people look out window during lunch
Cipriani detail
Paolo and friend outside train in Innsbruck
Venetian Lion
Villa view

Romantic Italian Holiday – London to Florence

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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.

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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: Florence to London 

Map of the London, Paris, and Florence journey

Countries Visited

  • Italy
  • Switzerland
  • France
  • Great Britain


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Day 1: Depart London

Board the gleaming carriages of the Belmond British Pullman train at London Victoria station. Your friendly steward will show you to your reserved seat. Sit back and enjoy a three-course brunch served with a Bellini as you travel throughout the English countryside.

After crossing the Channel, board the blue and gold carriages of the Venice Simplon-Orient-Express and settle into your private cabin. Soon, it is time to dress for dinner. Why not sip a pre-dinner cocktail before making your way to one of the magnificent restaurant cars? Here you will be served a delicious four-course dinner, prepared by skilled French chefs. After dinner you may want to linger in the bar car, listening to the sound of the baby grand piano. When you are ready, retire to your cabin, which has now been transformed into a cozy bedroom.

Day 2: Arrive Venice

Awaken as breakfast is served in your cabin at a time to suit you. Spend the morning in the Bar Car chatting to fellow guests over coffee. Enjoy a leisurely three-course lunch served in another of the beautiful restaurant cars. While away the afternoon with a visit to the on-board boutique to purchase souvenirs or admire passing scenery as the train travels through the Italian Dolomites. Later, afternoon tea is served in your cabin as you travel through the Brenner Pass. All too soon it is time to prepare to disembark as the train crosses the Venetian Lagoon and pulls into Santa Lucia station around 6 p.m.

On arrival, you will be transferred to the legendary Belmond Hotel Cipriani. (Transfer may be shared with other Orient-Express guests.)

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.

The remainder of the evening is at your leisure to explore the hotel, an attraction in itself. It offers several dining venues— our favorites were the formal Oro restaurant and the very popular and informal “Cip’s Club.” (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, saltwater, 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 3: Venice

Take breakfast in one of the Cipriani’s restaurants, or, perhaps privately on your balcony or terrace. 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 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 4: Florence

After breakfast at your hotel, you will be transferred by private boat to Venice’s Santa Lucia station, where you board the high-speed Eurostar Italia train to Florence mid-morning. Relax in your reserved, first-class seat for the two-hour journey through the beautiful Tuscany countryside. The price of your ticket includes complimentary beverages and snacks from the trolley.

Your private car and driver will meet you upon arrival at Firenze Santa Maria Novella 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 5: 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 6: Florence

Your journey ends in Florence today. Perhaps you want to extend your exploration of Italy, or linger in Florence…we can assist with additional arrangements.

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.