Brunello wine tours, Capri, Hertz and a lunch place in Val D’Orcia

For #3 - enjoyed a nice casual picnic lunch at Cugusi, a pecorino cheese producer just west of Montepulciano off the SP146 road which you would take to Pienza.

They have an impressive range of their own cheeses along with prosciutto, salami, snacks, and drinks. October might be a little cool outside but the tables have an impressive view of Montepulciano.

For #4, we drove ourselves but I would recommend a visit to Ciacci Piccolomini on your Brunello tour. I wish we’d bought a few more bottles to bring home!

This board has some reports (2023) of construction problems at the Positano ferry dock and heavy crowding on busses as a result. Presumably that might be solved by October.

Are you planning to spend the day walking (a lot) on Capri, or just boat around it and return? Capri is quite different from Positano. We skipped the Blue Grotto and were glad we did. To my mind, Positano is not that interesting an "explore." The worst similarity between Capri and Positano would be the same overpriced boutiques! But Capri has much more to see and do.

I don't deny that I wanted to "see Positano" and I'm glad we spent a few hours there. Opinion.

I'm in Tim's camp on the Positano vs Capri subject. We were pretty much done with Positano after a couple of hours but spent 2 nights on Capri and found plenty to keep us interested/occupied. Yep, we skipped the Blue Grotto too, with no regrets, as well as the posh boutiques, beaches (such as they are) and boat tours. There are any number of scenic treks to be had on foot, as well as the chairlift in Anacapri to the top of Mt. Solaro, the ruins of an Emperor's villas to explore as well as a 14th century Charterhouse, colorful ceramics to browse, and, well, lots to do. Need some down time? Pull up a chair at one of the island bars, order up an adult beverage and do some people watching. :O)

No tours needed! Explore your options, and just follow the directions for striking out on your own.
https://www.capri.net

Working on plans for October in this area. Might try Montalcino Wine Tours.

Thank you very much for the replies.

Ksea, Cugusi sounds wonderful as does Ciacci Piccolomini. It makes me so happy to make a list of recommended places. Did you bring wine home in your checked suitcase or have them ship?

Thank you Tim and Kathy - from your description, I think I'm going to encourage us to go to Capri, skip the Blue Grotto and spend the time exploring.

Wclosordo, thank you for the tip about Montalcino wine tours. I will look into them.

The people on this forum are amazing and so kind to give information and advice. Truly appreciate it.

Everything you need to know about Florence car rental: https://tinyurl.com/4zbp6stt

Read this about driving in Italy [and about ZTLs, limited traffic zones]; avoid leaving anything of value in a vehicle when parked: [and have an IDP, which is required]:

https://mominitaly.com/driving-in-italy/

You should be taking a train from Naples to Chiusi [25 minutes longer than Florence], picking up an Avis car and driving 45 minutes to Montepulciano [vs 1.5 hours from Florence], and returning the car in Florence.

Most wineries will ship, pretty sure Ciacci does. Make sure your state allows shipments, not all do. In hindsight that would’ve been the easiest way (and cheaper if you get 6/12 bottles from the same producer). Maybe next time! Where I am the standard Ciacci Brunello sells for about $20-25 more than in Italy, so with shipping you’re still coming out ahead. Even better values on the high end bottles, and then there are bottles you just can’t find easily in the US which make for a special souvenir.

We bought bottles from several wineries and consolidated into one shipment using the mail boxes etc location in Montalcino recommended by our hotel. They arrived perfectly fine after about 6 weeks. If you have the time and want to sample several wineries this is a good solution.

It's only an opinion, but our crew of four universally held our day excursion in Capri as the best singular experience of our 17 days in Italy.

We did a semi-private boat through Mondo, which included 10 guests total (12 guests max for the boat). We left first thing from Sorrento, and our skipper could not have been better. The trip delivered us to Marina Piccolo, where we navigated our way via the scary crazy little buses up to Anacapri and the chair lift to Monte Solaro. Absolutely gorgeous, and getting there was such an adventure. (you could splurge for a taxi and perhaps a less harrowing ride). Our boat trip provided a delicious caprese sandwich, so we bought a drink from the cafe at the top of Monte Solaro and had perhaps the best views ever for a family picnic. We enjoyed the 4 hours total that we had to wander, and unless you wanted to spend more time in the pricy shops we found the time period adequate.

Our group was collected from Marina Piccolo, and then our skipper continued the tour by boat around the island of Capri. We had a stop over in a little cove where all but the skipper took a swim in the Mediterranean. Goggles provided; gorgeous fish below. The skipper dropped a bit of food for the fish to gather so we could get a really good look. Water was...brisk!...but it was a glorious experience. We'll remember it always - which is in my mind the point of travel!

After the dip, we continued around to the Blue Grotto. I know others here have poo pooed it, but again we loved it. The experience of tumbling into a little rowboat, riding over to the "cash register" on a nearby boat for the entry fee, and gliding through that narrow opening were all great fun. It's gorgeous inside, and I can't help but note that all 10 of us on the boat opted in to the blue grotto. No one voiced regrets - on the contrary there was plenty of gushing about how glad we were to have done it. The original plan was to head to the blue grotto first, but our skipper offered to put it at the end of the trip for the smaller afternoon crowds. We were early enough in the morning to be near the front of the line for rowboats, but he suggested that we would spend less time waiting in the afternoon so we took his advice. Additionally, if you're there in October and it's too cold to swim, you might really consider gliding into the grotto if the weather/seas permit.

Our boat tour included interesting spots along the mainland, including some roman ruins and a waterfall, the green grotto, the Faraglioni, a complete circuit around Capri pointing out items of interest and a dash of history, and all the aforementioned stops.

My crew ranked this as their favorite day for the perfect combination of beautiful sites, a break from museums/cathedrals (which were also much enjoyed) and the opportunity to have experiences instead of just observations.

Apologies for the lengthy post - but if we were in person we would absolutely recommend a similar experience on Capri.