About your itinerary
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Don't forget that if something isn't quite right we can make changes to the itinerary.
Thank you for your email letting me know more fabulous pals are looking to join you for what is sure to be a memory of a lifetime! I am delighted to enclose your revised itinerary.
You will now see your trip starts in Florence, with three nights spread across four rooms during your time here. As before, we have your Chianti Safari, perfect for exploring Tuscany and its incredible wine & foodie fantasies.
In Rome, I have changed your hotel based on rates to the fabulous Fragrance St Peter – still a great hotel perfectly located, but with a slightly lesser rate so I could fit in what is yet to come! I have kept in your fabulous cooking class which I am sure will leave you all laughing, before heading to Naples for your Amalfi Coast experience.
To really do it right, I opted for your spot to be in the breathtaking town of Positano – this instagram perfect clifftop town offers a stunning beach and so many gorgeous restaurants and places to eat. You will be staying just a 15 min walk from town in the charming & gorgeous Hotel Vittoria Positano. This sweet 3* offers amazing views and the best way to maximise how much you are all looking to spend.
I also have added in an optional private full-day tour to Capri (price currently not included) to give you an idea of what we can do, however as we were at the region of $2,908.88 per person, I thought I best wait till I heard back following your thoughts from your friends & partners.
As the Amalfi is so pricey, it would be really hard to bring this below $2.5K per person, unless we were to potentially take one night off another city, or remove another altogether. I managed to guarantee a 2024 rate for your stay in 2025 from my contact at Hotel Vittoria to try my best to bring costs down for you, saving a fair few hundred per person, but this is only valid until Wednesday next week so if you love it, we will need to move swiftly to lock it in.
Deposit-wise, we are looking at $715.00 per person. Excited to connect early next week to chat everything through and hopefully I have nailed it!
Best travels,
Maria Gardner 
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 14th May 2025
Welcome to Florence
Welcome to Florence
Cradle of the Renaissance, romantic, enchanting and utterly irresistible, Florence (Firenze) is a place to feast on world-class art and gourmet Tuscan cuisine.
Few cities are so compact in size or so packed with extraordinary art and architecture masterpieces at every turn. The urban fabric of this small city, on the banks of the Arno river in northeastern Tuscany, has hardly changed since the Renaissance and its narrow cobbled streets are a cinematic feast of elegant 15th- and 16th-century palazzi (palaces), medieval candle-lit chapels, fresco-decorated churches, marble basilicas and world-class art museums brimming with paintings and sculptures by Botticcelli, Michelangelo et al. Unsurprisingly, the entire city centre is a Unesco World Heritage Site.
Italy's fashion industry was born and bred here. Homegrown designers Guccio Gucci and Salvatore Ferragamo opened haute-couture boutiques in Florence in the 1920s and shopping in the Tuscan capital has been stylish ever since. A-lister fashion houses lace Via de' Tornabuoni and a Pandora's box of specialist boutiques selling all manner of beautiful objects parade alongside family-run botteghe (workshops) in a glorious tangle of medieval backstreets. Watch fourth-generation Florentine goldsmiths and shoemakers at work, buy artisan scents evocative of the Florentine countryside and Tuscan sea breeze, and know the tag 'Fiorentina' is one of the finest international labels going.
Quality produce sourced locally, seasonally and sustainably is the holy trinity and Florentines share an enormous pride in their culinary tradition. Their city, surrounded by wine-rich hills, is a gourmet paradise where eating and drinking exceedingly well is mandatory. Be it a traditional bowl of earthy ribollita (bean, bread and veg soup), a tripe panino at a family-run food truck or a blue T-bone steak served in a market trattoria unchanged since 1915, dining in Florence is timeless and memorable. Raw cuisine, fish bistros, craft cocktails and the dazzling creativity of modern young Tuscan chefs add contemporary edge.
Stand on a bridge over the Arno several times in a day and the light and mood changes every time. At sunset hike to Piazzale Michelangelo to be dazzled by a palette embracing every known shade of soft pink, orange and fiery amber. Surprisingly small as it is, Florence looms large on the world's 'must-sees' list – and not just for its unmatched treasure chest of art. Rich in culture, backdropped by history and anchored by family, faith and food, the Florentine lifestyle is enviably sweet. Enjoy a go-slow afternoon passeggiata, indulge in an aperitivo at dusk, savour la dolce vita…
Private Vehicle from FLR to Kraft Hotel
Private Vehicle from FLR to Kraft Hotel
Upon your arrival into Florence, you will be greeted by two transfers and taken into the city ready for a fabulous three nights!
Kraft Hotel for 3 nights
Kraft Hotel for 3 nights
Located in a quiet but central neighbourhood in Florence near the Arno River, this modern, LGBTQ+ friendly hotel is just steps away from the historic city centre where you can discover fabulous architecture and world-famous art collections, the celebrated Duomo and bustling piazzas. Once the day is over, head back to the hotel to relax on the rooftop terrace and bask in the magnificent atmosphere of the city.
Its romantic rooftop dining terrace is a guest favorite for enjoying the free decent breakfast buffet or evening drinks. Dinner from an a la carte Mediterranean and Italian menu is also served here, and the panoramic city views are breathtaking. All of Kraft Hotel's guest rooms have an array of modern comforts including a minibar, tea/coffee facilities, and free Wi-Fi. The heated rooftop dipping pool is also a delightful city rarity.
Your room: Classic Room
2 x Classic Doubles & 1 x Classic Twin
Kraft Hotel's Classic Rooms offer a delightful spot from which to explore the city of Florence and it's surrounding highlights. Featuring comfortable double beds and modern bathroom amenities, all rooms are decorated in warm tones and elegantly furnished both with antique furnishings in style "maggiolini" and Luigi XV and XVI, as well as the most modern interior design.
Kraft Hotel for 3 nights
Kraft Hotel for 3 nights
Located in a quiet but central neighbourhood in Florence near the Arno River, this modern, LGBTQ+ friendly hotel is just steps away from the historic city centre where you can discover fabulous architecture and world-famous art collections, the celebrated Duomo and bustling piazzas. Once the day is over, head back to the hotel to relax on the rooftop terrace and bask in the magnificent atmosphere of the city.
Its romantic rooftop dining terrace is a guest favorite for enjoying the free decent breakfast buffet or evening drinks. Dinner from an a la carte Mediterranean and Italian menu is also served here, and the panoramic city views are breathtaking. All of Kraft Hotel's guest rooms have an array of modern comforts including a minibar, tea/coffee facilities, and free Wi-Fi. The heated rooftop dipping pool is also a delightful city rarity.
Your room: Triple Room
Your Triple Room offers a lovely double bed and a pull-out bed, perfect for groups of friends or throuples. Your ensuite offers an inviting shower with luxury amenities throughout.
Friday 16th May 2025
Chianti Safari: Off Road Tuscany Food & Wine Tour from Florence
Chianti Safari: Off Road Tuscany Food & Wine Tour from Florence
Today you will be leaving Florence for a full day exploring the beauty, the food and the wine of the iconic Chianti Region in a super fun way. From your hotel, make your own way to the meeting point where you will be greeted by your guide to start the day.
Get a true taste of Italy's famous Chianti region on this full-day wine and food tour departing from Florence. Led by an expert guide, travel through the Tuscan hills by a 4×4 off-road vehicle, stopping to visit a wine estate and historic villa, and a cellar specializing in bottles of Chianti Classico.
Your first stop of the day is at a winery belonging to one of the most prominent Italian families. Taste wines paired with cured meats and olive oils, and enjoy a guided tour of the historic wine cellars. Travel to the olive mill through the villa's underground tunnels, as well as to the garden.
Afterwards, head to a Tuscan winery restaurant and settle in for a 3-course meal, including regional specialties such as different types of fresh pasta and glasses of fine Chianti wine. (See the Itinerary for a sample menu).
The adventure continues as you continue your drive through the incredible countryside on our way to your final stop of the day. Here you will take a tour of the impressive villa and walk around the stunning grounds, soaking in the unique beauty and views, whilst learning more about wine before you sit for the final tasting of three wines paired with cheese. The perfect end to a truly unforgettable day.
Saturday 17th May 2025
Train from Florence Santa Maria Novella to Rome Termini
Train from Florence Santa Maria Novella to Rome Termini
After a beautiful three nights in the heart of Florence, you will make your own way to the train station to board your train to Rome. The journey takes approx 1.5hrs through the countryside, and I have upgraded you to 1st Class for additional comfort.
Proposed Train Times
Departs: 11:28AM, Florence
Arrives: 1:05PM, Rome Termini
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.
Fragrance St. Peter for 3 nights
Fragrance St. Peter for 3 nights
Fragrance St. Peter is a brand new stunning hotel located in the heart of Rome, a stone's throw from the Vatican Museums and St. Peter's Basilica. A historical structure, once a convent, was reinvented and adapted to offer a stay in welcoming and relaxing rooms. It has different types of accommodations, suitable for every need and desire. It offers a terrace overlooking the "Cupolone" and a relaxing winter garden, as well as convenient private parking.
The Monte del Gallo neighbourhood is adjacent to the Vatican and it seems that the area was part of the vast properties of Agrippina, Nero's mother, who also owned the Vatican and had houses and villas on the Janiculum. Monte del Gallo is a human-sized neighbourhood, warm and kind, elegant and popular at the same time. It takes just a few steps to immerse yourself in the atmosphere of Porta Cavalleggeri and Piazza San Pietro.
Your room: Triple Room
Your Triple Room offers a lovely plush double bed, with a pullout double sofa bed with spacious surroundings. Refresh in your ensuite bathroom with local amenities throughout.
Fragrance St. Peter for 3 nights
Fragrance St. Peter for 3 nights
Fragrance St. Peter is a brand new stunning hotel located in the heart of Rome, a stone's throw from the Vatican Museums and St. Peter's Basilica. A historical structure, once a convent, was reinvented and adapted to offer a stay in welcoming and relaxing rooms. It has different types of accommodations, suitable for every need and desire. It offers a terrace overlooking the "Cupolone" and a relaxing winter garden, as well as convenient private parking.
The Monte del Gallo neighbourhood is adjacent to the Vatican and it seems that the area was part of the vast properties of Agrippina, Nero's mother, who also owned the Vatican and had houses and villas on the Janiculum. Monte del Gallo is a human-sized neighbourhood, warm and kind, elegant and popular at the same time. It takes just a few steps to immerse yourself in the atmosphere of Porta Cavalleggeri and Piazza San Pietro.
Your room: Classic Double
2 x Classic Doubles, 1 x Classic Twin
Your Classic Double room offers a cozy and intimate, elegantly furnished and complete stay with all the amenities. Enjoy your ensuite bathroom with local amenities from the hotel.
Monday 19th May 2025
Traditional Pasta with Cocktails Drunken Cooking Class | Small-Group
Traditional Pasta with Cocktails Drunken Cooking Class | Small-Group
I know you guys were keen on a fabulous and fun cooking class, and no time in Rome is complete without a Drunken Cooking Class – the coolest school in town! That's right, learn to cook with a cocktail in hand, in the heart of Rome. What could be better?
In this cooking class, you’ll experience two of the best things about Rome – the food, and the drinks. The Spritz dates back as far as the 1800s, so when it comes to sparkling drinks, the Italians really do know what they’re talking about. As for the food – well, there’s nothing on earth like Italian food. Especially pasta. And in this class, you’re going to learn how to perfectly make both.
During the class, you’re going to make three of Italy’s most famous spritzes: Aperol, Campari and Limoncello.
Whilst your mixologist host teaches you how to make these staple Italian drinks you will also get hands-on with cooking your own fresh Italian Pasta. Then, you’ll learn one of Italy’s most famous sauces – carbonara or cacio e pepe, it’s up to you! Simply smother your pasta in it and enjoy!
Then it’s time to eat. Settle down with your new foodie friends, your third refreshing spritz, and enjoy a delicious meal. That’s how the Romans do it.
Tuesday 20th May 2025
Train from Rome Termini to Naples Central
Train from Rome Termini to Naples Central
After a gorgeous three night stay in Rome, it will be time to head to the Amalfi Coast. Make your own way to the train station for your train journey down to Naples, where your driver will be awaiting you on the other side. I have upgraded you all to First Class for extra comfort.
Proposed Train Times
Departs: 11:55AM, Rome Termini
Arrives: 1:10PM, Naples Centrale
Private Vehicle from Naples Centrale to Hotel Vittoria Positano
Private Vehicle from Naples Centrale to Hotel Vittoria Positano
Upon your arrival into Naples, you will be greeted by one of our friendly drivers and invited into your private vehicle to head to Sorrento, ready for an amazing stay with incredible views on the Amalfi.
Hotel Vittoria Positano for 3 nights
Hotel Vittoria Positano for 3 nights
The Hotel Vittoria is located in the upper part of the Fornillo district , one of the oldest in Positano. From its high position it enjoys a splendid panorama of the coast and the town and offers its customers the warm, familiar hospitality typical of a family-run hotel.
The center of the town of Positano can be easily reached in 15 minutes by walking along a street dotted with restaurants and boutiques or using the public shuttle service. Fornillo beach can be reached on foot in a few minutes.
Choosing the Hotel Vittoria for your holidays on the Amalfi Coast means spending a stay in absolute relaxation and tranquility without being too far from the sea and the centre. The hotel is also the ideal starting point for excursions that will allow you to discover the other towns of the Amalfi Coast such as Amalfi, Ravello, Atrani, Maiori, Minori but also Sorrento, Pompeii, Herculaneum and Capri.
Your room: Classic Triple Room
Your Classic Triple Room offers a cosy double with a sofa bed, as well as a beautiful terrace overlooking the gardens and mountainside. Your ensuite bathroom is perfect to refresh with your shower, and local amenities.
Hotel Vittoria Positano for 3 nights
Hotel Vittoria Positano for 3 nights
The Hotel Vittoria is located in the upper part of the Fornillo district , one of the oldest in Positano. From its high position it enjoys a splendid panorama of the coast and the town and offers its customers the warm, familiar hospitality typical of a family-run hotel.
The center of the town of Positano can be easily reached in 15 minutes by walking along a street dotted with restaurants and boutiques or using the public shuttle service. Fornillo beach can be reached on foot in a few minutes.
Choosing the Hotel Vittoria for your holidays on the Amalfi Coast means spending a stay in absolute relaxation and tranquility without being too far from the sea and the centre. The hotel is also the ideal starting point for excursions that will allow you to discover the other towns of the Amalfi Coast such as Amalfi, Ravello, Atrani, Maiori, Minori but also Sorrento, Pompeii, Herculaneum and Capri.
Your room: Classic Double Room
2 x Classic Doubles & 1 x Classic Twin
Located on the second floor, your Classic Double Room offers a balcony overlooking the sea and Positano. The balcony is equipped with a table and chairs. Very bright, furnished in Mediterranean style, your room is where the colors of blue and white prevail.
Thursday 22nd May 2025
Optional: Full-Day Capri Tour by Boat from Positano | Private
Optional: Full-Day Capri Tour by Boat from Positano | Private
Optional Tour
Price Not Included
Enjoy a half day or a full day trip and unveil the unforgettable beauty of Capri island, you will admire a scenic panorama, while getting the opportunity to swim in the most pristine and beautiful water you’ve ever seen, meet many fishes and get a stroll in one of the most celebrated shopping avenue in Italy.
You will meet your skipper, at the port, you will get on board of your private boat, ready to sail towards one of the most magnificent island in the world. Your skipper can tailor every detail of your excursion, you can decide to spend more than a few hours on the island, or you can opt for dive in each stunning location around the island.
This boat tour could start from Marina Grande (Positano) at your preferred time and after a few minutes sailing you will admire the delightful Li Galli islands, three small islands where, according to the legends, Ulysses met the sirens.
You will then move towards Punta del Capo, where is visible on a large boulder overlooking the sea, the welcoming bronze statue of “Gennarino, O ‘Scugnizzo di Capri”. The second step will be the White Grotto, a real captivating white-colored sea cave on the eastern coast of Capri. Stark white stones and turquoise waters, stalagmites and stalactites create an enchanting atmosphere.
After a while the captain will show you Villa Malaparte, the house on Punta Massullo, one of the best examples of Italian modern and contemporary architecture. It was the home of a famous Italian (and Tuscan) writer: Curzio Malaparte. He himself contributed with his drawings and his intuitions to this modern, linear and prestigious project.
Time for the Scoglio del Monacone and for the Faraglioni, three spurs of rock which rise up out of the sea. Their names are: Stella, Faraglione di Mezzo, Faraglione di fuori, or Scopolo. If you are very lucky you could observe a Podarcis sicula coerulea: these rocks are the only place in the world where you can find this blue lizard!
You can choose to swim here (you can do it anywhere, the water of Capri is magnificent in every centimeter of the coast!), or reserve this possibility for the next stop: the Green Grotto.
The Green Grotto is one of the most exciting highlight of the Capri boat tour, the place where, thanks to the reflection of the light between the rocks and the seabed, the poetic emerald green color of the water inside is so intense that you will feel a strong desire to dive among these waters. And you can, so, what are you waiting for?
After an amazing time out at sea, with the chance to disembark onto Capri itself, you will be ready to head back to Positano for a lovely final evening.
Friday 23rd May 2025
Transfer from Hotel Vittoria Positano to Capodichino Airport
Transfer from Hotel Vittoria Positano to Capodichino Airport
After a gorgeous three night stay in Positano, it will be time to head back to the US. Your private vehicles will collect you from your hotel and drive you back to Naples in enough time for your flight home.
What's Included
Your itinerary includes
- Private Transfers to/from Airports
- Stunning 4* Accommodations
- All breakfasts included
- 4 x Rooms throughout
- Private & Semi-Private Tours as listed
- Train Journeys throughout
- Upgraded First Class
- 24/7 emergency concierge service
Your itinerary excludes
- Optional Tours
- International flights
- Lunches & Dinners off ship (unless specified on tours)
- Hotel Pick-ups on Tours
- Travel insurance
- Resort Fees / City Taxes
- Visas (if applicable)
- Gratuities
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.