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Adventures in Italy. My Quick List and Top Picks

- Maranda Pleasant

Roadtripping Through Southern Italy

We rented a car in Rome and spent five weeks in the Italian countryside traveling, exploring and getting lost with no real plan. I had dreamed of exploring the famous Amalfi Coast since I was a child, and it did not disappoint. Rent a convertible and drive as slowly as you can.

Here are a few of my favorites.

The Amalfi Coast

Always visit in May, early June, September or early October for the most relaxing, quiet visits. It is breathtaking, and every picture is a postcard. Between June 15 and August 31, we head to the countryside.


Start in Positano and stay at the Poseidon Hotel. Borrow their complimentary vintage 1970-something Beetle convertible for a drive up the coast to Ravello, stopping at every small beach and town to swim and explore. It might be the most breathtaking drive I’ve ever had. Hire a small boat at the beach for about $130 and they’ll take you to all the hidden grottos and caves for a quick swim in their famous turquoise water. Arrive before June 15th or after September 8th for a less crowded visit.


You can’t do Amalfi without a couple nights at Hotel Villa Cimbrone. It’s surreal, otherworldly, transcendent and it transports you. The gardens, pool and sea views, and outdoor restaurant are all you need for a couple days.

Things I Wish I Had Known:

  1. Steer clear between June 15 and August 31. It becomes overrun with tourists and unmanageable.

  2. Bypass Sorrento + Naples and go straight to the Amalfi Coast.

  3. Skip Capri. It’s more marketing than mystique. It’s alright for a quick day trip, except for July and August. If you must go, try Casa Morgano Hotel for last minute rates. Steer clear of the restaurants at the pier, right off the boat. Capri is best experienced by boat, so wrangle some friends and splurge.


My number one pick for Tuscany: Hotel Lupaia in the hills of the Chianti region near Montepulciano.

It is an experience. The sunsets are stunning. We had to force ourselves to leave. They prepare personalized dinners and a homemade breakfast with one of the top chefs in the region. The gracious Austrian owners make the best cocktails with their homemade elderberry syrup they harvest in Austria.


  1. Rent a car in Rome that can handle unpaved roads.

  2. Skip the bigger towns and stick to the beautiful Tuscan countryside.

Roaming in Rome

We loved it so much that we I tripled our time here. Throw away the tourist map. Lose yourself strolling through this ancient city drinking four-dollar glasses of Champagne and falling in love with the people.

10 Tips:

  1. Look up the rooftop bars in the most expensive hotels. These are always great places to watch the sunset surrounded in luxury before you go back to your affordable apartment rental.

  2. Hotel rooms are pricey and extremely small, so booking an apartment is a good idea especially if you need a kitchen.

  3. I book with Europcar and always get the full coverage insurance. It’s the most affordable car rental and the insurance covers everything. We had an Italian cyclist hit us from behind, knocking our bumper off. I’m still baffled. You’ll be glad you’re covered. Envision us duck tapping our bumper back on hours later, in the rain, with the assistance of a local police officer. Good times.

  4. If you ever need a last minute room, the HotelTonight app can bring you sweet deals under $150.

  5. Espresso lovers, you’ll be in heaven. Even Italian gas stations have $8000 espresso machines.

  6. Vegans rejoice, you can find fettuccine carbonara at Origano.

  7. Consider trying their half marathon. It was the most scenic and gorgeous one we’ve ever run, and the most charmingly disorganized.

  8. Check out their organic grocery stores like NaturaSi.

  9. The best vegan hazelnut gelato of your life is waiting at Grezzo Raw Chocolate.

  10. The raw, plant-based Ecru restaurant serves Michelin-star quality eats in a cafe setting.

Places We Wished We Had Skipped


It’s like a shopping mall on an island, with all the kids you didn’t like in high school, who are still trying to impress their friends.


I know I’ll get hate mail for this, but we just couldn’t see the intrigue. We found more tourists and American students than Italians. The lines are long, it’s pricey, and it felt dirty and unappealing. It can’t compare to the gorgeous countryside. If you love spending all day in museums, this might be for you.


It feels commercial and void of charm. We just didn’t understand the hype. Italians vacate in August, and the city shuts down.


It’s built on nuclear waste (seriously), with toxic water and soil. Plus, the petty crime rate is pretty high, there’s no parking, and you better hold on to your valuables. Sounds like a perfect vacation. My partner loves it, mainly because he’s intrigued by mafia stories and Napoleon pizza. I couldn’t wait to get to Tuscany. Holidays should be relaxing, right?


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