Italy Honeymoon Itinerary: Tuscany Region

Advisor - Caroline Bernthal
Curated By

Caroline Bernthal

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  • Italy

  • Tuscany

  • Active Travel

  • Honeymoons

  • Food & Wine

  • Romantic

  • Outdoors

  • Local Food

A meandering old Italian street.
Curator’s statement

The Italian way of life is all about slowing down and enjoying the sweetness of doing nothing. To me, nothing sounds sweeter than a honeymoon (or anniversary!) with the one you love savoring the moment and embracing the Italian way of life. And while you won't exactly "do nothing" - sipping Chianti, looking over the Tuscan countryside or getting lost in the streets of Firenze can have that effect. Here's how to savor the sweet Tuscany region on the perfect romantic trip.

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Where to stay

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COMO Castello Del Nero

Spacious rooms with original 18th century frescoes overlooking the surrounding hills, woods, lawns and lines of Tuscan cypress trees of the Chianti wine region.

Castello di Casole

La dolce vita brought to life on 4,200 acres of fairytale Tuscan countryside.

Fora Perks
  • $100 food / beverage credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

Castello Banfi Il Borgo, Relais & Chateaux

Castle accomodations on a hillside in Tuscany.

Fora Perks
  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

  • VIP welcome & amenity

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Advisor - Caroline Bernthal

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Day 1: Getting to Know Tuscany

Views of rolling hills of Tuscany.

Your first day in Tuscany should be spent relaxing at your gorgeous hotel — my preference is a luxury castle stay. Most offer beautiful views of the countryside, pools and spa amenities and unique experiences specific to the region. My favorite is truffle hunting. You will tag along with the famous truffle hunter dogs and watch them find magic! Many experiences offer a special truffle themed lunch as well. For the afternoon, enjoy a wine tasting before a delicious Italian dinner.

Day 2: Florence

Florence Cathedral

Spend the day exploring the city and all of its masterpieces: The David, the Duomo, Uffizi Gallery and Ponte Vecchio. Depending on the time of year, some of these experiences are best with a guide and a skip the line option. Florence Food Tours is another great way to see a variety of things and try many local flavors. Don't forget to visit a famous wine window (used for hundreds of years in Florence - owners can avoid opening a shop and taxes but also was popular during plaque (and COVID!). Head to Piazzale Michelangelo for sunset.

Day 3: Cinque Terre

Angolo di paradiso italiano

The infamous five villages built into the coastal cliffs. The hike between the five villages will take a full day so plan an extra early start. Also, you now need to reserve a pass in advance so be sure to plan ahead with advisor who know the region and can help! If hiking the five isn't right for you, spend the day exploring one or two villages and take the train between. Have your camera ready!

Day 4: Wine

An outdoor restaurant

You can't miss the delicious wine of the region. Hire a driver for the day and bop between several wineries for tours and tastings. Don't skip lunch! Many of the wineries offer incredible lunch menus complete with wine pairings.

Day 5: Small Towns

A small town street in Italy.

The Tuscan region is scattered with some really beautiful, medieval villages. Depending on where you are staying, you can easily visit several in a day! My favorites are Lucca, Siena, Volterra, San Gimignano, Castellina in Chianti and Montepulciano.

Need to Know

For more travel tips, check out Travel Advisor Jennifer Schwartz’s guide, Guide to Picturesque Picnics In and Around Rome.

Advisor - Caroline Bernthal

Travel Advisor

Caroline Bernthal

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This guide is part of our ongoing series on travel to Italy.