14-Day Italian Getaway: Discovering Florence, Sorrento, Positano, and Rome

Day 1: Travel to Rome

New York, USA to Rome, Italy on May 21, 2025

8:00 PM

Flight to Rome

Depart from New York City (JFK) on an overnight flight to Rome. Enjoy in-flight entertainment and rest before your Italian adventure.
USD700, Approx 8 hours
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Day 2: Explore Florence

Florence, Italy on May 22, 2025

10:00 AM

Check into Hotel Art Firenze

Your four-star hotel located near the Uffizi Gallery offers comfortable accommodation for four adults.
EUR400, 1 hour

11:30 AM

Visit the Uffizi Gallery

One of the most famous art museums in the world, showcasing masterpieces from Da Vinci and Michelangelo.
EUR20, 2 hours

1:30 PM

Lunch at Mercato Central

A vibrant market with plenty of food stalls offering local ingredients and traditional Italian dishes.
EUR30, 1 hour

2:30 PM

Stroll across Ponte Vecchio

This iconic bridge lined with jewelry shops offers stunning views of the Arno River.
Free, 1 hour

4:00 PM

Visit Duomo Cathedral

Climb to the top for a breathtaking view over Florence and explore this architectural marvel.
EUR15, 2 hours

7:00 PM

Dinner at Trattoria Mario

Enjoy traditional Florentine ribollita or Bistecca alla Fiorentina in this local favorite.
EUR60, 1.5 hours
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Day 3: Art and Culture in Florence

Florence, Italy on May 23, 2025

9:00 AM

Breakfast at Caffè Gilli

Try a classic Italian breakfast of cornettos and cappuccino at this historic café.
EUR12, 1 hour

10:30 AM

Visit Accademia Gallery

Home of Michelangelo's David, a must-see for art enthusiasts.
EUR12, 1.5 hours

1:00 PM

Lunch at Osteria Vini e Vecchi Sapori

A cozy spot serving hearty pasta dishes made from family recipes.
EUR40, 1.5 hours

3:00 PM

Explore the Boboli Gardens

A stunning park filled with sculptures, fountains, and beautifully manicured gardens.
EUR10, 2 hours

5:30 PM

Enjoy a Gelato at Gelateria dei Neri

Sample some of the best gelato in Florence with unique flavors.
EUR5, 30 minutes

7:00 PM

Dinner at Il Santo Bevitore

A modern eatery known for its innovative take on Tuscan cuisine.
EUR70, 2 hours
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Day 4: Wine Tour in Tuscany

Tuscany, Italy on May 24, 2025

8:30 AM

Join a Wine Tour

Explore the beautiful wineries of Tuscany, learn about the wine-making process and taste some exquisite wines.
EUR150, Full day

1:00 PM

Lunch at a Vineyard

Enjoy a traditional Tuscan meal paired with fine wines at a local vineyard during your tour.
Included, 1.5 hours

6:00 PM

Return to Florence

Relax and unwind after a day of wine tasting in the Tuscan hills.
Included, 1 hour

7:30 PM

Dinner at La Giostra

A romantic restaurant offering delicious Tuscan cuisine and a lovely atmosphere.
EUR80, 2 hours
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Day 5: Cultural Highlights in Florence

Florence, Italy on May 25, 2025

9:00 AM

Breakfast at Pasticceria Nencioni

Start your day with rich pastries and a strong Italian espresso in this local bakery.
EUR10, 1 hour

10:30 AM

Visit Palazzo Vecchio

Explore Florence's town hall and its stunning rooms, frescoes, and outdoor courtyard.
EUR10, 1.5 hours

1:00 PM

Lunch at La Carraia

Known for their delicious and authentic Tuscan sandwiches and panoramic views of the river.
EUR25, 1 hour

2:00 PM

Cooking Class

Participate in a fun cooking class and learn how to make classic Italian dishes.
EUR100, 3 hours

6:00 PM

Enjoy an Aperitivo at Locale Firenze

Discover the Italian tradition of enjoying a pre-dinner drink and enjoy delicious small bites.
EUR40, 1.5 hours

8:00 PM

Dinner at Il Latini

Feast on traditional Tuscan dishes in a lively, local atmosphere.
EUR65, 2 hours
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Day 6: Travel to Sorrento

Sorrento, Italy on May 26, 2025

8:00 AM

Check out and Travel to Sorrento

Take a scenic train ride from Florence to Sorrento, enjoying stunning views of the Italian countryside.
EUR40, 3 hours

11:30 PM

Check into Hotel Antiche Mura

A four-star hotel offering comfortable rooms with convenient access to the main square.
EUR360, 1 hour

1:00 PM

Lunch at Ristorante Tasso

A charming restaurant known for its fresh seafood dishes and classic Neapolitan cuisine.
EUR50, 1.5 hours

2:30 PM

Explore Sorrento’s Town Center

Wander the streets filled with shops, cafes, and beautiful piazzas.
Free, 2 hours

5:00 PM

Limoncello Tasting

Visit a local factory to learn about limoncello production and savor some tasty samples.
EUR10, 1 hour

7:00 PM

Dinner at Ristorante da Filippo

Savor authentic Italian cuisine in this family-run restaurant known for its wonderful ambiance.
EUR60, 2 hours
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Day 7: Day Trip to Capri

Capri, Italy on May 27, 2025

8:00 AM

Boat to Capri

Take an early ferry from Sorrento to the breathtaking island of Capri.
EUR30, 40 minutes

9:00 AM

Visit the Blue Grotto

Discover the magical waters of the Blue Grotto on a guided boat tour.
EUR20, 1.5 hours

11:00 AM

Explore Anacapri

Wander around the charming streets of Anacapri and visit the Villa San Michele.
EUR10, 2 hours

1:00 PM

Lunch at Da Gemma

Enjoy a local meal with stunning views of the island at this cliffside restaurant.
EUR40, 1.5 hours

3:00 PM

Chairlift to Monte Solaro

Take a chairlift to the highest point on Capri for panoramic views of the Bay of Naples.
EUR12, 1.5 hours

5:30 PM

Return to Sorrento

Catch the ferry back to Sorrento after a delightful day.
EUR30, 40 minutes

7:00 PM

Dinner at Il Buco

Indulge in fine dining with local flavors and a great wine selection in a cozy atmosphere.
EUR75, 2 hours
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Day 8: Travel to Positano

Positano, Italy on May 28, 2025

8:00 AM

Check out and Travel to Positano

Take a stunning drive along the Amalfi Coast from Sorrento to Positano, enjoying breathtaking views.
EUR30, 1 hour

9:15 AM

Check into Le Sirenuse

Experience luxury accommodations with breathtaking views of the Mediterranean.
EUR800, 1 hour

11:00 AM

Explore Positano’s Beach

Spend the afternoon relaxing on the scenic beach or taking a dip in the blue waters.
Free, 3 hours

2:30 PM

Lunch at Chez Black

Taste the famous pizza and seafood dishes right on the beach.
EUR45, 1.5 hours

4:00 PM

Wander Through the Charming Streets

Discover the colorful, cascading villas, shops, and art galleries scattered throughout Positano.
Free, 2 hours

7:00 PM

Dinner at La Sponda

Indulge in gourmet cuisine while enjoying enchanting views of the sea.
EUR100, 2 hours
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Day 9: Relaxation and Exploration in Positano

Positano, Italy on May 29, 2025

8:30 AM

Breakfast at the Hotel

Enjoy a lavish breakfast provided by your hotel, featuring local delicacies and fresh pastries.
Included, 1 hour

10:00 AM

Boat Tour Along the Coast

Experience stunning coastal views and the chance to swim in hidden coves while on a private boat tour.
EUR100, 4 hours

2:30 PM

Lunch at Da Vincenzo

Enjoy a delicious meal featuring traditional Italian dishes and stunning coastal views.
EUR60, 1.5 hours

4:00 PM

Visit the Church of Santa Maria Assunta

Admire the famous dome and art within this iconic church located in the heart of Positano.
EUR5, 1 hour

6:00 PM

Shopping and Leisure

Explore the local boutiques and artisan shops for unique souvenirs while enjoying the pleasant atmosphere.
Free, 1.5 hours

8:00 PM

Dinner at Il Capitano

Dine on fresh seafood and other Italian specialties while enjoying sea views.
EUR70, 2 hours
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Day 10: Travel to Rome

Rome, Italy on May 30, 2025

8:00 AM

Check out of Hotel and Travel to Rome

Enjoy a scenic drive from Positano to Rome, where you'll head directly to the airport for your flight.
EUR200, 3 hours

11:30 AM

Arrive at Rome Airport

Prepare for your departure as you check in for your flight back to New York.
Included, 1 hour
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Day 11: Return to New York

Rome, Italy to New York, USA on June 1, 2025

1:00 PM

Flight Back Home

Depart Rome, taking with you memories of an unforgettable Italian adventure.
USD800, Approx 8 hours
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