Cue a drumroll as I’ve finally finished booking the accommodation for my Italian holiday. Which is – after all – now just over three weeks away!
I became a little flummoxed by fear (or apathy) despite knowing I really needed to lock down an itinerary and book hotels / apartments. It may well be my one and only trip to Italy so I really wanted to get it right. But of course, ultimately it also just needed to be DONE.
Sorrento
I’m flying into Rome and plan on jumping on a train and heading straight to Sorrento. Well, I plan to catch a train to Naples and it’s been suggested I then find a tour / driver / car to head to Sorrento.
I’ve got 3 nights in Sorrento, so two full days and it’s my intention to book in advance: a half-day tour to Pompeii (etc); and a full-day boat cruise type thing to Positano and Capri.
I want to book both trips before I leave. Work is going to be nightmarish for the weeks until I finish so I’m a little worried I’ll (otherwise) arrive in Italy and want to sleep or lie in bed for days on end!
Florence & Tuscany
From Sorrento I’ll catch a train via Rome to Florence, where I’ll have two nights at a hotel. Another person on my writing retreat had to cancel her trip so her room at the hotel was up for grabs and I’ve taken her booking for two nights before I head to Tuscany and one night after.
I have no idea as yet what I’ll do in Florence, but the room-canceller’s friend (who I’ve met online) will be staying there as well so there’ll be someone with whom I can take tea. (ie. Drink wine and be merry. #Inrelatednews I hope Chrissy drinks!)
Then of course the event this whole trip is planned around – the week-long writing retreat in Tuscany.
Cinque Terre
After a week of creativity I’ll overnight in Florence before catching yet another train to Cinque Terre for two nights. I finally decided to stay in Manarola, the second of the five towns (as you head north). I’d asked quite a few people for advice and then got overwhelmed with options on offer so procrastinated for a fortnight until fewer were available!
From there it’s onto Venice…. and you’ll notice I’m being vague about how I’m getting there but I’m assuming it’ll involve a train. Again. Or several. I haven’t been arsed looking at the intra-country travel stuff yet, but swear I’ll do so before I leave. Perhaps.
Venice
I’m staying at an Airbnb place in Venice, it’s just a room but on a canal (which probably isn’t unusual) and looks very grand. And old. My intent for the trip is to soak up the atmosphere so I’m trying to stay at places different to what I’d usually get here. (I suspect I’ll crave my modern house, bathtub & comfy sofa by the time the three weeks are over!)
I have no idea what I’ll do in Venice but I’m sure it’ll involve a gondola and wine. Sadly I’m travelling alone so I won’t be reenacting the scene from a favourite and much-remembered childhood movie A Little Romance (my first taste of Italy and commencement of my girl-crush on Diane Lane!).

Pic via Listal.com
Rome
From there I’ll catch yet another train to Rome. I’ve booked an Airbnb apartment there recommended by Styling You and it looks handy to all of the important stuff. I’ll force myself to do a few touristy things but suspect my time there will also just involve people watching, wine drinking and finding gluten-free food options.
Speaking of which, in addition to some day trip bookings, before going I need to:
- download an Italian language lesson app so I can at least utter a few words here and there (Am thinking wine, chocolate and gluten are important.); and
- speaking of gluten, I also need to download a coeliac app or bookmark some websites offering dining tips to coeliacs like myself or those on a gluten-free diet!
So there you have it. I’m kinda ready. Of course I’ve not thought about what I’ll pack or anything like that, but I have taken out travel insurance so already winning at this responsible traveller / adulting thing.
Anything I’ve not thought of? Or any tips?
The Lovin’ Life team includes:
August 16, 2018
How VERY exciting, especially your Airbnb in Venice!
August 17, 2018
I know. I got a bit worried later I couldn’t find the link to the place and was worried I’d been duped in some way. I suspect it’ll be a bit old and basic but that’s what this kind of experience is all about isn’t it?!
August 16, 2018
This all sounds super fabulous! I can’t wait to hear about it, see your pics etc. And duolingo is my pic re language apps.
August 17, 2018
Oh thanks for the trip re duolingo!
August 16, 2018
It’s a fabulous itinerary. There is no shortage of things to see and do in Florence and Venice. Just try to get a power nap or rest when you arrive so you can enjoy the destination.
August 17, 2018
Yes, I’m thinking the Tuesday (after my arrival) should be a half-day tour of Pompeii so I def have time for a nanna nap. I was initially spending an extra day in Sorrento (to unwind) but as I’ve taken over someone’s accommodation in Florence my schedule changed a little !
August 16, 2018
Oh it all looks so good. I’d love to see Pompeii. And yes, gondola and wine is compulsory. I loved doing that. Highlight of my time in Venice.
August 17, 2018
People seem to be recommending a water taxi rather than gondola. I don’t really care either way, it’ll just be so very different to life here that it’ll be wonderful!
August 17, 2018
But which is iconic? 🙂 The taxis are practical, the gondola is a bucket list type thing.
August 17, 2018
Hmmm… will see. Sitting by myself in a gondola doesn’t sound v.exciting – though guess I’d be instagramming it to death!
August 16, 2018
OMG….aren’t you just SO excited. Heck, I’m excited for you, and I’m not even going!! But aren’t we lucky we can download apps to get us around and through the mazes like these?? What in the heck did we do before apps??
XOXO
Jodie
http://www.jtouchofstyle.com
August 17, 2018
I know! I think Trip Advisor even has handy info re gluten-free options, but I did see mention of an app (and think there’s something similar here in Australia) so I’ll make use of that! And I’m thinking a translation app will also be handy! I speak some Portuguese but know Italian is different.
August 16, 2018
How fab, fab, fab! We were in Venice and Cinque Terre a couple of years ago. Check out what’s on at the Opera House in Venice,Teatro La Felice – we went to see La Traviata, and even though I’m not really into opera, just being there was amazing, and it wasn’t dear. Mind you, we picked cheap seats. Our highlight of Venice. Lots of little orchestral concerts. Gondola rides are horrendously expensive – the boat ‘trains’ give you just as good a view for a fraction of the cost. Enjoy.
August 17, 2018
Oh, I’m not a fan of opera either, but somewhere like that it’d be great! (And the cheap seats sound ideal!) 😉
August 16, 2018
OMG you are so much braver than me, I would have to have so many more details bolted down by now. I hope you have a wonderful trip just the same and don’t arrive too tired. Venice is magnificent – consider taking the ferry rather than a gondola and go out to Murano and Burano if you have time. But just enjoy!
August 17, 2018
My biggest worry is that I’ve got a pretty tight connection in Dubai and so any delays and then catching a train from Rome to Naples to get to Sorrento. I don’t worry to be arriving TOO late in the day when I don’t know what I’m doing and jetlagged. I’d book the connecting train but can’t be sure my flight won’t be delayed or it’ll take a while to get out of customs etc…
August 16, 2018
I think you’ve stolen my Italy itinerary. We visited all of these places and stayed in a couple of Airbnbs. We stayed at Monterosso at Cinque Terre, Siena and Castellini in Chianti,Tuscany, Positano on the Amalfi Coast. I absolutely adored Italy and I think you will too. I hope you have a wonderful holiday Deb.
August 17, 2018
I thought about Positano Kathy Sorrento seemed more central and easier to get to from Naples on the day of my arrival. My dream Italian holiday only ever involved Amalfi Coast, Cinque Terre and Tuscany and a week or so in each place, so this is a more condensed version obviously!
August 16, 2018
Wow! You are amazing to have organized all that and to be doing it all alone. You are so much braver than you give yourself credit for and I truly believe it’s going to be the trip of a lifetime. So excited for you 🙂
August 17, 2018
I traveled alone when I lived overseas before so am kinda used to that and remember going to Zimbabwe, Vietnam and similar without even pre-booking accommodation but then again I think the 1990s were very different in that respect!
August 16, 2018
Super excited for you Deb (and I don’t even know you)!! I loved every minute of Italy and really hope to return one day. I hope you have time for the San Lorenzo markets while you’re in Florence, and of course iconic David (and his perfect butt). The Amalfi Coast is just gorgeous, doesn’t really matter where you are. The steps are a challenge if you have heavy bags though, but that’s the case in many European destinations!! I found train travel super easy in Italy. You’re bound to have an amazing time!! Look forward to reading your Italy posts in due course, and seeing some beautiful photos xx
August 17, 2018
Ah yes, I kept reading reviews about having to carry luggage up steep hills and steps so took that into consideration when booking my accommodation. I’m trying to travel light but sadly have more than just hand-luggage. I’m getting really excited about it now!
August 16, 2018
I think you have a great balance there of “pre-organised” with “let’s see when I am there”. Really good plan! It is great to know it is going to happen and I am very happy for you. Denyse x
August 17, 2018
Yes, I figure I’ll pre-book a couple of early day tours and then talk to people and find out what companies are the best etc… And everyone says it’s cheaper to book trains beforehand but the only one I’d really like to book would be the first (so I didn’t have that stress on arrival to the country) but loath to commit to a time when I’m not sure if the flight will be on time / how long it will take to get through customs etc…
August 16, 2018
How exciting. I was so relieved when I got all of our accommodation locked in for our 2 week Tassie trip. Mostly airbnb’s and places that are, like you also chose, different from home. We have a pretty comfy bedroom and ensuite at home, so it makes choosing accommodation (especially on a budget) a bit of a challenge.
Regarding gluten, a friend of mine who has celiac disease recently did a walk from Sienna to Rome and found gluten free food quite readily available in Italy. There is a card online that you can print out to present at restaurants if you want to be sure. One of her comments was “if in doubt, just eat gelato”
As much as you want to make the most of your time, make sure you do allow yourself a little down time, or you’ll get home exhausted!
August 17, 2018
I’m the same Tracey – my place is quite comfy and has nice views of the ocean so makes it hard for places I visit to measure up so I figure I’ll immerse myself in the discomfort of past-years / centuries. But I was pretty keen to have my own bathroom everywhere I booked and (other than Venice) have gone for hotel rooms or ‘whole apartments’ so I get some privacy. I’ll probably not arrange any tours for Cinque Terre or Venice and only do a couple of touristy things in Rome so think I should get a bit of down-time!
August 17, 2018
My bags are packed and I’m read to go, Deb! I love Italy, and being married to an Italian we have visited often. My daughter (his stepdaughter) and her husband eloped and were married in one of the small villages of Cinque Terre by the Town Mayor. Just her, Ian and her best friend and his best friend. She looked so happy in the photos and the backdrop was gorgeous. Have a wonderful time and you have certainly the best of Italy itinerary planned. x
August 17, 2018
Oh I didn’t know your husband was Italian! And I love the idea of the elopement. No chance of that for me of course! 🙂
August 18, 2018
Yes he was born just outside of Naples and they came to Australia when he was 4 years old – he is now 70. He still has an aunt and cousins who we visit. My daughter looked lovely and so happy and who wouldn’t getting married in such a beautiful place. Enjoy your holiday and can’t wait for the photos. You never know you might meet someone, it’s never too late 🙂
August 17, 2018
I spent couple of years overseas and the one place I didn’t go but would have loved was Italy. It sounds amazing.
August 17, 2018
It’s really the only place I’ve wanted to go so glad I’m finally getting there!
August 21, 2018
Wooo hoooooo!!!! Can’t wait for the Italy posts! Plan to be there next year with a bit of luck. C is over that way at the moment. Actually, she’s done Paris and is now in Amsterdam and will do Greece, Not sure about Italy. Anyway, can’t wait for your posts. Will help me plan my trip.
August 21, 2018
I’ve tried to find accommodation with wifi but not sure I’ve been entirely successful though hope to be online for some posts and writing.