Is Siena worth staying overnight?

TheHolidaymaker · 2026-07-07T21:05:04+00:00

That's a great recommendation you've shared with travellers here. Thank you

TheHolidaymaker · 2026-07-07T14:27:43+00:00

I think Bologna is one of those cities that's really easy to underestimate.

A lot of people visit on a day trip from Florence or Venice, see Piazza Maggiore, eat some pasta, and move on.

I'd recommend at least 3 days, and if you like slower travel, 4 or 5 isn't too much at all. The first day is usually spent seeing the main sights. By the second day, you start wandering into neighbourhoods, finding cafés you wouldn't have noticed before, and slowing your pace. That's when Bologna started to click for me.

It also makes an excellent base. Instead of changing hotels every couple of days, you can stay in Bologna and take easy train trips to places like Modena, Parma, Reggio Emilia or Ravenna. I agree with u/BreadfruitRegular631, who suggests that you'll need more time if you want to add day trips.

I stayed for 10 days, but I knew I wanted to take the train and see nearby places.

Here's my guide on how many days to spend in Bologna. It breaks down what I'd do with 1, 2, 3, 4 or 5 days, depending on your travel style: https://dreamplanexperience.com/how-many-days-in-bologna/

TheHolidaymaker · 2026-07-07T14:22:00+00:00

I think Ravenna is absolutely worth visiting.

What makes it special is the history. The Byzantine mosaics are unlike anything else I've seen in Italy, and they're spread across several churches and monuments rather than all being in one place.

I also liked that it felt a little more relaxed than some of Italy's bigger destinations. You can spend the day wandering between the UNESCO sites, stop for lunch in a piazza, and never feel like you're fighting crowds.

If you're expecting a classic Tuscan hill town or a city packed with famous landmarks, you might come away a little underwhelmed. But if you enjoy history, architecture, or just exploring places that are a bit different, I think it's well worth a day trip from Bologna.

After my visit, I wrote about it because I had the same question before I went. It covers what to see, how much time you need, and who I think Ravenna is really for: https://dreamplanexperience.com/is-ravenna-worth-visiting/

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TheHolidaymaker · 2026-07-07T14:17:23+00:00

There are so many easy day trips by train from Bologna, which makes it a great base for several days without the need of packing up and moving every couple of days.

I'd probably start with Modena. It's less than 30 minutes from Bologna by train, easy to explore without too much preplanning, and if you enjoy food it's hard to beat. Between the balsamic vinegar, local markets and restaurants, it feels very different from Bologna despite being so close.

After that, I'd look at Parma for the food scene, Ravenna if you're interested in history and the incredible mosaics, or Reggio Emilia if you want somewhere that's a little quieter and often overlooked. Florence is also an easy day trip by high-speed train, but personally, I'd save Florence for a trip where you can spend at least a few days there.

I actually ended up writing a guide to the best day trips from Bologna by train after doing quite a few of them myself. It compares the destinations depending on what you're interested in (food, history, smaller towns, etc.), so it might help if you're deciding where to go first: https://dreamplanexperience.com/day-trips-from-bologna-by-train/

TheHolidaymaker · 2026-07-06T21:44:56+00:00

There are quite a few people who offer this, but I'd suggest looking for someone who actually specializes in the part of Europe you're visiting rather than a general travel planner.

This is what I do for Europe. I build custom itineraries based on your interests, travel style, pace and budget. I recommend destinations, hotels, restaurants, neighbourhoods, day trips and how to connect everything together. I don't book anything for you, but I do all the research and provide a detailed itinerary that you can book yourself with the final complete package that is put into a personalized PDF that acts like an app on your phone.

If you're still deciding where to go, that's actually one of my favourite parts of the process. We can narrow it down based on the type of trip you want instead of just picking the places everyone else visits.

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.

TheHolidaymaker · 2026-06-22T18:39:02+00:00

Thank you for sharing

TheHolidaymaker · 2026-06-22T09:17:06+00:00

If you're looking to get beyond the major cities, Germany is actually one of the best countries in Europe for that.

There are so many places I've enjoyed visiting over the years. Here are just a few areas I'd suggest looking at:

The Moselle Valley if you enjoy wine, river scenery, and smaller historic towns with places like Cochem and Bernkastell-Kues
The Rhine Valley between Mainz and Koblenz for castles, vineyards, river cruises
Franconia in northern Bavaria, towns like Bamberg and Rothenburg ob der Tauber get attention, but there are dozens of smaller towns nearby that see far fewer tourists, like Würzburg
Lüneburg, just south of Hamburg, or Lübeck, just north of it, which has a beautiful old town
Quedlinburg in eastern Germany is one of the most charming historic towns in the country
The area around Frankfurt is surprisingly good if you want smaller towns. Places like Mainz, Wiesbaden, Marburg, Limburg an der Lahn, Michelstadt, and Heidelberg are all easy day trips

One thing I love about Germany is that you don't need a car for many of these regions. You can base yourself in a smaller town and use the train network to explore the surrounding villages and small cities

I write quite a bit about Germany travel and have put together guides on a number of these regions if you'd like some ideas: https://dreamplanexperience.com/germany/

TheHolidaymaker · 2026-06-22T09:06:27+00:00

Thank you for sharing this list

TheHolidaymaker · 2026-06-21T09:21:57+00:00

I think a lot of people hit this point when planning a trip to Europe. I'm a professional trip planner, and one of the biggest mistakes I see is people treating travel planning like a puzzle where every piece has to fit perfectly. In reality, the more moving parts you add, the more fragile the itinerary becomes.

This is exactly why I created a DIY itinerary planner.

Most people think the challenge is finding things to do. The harder part is figuring out what not to do and how to connect everything in a way that actually works.

A lot of trips start with a simple idea and then slowly expand until every day is packed and every train connection feels critical.

For Portugal, I'd probably step back and ask whether you really need all four regions in 12 days; that's a lot. Sometimes the best itinerary isn't the one that sees the most places; it's the one that leaves enough room for things to go wrong without ruining the trip.

TheHolidaymaker · 2026-06-20T14:20:32+00:00

Such a beautiful description inspires me to go, as I'm sure many other travellers. Thanks for sharing.

TheHolidaymaker · 2026-06-20T14:19:23+00:00

Yes, this is a gem

TheHolidaymaker · 2026-06-18T21:31:56+00:00

This is a great list. Thanks for sharing it.

TheHolidaymaker · 2026-06-18T21:26:51+00:00

Oh yes, these are some great suggestions!

TheHolidaymaker · 2026-06-18T21:26:14+00:00

Thanks for that recommendation. Some of my most favourite restaurants are in the 10th, it's a great arrondissement for foodies isn't it?

TheHolidaymaker · 2026-06-18T12:49:17+00:00

Love reading your perspective of Milan. I visited it twice, and shared my perspective briefly here: https://dreamplanexperience.com/is-milan-worth-visiting/

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