Holiday like a VIP!

Fly business class, stay in luxury hotels, dine in fabulous restaurants, executive car transfers, discover Italy’s history with personal guides PLUS €2,500 spending money

All that’s needed is a passport and a packed suitcase! Sit back and relax, the Win VIP Holidays team will take care of the rest!

Winner announced in a live draw September



18:00 British Summer Time

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Watch it live & live life like a VIP!!

  • Exclusive Airport Lounge Access
  • Return Business class flights to Florence
  • 8 x night stay in luxury hotels
  • Personal Driver and Executive Car
  • Dine in Michelin star restaurant
  • Fully guided personal excursions or personal time
  • €2,500 spending money

Tickets £10 or postal entries available.

Valid for travel between September 2022 to October 2023*

Minimum 6,000 tickets to award the holiday or alternative cash prize awarded  T&C’s-alternative prize.

For full competition details see our T&C’s,

See our FAQ section for further competition details

This stunning and luxurious holiday will take our lucky winner and their travel partner to some of Italy’s famous towns and cities discovering hidden gems that are some of its best kept secrets.

You’ll experience everything like a VIP for 8 nights with a 5 star experience from the minute you arrive at the airport!

On arrival you’ll be greeted by your own executive car and driver to transfer you to your multiple destinations. You’ll enjoy some amazing architecture, retail therapy (those famous Italian brands), mouth-watering cuisine and top class hotels.

From Florence to Lucca to Pisa. Then Porto Venere to Santa Margherita and finally to Portofino.

What more can you wish for? Here’s a more detailed itinerary

Day 1 and 2 – Florence

  • Arrive at the airport and enjoy access to the lounge before boarding your business class flight
  • Touchdown in Florence to be greeted by your executive car and driver who’ll whisk you off to your first 5 star in the heart of Florence for two nights
  • Unpack and enjoy some bubbly in your room before enjoying some free time to take in the amazing architecture surrounding you.
  • Get ready for dinner – you’ll be dining in one of this city’s best restaurants where your table awaits for your taste buds to be amazed with some mouth-watering Italian cuisine.
  • After a restful night, you can enjoy a leisurely start before meeting your personal city guide (optional) who’ll show you some of the sights that inspired Michelangelo. You’ll visit the huge dome on Brunelleschi’s Red Cathedral, and the Galleria Dell ‘Academia to see David in all his glory
  • Have the afternoon to browse the world class designer retail shops or perhaps sip some Italian wine and watch the world go by. Then enjoy your second night before your driver takes you on the next part of your VIP Holiday.

Day 3 Lucca and Pisa

  • Driving through the beautiful Tuscan countryside, you’ll gasp at some of the most amazing scenery before arriving in Pisa where you can spend time visiting its famous leaning tower and have a spot of lunch.
  • Then it’s back on the road to explore Lucca, which is often referred to as a secret gem of Tuscany. There you will dine in one Lucca’s Michelin star restaurants — almost certainly the best in Tuscany. Why not take a post dinner stroll to Piazza dell’Anfiteatro a former Roman amphitheatres  before retiring in another of Italy’s luxurious hotels.

Day 4 and 5 Porto Venere – Gateway to Cinque Terre

  • Following a leisurely breakfast, your driver will be ready to take you to the breath-taking Italian Riviera where you’ll arrive in Porto Venere, the gateway to Cinque Terre.
  • Enjoy the day at your leisure exploring or relaxing on one of the local beaches. Spend the evening strolling around the port overlooking the gulf of poets and the many fine Italian and fresh seafood restaurants.
  • Before you retire in yet another 5 star hotel, be sure to get a view of the sunset – it’s simply amazing
  • After breakfast, your private boat taxi awaits to take you and your personal guide (optional) on a trip along some of the most dramatic coastal scenery in Italy. You’ll disembark at the world heritage site of Cinque Terre where you’ll stop in your tracks at the spectacular and colourful fishing villages with the narrowest streets only wide enough to fit a mule!

Day 6 and 7 Santa Margherita

  • Following a short transfer, you will arrive at the charming seaside town framed by lush green hills. Relax at the hotel’s private beach and swim in the crystal clear waters of the Med as you look out at the super yachts that adorn this tranquil part of the riviera. Enjoy dinner on the spacious terrace that overlooks the Gulf of Tigullio and the bay of Santa Margherita. The flavours of Ligurian cuisine offer a unique sensory experience: the highest quality and freshest ingredients are based on the region’s culinary tradition
  • Awake in the heart of Liguria with a sumptuous breakfast overlooking the Italian Riviera. Enjoy the day at your leisure.

Day 8 Portofino

  • Your VIP Holiday may nearly be over, but we think we’ve saved the best until last – Portofino. We think even the trees are handsome at its exclusively chic harbour!
  • Take a leisurely stroll up to the historic house museum, Castello Brown, for amazing views on the tranquil marina complete with Super Yachts as big as skyscrapers
  • Then enjoy a spot of lunch in one of the many waterside restaurants, and take a souvenir home to remember this amazing trip (We can recommend the Portofino Gin).
  • Retire to your hotel and enjoy an aperitivo as the sun sets and reminisce about your past few days.
  • With your suitcase packed, your driver will meet you to take you back to Florence for your flight home. Arrivederci!

*Trip to be taken within 12 months of winning, subject to availability. Win VIP Holidays will endeavour to accommodate specific date requests where possible, but this is not guaranteed. Black out dates apply July/August

Win VIP Holidays as seen in:

The Times
Lonely Planet
House Beautiful
Liverpool Echo
Mail Online
The Sun
The Scotsman
Bournemouth Echo
Dorset Echo
Al Arabiya
Elle Espana
Trip Advisor