keep a close eye on it if wanting to use this resource for booking your Colosseum underground or Forum/Palatine/Colosseum tours.

Awesome! These reply help tremendously! One other thing I was considering since we are arriving in Venice and this will be our first trip to Italy is it worth the splurge on a private water taxi? We are staying in a VRBO and are meeting the owner of it at the Rialto Stop. And if so what company have you used or recommend.

also what’s the best way to get to the train station for our departure to Florence when in Venice.
Thanks

Also, once you arrive in Pompeii, it may take half an hour or more to get to the front of the ticket line before you even get in the gate.
I would schedule at least 5 or 6 hours for Pompeii.
It really is enormous and deserves more than a couple of hours.
Just get your driver to pick you up later.