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Preparing Italian Summer: Villas, Vines & Flavors
Italian Summer: Villas, Vines & Flavors
📍 Italy
📅 17th to 24th August
💲 2,5002,350
🏃♂️ Physical Rating: Low
🎭 Food, Wine & Cultural Immersion
Your Trip Leader
Brynn Tweeddale
Food Enthusiast & Travel Creator
Hi, I'm Brynn! I'm a Denver-based content creator and photographer known for sharing hidden culinary gems and adventures all around the world. By seeking out experiences outside my comfort zone, I've travelled from the peak of Mount Kilimanjaro to the remote rainforests of Peru and all across Europe and Asia. I'm excited to be your host for this trip and can't wait to share what Italy has to offer with you!
Specialties:
- Travel photography
- Finding authentic experiences
- Always having an itinerary
Fun Fact: I hiked almost 20,000ft to the peak of Kilimanjaro after only training for a month. Would not recommend!
Expedition Overview
This curated journey will take you across three of Italy's most iconic and delicious regions: Lazio, Umbria, and Tuscany. Each one offers its own rich culinary heritage, unique wines, and unforgettable landscapes. Along the way, you'll explore the soul of Rome, Orvieto, Florence and Siena four extraordinary cities that blend history, culture, and deep-rooted food traditions.
Led by local guides, you'll be introduced to hidden gems and authentic flavors, the kind Italian people grow up with, passed down through generations. From street food in Rome to countryside wine tastings in Tuscany, this experience goes far beyond tourist fare and dives into the true heart of Italian life.
We'll stay in a modern, brand new hotel in the heart of Rome to then move into a beautiful countryside villa on the Chianti's hills, chosen for its charm, views, and location.
Experience Italy's Culinary Magic






Itinerary
Where You'll Sleep






During this expedition, you'll experience two distinct styles of accommodation. In Rome, you'll stay at a modern, brand new hotel conveniently located in the city center, with a rooftop pool, providing easy access to all the major attractions and culinary hotspots.
For the second half of your journey, you'll be based at the stunning Castle and Wine Resort in the Chianti Hills, surrounded by vineyards and olive groves. This historic property offers a perfect blend of authentic Tuscan charm and modern comfort, with beautiful grounds where you can enjoy morning walks through the vineyards or evening aperitivos with panoramic views.
✅ What's Included
- 7 nights in hotels/villas (shared twin/double rooms)
- Daily breakfast
- Welcome Dinner
- Rooftop Aperitivo in Rome
- Dessert Crawl in Rome
- Lunch in Orvieto/Pitigliano
- Wine tasting in Chianti
- Farewell dinner
- Guided tour in Rome (2 days)
- Guided tour in Vatican (1 day)
- Guided tour in Florence (1 day)
- Guided tour in Siena (1 day)
- Rome - Orvieto - Florence - Siena - Rome transfer in comfortable AC private minivan
- Planning and on-site support
- Translator
- Travel insurance
🚫 What's Not Included
- Flights to/from Italy
- Transfer from Rome airport to hotel (easily reachable by metro/train, bus or taxi)
- Meals outside of listed inclusions
- Optional activities (e.g., rooftop drinks, museums)
Booking & Logistics
Experience & Expectations
Creative & Photography
Pricing & Insurance
Expedition Details
When
August 17 - 24, 2024
Duration
8 Days, 7 Nights
Price
$2,500$2,350
Group Size
8 travelers
Physical Rating
Low
Focus
Food, Wine & Cultural Immersion
Bases
Rome & Tuscany Countryside