‘In fair Verona, where we lay our scene’… There’s a reason Shakespeare chose an Italian city as the setting for Romeo and Juliet. Italy was made for two. From culture-rich towns and cities to Tuscan vineyards and the picture-perfect Amalfi Coast, the options for an Italy romantic holiday are endless. Relax on sunny beaches, explore quaint villages or indulge in Italian gastronomy. Just picture yourself and your other half tucking into a large gelato with two spoons, or sharing a bowl of spaghetti Lady and the Tramp style. Whatever your style of romance, our Italy experts will customise the perfect holiday for you.

Italy Romantic Escapes Ideas

A few suggestions to get the holiday planning process started

  • Stay Italy – Naples – Pompeii

    From Palazzos to Pompeii - An Authentic Long Weekend in Naples

    Spend a long weekend discovering Naples’ ancient streets, elaborate architecture and stunning coastline

    4 days, from £1500 to £2150

  • One Country Italy – Turin – Piedmont

    Turin and Piedmont - Flavours of an Unexplored Italy

    Uncover a series of hidden gems on this six-day journey through a sleepy corner of northern Italy

    6 days, from £1750 to £2400

  • One Country Italy – Sorrento – Amalfi Coast

    A Long Weekend in the Mediterranean - Explore the Sun-Soaked Coast of Sorrento

    Spend a dreamy long weekend in Sorrento, savouring seaside beauty, Italian culture and the magical Amalfi Coast

    4 days, from £1850 to £2950

  • One Country Italy – Venice

    A Classic Weekend in Venice - Winding Canals and Wonderful Cuisine

    Immerse yourself in the magical romance of Venice, from its iconic canals to its ornate architecture

    4 days, from £1900 to £2450

  • One Country Italy - Sicily - Palermo

    A Short Break in Palermo - Discover the Rich History and Culture of Sicily

    Enjoy a weekend break in Palermo, sampling the Sicilian lifestyle through its historic landmarks and culinary delights

    4 days, from £2100 to £3100

  • One Country Italy – Ragusa – Syracuse – Taormina

    Ragusa, Syracuse & Taormina - The Most Beautiful Places in Sicily

    Explore Sicily by road, from charming Ragusa and ancient Syracuse to the stunning coastal views of Taormina

    7 days, from £2350 to £3200

  • One Country Italy – Florence – Chianti – Cortona – Perugia

    Vineyards, Food and Frescoes - Italian Road Trip in Tuscany and Umbria

    Hit the road for nine days of rolling countryside, medieval towns and authentic Italian cuisine between Tuscany and Umbria

    9 days, from £2400 to £3600

  • One Country Italy – Bologna – Parma – Ravenna – Padua

    A Taste of Italy - Emilia-Romagna from Bologna to Padua

    Embark on a nine-day Emilia-Romagna road trip, discovering historic cities, Renaissance art and culinary gems

    9 days, from £2600 to £3850

  • One Country Italy – Alghero – Oliena – Costa Smeralda – The Maddalena Islands

    Secret Sardinia - Coast and Countryside in the Mediterranean

    Experience the best of Sardinia’s coast and countryside, across four distinct yet equally enchanting locations

    7 days, from £2700 to £3900

Italy testimonials

30 reviews
4.7 / 5
"Emily really understood what mattered to us and created a trip that felt completely personalised and thoughtfully organised. We had time to relax in Naples after each excursion, our transport provider was friendly and always on time, and it was a pleasure to be looked after by a local, who added an authentic touch to the whole trip. Visiting Herculaneum and Pompeii was a particular highlight - our guide was truly exceptional, making the visits truly memorable with an excellent command of English and an impressive knowledge of world history as well as the sites themselves."
L - UK
Published on 23rd February 2026
"Our Concierge was brilliant and super helpful - we'd recommend travelling with Original Travel based on her help alone! The Concierge was a new thing for us as previous travel companies did not have this feature, and we thought this was invaluable. We particularly enjoyed the food tour in Ragusa, seeing Mount Etna, driving in Ortigia and the sunset in Marsala. It is the first time we have used Original Travel and we were very happy with the service."
M - UK
Published on 29th September 2025
"Emily really listened and understood what I was looking for, and developed a fantastic itinerary based on that. The personalised tour of Siena was a real highlight - I had asked if we could see some James Bond filming locations, and our guide took a lot of time to review the films and take us to the exact streets, balconies, doorways and squares seen in the films. We all loved it, especially our boys, who are James Bond enthusiasts."
G - UK
Published on 29th September 2025

Our Italy experts will create an Italy romantic holiday that’s unique to you and your other half. But just to give you some inspiration, here are a few experiences you might enjoy on your trip:


Indulge your inner sommelier

No Italy romantic holiday would be complete without a trip to a vineyard. Tuscany, Italy’s most famous wine region, is a landscape of rolling hills and incredible views. It’s home to the notable Sangiovese variety of wines: Chianti, Brunello di Montalcino and Vino Nobile di Montepulciano. Enjoy a wine tasting to sample all these local varieties and maybe buy a few bottles to bring home with you.


Potter around Positano

Positano is arguably the most iconic village on the Amalfi Coast, a strip of coastline so spectacular it’s been granted UNESCO World Heritage status. With the Mediterranean Sea to one side and the peaks of the Lattari Mountains to the other, Positano’s colourful architecture is scattered up the cliffside, with incredible views out to sea from the top. Spend your Italy romantic holiday exploring the town, its markets and local water-side restaurants.


Escape to the lakes

Italian lakes are a sight to behold. Lake Como and Lake Garda may be the most famous, but they are certainly not the only ones worth visiting. Whichever you choose on your Italy romantic holiday, you’ll be treated to the beautiful contrast of a dramatic mountain backdrop and peaceful, glistening waters. For the more adventurous or sporty couple, the lakes also offer all kinds of water sports to try.