Venice and Tuscany 14-Day Trip Itinerary

Arrive at Venice Marco Polo Airport

After your flight from JFK, arrive at Venice Marco Polo Airport (VCE).

Water Taxi to City Center

Take a private water taxi directly from the airport to your hotel, offering a scenic introduction to Venice.

A romantic and convenient way to reach your accommodation. Prices vary by destination.

Hotel Check-in & Freshen Up

Check into your chosen hotel in Venice and take some time to settle in.

St. Mark's Square & Doge's Palace Exterior

Begin your Venetian adventure with a stroll through the iconic Piazza San Marco, admiring the Doge's Palace and St.

Mark's Basilica from the outside.

Be aware of crowds, especially during peak hours. Enjoy the bustling atmosphere.

Romantic Gondola Ride

Experience the quintessential Venetian romance with a private gondola ride along the charming canals.

Romantic Venetian Dinner

Savor your first authentic Italian dinner in Venice at a charming local restaurant, enjoying fresh seafood or classic pasta dishes.

Consider making reservations, especially for popular spots.

Semi-Private Venice Market and Cicchetti Food Experience

Discover the essence of Venice on a gastronomic journey, limited to just six individuals.

Led by a local guide, immerse yourselves in the rich culinary traditions of the city, sampling authentic Venetian cicchetti.

This intimate tour offers a true taste of local Venetian life and food. Product Code: 6718P44

Rialto Bridge & Market Exploration

After your food tour, explore the vibrant Rialto Market and walk across the iconic Rialto Bridge, enjoying panoramic views of the Grand Canal.

Lunch in San Polo

Enjoy a casual lunch in the San Polo district, known for its authentic bacari (wine bars) and less touristy eateries.

Professional Photographer in Venice, Italy

Experience Venice through the lens of a professional local photographer, guiding you to iconic landmarks and secret spots for high-end, timeless portraits – perfect for your honeymoon memories.

Skip blurry 'stranger photos' and get stunning professional shots. Product Code: 259677P1

Sunset Kayak Tour in Venice

Sail under Venetian bridges and along canals on an intermediate workout tour, discovering the city from a unique perspective as the sun sets. An unforgettable and active honeymoon experience.

Ideal for couples who enjoy active exploration. Product Code: 389918P5

Dinner in Cannaregio

Enjoy a delightful dinner in the Cannaregio district, known for its vibrant atmosphere and excellent eateries, away from the main tourist crowds.

Secret Venice, an Unusual Walk - Private Walking Tour

Discover the hidden parts of Venice with a private local guide.

Explore authentic Venetian neighborhoods, uncover intriguing stories, and find wonderful, less-traveled locations.

A unique way to see Venice beyond the typical tourist path, perfect for honeymooners seeking local insights. Product Code: 128739P3

Souvenir Shopping or Last Coffee

Enjoy a final stroll through Venice, perhaps picking up some unique souvenirs or savoring a last coffee by a canal.

Farewell Venetian Lunch

Enjoy a final traditional Venetian meal before departing for Tuscany.

High-Speed Train to Florence

Take a high-speed train from Venice Santa Lucia to Florence Santa Maria Novella station, connecting you efficiently to the heart of Tuscany.

Pick Up Rental Car in Florence

Pick up your rental car near Florence Santa Maria Novella station, which will give you the flexibility to explore Tuscany at your own pace.

Ensure you have an International Driving Permit. Check with your accommodation about parking.

Drive to Tuscan Accommodation

Enjoy a scenic drive through the Tuscan countryside to your chosen agriturismo or villa, perhaps near Siena or in the Chianti region.

Check-in & Dinner at Agriturismo

Arrive at your charming Tuscan accommodation, check in, and enjoy a traditional Tuscan dinner, often served directly at agriturismos using local ingredients.

Many agriturismos offer delicious home-cooked meals; inquire about dinner options upon booking or arrival.

Chianti Wine Tasting Tour

Embark on a guided tour of the Chianti wine region, visiting a local vineyard for a tasting of renowned Chianti Classico wines and learning about the winemaking process. This is a private tour or small group for an intimate honeymoon experience.

Many tours include a light snack or lunch. Book in advance. Consider arranging a driver if both wish to partake in tastings.

Lunch in Greve in Chianti

Enjoy a traditional Tuscan lunch in Greve in Chianti, a charming market town often considered the gateway to the Chianti region.

Explore San Gimignano

Drive to and explore the medieval hill town of San Gimignano, famous for its well-preserved towers and historic architecture. Climb the Torre Grossa for panoramic views.

Try the award-winning gelato at Gelateria Dondoli in the main square.

Relax at Your Agriturismo

Return to your accommodation to relax by the pool, enjoy the scenery, or simply unwind after a day of exploration.

Authentic Tuscan Dinner

Indulge in another delicious Tuscan dinner at a local osteria or back at your agriturismo, enjoying regional specialties and local wine.

Siena Exploration: Piazza del Campo & Duomo

Spend the morning exploring the magnificent city of Siena.

Visit the Piazza del Campo, famous for the Palio horse race, and marvel at the stunning Siena Cathedral (Duomo di Siena).

Consider booking Duomo tickets online to skip queues. The 'OPA Pass' includes access to several cathedral complex sites.

Lunch in Siena

Enjoy a leisurely lunch in Siena, perhaps with a view of the Piazza del Campo or in a hidden alleyway.

Scenic Drive through Val d'Orcia

Take a breathtaking scenic drive through the UNESCO World Heritage-listed Val d'Orcia region, stopping at picturesque viewpoints and charming towns like Pienza (known for Pecorino cheese) or Montalcino (famous for Brunello wine).

The landscape is incredibly photogenic, especially in late summer. Perfect for a leisurely honeymoon drive.

Sunset Aperitivo at the Agriturismo

Enjoy a relaxing aperitivo at your agriturismo or a nearby winery, savoring local snacks and drinks as you watch the sunset over the Tuscan hills.

Tuscan Cooking Class & Dinner

Participate in a hands-on cooking class focused on traditional Tuscan dishes, followed by enjoying the meal you prepared.

A perfect culinary experience for honeymooners.

Many agriturismos offer on-site cooking classes. Book in advance, as these are popular.

Explore Siena

Wander through the historic center of Siena, a UNESCO World Heritage site.

Visit the Piazza del Campo, the Palazzo Pubblico, and the Siena Cathedral. Enjoy the medieval atmosphere and charming streets.

Siena's Duomo (Cathedral) is a must-see, consider buying tickets online in advance. Wear comfortable shoes for walking.

Lunch in Siena

Enjoy a traditional Tuscan lunch at a local trattoria in Siena, savoring regional specialties.

Chianti Wine Tasting Experience

Head into the picturesque Chianti Classico region for a delightful wine tasting tour at a local vineyard.

Learn about the winemaking process and sample renowned Chianti wines.

Many wineries require reservations, especially for private tours. Consider booking a 'Tours in Tuscany - Private Tours' from TripAdvisor if you want a guided experience.

Dinner at Agriturismo

Enjoy a romantic dinner at your agriturismo or a nearby countryside restaurant, savoring farm-to-table Tuscan cuisine and local wine.

Tuscan Cooking Class

Immerse yourselves in Tuscan culinary traditions with a hands-on cooking class.

Learn to prepare classic dishes like pasta, sauces, and dessert, culminating in enjoying your creations for lunch.

Many cooking classes include a visit to a local market. This is a wonderful honeymoon activity to do together!

Explore San Gimignano

Visit the medieval hill town of San Gimignano, famous for its well-preserved towers.

Climb the Torre Grossa for panoramic views, stroll through Piazza della Cisterna, and enjoy gelato.

Try the award-winning gelato at Gelateria Dondoli in Piazza della Cisterna. It can get crowded in the afternoon.

Relaxed Evening & Dinner

Return to your agriturismo for a relaxed evening and enjoy another delightful Tuscan dinner.

Spend time enjoying the tranquility of the countryside.

Scenic Drive through Val d'Orcia

Take a scenic drive through the stunning Val d'Orcia region, a UNESCO World Heritage site known for its rolling hills, cypress trees, and picturesque villages.

Stop for photos at iconic viewpoints.

This is a perfect area for photographers. Look for the famous winding road with cypress trees near Monticchiello.

Pienza & Pecorino Tasting

Explore Pienza, a 'perfect Renaissance town,' renowned for its Pecorino cheese.

Stroll through its charming streets and enjoy a tasting of various Pecorino varieties.

Look for shops offering free tastings of Pecorino cheese, often served with local honey or jams.

Montepulciano & Vino Nobile Tasting

Visit Montepulciano, a beautiful hilltop town famous for its Vino Nobile di Montepulciano.

Explore its main square, Piazza Grande, and descend into an underground cellar for a wine tasting.

Many wineries have cellars directly beneath the town's streets. Look for tastings combined with local meats and cheeses.

Farewell Tuscan Dinner

Enjoy a final, memorable dinner in the Tuscan countryside, reflecting on your wonderful experiences.

Perhaps a restaurant with stunning views.

Travel from Tuscany to Rome

Take a high-speed train from Florence (a short drive from central Tuscany) to Rome Termini.

This is an efficient and scenic way to travel.

Hotel Check-in & Freshen Up

Arrive in Rome, check into your centrally located hotel, and take some time to settle in and freshen up after your journey.

Choose a hotel near public transport or within walking distance of major sites for convenience.

Roman Welcome Lunch

Enjoy your first Roman lunch at a casual trattoria near your hotel, trying local pasta dishes like Cacio e Pepe or Carbonara.

Pantheon & Piazza Navona

Begin your Rome exploration with two iconic landmarks.

Visit the ancient Pantheon, then stroll to the beautiful Piazza Navona with its famous fountains and street artists.

Entry to the Pantheon is generally free but may require timed entry during peak seasons. Piazza Navona is great for people-watching.

Trevi Fountain & Spanish Steps

Continue your walk to the breathtaking Trevi Fountain to toss a coin, then head to the Spanish Steps.

These are popular spots, especially in the late afternoon/early evening.

Expect crowds at both locations. Best visited early morning or late evening for fewer people.

Romantic Dinner in Rome

Enjoy a romantic dinner at a charming Roman restaurant, savoring traditional dishes in a cozy atmosphere.

Vatican Museums & Sistine Chapel

Embark on a guided tour of the immense Vatican Museums, home to priceless art collections, including the Raphael Rooms and the breathtaking Sistine Chapel.

Book 'skip-the-line' tickets or a guided tour well in advance to avoid long queues. Dress code: shoulders and knees must be covered.

St. Peter's Basilica

After the museums, enter St.

Peter's Basilica, one of the largest churches in the world. Admire Michelangelo's Pietà and the stunning dome (optional climb for panoramic views).

Entry is free, but security lines can be long. Dress code strictly enforced. Climbing the dome has an additional fee.

Lunch near Vatican

Enjoy a casual lunch at a restaurant or café in the Borgo neighborhood near Vatican City.

Colosseum & Roman Forum Tour

Take a step back in time with a visit to the iconic Colosseum and the vast archaeological area of the Roman Forum and Palatine Hill.

Consider a combined guided tour for deeper insight.

Book a guided tour or 'skip-the-line' tickets in advance, as this is Rome's most popular attraction. Wear comfortable shoes and bring water.

Evening Stroll & Dinner

Enjoy an evening stroll through illuminated Rome, perhaps in the charming Trastevere neighborhood, followed by a romantic farewell dinner for this part of your trip.

Borghese Gallery & Gardens

Immerse yourselves in the stunning art collection of Bernini and Caravaggio in the Villa Borghese, followed by a leisurely stroll through the beautiful gardens.

Advance booking is essential, as tickets are limited and assigned to specific time slots. Consider a guided tour for deeper insights.

Authentic Roman Cooking Class

Enjoy a hands-on experience learning to prepare classic Roman dishes like pasta carbonara or cacio e pepe, culminating in enjoying your delicious creations.

Many classes offer market visits beforehand. A perfect way to bring a taste of Italy home with you. Booking in advance is highly recommended for popular classes.

Dinner in Trastevere

Spend your last evening in Rome enjoying a romantic dinner in the charming, bohemian neighborhood of Trastevere, known for its narrow cobblestone streets and authentic trattorias.

Wander through the lively streets after dinner, enjoy a gelato, and soak in the Roman atmosphere. Reservations are advised for popular restaurants.

Travel to Amalfi Coast (Positano)

Start your scenic journey from Rome to the iconic Amalfi Coast.

Take a high-speed train from Rome Termini to Naples Centrale, followed by a private transfer or ferry to Positano.

Check-in & Relax in Positano

Arrive in the picturesque cliffside village of Positano.

Check into your hotel and take some time to unwind, admire the views, or relax by the pool.

Many hotels in Positano are built into the cliffside, offering stunning views but often requiring stairs. Pack light and wear comfortable shoes.

Wander Positano's Streets

Take a leisurely walk through the charming, winding streets of Positano, browsing local boutiques for fashion, ceramics, and limoncello.

Don't miss the Chiesa di Santa Maria Assunta, with its iconic majolica-tiled dome. Enjoy the vibrant atmosphere as the sun begins to lower.

Sunset Dinner in Positano

Indulge in a romantic dinner at a restaurant with panoramic views of Positano and the Tyrrhenian Sea as the sun sets.

Popular restaurants like Da Vincenzo or La Sponda often require reservations far in advance, especially for prime tables with a view.

Coastal Boat Tour

Embark on a semi-private boat tour along the Amalfi Coast, enjoying breathtaking views of the coastline, hidden coves, and perhaps a swim in the pristine waters.

Many tours offer stops for swimming or visiting Grottos. This is a fantastic way to see the beauty of the coast from a different perspective.

Ravello Gardens & Views

Travel to the enchanting hilltop town of Ravello, known for its tranquil atmosphere and stunning garden villas, Villa Rufolo and Villa Cimbrone.

Enjoy panoramic views from the Terrace of Infinity at Villa Cimbrone and the scenic gardens of Villa Rufolo. Ravello offers a more peaceful ambiance than other coastal towns.

Romantic Amalfi Dinner

Enjoy a final romantic dinner on the Amalfi Coast, perhaps in Ravello for a refined experience or back in Positano to savor the evening ambiance.

Consider fresh seafood, local pasta dishes, and fine Italian wine to celebrate your honeymoon.

Leisurely Breakfast & Souvenirs

Enjoy a final leisurely breakfast with a view in Positano.

If time allows, pick up any last-minute souvenirs or enjoy a last stroll.

Consider local limoncello, ceramics, or handmade leather goods as mementos of your trip.

Transfer to Naples International Airport

Private transfer from Positano to Naples International Airport (NAP) for your return flight.

Depart Naples (NAP) to JFK

Check in for your international flight from Naples International Airport (NAP) back to New York (JFK), concluding your unforgettable Italian honeymoon.

Arrive at the airport at least 3 hours before an international flight. Enjoy your memories from Italy!