10 Day Tour of Italy: Florence, Cinque Terre, Lake Como and Tuscany

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Advisor - Shiana Bradshaw
Curated By

Shiana Bradshaw

  • Food & Wine

  • Florence

  • Cinque Terre

  • Lake Como

  • Tuscany

  • Arts & Culture

  • Local Culture

  • Local Food

Advisor - 10 Day Tour of Italy: Florence, Cinque Terre, Lake Como and Tuscany
Curator’s statement

Italy is a feast for the senses, and nowhere is its magic more alive than in Florence, Lake Como, Cinque Terre and Tuscany. Wander through Florence’s Renaissance heart, soak in the serene beauty of Lake Como’s alpine waters, explore the vibrant cliffside villages of Cinque Terre and savor world-class wine and golden sunsets across Tuscany’s rolling hills. Each destination offers a soul-stirring blend of art, nature and timeless charm.

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Where to stay

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Day 1: Arrive in Florence

Arrive in Florence (Firenze) and check into a centrally located boutique hotel (e.g., Hotel Brunelleschi or AdAstra).

Evening: Casual dinner and stroll around the historic center.

Optional: Aperitivo with a view at La Terrazza at Hotel Continentale.

Day 2: Explore Florence's sites & Oltrarno

Morning: Visit Uffizi Gallery and Palazzo Vecchio.

Afternoon: Explore Oltrarno, known for artisan studios and lesser-known gems like Basilica di Santo Spirito.

Evening: Wine and small bites tour with a local sommelier guide in Florence’s wine bars.

Day 3: Monterosso al Mare

Morning train from Florence to Monterosso al Mare (about 2.5–3 hours with one connection).

Check into a scenic hotel or Airbnb with coastal views.

Afternoon: Beach time or light hike to Vernazza.

Dinner: Fresh seafood and local Sciacchetrà wine.

Day 4: Boat tour in Cinque Terre

Boat rental or private boat tour of the Cinque Terre coastline. Swim, sunbathe and enjoy lunch in Manarola or Riomaggiore.

Evening: Sunset dinner with a view — try Ristorante Miky or Nessun Dorma.

Day 5: Tuscany

Train or private transfer to Tuscany/Chianti area (e.g., Greve in Chianti, Radda or Montepulciano).

Stay at a vineyard estate like Castello di Ama, Borgo Santo Pietro or Castello di Spaltenna.

Afternoon: Settle in and wine tasting at the estate.

Dinner: Farm-to-table meal on-site or at a Michelin-starred spot nearby.

Day 6: Cooking, wineries & art

Morning: Hands-on cooking class at a local agriturismo or estate.

Afternoon: Visit multiple wineries, tasting Chianti Classico, Vino Nobile di Montepulciano or Brunello di Montalcino depending on location.

Optional: Art stops at local sculpture gardens or artist studios.

Day 7: Day trip to Gimignano or Pienza

Day trip to San Gimignano or Pienza (both are scenic, artistic and offer great food/wine).

Explore villages, visit artisan shops and enjoy leisurely meals.

Option: Stop at a local ceramic studio or gallery en route.

Day 8: Return to Florence

Train back to Florence (3–4 hours).

Check into a chic hotel (e.g., Hotel Lungarno).

Florentine steak dinner and rooftop drinks at SE·STO on Arno or La Ménagère.

Add-on experiences

Artisan experiences: Leather workshop or a painting class in Florence or Tuscany.

Hot air balloon ride: Over the Tuscan hills for a surreal view.

Wellness: Spa day at a thermal bath (e.g., Bagno Vignoni).

Need to know

Any piece of this trip can be modified to your liking. I look forward to making this a memorable trip!

Advisor - Shiana Bradshaw

Travel Advisor

Shiana Bradshaw

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