About your itinerary
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Don't forget that if something isn't quite right we can make changes to the itinerary.
Dear Abbye & Jen,
Welcome to Italy
I am incredibly excited to present you with your spectacular Italian honeymoon, giving you the opportunity to explore the dreamy cities of Rome and Sorrento as well as some bonus time in the stunning Tuscan countryside in the scenic Siena.
I have curated a stunning itinerary that maximises your time in each destination, including an array of beautiful boutique hotels, bucket-list tours, and upgraded trains from place to place.
Your itinerary begins with 3 nights in Rome at the not only beautiful but perfectly located Leon's Place. I have included breakfast for you here so you are filled and ready for the day's exploration. I know how much you love history and I wanted to include some tours that really highlight the history of Rome.
You will start off your tours with a Jewish Ghetto & Trastevere Tour, a great way to explore two of Rome’s most historically rich neighborhoods. It's then an early rise the next day but it will be 100% worth it with your early entry into the Vatican, meaning you'll be amongst the first people to enter the museums and you'll get to see the Sistine Chapel, in all its glory. I have also included your Colosseum tickets for this afternoon for you to enjoy a behind-the-scenes access tour.
Knowing that you love smaller towns over the big cities, I had to include some time in Siena, situated on the Tuscan hillside. Rich in history and lovely landscapes I know this is going to be the perfect place for your time in Tuscany. I have arranged a stay in a converted monastery just a short distance from Siena itself.
While in Siena I have arranged some tours and experiences for you both, starting with an amazing cooking class with wine tasting. I have chosen this particular experience for you due to its location and beautiful views. I know you also like to walk around and get to know the local culture so I have included a private walking tour with one of our amazing guides taking in the local life, churches, and monuments as well as Siena's history.
To round off an already beautiful stay, you'll enjoy some time on the iconic Amalfi Coast at the Grand Hotel Ambasciatori in Sorrento. While in Sorrento I wanted to include some amazing experiences for you while keeping some free time for you to relax and enjoy eachothers company. I have therefore decided on an amazing tour of Capri, as this is not to be missed, and as your itinerary draws to an end you'll have a perfect honeymoon end to your trip with a lovely sunset boat trip just for the two of you.
I have ensured that while in Sorrento you will have a gorgeous room as I have upgraded you to the panoramic ocean view junior suite. You'll be able to enjoy an Aperol or a glass of fizz while you watch the sunset from your balcony.
With all of your transfers between places, dreamy accommodation, breakfasts as well as your tours you really won't have to worry about a thing. I will be on hand to ensure everything runs seamlessly from start to finish.
Having pulled some strings with my contacts to honor 2024 pricing, do let me know if you love what you are seeing and hopefully, we can take advantage of these for you.
I have absolutely loved pulling this together for you and I hope you love it too! I'm SO excited to catch up tomorrow. Feel free to reach out if you have any questions in the meantime.
Have a great day and enjoy!!
Best wishes,
Samantha McCormack 
Your Itinerary In Detail
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This itinerary has been tailor-made for you. No two itineraries are the same and we are always able to make changes if something isn't quite right.
Wednesday 23rd April 2025
Welcome to Rome
Welcome to Rome
A heady mix of haunting ruins, awe-inspiring art and vibrant street life, Italy’s hot-blooded capital is one of the world’s most romantic and charismatic cities.
Rome is the biggest and arguably the most fascinating city in Italy. You could spend a month here and still only scratch the surface. It’s an ancient place, packed with the relics of over two thousand years of inhabitation, yet it’s so much more than an open-air museum. Rome’s culture, food, and people make up a modern, vibrant city that is deserving of all the visitors that travel there every year. As a historic centre, it is special enough; as a contemporary European capital, it is utterly unique.
Private Vehicle from Rome Fiumicino Airport to Leon's Place
Private Vehicle from Rome Fiumicino Airport to Leon's Place
Upon arrival at Rome Airport, you will be met by an Out Of Office representative and privately transferred to Leon's Place, perfectly located to enjoy everything Rome has to offer.
Leon's Place for 3 nights
Leon's Place for 3 nights
This stylish hotel has a real boutique feel as well as a blend of traditional charm and modern luxury. It also has an enviable setting close to the Piazza della Repubblica, Via Veneto, Villa Borghese Gardens and the Via Condotti shopping area. The cool interior features of this chic property have contrasting tones and details that blend perfectly with the building’s historic charms – this is contemporary Italian design at its finest.
The hotel is home to the glamorous ‘Visionnaire Cafè which prides itself on creative cocktails and mouth-watering hors d’oeuvres. The bar and its shaded courtyard are the perfect places to sip a refreshing glass of prosecco after a busy day spent discovering famed Roman attractions such as the Trevi Fountain and the Spanish Steps. You can also make use of the hotel’s leisure facilities which include a steamroom, Jacuzzi and massage services.
The modern feel of the rooms is reflective of the hotel as a whole. The grey and white tones and space-maximising mirror details are complemented by chic and comfortable furnishings. The Classic Rooms offer a great value choice while the Deluxe Rooms are more spacious.
Your room: Classic Room
The luminous bedrooms of Leon's Place are spacious and elegantly furnished, with a study in precious materials combined with the modernity of the spaces. Each classic room is curated in detail, with a unique design, high decorated ceilings and beautiful marble bathrooms.
Thursday 24th April 2025
Jewish Ghetto & Trastevere Tour | Semi-Private Experience
Jewish Ghetto & Trastevere Tour | Semi-Private Experience
Your Jewish Ghetto & Trastevere Tour starts in Piazza Trilussa at the fountain of Ponte Sisto, which leads you to the charming streets of the Trastevere neighborhood. Known for its narrow, quaint streets, and abundance of tasty restaurants, this area used to be the home to a large Jewish community that dates back to the Roman Republic until the end of the Middle Ages. Your expert guide will share with you fascinating and enriching stories about this enchanting area of the city. In Trastevere, you will visit one of Rome’s most ancient Churches, the Basilica of Santa Maria, to admire its beautiful golden mosaic interior.
Your Trastevere Tour continues by crossing the famous island in the River Tiber, the Isola Tiberina. This small island is filled with the greatest secrets of Rome’s origins. From the island, you will get a glimpse of Rome’s most ancient bridge, Ponte Fabricio, which your guide will point out to you.
The last stop of this semi-private tour is the Jewish Ghetto, stopping first in front of the Great Synagogue of Rome. Your guide will share with you its history. Should you like to go inside, you can do so at the end of your tour. You will hear stories of the oppressive foundations of this area, where its inhabitants lived in overcrowded and unjust conditions, and the eventual destruction of the ghetto walls and absurd regulations. Enjoy stories from Ancient Rome as you admire the Teatro Marcello and the temple built by Augustus Caesar that sits just next to it.
You will finish your tour in the heart of the Jewish neighborhood, where your guide will join you in savoring the moment with an espresso or gelato on us!
Friday 25th April 2025
Semi-Private Early Morning Vatican Tour
Semi-Private Early Morning Vatican Tour
Your Semi-Private Early Morning Vatican Tour will begin near the Vatican Museums’ entrance. Here you will meet your professional and charismatic tour guide. Yo'llu to be among the first to enter the storied halls of the Vatican Museums and see the Sistine Chapel, in all its glory.
The tour will begin with the Pinecone Courtyard and Octagonal Courtyard. Learn about the greatest statues of antiquity. From the mysterious composition of the Greek statue of the Laocoon, to the Apollo Belvedere and the Belvedere Torso, which despite it’s ruined state, inspired generations of artists. Then, stop to admire the art and decoration of the Gallery of the Maps and the Gallery of the Tapestries.
Then, onto to the world-renowned Sistine Chapel, Michelangelo’s masterpiece. Because this Chapel is the number one attraction inside the Vatican, LivTours believes it is important to give guests the time and space they need to fully appreciate it. Stand in amazement as you gaze onto Michelangelo’s awe-inspiring ceiling frescoes. Wonder over the breathtaking “The Last Judgement” before the major surge of crowds.
Your tour will continue by visiting the Raphael Rooms before the rush of tourists. Guests will be privy to some of the most important works of art in the museum – all without the rush of the usual crowds around them. With your tour guide by your side, you’ll learn about the intriguing stories and meaning behind the paintings that adorn the walls of the pope’s private apartments.
Once you’re done, you’ll head directly into St. Peter’s Basilica. This VIP access saves time and allows you to skip-the-line. Once inside, you’ll be greeted by the breathtaking space, which is the largest Catholic church in the world. Two of the glorious works of art that you will get to see up close include Michelangelo’s Pietà and Bernini’s Baldacchino. Before you leave St. Peter’s Basilica, your guide will tell you about the Papal Tombs and share how to access the dome of St. Peter’s. Conclude your Early Morning Vatican Tour by walking around Piazza San Pietro Square and taking in the grandeur that is St. Peter’s.
Colosseum Tour with Underground, Arena & Gladiator Gate with Roman Forum
Colosseum Tour with Underground, Arena & Gladiator Gate with Roman Forum
Your tour will begin as you approach the Colosseum, exploring its architecture and discovering why Emperor Vespasian took the unusual step of building an amphitheater within the city walls. With this tour, you won’t have to wait in line for tickets, just a quick security check before you are standing inside the Colosseum, under the arches where spectators used to enter to experience the most brutal of entertainments.
This tour will take you to two restricted access areas inside the Colosseum: the underground area and the Arena Floor. You’ll understand what it was like for the gladiators underground in the semi-darkness, surrounded by terrified animals, waiting to be hoisted up to stand in front of the crowds. From the Arena Floor, you’ll have an incredible view of the entire amphitheater, as the gladiators did when they walked through the Gladiator Gate to the deafening roar of 50,000 cheering spectators.
And what about the people who came to watch the games at the Colosseum? In the part of the Colosseum open to the general public, you’ll visit the first tier and look down onto the arena, get your first glimpse of the Forum, and visit the Imperial box.
Outside, you’ll pass the Arch of Constantine and skip the line into the Roman Forum. With stories that educate and entertain, your guide will bring the complexity of more than 2000 years of history to life. You will see the most famous sites of the Forum, including the Arch of Titus, the Temple of the Vestal Virgins and the spot where Julius Caesar was cremated.
Saturday 26th April 2025
Train from Rome (Termini) to Florence (Firenze Santa Maria Novella)
Train from Rome (Termini) to Florence (Firenze Santa Maria Novella)
This morning you will catch a local taxi / Uber to Rome's Termini Station, in time for your direct train up to Florence. Schedules haven't been released for April 2025 just yet, but I have included estimated times below:
Departure: 11.05 am
Arrival: 12.31 pm
The train takes around 1h 26m, offering dreamy views of rural Italy en route. On the other side, you will take a local taxi / Uber to your hotel.
Private Vehicle from Florence (Firenze Santa Maria Novella) to Certosa Di Maggiano
Private Vehicle from Florence (Firenze Santa Maria Novella) to Certosa Di Maggiano
On arrival in Florence, head to the pre-determined meeting location to meet your driver. You'll then be invited into your private transfer and taken to the historic town of Siena.
En route enjoy a 75-minute stop at Colle Val d'Elsa.
Colle Val d'Elsa
Colle Val d'Elsa
This charming Italian town and commune in Tuscany is renowned for its production of crystal glassware and art, amounting to 15% of the world’s total production. But long before its industrial sector became what it is today, Colle di Val d’Elsa was rocked by a turbulent past. Due to its position, close to both Florence and Siena, the town has seen several notable conflicts including a famous battle during the wars of the Guelphs and Ghibellines in 1269, and a siege by Neapolitan troops in 1479. The oldest part of the town is the “colle alta”, the higher part, with a well-preserved medieval center. Visitors will enter through the ancient and monumental Porta Nova and following the narrow, winding lanes as they admire the 15th- and 16th-century noble houses and tower houses, making their way to Palazzo Campana, which marks the entry to the oldest part of Colle – the castle.
Welcome to Sienna
Welcome to Sienna
Siena is a city where the architecture soars, as do the souls of many of its visitors. Effectively a giant, an open-air museum celebrating the Gothic, Siena has spiritual and secular monuments that have retained both their medieval forms and their extraordinary art collections, providing the visitor with plenty to marvel at. The city's historic contrade (districts) are marvelous too, being as close-knit and colorful today as they were in the 17th century, when their world-famous horse race, the Palio, was inaugurated. And within each contrada lies vibrant streets populated with artisanal boutiques, sweet-smelling pasticcerie (pastry shops) and tempting restaurants. It's a feast for the senses and an essential stop on every Tuscan itinerary.
Certosa Di Maggiano for 3 nights
Certosa Di Maggiano for 3 nights
Minutes away from the center of Siena, in the beating heart of Tuscany, there is a place where time has stopped and relaxation is guaranteed. It is the Certosa di Maggiano, an antique monastery where beauty, design, tradition, and nature co-exist in total harmony.
Vieri Michelangioli and Gaia Marconi are the new managers of La Certosa – partners in life who blend his lifetime of experience in the hotelier business with her creativity and unique approach to hospitality in order to create a colorful and passionate atmosphere for those who pass through their doors.
A fairytale two steps away from the bustling city. Refuge from daily life immersed in shades of green. A place where beauty is found in every corner, including our imperfections.
Your room: Deluxe Room
Your deluxe room offers a unique feel entwining contemporary details with whimsical elegance. Overlooking gardens and olive groves perfectly combines comfort and design with a beautiful landscape. The perfect combination of soft linens and cool floors and a scrumptious king-sized bed will be sure to ensure a dreamy stay.
Sunday 27th April 2025
A Brunello Cooking Class with Vineyards View
A Brunello Cooking Class with Vineyards View
Today you will discover the fine food and wine of the Siena region with your own private guide on a full-day tour in Tuscany. Taste some of Tuscany’s great wine and cheese, take a cooking class, go to wine estates, and have a delicious lunch.
Your private chef is ready to show you how Tuscans get down with food. And after your hard work in the panoramic outdoor kitchen overlooking the rolling vineyard hills, you deserve a private wine tasting, along with a tour of the 13th-century Tuscan castle that now hosts the famous Tricerchi wine cellar.
Finish the perfect day on the sun-kissed terrace overlooking the breathtaking wine country!!
Monday 28th April 2025
Private Secret Siena Walking Tour
Private Secret Siena Walking Tour
Today you will meet your guide at Piazza del Campo and set off your walking tour in the morning or afternoon. As this is a private tour, the 3-hour itinerary can be customized to your interests.
Designed for visitors with more in-depth knowledge of Siena, the personalized route takes you past churches and other monuments that do not require an entrance fee. (Admission to museums is your own expense.) Learn about Siena’s golden age of architecture and discover cultural treasures that take you beyond a typical tour of the medieval town.
Off the beaten path, you'll head down alleys and streets that immerse you in local life as well as Siena's history. Hear fascinating tales about resident artists and neighborhoods such as the 17 contrades (districts) along the Palio di Siena, a horse race held in the town’s main square twice a year. Visit the Church of the Madonna di Provenzano and the Basilica di Santa Maria dei Servi, a beautiful church that holds Siena masterpieces.
You'll come across panoramas of town and have the opportunity to take some unusual pictures. Continue to the medieval Fountain of Fontebranda, where your guide will illustrate the peculiar geology of the area and how water has shaped these hills and their civilization.
Tuesday 29th April 2025
Private Vehicle from Florence (Firenze Santa Maria Novella) to Certosa Di Maggiano
Private Vehicle from Florence (Firenze Santa Maria Novella) to Certosa Di Maggiano
On arrival in Florence, head to the pre-determined meeting location to meet your driver. You'll then be invited into your private transfer and taken to the historic town of Siena.
En route enjoy a 75-minute stop at Colle Val d'Elsa.
Train from Florence ( Firenze Santa Maria Novella) to Naples
Train from Florence ( Firenze Santa Maria Novella) to Naples
It's time to head to the stunning shores of Amalfi. Schedules haven't been released for April 202 just yet, but I have included the following.
Departure: 10.43 am
Arrival 1.43 pm
The journey takes around 3h.
Welcome to Sorrento
Welcome to Sorrento
A small resort with a big reputation, Sorrento is a town of lemons, high-pedigree hotels and plunging cliffs that cut through the heart of the historical core.
The town’s longstanding popularity stems from its location at the western gateway to the Amalfi. It’s also on the train line to Pompeii and has regular fast-ferry connections to Naples and Capri.
Tourism has a long history here. It was a compulsory stop on the 19th-century 'Grand Tour' and interest in the town was first sparked by the poet Byron, who inspired a long line of holidaying literary geniuses – including Goethe, Dickens and Tolstoy – to sample the Sorrentine air. The romance persists. Wander through Piazza Tasso on any given Sunday and you’ll be exposed to one of Italy’s finer passeggiatas (strolls), snaking past palatial hotels, magnificent marquetry shops and simple Campanian restaurants serving gnocchi alla sorrentina finished off with a shot of ice-cold limoncello.
Private Vehicle from Naples Train Station to Parco dei Principi
Private Vehicle from Naples Train Station to Parco dei Principi
On arrival in Naples, you'll be met by your driver at a pre-determind location and invited into your private transfer to take you to the stunning shores of Sorrento.
En route, you'll take a pit stop at the historic Pompeii.
Pompeii
Pompeii
In 79 AD, waves of volcanic runoff and ash buried Pompeii, one of the Rome’s most active and splendid cities. The speed and magnitude of the event left the city frozen in time, preserved as it was.
Today, excavations of the ancient metropolis have revealed some of the most significant insights into Roman art, customs, trades, and the brick-a-brack of everyday life. Walking the 2000-year-old streets reveals a wealth of architectural styles. Pompeii didn’t segregate its neighborhoods based on income, so you'll find affordable apartments are next to lavish villas. The city’s best-preserved home is the House of the Vetti, where you can admire richly frescoed entertainment rooms, and a central courtyard where a pool is surrounded by a formal garden. The city enjoyed an abundance of water, and used an aqueduct-fed reservoir to supply everything from public fountains to a street-cleaning system.
Grand Hotel Ambasciatori Sorrento for 4 nights
Grand Hotel Ambasciatori Sorrento for 4 nights
Formerly the summer residence of a Piemonte nobleman, this splendid 19th-Century villa is now an elegant hotel boasting a dramatic setting. Perched on a clifftop, the views over the coastline and Bay of Naples are simply breathtaking. Sorrento is just a ten minute walk away, making this gem of a hotel a great base for exploring the local area. Soothe aching muscles in the outdoor pool with hydro-massage or relax under the shade of palm trees on the sun terrace. For a change of scenery, take the internal lift down to the private beach.
Restaurant Le Muse, which also houses the Vesuvio Terrace, has delightful views over the Bay of Naples, which are best enjoyed at sunset. When it's time to indulge in a refreshing cocktail or two you have a choice of three bars with different settings – overlooking the gardens, at the bottom of the cliff facing the sea or on the poolside terrace overlooking the sea.
All of the rooms are classically furnished. Double Balcony Garden View Rooms overlook the gardens, but if you long for a glimpse of the sparkling sea then it's worth upgrading to a Double Balcony Partial Sea View Room or a spacious Suite Balcony Sea View.
Your room: Deluxe Junior Suite Ocean View
Mediterranean colours and local ceramics highlighting the natural light of the room. These type of rooms carved in a rocky cliff overlooking the sea have the ability to feel both spacious and intimate. Every area is formed with space to rest and to relax starting from the balcony with a breathtaking view on the bay of Naples and Mount Vesuvius.
Not to mention the spectacular scenery of the Ischia and Procida Islands nearby as well as the whole outlined coastline. A Rock-cut elevator leads down from rooms' floor directly to the sea level at the private rocky beach with jetty and sundeck.
The Bathrooms with the dazzling design are very large and are featuring a double sink, bathtub, walk-in shower with a rainfall showerhead, separate toilet as well accessories like attentive complimentary toiletries, magnifying mirror, bathrobes, slippers, hairdryer, direct dial telephone just to mention a few.
Friday 2nd May 2025
Capri Tour | Semi-Private Full Day Experience
Capri Tour | Semi-Private Full Day Experience
Your amazing Capri Tour starts in Sorrento where you will hop on a ferry to Capri with your guide and other travelers on your semi-private tour. Famous for being the most exclusive and upmarket island in the Mediterranean, this is a day to rub elbows with the rich and possibly famous. Your local guide will have tickets ready, ensuring that you will board the morning ferry to the beautiful Island of Capri. Upon arrival, you will set off in a motor boat to go straight to the beautiful and famous Blue Grottoes. Weather permitting, you will stop at the blue grottoes and visit the interior.
Once back in the Capri port, your guide will organize an open-topped taxi to take you and your group up to the clifftop town of Anacapri. Anacapri might look like it is the top of the island, but to reach the peak you will need to take a short ski-lift ride. The view from the top of the island is just stunning and you will be able to capture unique photos of the stunning island, its crystal clear waters, and also the farther island of Ischia and the Gulf of Naples with Mt Vesuvius in the background.
Back down the hill by taxi to Capri with your local expert guide where you will enjoy a short walking tour of the town and the amazing gardens of Augustus. Your guide will leave you with suggestions for lunch (not included in the price of the tour) and some free time activities. This is sure to be the perfect day in Italy!
Private Amalfi Coast Sunset Yacht Cruise
Private Amalfi Coast Sunset Yacht Cruise
It's your final evening, and today's tour will be the perfect way to close your spectacular Italian honeymoon.
Enjoy a truly magical sunset cruise around the breathtakingly beautiful Amalfi Coast on this private sunset yacht cruise aboard OOO's super-luxury 2023 Tornado 38. With an open bar serving wine, beer, and prosecco, relax on the sun deck of this brand-new speedboat.
The 2023 Tornado 38 is designed to be fast, stylish, and the latest word in maritime luxury. Enjoy speeding out to sea, the wind in your hair, to watch the famously stunning sunset over the Amalfi’s charming coastal villages, the dramatic cliffs, ancient rock formations, tiny islands, and the vast ocean.
Saturday 3rd May 2025
Private Vehicle from Grand Hotel Ambasciatori Sorrento to Capodichino Airport
Private Vehicle from Grand Hotel Ambasciatori Sorrento to Capodichino Airport
It's time to head home along with all the wonderful memories you have made on this incredible adventure. This morning you will be picked up from the Grand Hotel Ambasciatori Sorrento and privately transferred to Naples Airport, in time for your return flight home.
What's Included
Your itinerary includes
- Private transfer from Rome Airport to hotel
- 3 nights at Leon’s Place, Rome
- Classic Room with breakfast
- Jewish Ghetto & Trastevere Tour | Semi-Private Experience
- Semi-Private Early Morning Vatican Tour
- Colosseum Tour with Underground, Arena & Gladiator Gate with Roman Forum
- Train from Rome to Florence
- Upgraded seating
- Private transfer from Florence to Siena
- Via Colle Val d’Elsa
- 3 nights at the Certosa Di Maggiano
- Deluxe Room with breakfast
- A Brunello Cooking Class with Vineyards View
- Private transfer from Siena to Florence
- Train from Florence to Sorrento
- Upgraded seating
- Private transfer from Naples train station to the Grand Hotel Ambasciatori
- Via Pompeii
- 4 nights at the Grand Hotel Ambasciatori, Sorrento
- Upgraded Deluxe Seaview, with breakfast
- Capri Day Trip
- Private Amalfi Coast sunset cruise
- Private transfer from hotel to Naples Airport
- 24/7 emergency concierge service
Your itinerary excludes
- International flights
- Transfer to train stations in Rome
- Local hotel taxes
- Visas (if applicable)
- Travel insurance
Important Information
Travel Advice
It is important to seek independent and up-to-date advice when travelling to any foreign country. Many of our customers ask us to keep them up-to-date on the existing legal position regarding LGBT rights in the country to which they are travelling. You can find up-to-date details on our website under the country which you are travelling to. They are provided as a guide only and laws can change frequently. You should seek advice from the relevant authorities and embassies before travel (if applicable).
Travel Insurance and Terms and Conditions
It is a condition of booking with Out Of Office that you have adequate insurance cover for your trip at the time of booking. Please also ensure you have referred to our terms and conditions which can be found at www.outofoffice.com/terms-and-conditions. Please note that as each booking is tailor-made for you we only confirm the itinerary once we have received a deposit. There is a small chance that availability on some items quoted may change. If this is the case we will book similar accommodation and let you know.