ITALY SUMMER 2026

Tuscany, Italy

Embark on an unforgettable journey through Tuscany, exploring medieval towns like Siena and Greve in Chianti, and discovering hidden gems. Indulge in wine tastings at prestigious Chianti wineries, relax on the Tuscan coast, and set sail on a sunset catamaran cruise. Enjoy authentic meals, explore artisan workshops, and create unforgettable moments with your friends.

Day 1

  • Afternoon - Arrive, unpack, and rest.

  • Evening - Walk to a nearby restaurant or order in.


Day 2: Cooking Class and Local Flavors

  • Morning - Participate in a hands-on Tuscan cooking class at your villa or a nearby farmhouse. Learn to prepare classic dishes like fresh pasta, sauces, and desserts.

  • Afternoon - Enjoy the fruits of your labor with a leisurely lunch. Take it easy in the afternoon to adjust to the time change.

  • Evening - Explore a local village or town for a casual dinner.

    • Montepulciano Area

    • Notes: Most historic Tuscan towns have limited parking within their walls. Look for parking areas outside the walls and be prepared to walk a short distance. Pay close attention to parking signs, as fines can be issued.

    • Dinner at Osteria Acquacheta or Trattoria di Cagnano (has outdoor seating).

Day 3: Wine Country and Historical Charm

  • Morning - Drive to the Chianti region for a wine tasting at two of the following highly rated Chianti wineries: Marchesi Antinori, Castello di Brolio (Ricasoli), Castello di Querceto. Enjoy a tour of the vineyards and cellars.

  • Afternoon - Explore the charming medieval town of Greve in Chianti, known for its triangular piazza.

    • Grab a snack (wine and a charcuterie spread) at Antica Macelleria Falorni. This is more than just a butcher shop; it's a culinary experience. Located right on Piazza Matteotti, it's a historical institution.

  • Evening - Enjoy a casual dinner at a Trattoria in the Chianti region.

    • Dario Cecchini's (Panzano in Chianti) - This is a very unique experience, and is very highly rated for the experience. It is not a formal restaurant, but a very fun and authentic experience. It is very highly rated by food lovers.


Day 4

  • Morning - Indulge in a relaxing spa day at the villa. Arrange for a masseuse to provide in-house massages and treatments. Note: I like this more than you all going to the spa. We can arrange for multiple people to come in to give massages at your villa.

  • Afternoon - Enjoy time relaxing by the villa pool, or exploring nearby trails.

  • Sunset - Enjoy a sunset photo shoot at a scenic location, such as a hilltop overlooking the Tuscan countryside.

  • Evening - Enjoy a fancy dinner at Enoteca Pinchiorri, a restaurant that holds the prestigious distinction of being a three-Michelin-starred establishment.


Day 5

  • Morning - Day trip to Siena. Explore the Piazza del Campo, the heart of Siena, and visit the Duomo (cathedrals).

    • Breakfast at Siena (They offer a classic Italian breakfast experience, with delicious pastries like ricciarelli and cavallucci, paired with excellent coffee).

  • Afternoon - Arrange for a reputable tattoo artist to come to the villa or have transportation to a shop, for the group tattoos.

  • Evening - Enjoy dinner at a Trattoria in Siena (Osteria Le Logge), or back at the Villa.


Day 6

  • Morning - Drive to the Tuscan coast for a relaxing beach day. Enjoy the sun, sand, and sea.

  • Afternoon - Board a catamaran for a sunset cruise along the Tuscan coast. Enjoy dinner and drinks on board while watching the sunset.

  • Evening - Return to the Villa.


Day 7

  • Morning - Day trip to Florence. Spend the morning shopping for leather goods, jewelry, and other Italian treasures. Including visiting ‘wine windows’.

  • Afternoon - Explore the Oltrarno district for artisan workshops, or explore the Pitti Palace gardens.

  • Evening - Enjoy a second fancy dinner at a Michelin-starred restaurant in Florence.


Day 8

  • Morning - Enjoy a leisurely breakfast at the villa.

  • Afternoon - Drive to Florence Airport (FLR) or Pisa International Airport (PSA) for your departure.

Rome, Italy

For your personal Rome segment, prepare to be immersed in the heart of history and culture. You'll explore iconic landmarks like the Colosseum and Roman Forum, experiencing the grandeur of ancient Rome. A visit to Vatican City will reveal the magnificence of St. Peter's Basilica and the artistic wonders of the Vatican Museums, including the Sistine Chapel. Beyond the historical sites, you'll have time to soak in the city's vibrant atmosphere, toss a coin into the Trevi Fountain, stroll through picturesque neighborhoods like Trastevere, and indulge in authentic Roman cuisine. This portion of your trip offers a perfect blend of sightseeing and cultural immersion, creating unforgettable memories just for the two of you.

Rome

Day 1

  • Afternoon - Arrive in Rome and settle into your next place in Rome.

  • Evening - Dinner out at a nearby establishment.

Day 2: Ancient Rome

  • Morning: Colosseum: Start your day early to beat the crowds. Roman Forum and Palatine Hill: Explore the ruins of ancient Rome. We can arrange a tour and golf cart tour around the city. This is a super easy way to get around.

  • Afternoon: Altar of the Fatherland: take in the impressive architecture. Walk along Via dei Fori Imperiali.

  • Evening: Trastevere: Enjoy dinner in this charming neighborhood. Dinner at Mimì E Cocò Trast.

Day 3: Vatican City and Historical Center

  • Morning: Breakfast at a local cafe and then spend the morning at the Vatican Museums, Sistine Chapel, St. Peter's Basilica: Marvel at the grandeur of this iconic church. The line for this is INSANE, so it’s important that we schedule an early morning visit to avoid that experience in the heat.

  • Afternoon: I suggest an easy lunch and relaxed afternoon.

  • Evening: Piazza Navona: Enjoy the lively atmosphere. See the Pantheon, an amazing piece of ancient architecture at night. Dinner at the Camillo A Piazza Navona Dal 1890.

Day 4

  • Morning: Breakfast near the Trevi Fountain at the Trecaffe’ - Via dei due Macelli. Then head over to the Trevi Fountain to make a wish. The Trevi Fountain, designed by Nicola Salvi and completed in 1762, is a Baroque masterpiece and one of the most famous fountains in the world. Legend has it that tossing a coin over your shoulder into the fountain ensures a return to Rome. Then sit on the Spanish Steps: Relax and people-watch for a bit. You won’t regret it.

  • Afternoon: There are a lot of cute shops and places to eat and drink nearby. Take a leisurely walk around that area before heading back to your hotel to get ready for your evening food tour.

  • Evening: You can discover Rome's culinary scene by joining one of its many enjoyable food tours, which feature stops at several excellent restaurants.

Day 5

  • I like to leave the last day of a trip as a ‘choose your own adventure day’. You may want to shop more, eat at a place you’ve noticed while exploring, or revisit a historical site. Let me know and we’ll make it happen.

Day 6

  • Travel Day

Alternative Itinerary: Venice

Day 1: Arrival in Venice & Canal Charm

  • Afternoon: Arrive at Venice Marco Polo Airport (VCE). Take a water taxi to your hotel in Venice. Settle in and explore your immediate surroundings.

  • Evening: Enjoy a leisurely dinner at a traditional Venetian "osteria" near your hotel.

Day 2: Iconic Venice & Island Exploration

  • Morning: Visit St. Mark's Square, St. Mark's Basilica, and Doge's Palace. Book tickets in advance to avoid long lines.

  • Afternoon: Take a vaporetto (water bus) to Murano, famous for its glassblowing, and Burano, known for its colorful houses.

  • Evening: Enjoy a "cicchetti" (Venetian tapas) tour, sampling local delicacies and wines.

Day 3: Gondola Ride, Massages, & Hidden Venice

  • Morning: Experience a classic gondola ride through the canals.

  • Afternoon: Arrange for a masseuse to come to the hotel or a rented apartment, for in room massages.

  • Evening: Explore the quieter neighborhoods of Dorsoduro or Cannaregio, discovering hidden bridges and charming squares.

Day 4: Culinary Venice, Rialto Market, & Tattoos

  • Morning: Visit the Rialto Market, a vibrant hub of fresh seafood and produce.

  • Afternoon: Arrange for a reputable tattoo artist to come to the hotel or a rented apartment, or travel to a local tattoo shop.

  • Evening: Enjoy a fancy dinner at a renowned Venetian restaurant.

Day 5: Venetian Lagoon & Sunset Cruise

  • Morning: Take a boat trip to explore the Venetian Lagoon islands, such as Torcello, known for its ancient cathedral.

  • Afternoon: Relax, and prepare for the evening cruise.

  • Evening: Board a boat for a sunset cruise along the Venetian Lagoon. Enjoy dinner and drinks on board while watching the sunset.

Day 6: Prosecco Hills & Wine Tasting

  • Morning: Day trip to the Prosecco Hills, a UNESCO World Heritage Site.

  • Afternoon: Enjoy wine tasting at a local Prosecco winery, with stunning views of the vineyards.

  • Evening: Return to Venice for dinner.

Day 7: Padua Exploration & Artistic Treasures

  • Morning: Day trip to Padua. Visit the Scrovegni Chapel, with its stunning frescoes by Giotto.

  • Afternoon: Explore the University of Padua and the botanical gardens.

  • Evening: Enjoy a farewell dinner in Venice, savoring your last Venetian meal.

Day 8: Departure

  • Morning: Enjoy a final Venetian breakfast.

  • Afternoon: Take a water taxi to Venice Marco Polo Airport (VCE) for your departure.

I am partial to the Tuscany, Italy. Less expensive, options for Villa’s where you and your friends can stay together and enjoy the countryside, bring experiences to your location, and would be a is a little less expensive than Venice.

But it’s still an option to explore!