9 Day Honeymoon to Rome, Tuscany(Siena), & Florence Itinerary Advice

Not bad. But one suggestion is to reverse the order so your Rome time is at the end. If your flight is out of Rome, unless it is late in the day, you should be in Rome the night before so if all your Rome time is at the end you have one less hotel switch. You can probably go straight from the train station at the airport to Florence, but even if you need to change trains at Termini it's no big deal. You spend much of your jet lagged first day on the train and save sightseeing for when you are fresher. There is also a bus that goes directly from FCO (Rome airport) to Sienna. But only a couple times a day so depending on your flight arrival time you might be wasting some time waiting for it. But you can check the schedule on line and if it works for you I would do that.

But the amount of stuff you have planned for each day looks fine, and you are right to group the Rome sites geographically - one day for 'Ancient Rome', one for 'Vactican/St Peter's', and one for 'Heart of Rome' - which is basically what you have. Florence and Siena are small enough that you'll probably end up walking all over them each day so it doesn't matter as much what you do when.

Here's my photos (they are all labeled if you hover over them so you can see what's what)
Rome - https://andiamo.zenfolio.com/p632712636
Siena - https://andiamo.zenfolio.com/p41794234
Florence - https://andiamo.zenfolio.com/p798557837

Your trip would flow much better if you changed your path. This would eliminate that one nite stay in Rome.

Arrive FCO (fiumicino aeroporto) immediately train to Florence (Firenze SMN). If your lucky,
there are two direct trains a day right from the airport at 11:08 and 15:08. Travel time 2:14.
Otherwise you'd take the Leonardo Express to Roma Termini station then on to Florence.
Do not purchase these tickets early to save $$. If your plane is late or immigration is slow those tickets become worthless.

The rest of your itinerary looks well planned,
For your trip to Siena, take the bus, it drops you a short distance from the Campo.

Your return to Rome will be a 90 minute ride, from Florence, basically giving you an extra 1/2 day in Rome.

You'll have a wonderful honeymoon.

People who have tried it say that seeing Pompeii on a day-trip from Rome is a very long, tiring day. There's lots of good stuff south of Rome. I suggest planning to hit Pompeii on your second trip to Italy.

Concur with the thought to go directly to Florence on arrival in Italy and bunch all your days for Rome at the end.

Consider Ostia Antica as a destination vs Pompeii and save some wear and tear on yourselves.

Do Pompeii on a future trip.

Concur with the thought to go directly to Florence on arrival in Italy
and bunch all your days for Rome at the end.

I'll absolutely vote for this.

Also, is it possible to throw in a day trip to Pompeii from Rome in
this plan?

I'll say no. You already have less than the minimum I recommend for Rome (4 nights/3.5 days), and you'd have to scrap either your current day 2 or day 3 plan. That's not worth doing unless you have days to spend in the Naples/Sorrentine/Amalfi region itself (which you don't). Pompeii is not a 1/2 day trip to/from Rome.

-Day 5 - Siena (Bike Tour, Hiking, Wine Tour, Wine Festival, Olive Oil/Other Food Tour)
*Trip to San Gimignano possible?

No, you only have time for Siena.

-Day 6 - Half Day Sienna/Travel to Florence (Uffizi and Accademia Art Galleries, Cattedrale di Santa Maria del Flore, Palazzo Vecchio Town
Hall, Ponte Vecchio Bridge, David of Michelangelo)

You absolutely won't get all of this done with less than 1/2 day in Florence so you'd need to be selective. This is a full day's worth of stuff, and you haven't even included the rest of the Duomo's treasures, such as the baptistry (don not miss this one!) and museum.

please don't do a day trip from rome to pompeii

Thank you to everyone's reply! This was very helpful. I changed around my itinerary to the following and have decided not to try to fit in Pompeii:

Day 1 - Arrive in Rome & Travel to Florence
Day 2 - Florence
Day 3 - Florence
Day 4 - Travel to Siena
Day 5 - Siena
Day 6 - Travel to Rome
Day 7 - Rome
Day 8 - Rome
Day 9 - Leave

hey teal724
happy for your upcoming wedding and honeymoon to italy. you'll have a great time. doing your "homework" will do wonders and not getting too stressed out. the people on this forum are great, they will give you good bad and ugly advice as to what's feasible and what is far fetched. it's a big place and you don't want to over extend yourself. what are your dates for your honeymoon?
like your idea of going to florence first then rome at end of trip and not doing pompeii, long day trip.
couple sites to check for hotel/apartments:
booking.com (put in filters)
cross-pollinate.com
shortstay-apartments.com
windowsonitaly.com
read reviews, look at pictures closely (not sharing kitchen or bathroom), payment in euros or credit card on arrival, check arrival and departure times, early check in or can you leave luggage, don't want to be pulling until check in or out. we like to have a terrace to sit and relax with morning coffee or happy hour vino, appetizers, people watch, plan next day events. pack light, our last place we book with a washer/dryer (not all have dryers so just hang up overnight - get instructions for use, i usually bring a tide pod for convience).
look at cookly.me, florencecookingclasses.com, eatingeurope.com (classes and tours) eatwith.com some are offered in rome. walk around mercato centrale of florence, so much to see, do and eat. maybe take out for lunch or dinner in your place, don't forget the wine and corkscrew (we pack one in our suitcase)
siena rent a hotel room in city center and walk all over, slow pace enjoy the atmosphere. stop at a tourist info kiosk and look what's available. you don't really have that much time there.
rome: book your tickets early for what you want to see in rome. withlocals.com has a beautiful countryside day trip: castelli romani. oldfrascati.com (read about us and blog) family owned winery outside of rome, 30 minutes by train. walk the markets near roma termini train station and testaccio
this gives you lots to think about and search, any questions feel free to come back and ask.
aloha