< Designed Trips

The Trip

Uncover Italy's most idyllic natural landscapes with this incredible Designed Trip, spanning from north to south. Relax on the shores of one of the world’s most scenic lakes, marvel at Renaissance masterpieces, watch the sun set over vineyard covered hills, and dive into turquoise seas. Begin at Lake Como, spotting the grand villas of celebrities and diplomats from a traditional Venetian-style wood boat. Head south to the heart of the Renaissance, Florence. Stroll the cobblestone streets, learn the art of fresh pasta with a local chef, and see some of the world’s most famous art, including Michelangelo’s David. Continue on to the enchanting vineyard-covered hills of Chianti to taste some of Italy’s finest wines, hunt for truffles and experience cucina rustica. Travel south to the stunning Amalfi Coast, gazing upon azure seas and steep, lemon tree dotted cliffsides. Either choose to end your trip here, or add an additional 3 days in Rome where you’ll see the Eternal City’s most impressive sights, visit the Colosseum, and find the best Roman bites on a food tour of the city’s hidden eateries.

The Details

Price: 
  • 12 days from $4,167/person
  • 15 Days From $5,379/person
Duration:
  • 12 days -OR- 15 days
Inclusions:
  • Highly-rated boutique hotels
  • Transportation within Italy
  • Small-group experiences
  • ​​Curated Italy mini-guide
  • Trip preparation & support

The Itinerary

Lake Como
  • Day 1: Benvenuti in Italia - welcome to Italy! After collecting your luggage, relax as you travel north about 1 hour, 30 minutes, to the gorgeous Lake Como and your boutique hotel. Historically Italy’s playground for celebrities and diplomats, the shores of Lake Como are home to grand villas with private boats and quaint, colorful villages. Check in, pop the prosecco and relax. Your trip has just begun.
  • Day 2: ​Wake up beside one of the world’s most famous lakes. Enjoy a relaxed breakfast and your first Italian cappuccino before heading to meet your captain for a small-group boat tour of the lake. Head out on a traditional Venetian-style wood boat to admire the historic villas, picturesque towns, and discover the beautiful locations featured in the movies, including Star Wars and Casino Royale. The afternoon is yours. Relax and de-jetlag at your hotel, or head out to explore.
  • Day 3: Buongiorno! Today is free to do what feels right. Maybe enjoy a long, relaxed breakfast before heading out to explore the lake’s quaint towns, extraordinary villas and manicured gardens. Grab a water taxi or hop on a ferry to explore Bellagio, Menaggio, or Varenna; explore the grand Villa Carlotta, Villa Monastero or Villa Melzi d’Eril; or browse the shops in what is widely regarded as one of the best places in Europe to buy silk.

Florence
  • Day 4: After a transfer from the lake, hop on a high-speed train from Milan for the 2 hour journey south to historic Florence. Check in to your boutique hotel and wander the city’s ancient cobbled streets before digging in to your first Florentine dinner. 
  • Day 5: You’ll only need a light breakfast today as you’re spending the morning touring Florence’s best markets and eateries with a local guide. Get deeper into Florentine history and culture as you taste local delicacies and stroll the backstreets in search of hidden local spots. In the afternoon, uncover the city’s incredible artistic history at the Accademia Gallery, paying a visit to Michelangelo’s David.

Chianti
  • Day 6: Head to Florence Station to pick up your rental car. It’s time to hit the scenic roads of Tuscany and make your way to the vineyard-covered rolling hills of one of Italy’s most beautiful wine regions: Chianti. Check in to your boutique countryside hotel before taking the rest of the day to relax and unwind. Stroll through the vineyards or discover one of Chianti’s beautiful hilltop towns, then sit down to a rustic dinner as you watch the sun set over the vineyards.
  • Day 7: Wake up in the rolling hills of the Chianti region. This area is all about embracing La Dolce Vita - good wine, good food, slow pace and amazing views. After a relaxed breakfast, hop in the car and drive over to a small, family-owned olive oil mill. The Romans brought many things to Italy, including the first tools for pressing olives and efficient oil storage techniques, both of which have remained virtually unchanged until the last century. Meet the olive oil producer to learn about the cold pressing method, which uses large millstones to break open the fruit and a wooden press to separate the oil, before tasting various small-batch oils alongside a traditional Tuscan lunch. In the afternoon, visit a local winery to explore the ancient cellar and learn about the production of the region’s most prestigious wines. Then, sit down for a guided tasting of the winery’s estate wines, including the world famous Chianti Classico.
  • Day 8: Rise and shine! Today is all about the journey, as you head south to a lovely organic farm and winery in the Sienese hills for an early morning truffle hunt and cooking class. Meet a local truffle hunter and his trained dogs for a walk through the forest, learning the secret to finding delicious Tuscan black truffles. Afterwards you’ll join a small group in the farmhouse kitchen where you’ll be introduced to the techniques of Tuscany’s cucina rustica, preparing a variety of traditional dishes and pastas using black truffles. Sit down to a delicious lunch of your own making, paired with the property’s excellent estate grown wines.

The Amalfi Coast 
  • Day 9: Wake up, eat a big breakfast and drink a strong cappuccino to fuel your travel day. Hop in your car and drive back to Florence before taking a high-speed train 3 hours south to Naples, your gateway to The Amalfi Coast. Your private driver will be waiting for you, ready to whisk you away to your boutique hotel along this stunning coastline. On the way, you have the option to make a stop at a winery at the base of Mt. Vesuvius for a wine tasting and lunch before continuing on to the stunning Amalfi Coast. Check in, relax, and take in the incredible sea views.
  • Day 10: Buongiorno! You can’t visit the Amalfi Coast without a boat trip. Choose to cruise along the amazing coastline, passing the area's most famous cliff top towns and villages along the way, or head to the gorgeous island of Capri, often called “the jewel of Naples”. Your captain will take you and a small group to discover the turquoise Tyrrhenian Sea and the natural landmarks that make this area so famous. Once back on the mainland, grab a glass of wine before a relaxed dinner made with local ingredients.
  • Day 11: Today is all about  enjoying one of the most famous coastlines in the world. You’re free to do whatever you choose. Maybe head into Positano to explore the famous terraced village, swing by Fornillo Beach or the breathtaking Fiordo di Furore, or if you’re feeling adventurous, hike the famous ‘Path of the Gods’. Enjoy the day doing whatever feels right.
  • Day 12: Wake up, drink a cappuccino and enjoy a delicious breakfast. It’s your final day. Either talk to us about extending your trip with a 3-day visit to Rome, or hop on the plane for a flight home.

Optional Add-On: Rome
  • Day 12: If you choose to extend your trip, you’ll take a short transfer to Naples Central Station where you’ll hop on the high-speed train to Rome. After checking into your boutique hotel in the city’s historic center, meet up with a private local guide for an introduction to some of Rome’s most historic sights from a local perspective.
  • Day 13: Wake up for your first full day in the Eternal City, have a good breakfast and enjoy a delicious cappuccino before eating your way around the city on an authentic small group Roman food tour, sampling everything from ricotta pie, to pizza, to gelato and Roman suppli. In the afternoon, explore the city’s hidden squares and shops to your heart’s content.
  • Day 14: On your final full day in wondrous Roma, head to the Colosseum to explore the heart of the Ancient Roman Empire. Skip the line with your local guide and explore the incredible amphitheater that once held up to 80,000 spectators for the games and gladiatorial combat. Learn about the history of the building and life in ancient Rome at one of the world's most famous sites. The rest of the day is free to indulge in some end-of-trip gelato and maybe an Aperol Spritz before sitting down to your final Italian dinner.
  • Day 15: Enjoy your last cappuccino and savor the morning. It’s your final day, so head to the airport and hop on the plane for a flight home.

Pricing & Inclusions

Boutique
  • 3 hotel nights in Lake Como: Hotel Du Lac & Spa Bellagio, Boutique Hotel Bellagio, or equivalent
  • 2 hotel nights in Florence: The Artists' Palace, Antica Dimora de Benci, or equivalent 
  • 3 hotel nights in Chianti: La Pensione di Vignamaggio, Villa Le Barone, or equivalent 
  • 3 hotel nights on the Amalfi Coast: Hotel La Bougainville, La Barbera, or equivalent
  • Private transfer from Milan Airport to Lake Como
  • Small-group Lake Como boat tour
  • Private transfer from Lake Como to Milan
  • High-speed train from Milan to Florence
  • Small-group Florence market & food tour
  • Tickets to the Accademia
  • Car rental in Chianti, 3 days
  • Olive oil mill tour, tasting & Tuscan lunch
  • Chianti winery tour & tasting
  • Small-group truffle hunt & cucina rustica cooking class
  • High-speed train from Florence to Naples
  • Private transfer from Naples to the Amalfi Coast
  • Small-group Capri boat tour 
  • Private transfer from the Amalfi Coast to Naples
  • Curated Italy mini-guide
  • Trip preparation & support

Rome Add-On
  • 3 hotel nights in Rome: Condominio Monti, Damaso Hotel, or equivalent
  • Private transfer from the Amalfi Coast to Naples
  • High-speed train from Naples to Rome
  • Private intro to Rome tour
  • Small-group Roman street food tour
  • Small-group tour of the Colosseum

Exclusions
  • International Flights to Italy
  • Meals & activities not listed
  • ​Travel insurance

Boutique pricing
  • 12 days from $4,167 pp
  • 15 days from $5,379 pp

​*Pricing based on double occupancy and may vary depending on travel dates and total number of travelers. 
Luxury Boutique
  • 2 hotel nights in Florence: Corte Calzaiuoli Suites, Hotel Calimala, or equivalent
  • 3 hotel nights in Chianti: Borgo del Cabreo, Castello di Meleto, or equivalent
  • 3 hotel nights on the Amalfi Coast: Grand Hotel Tritone, Hotel Onda Verde, or equivalent
  • Private transfer from Milan Airport to Lake Como
  • Small-group Lake Como boat tour
  • Private transfer from Lake Como to Milan
  • High-speed train from Milan to Florence
  • Small-group Florence market & food tour
  • Tickets to the Accademia
  • Car rental in Chianti, 3 days
  • Olive oil mill tour, tasting & Tuscan lunch
  • Chianti winery tour & tasting
  • Small-group truffle hunt & cucina rustica cooking class
  • High-speed train from Florence to Naples
  • Private transfer from Naples to the Amalfi Coast
  • Small-group Capri boat tour 
  • Private transfer from the Amalfi Coast to Naples
  • Curated Italy mini-guide
  • Trip preparation & support

Rome Add-On
  • 3 hotel nights in Rome: Sentho Roma, The Fifteen Keys, or equivalent
  • Private transfer from the Amalfi Coast to Naples
  • High-speed train from Naples to Rome
  • Private intro to Rome tour
  • Small-group Roman street food tour
  • Small-group tour of the Colosseum

Exclusions
  • International flights to Italy
  • Meals & activities not listed
  • ​Travel insurance

Luxury boutique pricing​
  • 12 days from $5,595 pp
  • 15 days from $6,946 pp
​
​*Pricing based on double occupancy and may vary depending on travel dates and total number of travelers.
Luxury
  • 3 hotel nights in Lake Como: Grand Hotel Villa Serbelloni, Grand Hotel Tremezzo, or equivalent
  • 2 hotel nights in Florence: Hotel Lungarno, Helvetia & Bristol Firenze, or equivalent
  • 3 hotel nights in Chianti: Hotel Le Fontanelle, Borgo San Felice, or equivalent
  • 3 hotel nights on The Amalfi Coast: Borgo Santandrea, Convento di Amalfi Grand Hotel, or equivalent
  • Private transfer from Milan Airport to Lake Como
  • Small-group Lake Como boat tour
  • Private transfer from Lake Como to Milan
  • High-speed train from Milan to Florence
  • Small-group Florence market & food tour
  • Tickets to the Accademia
  • Car rental in Chianti, 3 days
  • Olive oil mill tour, tasting & Tuscan lunch
  • Chianti winery tour & tasting
  • Small-group truffle hunt & cucina rustica cooking class
  • High-speed train from Florence to Naples
  • Private transfer from Naples to the Amalfi Coast
  • Small-group Capri boat tour 
  • Private transfer from the Amalfi Coast to Naples
  • Curated Italy mini-guide
  • Trip preparation & support

Rome Add-On
  • 3 hotel nights in Rome: Hotel Locarno, Maalot Roma, or equivalent
  • Private transfer from the Amalfi Coast to Naples
  • High-speed train from Naples to Rome
  • Private intro to Rome tour
  • Small-group Roman street food tour
  • Small-group tour of the Colosseum

Exclusions
  • International flights to Italy
  • Meals & activities not listed
  • ​Travel insurance

Luxury pricing​
  • 12 days from $7,450 pp
  • 15 days from $9,310 pp

​​*Pricing based on double occupancy and may vary depending on travel dates and total number of travelers.

Optional upgrades

  • Private Lake Como boat tour with Prosecco on a traditional Venetian wood boat
  • Private Accademia Gallery tour with a local guide
  • Full-day olive oil & wine tour in Chianti with a private local guide and driver
  • Wine tasting & lunch at a winery on the slopes of Mt. Vesuvius
  • Private full-day Amalfi Coast boat tour on a traditional Gozzo boat
  • Private guided Colosseum tour in Rome

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From our home in Italy, this Designed Trip was developed based on our personal contacts, favorite hotels and authentic activities we've experienced first-hand.
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FAQs

WHAT IS A DESIGNED TRIP?
A Designed Trip is a pre-designed travel plan based on our personal, first-hand travel experiences in each destination. As they are pre-designed, our Designed Trips have been created as a turnkey travel option and can be booked and delivered in as little as one week. ​
CAN I MAKE ANY CHANGES TO A DESIGNED TRIP?
Absolutely! Pre-designed doesn’t mean there isn’t any flexibility. Whether you want to shorten or lengthen your trip, switch out a destination or change an activity, let us know. If, however, you want a trip built around your specific desires, a Custom Trip might be more appropriate. We can help you decide, so get in touch.
​HOW LONG DOES THE PROCESS TAKE?
Once you’ve selected your Designed Trip and chosen between a Boutique, Luxury Boutique or Luxury experience, your trip can be booked and delivered in as little as one week. If you would like to make some changes to your trip, such as including an alternative activity, shortening or lengthening your trip, then this can take a bit longer.
HOW DO I KNOW HOW MUCH MY DESIGNED TRIP WILL COST?
Once you have decided on your Designed Trip, your dates, and any adjustments we will provide a personalized itinerary and pricing for your trip. We have included base pricing on each Designed Trip page to give you an idea as to what the final cost might be, but prices can fluctuate depending on time of year and any personalization. Get in touch and we can help.
If you have any other questions, feel free to check out more FAQs or send us an email.