Italy Itinerary September/October - sanity check please!

That itinerary looks great. That's a lot of traveling and days filled with activities. At my age, I'd be exhausted trying to keep up. I'm sure the private tours and transfers will simplify things. My wife and I have been to many of those towns but have not immersed ourselves in quite as much wine. We've consumed a fair amount, though, and enjoyed it all. We especially enjoyed Alessandro's evening pub crawl in Venice during our 3-day visit there in 2015.

Day 16 looks like a really full day. We hiked the Path of the Gods from Bomerano to Nocelle in 2019. The views are amazing. I wish the trek had been twice as long, but after going down the 1,700+ steps and walking back to Positano, we were ready for a relaxing aperitivo/happy hour.

Have a wonderful trip.

Your research and itinerary are excellent! A few changes here to enhance it.
Day 2, Burano and Torcello would be a better choice than crowded , tourist filled Murano. To purchase high quality locally blown glass go to Carlo Moretti’s store L’Isola in Venice. We have purchased several pieces from him.
Day 9. Panzano. Are you having lunch at one of famous butcher Dario Chicchini’s restaurants?? He has several restaurants; one has a Michelin star. Quite a story. Was featured on Top Chef.
We spent a week in Panzano, loved it there.
13. I would prefer to stay in Sorrento , not going out on a boat at sunset. Have dinner , if you love seafood, at Bagni Delfino down at the fishing marina. The fresh seafood is terrific. Reserve ahead.
Day 15. Capri, of course it is easy to do on your own. I can’t even envision taking a tour there.
Capri deserves an overnight stay. We spent three nights there. The least favorite part of our trip to Capri was the boat ride around the island.
We stayed in the area between the Giardini Agosto and Punta Tragara , all pedestrian pathways, not far from Capri Town but uncrowded, lovely. Consider staying at Hotel La Minerva with it’s stunning sea views and fabulous owners. . Wonderful nearby dining options too.

Love your itinerary! It sounds amazing! I’m going to bookmark this and love @suki recommendations.
I spent a lot of time in Italy quite some time ago for work. It’s such an amazing place. Love your destinations plus the private tours sound incredible!
Now- my husband has never been, either. He travelled quite a bit with me when I was working in Europe- not sure how Italy was left out of the picture!
This year we are doing our first tour ever- going with friends. I opted to choose the Rick Steves best of Italy in 17 days trip. Just thinking with 4 total this might be a good option.
I hope that you write a trip report after! Love the luxurious tone of this trip- so fun! Right up my alley- I think it sounds amazing! Sorry I don’t have more advice but just wanted to give you a thumbs up!
Lisa

You’ve obviously done a lot of planning and research! Kudos! It might just be me but I would want an unplanned day or a few afternoons/mornings to rest and relax about midway through. As Rick says, plan so you can be spontaneous!

Glass Week in Venice runs Sept 17-25 this year. I haven't checked recently to see whether there's info online yet, but this may give you even more opportunities to see glass without going to Murano if you arrive during that period. Note that there is not just one factory on Murano; there are many furnaces. There is only one glass museum there. I love glass and have scheduled myself in Venice for over a week so I can try to see everything. For a regular tourist with less than two non-jetlagged days in Venice, I'm not sure going to a bunch of Murano glass shops is a good use of the time required. I suspect you'd enjoy just wandering around more.

The Art Biennale may still be running during your visit, too.

@Lew - Thanks for the recommendation for Alessandro's pub. I had actually looked into this but with our timing in Venice wasn't sure it would fit as feel we will be ready to crash early on arrival day from jet lag and planning a nice dinner for our second night there before we depart the next day however I know cicchetti's are a big thing in Venice so we were thinking we could do a self-guided hop around to a few that Rick Steve's recommended early on arrival day ourselves and then crash :).
Thank you for the Day 16 feedback as well. We were thinking about avoiding the 1,700 steps down from Nocelle to Positano. Once we hiked into Nocelle we were thinking about getting lunch at La Tagliata and then using their car service afterward back down to Positano. Do you think you get all the views from the walk itself or is the 1,700 steps down definitely worth it (and the strain on the knees haha?)

@Suki - Thank you for this great feedback! Will definitely look into Torcello and the shop you recommended. Also saw @acraven post above about it being Glass Week in Venice so will need to look into what events they might have going on as well that could be of interest to us.
I had another post in this forum about Dario Chicchini's restaurant. Got some feedback that it was becoming a tourist trap lately with all the publicity from TV series. We were thinking simply to opt for a wine-pairing lunch at a local vineyard in the region based on our driver's recommendation for that day.
Sounds good about Sorrento day....will look into Bagni Delfino as well. Only restaurant I was set on so far for Sorrento was O'Parrucchiano as I ate there a few years ago and it was an absolutely fantastic experience and one I want my husband to experience as well!
I hear you on the overnight stay for Capri, I was just really worried about all the moving around we are already doing. I think it we weren't doing the overnight stop in Bologna for the Italian Day's tour we definitely would opt for at least 1 if not 2 nights in Capri but we might have to reserve that for our next Italy trip to avoid adding yet another hotel to the mix.

@Lisa g I will definitely write a trip report when we return! And yes, this is definitely on the more luxurious side of things - kid-free and probably won't get the opportunity to go on a trip like this without the kids again for awhile so taking full advantage of the opportunity and time to fully relax and enjoy all that Italy has to offer.

@ksinclair - I hear you and definitely need to think about that a little more. I think the days where we have private drivers provides some flexibility in this regard as we can move as fast or slow as we want on these days and choose to spend more or less time in a town pending on our interests.

@craven - I was not aware of Glass Week in Venice and we will be there during that timeframe so I will definitely look into the events scheduled and that might be the perfect way for us to get a great introduction/experience to Murano glass. And yes, need to factor in the jetlag at the beginning of the trip...working in our favor is the fact we have two very young children so we are used to functioning on little sleep haha

I’m so thankful you posted this! I went to Italy the summer before my senior year in high school and loved it, but it was a blur. I’m going on my honeymoon and he has never been so I’m “showing him the ropes” :) Planning everything has been overwhelming so I love this extra help! We are flying into Venice, to Florence, Rome, stoping by Pompeii, then Capri. Pretty much 2-3 nights each place except just one night in Venice. My biggest confusion is navigating how to get around (private car vs bus). Thoughts?

Hi Amanda,
I’ll just add a few favorites: Montepulciano- Our tour group visited Cesare the Coppersmith. Several of us purchased his “grape wine cooler” & had it shipped home. It sits on our dining room table as a wonderful memory. We followed a similar route. Sounds like a great itinerary! As far as Venice we deleted Murano. We felt we saw all the glass we needed to see in Venice. We really enjoyed Burano & Torcello on the same day. We were in Venice during the Venice Film Festival in 2018 and went to Lido during the festival. We enjoyed Capri, but skipped the Blue Grotto. We loved the chairlift at Anacapri. The views are stunning. We stopped at Civita di Bagnoregio and enjoyed the lovely village, lunch & wine. Hope you will share a trip report. Enjoy your trip!

Just a thought on your Capri trip. I am not crazy about boats but I arranged for a private boat tour around Capri for my husband and myself and it turned out to be the highlight of our trip. Salvatore is wonderful and was able to get us into the blue grotto without a wait. Note that it is not aways open due to the condition of the sea. He provided us with a lot of history and even snacks and drinks. So romantic too! My son and his wife also did the tour on their honeymoon and they stopped along the way to swim. Here is his website https://www.tripadvisor.com/Attraction_Review-g187783-d6537512-Reviews-Capri_Trip-Capri_Island_of_Capri_Province_of_Naples_Campania.html#REVIEWS

@sarahcwortmann - Congratulations! I'm not sure when you are going but I definitely plan to post a review following our trip when we get back. I have been to Italy many times in the past...can't say I ever took a bus. I have taken the train many times which is super efficient. This trip we opted for private transportation for all legs except from Venice to Bologna where we are taking the train. If money allows the private transportation offers much greater relaxation/flexibility/enjoyment in my opinion. We have used Gianluca Savarese with Private Day Tours for our transfers/transportation needs in and around the Amalfi Coast on past trips and he's helping us again for this trip as well - we love him and he's super responsive and knowledgeable. Also, based on recommendations from various others in this group we have booked private transfers/day trips with Luca Garrapa with Hills and Roads and Filippo with Tuscany Car Tours for our upcoming trip (both based in Florence/Tuscany area). The Grape Tours on our itinerary above also highly recommended - my parents did Grape Tours' Tuscany wine tours back in 2015 and absolutely loved so we are partaking in 3 of their 4 day offerings as part of our trip this go around. Again, congratulations and hope you have a wonderful time!

@Janis - thank you for the recommendations. I will definitely look into Cesare the Coppersmith for when we are in Montepulciano. I've also heard similar remarks on Murano so looking into doing Burano and Torcello instead as you have suggested.

@Kathleen - thank you so much for the recommendation for Salvatore. I did Capri a few years back but did not get to do a boat tour/blue grotto on that trip as the weather didn't cooperate. We have reached out and booked with Salvatore for a morning boat ride and Blue Grotto so hoping the weather is good this go around!

Lovely! Can I ask what private driver you are using for your transfer from Florence to Montepulciano?

@rlhill1979 - we are using Filippo with Tuscany Car Tours to get from Florence to Montepulciano with stops along the way in the Chianti region. We are also using Luca with Hill and Roads for transportation needs while in the Val D'Orcia. Both come highly recommended by a number of people in this forum.

Hi Amanda. -
My goodness, what an exciting adventure you have planned! It's much, much heavier on scheduled tours/activities than we would like (I'd be exhausted halfway through) but it's YOUR trip so there ya go. A couple of comments?

Day 4: Italian Day's Food and Wine Tour; evening train to Florence
(might consider private driver for simplicity?) and check into Westin
Excelsior

No need for a transfer, IMHO. Take a train

Day 8: Pitti Palace / Boboli Gardens in the AM, markets mid-day, Duomo
(and climbing dome) late afternoon

The Pitti is an interesting choice. I'll caution that unless you really, REALLY like art, your eyes will be crossed by the time you reach room 16 (out of 28) of the Palatine Gallery. That doesn't include the 14 rooms of the Royal Apartments (if open), the Modern Art Gallery, and the Treasury, I am an art lover and even I was crossed-eyed after a point! The gardens are also vast and, well, not the sort of flower-y thing you might be expecting. All-in-all, together they're a devourer of energy and time, and really could use more than just one day to fully appreciate.

You might consider some of the smaller museums that are more easily digested lest you be too tired/overwhelmed for anything else that day? Would also love to see you get up to Piazzale Michelangelo and San Miniato for some of the best views in Florence + a look at a very old and important church.
https://www.visitflorence.com/florence-monuments/piazzale-michelangelo.html
https://www.visitflorence.com/florence-churches/san-miniato.html

As a lover of Florence, I'm a little distressed that you're planning to spend so little time IN the city but it looks like 🍷 is your thing, eh? Oh, and you do know that you'll need a reservation to climb the dome at the duomo, right?

Day 12: Private transfer Montepulciano to Sorrento with stops along
the way: Fortress Radicofani; Bolsena; and Civita di Bagnoregio; check
into Grand Hotel Ambasciatori

Oof. I'll just assume that you know how $$$ this will be? It's a loooong way between these two locations.

Day 15: Capri (thinking on our own...is that possible?) - Blue Grotto,
Anacapri chair list, exploring the towns. If we looked into a short
tour around the island that included stop at Blue Grotto do you have
recommendation for Company you have used to set this up?

Yes, you absolutely can do Capri on your own! We have. I'll also 2nd the vote for spending at least one night there as evenings and early mornings, when the hordes of day-trippers are not around, are some of the more enjoyable hours. That does, however, pretty much mean giving up your Day 14 or 16 plan as you'll want to maximize your time on the island.

I'll say yes to the chairlift, and a resounding no to the Blue Grotto. We skipped it, based on reviews and the amount of time/effort the thing can take for a mere few minutes inside, and have never been sorry.

https://www.tripadvisor.com/Attraction_Review-g488299-d195537-Reviews-Blue_Grotto-Anacapri_Island_of_Capri_Province_of_Naples_Campania.html

If you've not found it yet, Capri has a very good website; spend some time with it, and no need for any of the guided tours advertised.
https://www.capri.net

@Kathy - Wow! Thank you for the great insight and suggestions. I appreciate your candidness on the Pitti Palace - neither of us are huge art lovers so maybe we should just opt for RS's self-guided Oltrarno walk to explore that area but skip touring the inside of the Pitti Palace :). And yes, Piazzale Michelangelo and San Miniato are on the list - the office where we return after wine tour on Day 5 is on the river right below so planning to walk up, explore and watch the sunset from up there that evening.
Yes, Day 12 is $$$...but we opted for ease and relaxation on this trip as it'll probably be quite some time before we get to do a trip of this extent again given we have two young children that my parents are graciously helping us out with to make this trip possible.
And thanks for the insight on Capri. I did a day trip there previously with my family but it's been awhile. We didn't do Blue Grotto on that trip as was closed due to weather but the chair lift was fantastic and looking forward to doing that part again with my husband on this upcoming trip.

We opted for ease and relaxation on this trip as it'll probably be
quite some time before we get to do a trip of this extent again given
we have two young children that my parents are graciously helping us
out with to make this trip possible.

I completely understand! Hope you both get some precious R&R between your tours!😴

We went to Italy for our 30th anniversary in June and followed a lot of Rick Steves tips. Highly recommend Capri, and an overnight if you can manage it since the hoards have to leave for the final boat at 6:30 and then it gets so much nicer and quieter and more Italian. Capri also has a thrilling mountain road to Anacapri if you can manage a Vespa style scooter, just don't learn to ride it there. The guardrail and wall are good and high and sturdy, and there are pulloffs to admire the vertiginous view. My wife and I managed it, and I'd only ridden once before just for practice. The view from the top of the chairlift was so awe inspiring, it's my screensaver now. Do NOT miss that. The Blue Grotto rowboat guys are shameless and will hound you for a 20 Euro tip per person, but you can just give them 2 Euro and they will let it go after asking 2-3 times. (This is Rick's advice btw.)

Positano and Amalfi are lovely though massively crowded. We chose the "fjord beach" at Furore and Marina di Praia for our swimming stops and it felt less mobbed with our fellow Americans. In all I was greatly surprised by how many USA accents we encountered -- often it seemed they far outnumbered Italians.