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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Day 1: Getting to Know 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
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
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
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
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.
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Travel Advisor
Caroline Bernthal
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For more travel tips, check out Travel Advisor Jennifer Schwartz’s guide, Guide to Picturesque Picnics In and Around Rome.
This guide is part of our ongoing series on travel to Italy.