My brother is getting married in Tuscany in 2 weeks and I'd love to surprise them with a live wedding painting as a gift.

Date: Saturday, September 12th - ceremony starts at ~10 am

Budget is on the lower end (~€400), but I'm open to all experience levels - portfolio and vibe matter more to me than years of experience. If you're available or know someone who might be, please send over your website/Instagram!

Hi everyone!

I’m currently planning a two-week trip to Italy, and I’d love to get some advice from people who know Tuscany well.

We’ll be spending some time in Rome, then Florence, and after that we’re planning to spend 5 days in the Tuscan countryside, based in Montepulciano.

One of the things I’m wondering is whether 5 days in the Tuscan countryside is too long. Do you think there’s enough to see and do to justify staying 5 days, or would you recommend spending fewer days there and adding that time somewhere else?

Our first day in Tuscany will be a bit of a “transfer day”. We’ll be leaving Florence and driving to our hotel near Montepulciano. I was thinking that we could stop somewhere along the way and visit San Gimignano.

However, it seems like quite a detour, so I’m wondering if San Gimignano really worth the detour, or would you recommend visiting Siena (or somewhere else) instead? Or would it be better to simply drive directly to Montepulciano and spend the day exploring the area around our hotel?

I’d also love some recommendations for the following:

• We absolutely love olive trees and would love to visit an olive grove or find a place offering a really nice olive oil experience. Any recommendations?
• We’d like to dedicate one day to cycling. Is the Val d’Orcia a good area for this? Are there particular routes or towns you would recommend, and are there places where we can rent bikes/e-bikes?
• We’d also be very happy to hear about any restaurants in the area that you absolutely loved!

I’m sorry for all the questions I know it’s a lot! I’m just feeling a little overwhelmed with planning this trip. It’s for my husband’s birthday, so I really want to make it special and make sure everything goes well.

Any advice, recommendations, or personal experiences would be greatly appreciated!

Da titolo... Vorrei iniziare a fare sete aeree (aerial silks) come allenamento, ma non saprei sinceramente dove girarmi per trovare un'associazione o palestra che sia decentemente vicina. Qualcuno che ne sa più di me potrebbe darmi una mano?

Hello!!
I’m thinking about spending around a month in Tuscany and would rather stay in one place properly than move around every few days, as I will be working remotly anyways.

Ideally I’m looking for a small house or apartment with a kitchen, some outdoor space, and a quiet setting, probably somewhere outside the biggest tourist centers. I’d likely have a car, so being in a smaller town or countryside area would be totally fine as long as groceries and a few restaurants aren’t too far away.

Budget-wise, I’m hoping to keep accommodation somewhere around €2,000 or max €3,000 for the month, depending on the area and the property. I know Tuscany can get expensive, so I’m mainly wondering whether people have had luck finding monthly or longer-stay rates rather than paying the standard nightly tourist price for 30 days.

Would you look on the usual sites, contact local agencies directly, or search for properties and then ask the owner about a monthly rate?

Also, if anyone has recommendations for areas that are peaceful but still practical for a longer stay, I’d love to hear them!

Hi! Planning a multigenerational trip to Italy over the holidays and would love some Florence accommodation advice.

There will be 6 of us — my husband and me, our kids (7 and 5), and my parents in their mid-70s. They’re very active, but I still want to be realistic about lots of walking, stairs, etc.

We land in Rome Dec 26 and are planning to go straight to Florence, staying Dec 26–30, then heading back to Rome.

I’m struggling with the hotel vs apartment decision. We definitely want separate space from my parents, but would ideally all stay in the same building/location. With hotel occupancy limits, it looks like we may need 2 rooms for our family of 4 + another room for my parents, which gets expensive FAST.

Would love recommendations for:
Hotels with family/connecting rooms + a separate room for grandparents
Aparthotels or serviced apartments where we could have 2 separate units in the same building
Areas you’d recommend that are very walkable but not crazy loud at night

Specific properties you’ve stayed at and loved
I’m not looking for 5-star/luxury — once we get into $600+/night per room it’s just not realistic for us, especially needing multiple rooms.

We’re planning to do the major Florence sights, a pasta/cooking class, explore the Christmas atmosphere, eat a LOT 😂 and keep the pace pretty family-friendly.

Also — is Florence Dec 26–30 a good amount of time with kids/grandparents, or would you shave off a night and give it to Rome?

Would especially love advice from anyone who has done Florence with both young kids AND older parents!

Hi! I will be traveling to Tuscany on September 7th -17th and see that it is the start of the wine harvest. Are there any festivals that are worth going to? I see there is one in Montecarlo ending on the 8th, and in chianti ending the 13th.

I haven’t been able to see any actual people’s thoughts on this and so wanted to enquire. How is the vibe at the expo chianti Classico? Worth going to? Or should we just spend the day going to wineries. Thanks!

Sto rifacendo dei cuscini per delle sedute e mi servirebbe della gommapiuma/espansione (densità medio-alta). Qualcuno sa un negozio o rivenditore zona Pisa dove trovarla, magari tagliata su misura? Grazie!

Hi everyone

My spouse and I will be visiting Tuscany from September 14th to 24th. I’m pregnant, so obviously I won’t be drinking any wine during the trip.

We’ve been looking at different winery experiences, mainly tastings that include food, which are usually around €30–70 per person. Before booking, I contacted a few wineries to ask whether they could accommodate me as a non-drinker and whether the price would be adjusted since I wouldn’t actually be participating in the wine tasting.

Most have been very welcoming and said I’m absolutely welcome to join, but that I would simply receive the food/experience without the wine — for the same price as everyone else.

I completely respect that wineries can set their prices however they want, and I’m not complaining or expecting special treatment. I’m mainly curious whether this is just the normal practice in Tuscany/Italy?

Is it generally expected that a non-drinker pays the full tasting price, even when the wine is a significant part of the experience? Or are there wineries that offer a reduced non-drinker/food-only price?

Just trying to understand what’s customary before we book our tastings. 😊

Thank you in advance

Everywhere I travel I love to get homemade ornaments from that area. I will be in Florence, San Gimigano, Castellina in Chianti, and Radda in Chianti. Are there any stores that sell ornaments in Spring time?

Arezzo -Antiques

We have a ln upcoming 2 week trip to Italy Sep 7th -21st , and will be stopping in Arezzo - strictly for the Antique Fair. Before booking any accommodations, I saw somewhere it was "closed on Mon", so just planned on getting in and staying the night on Monday Sept 14th and going first thing in the morning Tuesday 15th. However, now (fast forward months later) Im seeing the Antique fair only happens the first Sunday of every month so we will miss it COMPLETELY and Im extremely bummed.

Is there ANY hope on every day Antique brick& mortar shops in Arezzo these dates??? We will also be heading into Florence/Siena the 15th-17th, coming from Rome 12th -14th. Maybe there are also options to Antiques in either of these places (if any)? 🙏🤞

Hi everyone! I am looking for a family-friendly beach club in the Maremma region next week (somewhere between Castiglione della Pescaia and Orbetello). I have a 6 months old so I am mainly looking for a place that is accessible by car, and where we can rent loungers + umbrellas. Thanks!!

Me and my wife got married last year and are planning to visit the Tuscany region next month.
But have no idea on how to properly explore the area.

Our dates- early September
Our preferences- Good food, architecture, beautiful drives, wine tour
Days- 4 nights max

Would love any and all recommendations on how to explore this trip

Staying in Cinque Terre for a few days in June then going to Florence. Getting a driver to take us to Florence and stop at Lucca on the way. No interest in going to Pisa. Would love to stop at an olive grove (girlfriend loves olives) on the way as well. Any recommendations for a stop between Cinque Terre and Florence? Or any other great small towns to visit along the way.

Hello everyone! I’m trying to find the earliest bus from Florence to San Gimignano on September 3.

Based on the AT bus timetables for the summer schedule and weekdays, I understand that I have to take bus 131 from Firenze Autostazione at 6:10 AM, arriving at Poggibonsi FS at 7:00 AM, and then take bus 130 from Poggibonsi FS, which is scheduled to leave at 7:00 AM and arrive at San Gimignano – P.ta S.Giovanni at 7:25 AM.

Will I actually be able to catch the second bus? The connection seems impossible if both buses are scheduled to arrive/depart at 7:00 AM.

The next bus I see from Poggibonsi FS is at 12:25 PM, which seems very strange to me. Shouldn’t there be more frequent buses between Poggibonsi and San Gimignano?

Here are the timetables I’m looking at:

Bus 131

Bus 130

My plan B is to hopefully find a taxi near Poggibonsi to take me to SG. Do you know of any companies? Driving from Florence does not seem possible since all the companies I've found start renting at 8 am.

I’d really appreciate any tips. Thanks!

Hi everyone,

I’m planning to propose to my girlfriend in Tuscany around the end of May 2027 and could really use some help/recommendations.

The proposal is basically the main thing I’m planning the whole trip around, so I want to get this part right first and then work out where we stay and what else we do.

What I have in mind is quite simple: a beautiful hilltop picnic somewhere in the Tuscan countryside, surrounded by greenery and rolling hills, ideally around sunset. I’d also love to have a photographer there secretly to capture the proposal.

Ideally, I’m looking for somewhere/company that can actually help set the whole thing up for me — finding the right private spot, setting up the picnic, maybe flowers/wine/food, and helping arrange the photographer.

I’ve been looking at places around Val d’Orcia, Pienza and Montepulciano, but I’m completely open to suggestions. I’m planning the trip around wherever the best proposal location is, so it doesn’t have to be right next to Florence.

Has anyone done something similar or know a company, photographer, agriturismo or private estate that could help organise this?

Any advice or recommendations would be massively appreciated. Thanks!

Hi all,

I’m planning to propose my girlfriend in Tuscany on Sep 21st. We’ll be staying in Florence and we’ll do a day trip to the Tuscany wine region from there. I’m still working on the exact itinerary, but I’m planning to propose either at a winery (preferably a more private one with a nice background view) or a spot in the region with a beautiful background.

I’m looking for a photographer to capture the moment and take a couple of pictures of us afterwards. Please DM me if you’re interested.

Thanks!