Italy - Cortona/Tuscany

Arriving in Tuscany (I suspect in any city here) can be quite scary for a single male traveler. What am I supposed to do! It’s not exactly cosmopolitan. Luckily I had a guide to my Tuscan adventures and a city that turned out to be charming…if you like that sort of thing.

First off, having lunch at a picnic table in the backyard of a local house, overlooking the Italian countryside is a pretty cool way to start a trip to any city. Cortona happens to be on the top of a rather large hill, completely surrounded by walls. It’s old as shit and you feel like you’ve gone back in time while you are there.

I suspect that the very thing that makes places like this attractive, are the very things that are going to destroy it in this age of globalization that we live in. That being said…my money is green. Dinner at Mario’s restaurant is like sitting in the chef and owner’s house. Having a true Italian lunch with tons of wine, 4 courses including pasta and grilled game, and people toasting all around you is just perfect (I am told you can’t go there if you aren’t with a local). Ate some fantastic Italian pizza (flat and crispy as hell), chilled with a bar owner who seemed to have very little interest in talking to me, and discussed the merits of fascism with the Marlborough man of Cortona.

This town is great, but without my companions, I would have left after a couple hours…

My second visit was just as good as the first. This time we spent an entire day exploring the local wineries. We went to some of the oldest wine cellars on earth (most from the Etruscan age). This was truly like going back in time, and some of those old oak barrels are bigger than houses. We also had “lunch”, which was really just the biggest bruscetta platter on earth, in a thousand year old wine cellar. It was a once in a lifetime experience. And of course, we truly had to have dinner at the new burger bar in the center of town (Beerbone). Cool spot, but the beef needs work (that being said, every country has their own tastes and this place seemed popular enough). Super nice people and lots of upside here me thinks.

Cortona Aug 2022 Update

Villa marsili is actually quite lovely. It’s old of course but they do a good job, and I rather enjoyed the short walk up to the center of town each day. You are still in the walls but on the edge. My parents probably wouldn’t love the walk. We got a suite with a panoramic view, and in a town of great views this one is pretty gd perfect. The breakfast was simply as cute as a button. So quaint and little and perfect. Mini croque madames? I mean come on!
Plus ask for the private parking for 8 bucks a night. Worth every penny.

Our 2019 trip brought some new things as we stayed a lot longer this time.

For this trip we stayed on a mountain overlooking lake Trasimeno. Beautiful area. We drove all around from that home base but one of the cool spots on the lake was Passignano where they have a nice market and you can also take a short ferry to Isla Maggiore. Not the most exciting place on earth but it’s pretty neat to see a place that is so isolated and has like 10 residents…not sure what is interesting about doilies though! House was in Lisciano Niccone in Perugia.

Tuoro was right down from out house and it’s charming.

Umbertide was not as close but their Wednesday market was fun and the town is cool enough…limited dining options though.

Perugia itself is worth a visit. Cool little town. Once you finally find parking and walk up it has a main drag along a ridge line so it’s very flat up there (humongous hills before you get to the ridge). We found an awesome pizza place directly in front of the cathedral on a side street. In their main square they also have a pretty famous porchetta stand that I thought was absolutely fantastic. We went to this on our second visit in 2022 and I was floored. This was also the visit where we mistakenly drove the car into the walled city. Don’t do this as you may never get back out :)

Multipuciano is like Perugia really, but in this case the highlight is always the walk through the Ricci winery and their hundreds of years old casks and thousands of years old caves and rooms. Pienza is a cool town nearby as well with tons of Pecorino shops, their specialty. A cool main road for shopping etc.

Castigleone de lago is a pretty small town on lake trasimeno with one Main Street, not unlike Pienza, but I think Pienza is better, but at least here you do have lakeside restaurants (but down a steep hill). The top of the hill is the Tuscan town, the bottom is lake living. Lunch with Laura was nice then walking up to the shops worked great.

Passignano was where we took the ferry to Isola de Maggiore (doiley island), but we went to it again for food and drinks on this trip. Lots of beachside stuff and lots of kid friendly stuff. A little sleezy maybe. It does get lively and you can have a drink right along the water, but maybe yeah, it’s a little trashy.

Isola, btw, is charming enough, and nice, like going back in time. But still I was ready to leave after 5 minutes :)

In the covid summer of 2021 (you couldn’t even go in 2020) we stayed in a villa in a nonexistent town called Ronzano. Very isolated but only about a 10 minute drive to Cortona.
The villa itself was a perfect very Italian style Villa.
The pool was cold as shit but was used it quite a bit anyway. The view on cortona and the surrounding countryside is hard to beat. The hot tub was bananas like a volcano erupting each time you turned it on. The pool room came in especially handy for late night drunkenness.

Update Aug 2022

Tellaro is not a place you need to stay in. It’s very much like Priana in the amalfi coast. Why stay next to rad places when you can stay in rad places. Here you have to walk down and uphill to do anything, and even their commercial areas are limited and not well connected. It’s charming and cute for sure, but a quick boat stop from Porto Venere or Lerici is all you need. Speaking of Lerici, we stopped there again this year by car (by boat last year) and we are thinking it’s pretty rad. Lots of restaurants, lots of beach clubs, lots of options. And get this, I went to a beach club that had an actual sand beach. Like for real man. It ain’t powder, but it ain’t rocks either!
Another problem was there are now so many Airbnb’s in Tellero that the “beaches” and restaurants do not have the capacity. If you want hot, no breeze, restaurants that have no availability, no real beach, walking up flights to go anywhere, and really old Italians everywhere, then this is the spot for you.
Btw, Tellaro beach is no beach at all, it’s a boat launch (like riomaggiore) with huge rocks nearby to sit on. The “better” beach is fianmuchera, which you can walk to but oh my is it not worth it. Sandy a bit, but only maybe 15 feet of coast and it’s packed. Top 5 worst beaches I’ve been to easily. And jellyfish. Nasty.
Our Airbnb was decent with spectacular views but like everything else it’s a haul to go anywhere or do anything.
It’s impossible to stay in this part of the gulf of poets when coming from the close to perfect town of Porto Venere or the pretty awesome town of Lerici.

Sienna is still one of my favorites by far. It is a must stop in my opinion. Kind of the perfect blend of shopping, restaurants, and old school living. Not too big like Florence. And not too small like Cortona. It’s my Goldilocks town. Not kidding. The main plaza is gigantic and completely pedestrian and surrounded by patios. Even on a continent of plazas and patios, this one is special, and I would say especially with a kid that wants to run around.
They cover the entire outside edge of the plaza with dirt and do a horse race each year. It’s pretty amazing.
I forgot to mention la prosciutteria last time which has famous sandwiches (it was closed last time but I could still taste their amazing sandwiches).
We also were feinding for a burger and found a decent one right off the square at Te Ke Voi. Overall you get local shopping here and bigger brands. You get a good mix of everything.
Siena and the Palio go hand in hand. We were there while they were setting up and practicing, so while we didn’t see the race, even just seeing the track is a sight to behold. So cool and crazy that they do that.

Julie says we should look into Bomarzo. Very cute town we drove through.

Hotel grand Continental Sienna
Finally great American style toilets (no water and a weird angle of the bowl makes for a lot of “maintenance” typically)! Haha! They have us in adjoining rooms which with the kid was perfection.
Location can’t be beat, but don’t drive in the wrong way like us jackwagons. We had no business dodging people on these amazing walled streets. The actual car entrance is very close and easy.
The adjoining rooms were simple perfection at its best, 2 rooms with doors behind one main door (love it), but god help the person that gets that single room and it’s not connected to a double. The breakfast was 26 euros and was well worth it if you aren’t in the morning mood for wandering.

The heritage suite at the Grand Hotel Continental did not disappoint. It’s huge with a big loft and a ceiling like the Sistine chapel. There was no amazing bedroom versus living room situation with the loft and the shower was pretty meh, but the 2 bathrooms and overall feel made it like a trip back in time while still being quite comfortable.

Portovenere is amazing. Maybe an hour west of Florence right on the coast below the Cinque Terre. Small but also with plenty of narrow streets with shops and restaurants. It can be pretty magical. This area is also the focaccia capital of the world so I was right as rain :) Focacceria, home run!
Grand Hotel Portovenere
If you aren’t getting a junior suite or better I think you’re really missing out. The beautiful balconies that look down on the commercial “center” are some of the best balcony experiences you are gonna get. Large with great views. So comfy. So perfect.
The hotel has some private boat trips that should be taken advantage of. I thought the nice boat at 1400 euros for 8 hours was a little pricey with too long a trip (small boats traveling fast get annoying quickly!). On the other hand I thought the lesser boat was great for 2 hours at 295 euros or 3 hours at 320 (no brainer on the 3 hours). You get to see the surrounding areas and lirici to the south. Seeing the 5 cinque terre towns takes 4 hours or more, and since we’ve been there multiple times we skipped heading north.
The hotel has “sporting” beach club. But this is Nice France style. There ain’t no sand to be found unless you bring it yourself

2022 update - Porto Venere is still wonderful. But don’t forget all the shit they gave us at the grand hotel this time trying to get our 5 year old into their best rooms. Not only has she stayed in those rooms with us before, but it’s the best room and exactly why you stay there. It’s huge compared to most and the balcony is to die for. I should mention that we did really like the small but gorgeous breakfast each morning, get it included.
We had a great time on the private boat but it had to be the slowest boat in town! The Moby Dick…a grand dame that might need to be retired. $750 5 hours (he gave us 6 hours) and 6 people. And I tipped a hondo. And wow did that restaurant, Torre Di Venere, at the end of the marina get us this time. Second time there and we dropped 750 this time. Wasn’t able to spend even half that at any other restaurant the entire trip, and we don’t dine at no slouches :)

July 2024 Update (I really need to break out Porto/Liguria)

Had the Scriptorum suite this time (cause of the 3 person occupancy). The room does have a living area completely separated from the bedroom. The balconies have overhangs that prevent easy sky viewing but it’s still pretty nice. Our room 402 was one of the corner versions so you could see the town and the gulf of poets which was rad. If you can’t see the town then it’s a waste of money I think. The cloister suites have the 2 person occupancy (yeah they take it seriously) but they are kind off bigger, and definitely better. Those balconies (even though they don’t look at the gulf) are too good to be true. Our other peeps had a basic room looking at the gulf (no town). I felt bad for them but at least they had our balcony to hang on.

Forte Dei Marmi
It just felt so experience specific, meaning if you chose the wrong beach club, you could be either very unhappy or very happy, but no matter what you do you’ll be wondering about what’s at the like 200 other beach clubs. At least that’s me. The grass is always greener lifestyle is tough I know, but this area is south beach style, and the scene can be everything!

Again I need to break out Liguria…but food tour September 2024

Hotel Shelley De Palme
This hotel was actually a pleasant surprise. While the lobby looks like classic crappy euro hotel shit, the rooms were updated and were clean and mod. The balcony was decent sized and looking at the water is always nice.
The view was not of the beach but of the marina, which is worse maybe. BUT it’s way closer to town.
That being said Lerici is not great and you confused it with the town of Amalfi I think.
There is not much there so don’t go back.
We did luckily hop on the ferry and hit riomaggiore and Porto venere for a full and amazing day.
To get to Pisa airport they charge 200 euros for the 45 minute drive. Confirmed as real by others but still ugh.
We went to la Spezia and walked the pedestrian thoroughfare also. This remains underwhelming and when we couldn’t get a car to take us to Lerici we hopped on a bus. Ugh and ugh.

Notes to self:

-If possible, visit one of the Olive Oil festivals. It’s like a miracle of delicious…and it’s free of all things.

Hotel Italia - Oct 2013, June 2016

Perfect location right in the center of town. Great staff who was more than helpful with everything. The view from the rooms on the high floors is the type of thing you would see on a postcard. Bed was fine and the room and hotel were remarkably quiet…like uncomfortably quiet maybe, though I slept so so well there.

They do have a little TV but it’s not facing the bed, instead it’s facing these two chairs that were made in the middle ages by some sort of genius sadist. But whatever, Italian TV before midnight sucks anyway.

The bathroom was fine but the shower was quite small…and I am not small, but I’m not so big either.

The rooftop “restaurant” was a nice spot for some included coffee and breakfast in the morning…but the breakfast was pretty boring and unattractive.

This place was perfectly quaint and hard to beat in Cortona.

***While the above is still true, upon my second visit we were stuck in the worst room in the hotel, and possibly the worst room in all of Italy. It was a dungeon. It was a disaster. My peeps tried so hard to improve the situation but there was some art group that booked before us (if they had just told me I could of canceled and booked somewhere else, but alas). The hotel did buy us a bottle of champagne, but it was a small token for such a ridiculous room. Might be the worst room I’ve ever stayed in, which is saying a lot for someone who has spent time in south east asia So this hotel can be perfect, but call ahead to make sure perfection doesn’t become despair.

Hotel San Michele - July 2019

So I finally switched it up from my typical Cortona hotel and I was pleasantly surprised! Now, to be fair, this is a small town in central Italy so you ain’t getting posh (although I have heard a very small posh place opened up or is opening soon), but this place turned out to be great.

The people, from the dude who kept helping us with luggage and cars and anything, to the front desk people to the breakfast people. So so nice.

The location is perfect, but as perfect as the other place. In this case they let you drive up to the front door to drop your bags off. If you choose they will park your car in their garages for 20 a night, we absolutely chose to do this and recommend the same.

The lobby is old and busted but they have a very nice outdoor courtyard and other nice touches.

The breakfast is small as you’d expect but they have another nice courtyard next to the breakfast room (on the 2nd floor) where you can relax and get ready for the day.

Ok, the rooms are not great. And the corridors are done up in scary religious paintings. At night you feel like you are in Disneys Haunted Mansion I shit you not. BUUUTTTT. They have a suite, and it is a perfect place to stay because of its incredible balcony. Huge, amazeballs view, private, relaxing, so perfectly Tuscan. We were so happy. Anyway, get this room.

**We also stayed in a villa in Umbria on this trip and in a pretty rad subterranean apartment right in the heart of Cortona. La Corte.