Server talking to guest on the Romantic Italian Holiday journey
Woman gazing out the window on the Romantic Italian Holiday journey
Server offering bread on the Romantic Italian Holiday journey
Fresh breakfast with orange juice on the Romantic Italian Holiday journey

Romantic Italian Holiday – Florence to London

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The Highlights

  • Two nights at the five-star Villa San Michele, a former monastery overlooking the Renaissance city of Florence
  • Two nights at the palatial Cipriani Hotel in Venice, perfectly situated just minutes from the Piazza San Marco, yet blissfully removed from the tourist crush
  • Double compartment Venice-Paris-Calais on the Venice Simplon-Orient-Express
  • Afternoon tea, wine and champagne on the British Pullman from the English Channel to London
  • Sumptuous breakfast daily at your hotels
  • Private guide/driver for half-day each in Florence & Venice
  • First-class, high-speed-rail tickets Florence-Venice
  • Airport/rail station/hotel transfers Florence & Venice

The Tour

Try this for Romance: two nights in Florence at the Belmond Villa San Michele, a former monastery turned five-star hotel; two nights in Venice at the Belmond Hotel Cipriani, iconic waterside pleasure palace overlooking the Grand Canal; two days and a night on the Venice Simplon-Orient-Express, capped off by afternoon tea on the British Pullman into London.

Perfect for honeymoons, anniversary celebrations, or any other occasion demanding over-the-top luxury and romance. Package includes hotels, breakfast daily, railway station/airport/hotel transfers, tours, Florence-Venice high-speed rail transfer, and more. Extend your celebration: add London’s romantic Milestone Hotel for a two-night stay and enjoy complimentary afternoon tea for two.

Special Report: View travel notes by Society owners Owen & Eleanor Hardy, who celebrated their 30th wedding anniversary on the Orient-Express Venice-Paris-London.

This itinerary is also available in the reverse direction: London to Florence

Map of the London, Paris, and Florence journey

Countries Visited

  • Italy
  • Switzerland
  • France
  • Great Britain


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Day 1: Florence

Your private car and driver meet you upon arrival at the Florence airport or rail station, and whisk you to the Belmond Villa San Michele (Superior room). Dating from the 15th century, with a façade attributed to Michelangelo, Villa San Michele must be one of the most romantic places in the world. This former monastery, nestled on a hilltop surrounded by trees and terraced gardens, overlooks the city of Florence. The Renaissance building is as much a part of Italy’s culture as the country’s greatest cathedrals and galleries.

This is a day for enjoying the sublime beauty of your surroundings. Stroll in the Italian gardens, filled with lemon trees and roses. Relax in the pool overlooking the city. And tonight, savor the superb Tuscan cuisine alfresco on the loggia. Just sitting at the table, covered in yellow linens and beautiful china and silver, admiring the Duomo below, is breath-taking. Or dine indoors at the Cloister, serving Tuscan and Italian specialties.

Day 2: Florence

Start your day with a sumptuous breakfast alfresco; an incredible buffet of Italian delicacies awaits you. It’s hard to pull yourself away from the gorgeous open-air restaurant, but you must try.

Today is for exploring Florence: Your car and guide will meet you at the hotel and are at your disposal for a personal, four-hour tour (either 9 a.m.-1 p.m. or 2- 6 p.m). Entrance fees not included.

Your guide is completely at your disposal; your touring program is limited only by your interests. Visit the Duomo, made of green, pink, and white marble; the Ponte Vecchio, bridging the River Arno, built in 1345; the Pitti Palace, Florence’s largest palazzo, and once the seat of the Medici family; the Uffizi Gallery, the world’s top repository of Renaissance masterpieces; Boboli Gardens or the adjacent, recently opened Bardini Gardens; or the Galleria dell’ Accademia, which houses Michelangelo’s “David.” The remarkable concierge Maurizio Ammazzini at the Villa can get tickets ahead of time for anything you wish and even arrange a personal shopper to take you to the neatest places. Please advise us upon booking: especially important are the Uffizi and the Galleria.

Spend the rest of your day wandering Florence’s narrow streets, shopping for jewelry or exquisite leather or paper goods; or simply taking in the sights with a cup of espresso and a fine Italian pastry in one of the city’s chic outdoor cafés.

Meet your complimentary shuttle back to the hotel right near the Duomo. It goes back and forth every 20 minutes.

Day 3: Venice

Following breakfast, your private car takes you to Florence’s railway station, Firenze Santa Maria Novella. Your driver will assist you with your bags to the platform and help you validate your rail tickets in the machine (you are responsible for getting your luggage aboard the train, unless prior arrangements are made.).

Once on board the high-speed Eurostar Italia — ES9404 — relax in your reserved, first-class seat. The price of your ticket includes complimentary beverages and snacks from the trolley. Departing at 10:30 a.m., you can sit back, relax and gaze at the passing Tuscan countryside. Arrival at Venice’s Santa Lucia station is at 12:33 p.m.

A hotel representative will be waiting to greet you and other guests at the head of the platform next to the engine (porterage services are not available at the Venice station, so please ensure you take all your luggage with you when leaving the train.)

No matter how many times you’ve been to Venice, arrival by rail is always an event in itself. As you pass outside the station door, you’re greeted by the Grand Canal, in all its glory, with your private boat and driver ready to take you to your hotel, the legendary Belmond Hotel Cipriani.

One of the world’s most famous hotels, the Cipriani is situated on Giudecca Island, five minutes by the hotel’s motor launch from Piazza San Marco. Your hotel room is a double, with garden view and terrace or balcony.

As in Florence, your Venetian holiday starts with your hotel, an attraction in itself. The rest of your day is reserved for enjoying the Cipriani. The hotel offers several dining venues— our favorites were the formal Fortuny restaurant and the very popular and informal “Cips.” (Both overlook water — the lagoon or Grand Canal. Allow the IRT Society to make your dinner reservations as soon as you book at these fantastic restaurants.)

Enjoy the full-size, salt water, outdoor swimming pool, tennis courts and the Casanova Beauty & Wellness center offering a range of Babor massages and other relaxing therapies. Stroll in the gorgeous garden, blooming with roses. The only problem with staying here: it’s hard to peel yourself away!

Day 4: Venice

Today is reserved for your prearranged, personal half-day tour of Venice, either in the morning or afternoon. You may request your guide take you on a walking tour of “La Serenissima”—the Most Serene Republic of Venice. Perhaps you’d like to include the city’s most famous sights: the Piazza San Marco, the Accademia Gallery, St. Mark’s Cathedral or the Doge’s Palace. Or maybe you’d prefer to travel further afield into the Venice where tourists rarely stray. Your guide will arrange the program to your liking.

The rest of your day is at your leisure. Nothing beats a ride on an ordinary “vaporetto”—water taxi—to take in the sights. Strolling along the city’s many canals and over its romantic bridges is endlessly fascinating. And be sure to leave plenty of time for a visit to the Café Florian, on St. Mark’s Square and founded in 1720. You’ll pay an extra 6 Euro per person for the privilege of listening to its orchestra, but the café’s gilded, mirrored, ornate interior resembles a ducal palace, and its espressos, pastries and light meals are meant for lingering over.

And when the crowds overflow Venice, you can pop right back to your hotel and its serenity in five minutes on the complimentary, 24-hour shuttle by vintage speedboat—another Cipriani plus. The hotel’s dock is right by San Marco’s Square. For five to ten minutes, you feel like a movie star. (We met several people on board this speedboat, who were coming to dinner at the Cipriani. They told us they rued the day they booked their hotel on the main island.)

Day 5: Venice Simplon-Orient-Express

Take breakfast today in one of the Cipriani’s restaurants, or, perhaps privately on your balcony or terrace.

Then a hotel representative will escort you by boat to Santa Lucia Station (please note that on occasions you may be transferred together with other Orient-Express passengers). You will be met at the station by representatives of the Venice Simplon-Orient-Express, who will take charge of your luggage and check you in for your 10:57 a.m. departure on one of the World’s Top 25 Trains.

As you settle in to your comfortable double compartment, the maitre ‘d will take your reservation for meals. We recommend asking for seating in each of the three gorgeous and very different diners. Soon, you will make your way to a sumptuous lunch. Enjoy your day on board as the train travels through the beautiful scenery of the Italian Dolomites and the Swiss Alps. Afternoon tea is served in your compartment. After a leisurely four-course dinner, you may want to relax in the lounge car, while conversing with other guests and listening to the strains of Cole Porter, George Gershwin and others, courtesy of the on-board pianist.

Day 6: British Pullman

Today, breakfast is served in your compartment. The train halts at Paris Gare de l’Est for approximately 30 minutes. A delicious brunch is served as you travel on towards the Channel. At Calais Ville, coaches will transfer you to the Shuttle terminal at Coquelles and through the tunnel and on to Folkestone, where you will join the British Pullman train for the journey to London.

Enjoy afternoon tea with wine and a glass of champagne. (Make sure you reserve time to walk the train and admire each of the unique, beautifully decorated antique cars. And don’t forget to visit the bathrooms; the tile floors are works of art in themselves.)

The train arrives into London’s Victoria station at 5:30 p.m.

Dates & Prices

2023 Dates

October 1 - 31

November 1 - 30

  • Please note prices are in British pounds. View approximate exchange rates.
  • Prices are per person.
  • Pricing subject to change based on hotel rates, travel dates and currency fluctuation.
  • Upgrades available to a Suite or Grand Suite on the Venice Simplon-Orient-Express available. Please inquire.
  • Single pricing available upon request.

2024 Dates

April 1 - 30

May 1 - 31

June 1 - 30

July 1 - 31

August 1 - 31

September 1 - 30

October 1 - 31

November 1 - 30

December 1 - 31

  • Please note prices are in British pounds. View approximate exchange rates.
  • Prices are per person.
  • Pricing subject to change based on hotel rates, travel dates and currency fluctuation.
  • Upgrade to a Suite or Grand Suite on the Venice Simplon-Orient-Express available. Please inquire.
  • Single pricing available upon request.

Our Process

This is a suggested itinerary for a wonderful private journey. It will be fully customized for you.  Please contact us at (800) 478-4881, or (502) 897-1725, or email us at, to schedule a brief conversation with one of our specialists  to discuss our process.


Upgrades Available: Villa San Michele and Hotel Cipriani: If you wish to upgrade to a suite or apartment, please call for rates, (800) 478-4881 within U.S., (502) 897-1725 elsewhere or email us.

Tours: We can work out just about anything you wish for your touring in these iconic cities. Examples are all-day Tuscany wine tour in Florence or half-day tour in Venice to Murano, Burano and Torcello. Note the Uffizi Gallery is always closed on Mondays. The Boboli Garden is closed the first and last Monday of every month. We will do our best to work around these and other closings.

London Extension:
Extend your Orient Express holiday celebration (pre- or post-tour) at “London’s most romantic hotel,” the Milestone. Owen and Eleanor recommend this boutique hotel for its afternoon tea, intimate restaurant, very personal service, and location: within walking distance of Buckingham Palace and directly across the street from Kensington Gardens.  The suites particularly are magnificent.

Milestone Hotel package:
Stay two nights, and receive complimentary afternoon tea for two on either day. Book a suite, and get two treats. Package can include private transfer from Victoria Station to hotel, just minutes away. Call for special rates, (800) 478-4881 within U.S., (502) 897-1725 elsewhere or email us.

Italy extension: Extend your Italian stay in any of these over-the-top Italian hotels: Portofino:Belmond Hotel Splendido and Belmond Splendido Mare; Amalfi Coast: Belmond Hotel Caruso; Taormina Mare (Sicily): Belmond Villa Sant’Andrea; Taormina (Sicily): Belmond Grand Hotel Timeo.