In the autumn of 2014, my future husband and I embarked on a romantic Tuscan Adventure we would forever remember vividly and warmly with our hearts and our stomachs. Here I will share with you some tips and an account of our adventure to help you plan your visit! We fell in love with Tuscany (it is very difficult not to do), and hope you will share the same love as we did.
For some background, here’s a quick overview of our travel specs / what we were looking for in our trip:
- Trip Duration: 4 nights
- Wanted to visit quaint medieval Tuscan towns & Cinque Terre (we avoided Florence and Sienna)
- Wanted to do something active & outdoors – we opted for a Bike Tour
- Wine, wine, wine, picturesque vineyards…… more wine
- Quiet B&Bs with fantastic views and friendly hosts
- Freedom to make our own adventures & schedule, hence hiring a car
Exploring Pisa
Our plane arrived in Pisa right around noon, giving us plenty of time to pick up our rental car and explore Pisa before heading to our B&B to unload and unwind.
Patience is hard to come by when first driving in Italy – so if you are renting a car, prepare to adjust to the Italian driving styles and to be a bit apprehensive until you get your bearings.
In Pisa we wandered around the streets, ate a fantastic lunch al fresco, had our first (of what would be many) gelatos, and explored the typical tourist sites. Pisa was great for an afternoon to tick the box of seeing the leaning tower, but it was a bit grimy and I wouldn’t have wanted to spend more than half a day here. Perfect amount of time.
We then travelled to our B&B which was absolutely incredible. The shot below was captured en route to our B&B, next to the incredible antipasto we enjoyed at dinner that evening.
The views were amazing, our host was so lovely, and she recommended we dine at a very small restaurant in the village close by, within walking distance. The owner of the
restaurant was extremely friendly and accommodating, the venue and set up was so romantic, and the food prepared was just to die for. We went to bed tired from our day of travels, with very happy bellies.
Exploring Small Towns of Tuscany
For our second day, we started with no set plans (except at some point we needed to get to our next B&B in Chianti), so we spoke to our B&B host during breakfast for some recommendations. We had a delicious breakfast with some wonderful views.
Upon the recommendation of our host, we decided to check out the two medieval towns of Volterra and San Gimignano before heading to Chianti. These two towns were stunning – both fantastic choices for soaking in all the feels of the quaint old towns of Tuscany.
Volterra was quite small, but much less crammed with tourists than we had anticipated. This was Arnie’s favourite stop, as you could just feel how old the town truly was. Our B&B host had mentioned something about vampires in Volterra to Arnie (and I wasn’t going to tell him it was regarding a scene from Volterra in the Twilight Series), which enticed his appetite for the eerie.
Also worth noting, Volterra is enclosed in castle-like protective walls, a necessity for the battles fighting Florentine and Medici ruling. As it is also very high in the hills, Volterra lends itself to fantastic views of the surrounding hillside.
San Gimignano, to contrast Volterra, was very much on the tourist track – but there is definitely a reason why. This is due to the breath-taking views and beautiful towers (there are 13!) present in San Gimignano. Although it might be more crowded, the views from San Gimignano are absolutely not to be missed.
When in San Gimignano, Arnie and I picked up some delicious fresh ingredients from a local shop, as well as artisanal crisps, dry cured meats, truffle tapenade, olives, and lots (….lots) of wine to try. We finished our evening by arriving quite late to our B&B and cooked our own feast using the goods we purchased at the shop earlier. This is typical for us, as we always try to book B&Bs where we can make our own dinner. This gives me the opportunity to craft a dish using fresh local ingredients; it also saves quite a bit of money on dinner, especially when we want to drink multiple bottles of wine!
Tuscan Bike Tour
The next morning, we had a delicious breakfast while waiting for our ride to the Tuscan Bike Tour we had arranged. We didn’t know it until that day, but there is a HUGE cycling culture in Italy, and Italians regard it as one of their most popular sports. When you have beautiful scenic landscapes along the whimsically winding roads at your finger-tips, jumping on a two-wheeler and peddling through the hillside would feel like a birth-right. And we were definitely excited to partake in some of the butt-busting action!
Our bike tour started in a small village in the Chianti region (the name of which is escaping me), and we quickly geared up and hit the road. The sun was shining her warmth on us while we chugged along, fresh air filling our lungs, the picturesque Tuscan landscapes seeping in through our eyes, giving us a sense of euphoria. It was absolutely incredible.
We made a pit stop on our tour at Castello di Brolio, a castle, one of the oldest businesses in the world, and the oldest winery in Italy. Here they produce some of the world’s finest Chianti from their impeccably harvested Sangiovese grapes. We were dying to try some, and almost died from happiness after we had our taste. I’ve since seen this wine for sale in shops in London at an exorbitant price, and we were very lucky to have been to this place in person (and by bike).
Following our bike tour, and our transport back to our B&B, we napped in the hammocks among the olive trees, drank more wine, then headed out for some dinner in the town of Chianti. As we were exhausted, this was a short-lived adventure, but the piazza at night time was nothing short of Italian romantic splendor.
Cinque Terre via Lucca
On our fourth day, we bid farewell to the enchanting views of the sun peering through vineyard mist at our hillside B&B in Chianti, and headed north on our way to Cinque Terre, a place that had been on my bucket list since I heard of its existence.
LUCCA
In passage to Liguria, we stopped in another small Tuscan town, Lucca, as it was recommended to us by one of my colleagues and it was conveniently on the way up north. Lucca was truly a gem, offering both the genuine medieval feel and aesthetics, while also feeling like it was a town where real people currently lived. This was much different than San Gimignano, for example, where the town felt like the primary inhabitants were tourists.
Lucca had much to offer for our quick visit, including ramparts like none other we had ever seen. The city walls in Lucca are covered with beautifully manicured lawns and a pleasant path along the top, where residents and visitors strolled, jogged, and cycled along. It was a delight to explore the city from this vantage point.
In Lucca you will also find the exquisite cathedral of San Martino, the typical medieval piazza del mercato, and quaint narrow streets and alleyways. In sum, Lucca was a pleasant pit stop on our journey, and we were very happy to have stopped here for lunch and for a few hours to explore.
As you move north from Tuscany to Liguria, the landscape evolves from rolling hills and vineyards to rockier, steeper slopes, with more densely packed dark green trees blanketing the scene. We stumbled across a few vineyards on our journey, and stopped in two of them. Here we tasted some incredible wines, and stocked up on some bottles to enjoy later that evening.
Our next B&B was a renovated farm house high in the hillside, over-looking a very small village in what seemed to be the middle of nowhere.
After checking into our B&B, we took the advice of our host and headed to the seaside town west of the Cinque Terre called Levanto. This was a picturesque Italian beach, where we stopped for a light dinner and cocktails at a bar in the sand, with a perfect west-facing view optimal for watching the sunset.
Once the sun had settled in for the night, Arnie and I found another local shop, stocked up on some snacks, and headed in for the night to drink our wine and munch on some Italian treats.
Cinque Terre & Portovenere
Our final day was spent touring the dramatic coast-line of Liguria, viewing the 5 towns (Cinque Terre) and a 6th town, Porto Venere.
We started in Monterosso, where you can drop your car and use the ferry service for the day. The ferry is a great way to get around, especially if you only have half a day to explore. The ferry takes you to all 5 towns as well as Portovenere, and it is very easy to hop on and hop off from all locations.
The sights of Cinque Terre from the ferry were exceptional, and the towns themselves were quite unique and special.
We stopped in Manarola to explore, and loved the small passage ways, the romantic restaurants, and the “beach food” that the Italian seaside had to offer, much different than the typical beach eats I was accustomed to.
We made our final stop in Portovenere, which was recommended to us from my Italian friend and colleague, as he and his girlfriend vacation in Liguria each sum
mer (lucky). Portovenere is not to be missed.
We first wandered through the lovely narrow alleys to a small chapel on a rock island, following the entrancing melody of an organ playing in the distance. Upon arrival at this chapel, we peaked our heads in to witness a couple getting married to the tune of Ave Maria. I know I may be overly romantic and emotional at times (I’m a Pisces, what can I say), but the scene was so beautiful, it brought tears to my eyes.
There is also a castle at the top of the cliffs with incredible views of the town. I believe there was a small entrance fee, but it is worth it.
After Portovenere, we had to say goodbye and left for Pisa to fly out. This adventure of ours was absolutely incredible, and I hope w have inspired you to make a trip! Best of luck ❤
Arnie & Amanda's Grand Adventure 
Leave a Reply