We hit the road bright and early in our rental car around 7:30 AM from Montepulciano. Our goal: reach Cinque Terre before the car rental place closes for lunch, but not before stopping to see the world’s most famous architectural mistake: the Leaning Tower of Pisa.
We made a breakfast stop at Filter, a cute Tuscan café with all the greatest hits: avocado toast, acai bowls, oat milk everything. Delicious coffee and beautiful.
After filling up, we made our way to the tower. It was around 9:45 AM, so the tourist swarm hadn’t descended yet. We snapped the classic “pretending to hold it up” photo (it is mandatory), and then peaced out before the bus tours rolled in.
Back in the car, we headed straight for La Spezia to return our rental car.
The downtown location of Avis had zero parking, so we did what any desperate, traveler would do: stopped in the middle of the road and hurled our bags to the sidewalk. An Avis employee ran out, jumped in the car, and sped off. Car return. Done just in time before they closed for lunch. We barely made it.
Avis called us a cab and 45 minutes later, we were winding along the coastline into Monterosso, our final stop.
The cab dropped us, and we walked to Hotel Pasquale. Just beautiful!
We checked into Hotel Pasquale, and instantly fell in love. Cozy rooms, sea views, and breakfast waiting downstairs every morning like magic.
The rest of the day we spent beach strolling and shopping.
Dinner was peaceful and breezy, and we ended the night walking along the shore, high-fiving ourselves for making it this far. And then, gelato!
Day 2: Cinque Terre Itinerary by Boat and Train
We kicked off the morning with another A+ breakfast at Hotel Pasquale. I’m talking: perfect coffee, fluffy eggs, buttery pastries.
Then it was boat day! We grabbed ferry tickets to Riomaggiore, with a plan to boat there, then train-hop our way back. We got discounted train tickets through Hotel Pasquale.
Pro tip: No need to buy the Cinque Terre train tickets in advance.
The ferry ride was colorful cliffside villages, turquoise water, … just like the photos.
Riomaggiore was stunning, and also — vertical. I swear this village is on the side of the mountain. Gorgeous! We walked around (a.k.a. climbed 7,000 stairs), sweat through every layer, and then jumped on a quick train to Manarola, where we had lunch.
Eventually, we trained it back to Monterosso, changed into swimsuits, and sprinted to the beach for a much-needed cooldown.
Dinner was at Pizzeria La Smorfia, recommended by Hotel Pasquale, which was everything our pizza-loving hearts could’ve dreamed. Wine, carbs, and a peaceful beach stroll to finish it off.
Day 3: Family Reunion + Beach Club Vibes + FAMILY MEET-UP!
Turns out, some of our family was on a cruise making their way through France, Spain, and Italy — and as fate would have it, they docked in Cinque Terre while we were in Monterosso.
We all camped out at Stella Marina Beach Club under those iconic orange and green umbrellas, living our absolute best lives. It was a full-day hang: swimming, sunbathing, pizza and Aperol spritz.
That morning, the jellyfish were out in full force — like they’d all RSVP’d the same beach club for the day. Two of our kids got stung within minutes of hitting the water, but thankfully the lifeguards were ready with some kind of magical potion that worked instantly. Pain was gone and they were back in the water in no time. Within a few hours the jelly fish were nowhere to be found.
Pro tip: If you checked a bag (or brought an extra tote just for souvenirs), load up on Italian skincare products. Every pharmacy here is a treasure trove of magical lotions, potions, and healing creams. I was living that carry-on-only life, which meant zero room for extras — and shipping costs are more than the products themselves. So if you’ve got the space, treat yourself. Your future self (and your skin) will thank you.
Lunch at the beach club hit all the right notes — beachy, breezy, and best of all, didn’t require shoes. Afterward, we strolled over to our favorite gelato spot.
It was such a great family day.
Dinner was at Il Casello over the water. Gorgeous views.
Day 4: Vernazza Girls' Day + Italian Rain
Woke up to rain, so the guys voted for a chill day — but the girls had other plans.
Vernazza Girls’ Day was on. Maven and I grabbed the train and had the best day exploring the village. Souvenirs were bought, all sorts of yummy Italian food were devoured, and every shop was cute!
We met up with the guys back in Monterosso for lunch, and yes… more shopping followed. It’s like the stores get cuter the more you look.
The rain had stopped just in time for dinner that night was tucked away in the trees at Lapo’s.
Beautiful views from our room at Hotel Pasquale.
Day 5: Back to Rome – The Final Stretch
We said goodbye to Hotel Pasquale with heavy hearts and heavier luggage (souvenirs hit hard). Breakfast then it was off to the train station — a mercifully downhill five-minute walk.
We trained from Monterosso to La Spezia, and then hopped into business class to Rome. We stayed at the La Guara Guest House in Rome before our flight out the next day.
Pro tip: Book your trains from Rome to Florence and La Spezia in advance. I bought tickets about 45 days prior.
We had a fantastic time in Monterosso! Read about our trip to Rome HERE, Florence HERE and Tuscany HERE.
If you love exploring the world’s most amazing stays, don’t miss our guide to the 10 Best Family Hotels in Exuma Bahamas for a tropical escape after your Italian adventure.
Drop me a line if you decide to go to Cinque Terre. I would love to hear from you.
