City and Beach Holidays in Italy Vacation Packages
Famous for its amazing food, impressive historical sites, highly regarded art, charming small towns and equally beautiful cities, countrysides and coastlines, it`s safe to say Italy`s offerings are unparalleled. The country boasts bustling cities as well as some of the most beautiful beaches in the world. It doesn`t matter if you prefer private bays with calm waters or glamorous holiday destinations crowded with celebrities and high-class restaurants, the beaches in Italy are fantastic in many ways and there is truly something for everyone.
Best Vacation Packages:
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9 nights from $1,269*More details›
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Cities to Explore
Areas to Explore
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The mild climate, the splendor of the coasts, the richness of its art and history, and the love for food make the Amalfi Coast and Neapolitan Riviera, the fascinating territory that it is.
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The Italian Riviera is a spectacular coastline on the Ligurian Sea extending from the Italian-French border to Capo Corvo, near La Spezia and offering luxuriant mountains to the north and east, and the sapphire blue Mediterranean to the south and west with medieval hilltop hamlets, panoramic vistas, vibrant seaside villages and unspoiled beaches.
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A voyage over an emerald sea, past characteristic coves and snow white sandy beaches lies enchanting Sardinia. This beautiful getaway surprises visitors with its blend of old-world traditions and a wild and pure nature.
More to Explore
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French Riviera
The southeast coast of Provence, France, is sprinkled with some of the world`s most popular beaches and destinations, including Nice, Monaco, Cannes, Saint Tropez and Menton.
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Mediterranean
The coastlines of southern Europe, the Middle East, and North Africa are shaped by the Mediterranean Sea. Not only does the Mediterranean have beautiful resorts and beaches on the mainland, there are literally thousands of islands to explore, each with their own beauty.
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Best of the Aegean
There is no better way to discover the ancient Aegean Civilization than taking a discovery trip around the Greek Islands.
SUGGESTED ITINERARIES
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Florence - Rome - Sorrento and Capri11 nights from $8,921*› - Flight into Florence and out of Naples
- Hotel for 3 nights in Florence
- Train from Florence to Rome
- Hotel for 3 nights in Rome
- Transfer from Hotel in Rome to Hotel in Sorrento via Herculaneum Archaeological Area
- Hotel for 2 nights in Sorrento
- Ferry from Sorrento to Capri
- Hotel for 2 nights in Capri
- Ferry from Capri to Naples
- Hotel for 1 night in Naples
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Milan - Venice - Florence - Rome by Train9 nights from $2,367*› - Flight into Milan and out of Rome
- Hotel for 2 nights in Milan
- Train from Milan to Venice
- Hotel for 2 nights in Venice
- Train from Venice to Florence
- Hotel for 2 nights in Florence
- Train from Florence to Rome
- Hotel for 3 nights in Rome
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Rail to Road: Milan - Venice - Florence - Rome and SorrentoMore details› - Flight into Milan and out of Naples
- Hotel for 3 nights in Milan
- Train from Milan to Venice
- Hotel for 2 nights in Venice
- Train from Venice to Florence
- Hotel for 2 nights in Florence
- Train from Florence to Rome
- Hotel for 3 nights in Rome
- Rental Car for 4 days
- Pick Up: Rome Downtown/Drop Off: Naples Airport
- Hotel for 3 nights in Sorrento
Driving Time
Rome - Sorrento: 3 hrs. 35 mins. approx.
Sorrento - Naples Airport: 1 hr. 40 mins. approx.-
Runway to Rail: Florence - Rome and Malta Island8 nights from $1,389*› - Flight into Florence and out of Valletta
- Hotel for 3 nights in Florence
- Train from Florence to Rome
- Hotel for 3 nights in Rome
- Flight from Rome to Valletta
- Hotel for 2 nights in Valletta
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Runway to Ride: Rome - Amalfi Coast and Malta Island10 nights from $1,611*› - Flight into Rome and out Valleta
- Hotel for 3 nights in Rome
- Rental Car for 5 nights
- Hotel for 3 nights in Amalfi Coast
- Hotel for 1 night in Naples
- Flight from Naples to Valetta
- Hotel for 3 nights in Valetta
Driving Time
Rome - Amalfi Coast: 3 hrs. 30 mins. approx.
Amalfi Coast - Naples: 1 hr. 30 mins. approx.-
Barcelona - Madrid - Rome by Air9 nights from $1,301*› - Flight into Barcelona and out of Rome
- Hotel for 3 nights in Barcelona
- Flight from Barcelona to Madrid
- Hotel for 3 nights in Madrid
- Flight from Madrid to Rome
- Hotel for 3 nights in Rome
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Venice - Pisa - Florence - Assisi - Sorrento - Rome (Self Drive)11 nights from $1,329*› - Flight into Venice and out of Rome
- Hotel for 2 nights in Venice
- Rent a car for 7 days
- Hotel for 2 nights in Pisa
- Hotel for 2 nights in Florence
- Hotel for 1 night in Assisi
- Hotel for 2 nights in Sorrento
- Hotel for 2 nights in Rome
Driving Time
Venice - Pisa: 4 hrs. 30 mins. approx.
Pisa - Florence: 1 hr. 20 mins. approx.
Florence - Assisi: 2 hrs. 5 mins. approx.
Assisi - Sorrento: 4 hrs. 30 mins. approx.
Sorrento - Rome: 3 hrs. 5 mins. approx.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Travel Guide
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Iconic Amalfi Coast
Few destinations capture the imagination quite like the Amalfi Coast. This UNESCO-listed stretch of southern Italy is a dizzying blend of dramatic cliffs, picturesque villages, and sparkling Mediterranean views.
Italy Customer Reviews
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An email sent out 2 weeks prior to trip would be nice, letting us know the email with travel details would be coming a week prior to the actual trip w ...Traveled on: 10/11/2026
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Everything was great, the hotels were very nice and centrally located and within walking distance to all the must see attractions in Rome, Florence an ...Traveled on: 10/7/2026
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The trip was great besides all of the trains in between cities left so early in the day that we only got 1 whole day in each city. Would have preferre ...Traveled on: 10/4/2026
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Let me think about that and get back to you with some useful information ...Traveled on: 9/30/2026
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Transportation was great! Hotels were fine, but you need to give them contact information! They all told me they had no way to reach out to me, aski ...Traveled on: 9/29/2026










