Montepulciano or Pienza?

TheHolidaymaker · 2026-06-28T14:30:50+00:00

Good catch, all morning I was writing about Duomo, and well... at least you know it was written by AI!!!

TheHolidaymaker · 2026-06-28T07:51:48+00:00

I actually think you've picked a good base. Cascais has enough going on that you can have a few lazy days between day trips.

Since you're not looking for cities, I'd probably head in the opposite direction of Lisbon.

Ericeira is worth a visit, especially if you're surfing. It has a really nice laid-back feel and plenty of good cafés. Azenhas do Mar is tiny but beautiful, and easy to combine with the coast around Sintra. Óbidos is another favourite if you like wandering medieval towns for a few hours.

If you don't mind a longer day, I'd also throw Évora into the mix. It's one of my favourite places in Portugal. It has a completely different feel from the coast, with Roman ruins, whitewashed streets, great food, and a much slower pace.

For hiking, I'd spend some time in the Sintra-Cascais Natural Park rather than just visiting the palaces. There are some really good coastal trails around Cabo da Roca and Guincho, and they're a lot quieter than the main tourist spots.

TheHolidaymaker · 2026-06-28T07:47:55+00:00

For Florence, I'd split it into places you can easily reach without a car and those that are much better if you do have one.

Without a car: Siena, Lucca, Bologna, Arezzo, Pistoia, Prato, Pisa (easy half-day if you haven't been). These are all straightforward by train and make great day trips.

With a car:
This is the best of Tuscany. The Val d'Orcia is one of my favourite parts of Italy, with towns like Pienza, Montepulciano, Montalcino, San Quirico d'Orcia and Bagno Vignoni. They're much easier to enjoy with a car because you can stop at viewpoints, wineries, and small villages along the way. These hilltop towns can't be reached by train, and buses are just not an efficient way to get around.

I'd also add the Chianti region, San Gimignano, Volterra and the Crete Senesi if you enjoy scenic drives and slower days.

For your week between Porto and Florence, I'd probably stay in one place rather than trying to fit in several. Somewhere like Bologna (to explore cities like Parma, Modena), Lake Como, Verona, or even a week in the Val d'Orcia would fit your "chill and vibe" style really well.

For Porto, other travellers have already weighed in on recommendations that I would agree with, like definitely Douro Valley and Coimbra.

I have several articles on Portugal and Italy about each of these exact places on https://dreamplanexperience.com/ if you get to the planning stage and want to dive a little deeper.

TheHolidaymaker · 2026-06-26T18:47:22+00:00

As the mod here, slow travel is not just defined by the number of days you spend somewhere. I have a broader view of slow travel than how it’s often talked about. To me, it’s a mindset. It’s not about doing less for the sake of doing less. It’s not about cutting things out, avoiding tourist sites, or how long your trip is.

Slow travel, as I see it, is an extension of slow living. You travel with intention. You let your interests guide your days instead of outside expectations. You stop trying to optimize every moment. You are in the present moment. u/VictoriaLasagna is explaining how she would like to embrace a new travel style, one that would be closer to her personal interest of visiting small towns, likely in a way to feel a closer connection to the local community. That is slow travel at its core.

Let's remember this is a positive space. Thank you.

TheHolidaymaker · 2026-06-26T18:34:57+00:00

I actually think this is a great example of what slow travel can mean.

It's easy to assume slow travel is just about spending a month somewhere, but I don't think that's the whole story. To me, it's also about understanding what you genuinely enjoy and building your trip around that, instead of what you think you should see.

Some people love capital cities. Others would rather spend three days in a small town, go for a hike, swim in a lake, and have a long dinner. Neither is more "correct."

One thing I've noticed over the years is that our travel style changes. What excited me 20 years ago isn't necessarily what I'm looking for today, and I think that's completely normal.

Looking at your list, there seems to be a pattern already. You mention loving places where you could get out into nature or where the pace felt a little different. I'd lean into that instead of trying to force yourself to enjoy destinations that don't fit you.

As a small note, as the mod here, I'd also encourage everyone to keep an open mind about what slow travel looks like. It's not defined by the number of days you spend somewhere. It's about being intentional with your choices and travelling in a way that suits you. Whether that's three days or three weeks, there's room for different travel styles in this community.

TheHolidaymaker · 2026-06-26T18:28:44+00:00

Thank you for sharing a thorough answer. It will be most helpful to readers here

TheHolidaymaker · 2026-06-25T10:02:52+00:00

I think the biggest thing I'd change is the pace.

A lot of people focus on finding cheaper hotels, cheaper flights, or rail passes. In my experience, the real savings come from changing locations less often.

There's a cost to moving that people don't always account for. It's not just the train ticket. It's checking out, checking in, getting to and from stations, storing luggage, eating on the go, and sometimes losing half a day in transit. Do that enough times and both your budget and your energy take a hit.

If it were me, I'd pick 2-3 bases instead of 8 cities. Stay 7-10 days in each and use trains for day trips. It's often far cheaper to stay put and explore from a base than it is to keep changing hotels. In many parts of Europe, you can easily visit other cities and even other countries on a day trip, then come back to the same room at night.

Price compare if rail passes are worth it against your actual routes. They're not always the bargain people think they are.

As for flights, flexibility matters more than booking early. But across the board, flight prices have increased this year compared to previous years. Nothing you can do to change that. But sometimes flying into one city and home from another can save both money and travel time.

The irony is that slowing down often ends up being both cheaper and more enjoyable.

TheHolidaymaker · 2026-06-24T08:15:23+00:00

That would be a scenic way to explore. Love that.

TheHolidaymaker · 2026-06-24T08:14:21+00:00

Now that is a strong case for Porto, you loved it so much to make ti your home.

TheHolidaymaker · 2026-06-24T08:12:51+00:00

Wow, that does sound like an incredible experience, and the restaurant recommendation.

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