About your itinerary
?
Don't forget that if something isn't quite right we can make changes to the itinerary.
I am incredibly excited to present you with your spectacular trip to Italy and Greece, giving you the opportunity to spend five nights wining and dining in a dreamy Tuscan villa, followed by nine nights of island hopping around the gorgeous Greek islands of Ios and Naxos – all in total luxury, of course.
To make your trip spectacular from start to finish, I have included an array of my all-time favourite properties – including a very special upgrade in Naxos over your birthday. I've been able to confirm 2024 rates and save over $3,500 compared to 2025, so I'd recommend we get these on hold ASAP if you love what you're seeing.
I haven't included international flights as May 2025 schedules haven't been released just yet. We'll be able to add these into your booking around a year in advance.
I'll give you a call this morning to talk everything through, and I'm SO excited to hear your thoughts.
Jaike Rowe 
Your Itinerary In Detail
?
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 7th May 2025
Welcome to Tuscany
Welcome to Tuscany
A highly seductive medley of Renaissance cities, rolling hills and terraced vineyards, Tuscany offers the quintessential Italian experience. From the olive groves and cypress alleys to the romantic villages perched on rocky outcrops, the landscape here has become a symbol of the country as a whole.
Its truffles, olives, wines and cheeses combine in a rich culinary tradition that makes dining a pleasure all of its own. Yet, the region's greatest treasures are the medieval masterpieces of Florence, Pisa, Siena and San Gimignano and the astonishing legacy of art and architecture they hold.
Car Hire Between 7th - 12th May
Car Hire Between 7th - 12th May
I have included car rental during your five nights in Tuscany, allowing you total flexibility to explore this spectacular part of Italy. I have included a midsize car that will comfortably seat the four of you.
You will collect your vehicle on arrival into Florence or Rome Airport, and then drive to the beautiful Villa di Piazzano. From Florence the drive takes around 1h 30m, and from Rome around 2h 30m.
Your car rental includes:
– Unlimited miles
– Full tank on collection, to be returned full
– Full damage and theft protection
Villa di Piazzano for 5 nights
Villa di Piazzano for 5 nights
Down-to-earth luxury at this Renaissance country estate in the Tuscan hills. When you arrive at Villa di Piazzano, you’ll experience a warm Italian welcome that’s made visitors feel at home for over 500 years. This historic estate was originally the hunting lodge of Cardinal Passerini, a favourite of the Medicis. Wild boar may still be a seasonal delicacy here, but today this luxury hotel is devoted to far more relaxing pursuits.
From the moment you’re greeted at the door, Villa di Piazzano begins to work its magic. Time seems to move more slowly – allowing every day to be spent exactly as you wish. Wander from your peaceful, heritage-inspired room to the sun-soaked pool. Or grab a bike and head out to tackle some of those Tuscan hills. When you’ve worked up an appetite, sit down to an ultra-local Italian feast at the restaurant, where the vegetables are plucked fresh from the hotel gardens.
Set on the border between Tuscany and Umbria, Villa di Piazzano puts you in pride of place for discovering the region’s highlights. Explore captivating medieval cities like Siena. Or hop over the border to pretty Perugia. Cortona, with its Renaissance piazzas and ancient Etruscan heritage, is just 10 minutes away by car – and there are always the hotel's e-bicycles if you fancy a picturesque pedal. Of course, you’d be forgiven for staying put – Villa di Piazzano casts a spell that’s hard to break.
Your room: Classic Double
These rooms are located in the main villa and adjacent buildings featuring a dreamy queen bed with signature bed linens ensuring a dreamy night's sleep. With complimentary amenities, ultra-comfort bathrobes, and slippers, you'll have everything you need for a luxury stay in the Tuscan hills.
Thursday 8th May 2025
Wine Tours in Tuscany
Wine Tours in Tuscany
I haven't included a pre-arranged wine tour as we're a little far out to book for 2025, but I have included some dreamy inspiration about the tours on offer around the region.
Tuscany is known for its beautiful vineyards and world-renowned wines. There are several vineyard tours available in the region that offer visitors the opportunity to explore the vineyards, learn about the winemaking process, and taste some of the finest wines in the world. Here are a few popular vineyard tours in Tuscany:
1. Chianti Wine Tour: The Chianti region is famous for its red wines, and there are many vineyard tours available that focus on this area. These tours often include visits to multiple wineries, where you can learn about the production process and sample different Chianti wines.
2. Brunello di Montalcino Tour: The Brunello di Montalcino wine is one of the most prestigious and sought-after wines in Tuscany. A vineyard tour in this region will give you the chance to visit wineries that produce this wine, learn about the unique production methods, and taste the rich and complex flavors of Brunello di Montalcino.
3. Montepulciano Wine Tour: Montepulciano is another famous wine-producing region in Tuscany, known for its Vino Nobile di Montepulciano. A vineyard tour in this area will allow you to explore the vineyards, learn about the winemaking process, and taste the elegant and full-bodied wines produced here.
Monday 12th May 2025
Flight on TBC
Flight on TBC
| From | To |
|---|---|
| Rome Fiumicino Airport (FCO) |
Athens International Airport (ATH) |
| Departs | Arrives |
| 12-May-2025 09:50:00 | 12-May-2025 12:45:00 |
| Airline | Cabin |
| ITA Airways | Economy |
Welcome to Athens
Welcome to Athens
Equal measures of grunge and grace, Athens is a spirited mix of history and edginess. The Greek capital rewards open-minded travelers with spontaneous discoveries.
As you wander through the winding streets of Athens, you'll be transported to a world of ancient myths and legends. The Acropolis, with its towering columns and majestic temples, will leave you in awe of the city's rich history and culture. The Parthenon, one of the most famous landmarks in the world, is a sight to behold, with its intricate carvings and stunning architecture.
But Athens is not just about ancient history. The city is also a hub of modern culture and innovation. The vibrant neighborhoods of Monastiraki and Psirri are home to some of the city's best restaurants, cafes, and bars. Here, you can indulge in delicious Greek cuisine, sip on local wines, and soak up the lively atmosphere of the city.
Private Transfer from ATH to Ergon House
Private Transfer from ATH to Ergon House
On arrival into Athens Airport, you will be met by a fabulous Out Of Office representative and privately transferred to Ergon House, ready for a few nights in the heart of the city.
Ergon House for 2 nights
Ergon House for 2 nights
Completing this holistic hospitality experience built on the foundations of Greek Food, Ergon House offers contemporary living spaces spread over the floors above the marketplace. All rooms include the hotel's signature breakfast and come in four sizes, with privileged access to communal kitchens and lounges, a gym and a panoramic rooftop terrace.
The spaces are a collaboration with leading local designers and artists – the tribute to Greece ever-present in natural materials, traditional craft and references to the vernacular, paired with a strong contemporary line.
Large, double-glazed windows invite all the spectacle and none of the soundtrack to views of the Parthenon and city, or the buzz of the Agora. Seamless service is a given and we’ve done away with in-room dining because the whole Ergon House experience places food centre stage.
So, while the curated minibar delicatessen should tide you over, the Agora awaits some of the best food in town, or fresh market ingredients with which to make your own magic in one of the dedicated kitchens.
Your room: Small Room
Every comfort you need is considered in SMALL’s compact space with custom mood lights, fittings and furniture, arranged in an open layout that is loosely screened by the retro chic of breeze blocks used on the Greek islands in the ‘60s. The twin beds or a raised four-poster bed reminiscent of the traditional ‘ontades’ of Pelion is the centrepiece to ultra-contemporary interiors that feature an open closet and wireless work area.
Natural daylight floods through large double-glazed windows with atrium views as well as a glass brick feature wall. In the wet areas, walnut parquets transition to grey marble and patterned tiles inspired by medieval ‘xysta’ motifs found on the island of Chios. Beautiful basins, hand-carved from time-worn marble steps, are a pleasing contrast to sleek, brushed brass fixtures in a bathroom stocked with natural products that are custom-made for Ergon House.
Tuesday 13th May 2025
Private Tour of Athens
Private Tour of Athens
Today you will enjoy a historic tour of Athens with one of our incredible LGBTQ+ guides.
Be ready to enter one of the most important archeological site in the world: Athens' Acropolis! Enter the Acropolis from the south slope to avoid the crowds and also to visit the Dionysus sanctuary and Dionysus Theatre built in the 5th century BC. On your way to the Acropolis, enjoy the marvellous view that unfolds before your eyes.
Explore the mighty Acropolis on foot to see the glorious Parthenon, the Erechtheion, the Propylaia, the Nike Temple, the Agrippa Monument and other highlights. Learn more about its history, observe the statues from archaic period, Caryatids, and of course the Parthenon hall. Afterwards continue to the Agora, among the ruins of public buildings where we will see the temple of Hephaestus, the best preserved temple of the ancient times. The tour ends with a short walk to the ruins of the Roman Agora, in the heart of Monastiraki flea market area.
Wednesday 14th May 2025
Private Transfer from Ergon House to Athens Piraeus Port
Private Transfer from Ergon House to Athens Piraeus Port
This morning you will be picked up and privately transferred to Piraeus Port, in time for your early departure to the dreamy island of Ios.
Ferry from Athens to Ios
Ferry from Athens to Ios
This morning you will catch a ferry from Athens Piraeus Port to Ios Port. The ferry takes around 4 hours, offering dreamy views of the Aegean along the way.
Departure time: 7 am
Arrival time: 11 am
Ferry provider: SeaJets
Vessel: Worldchampion Jet
Seats: Standard
Schedules haven't been released for 2025, but I have estimated the timings based on 2024.
Welcome to Ios
Welcome to Ios
Ios, a captivating island located in the Cyclades archipelago of Greece, is a true paradise for travelers seeking a perfect blend of natural beauty, vibrant nightlife, and rich cultural heritage.
With its stunning golden beaches, crystal-clear turquoise waters, and dramatic cliffs, Ios boasts some of the most picturesque landscapes in the Aegean Sea. Whether you prefer secluded coves or bustling beach clubs, the island offers a wide range of options to suit every taste. Mylopotas Beach, the most famous beach on the island, is a long stretch of golden sand with shallow waters, making it ideal for families and water sports enthusiasts.
Beyond its breathtaking natural beauty, Ios is also steeped in history and culture. The island is home to numerous ancient ruins and archaeological sites, including the ancient city of Skarkos, which dates back to the 3rd millennium BC. Exploring these historical sites offers a glimpse into the island's rich past and the opportunity to learn about its fascinating heritage.
When the sun sets, Ios comes alive with its legendary nightlife. The island is renowned for its vibrant party scene, attracting young travelers from all over the world. The main town, Chora, is a maze of narrow streets lined with bars, clubs, and restaurants, where visitors can dance the night away and enjoy live music until the early hours of the morning.
Liostasi Hotel & Suites for 3 nights
Liostasi Hotel & Suites for 3 nights
Chic design comes together with the beauty of nature at Liostasi Hotel & Suites, an enchanting boutique hotel that has been recently renovated to provide an opulent atmosphere with alluring island and sea views. It has a serene spa, a gym area, a delightful pool with a bar, and an award-winning restaurant all within easy access of Chora.
Simplicity and oneness with nature best describes the experience at Liostasi Hotel & Suites. Minimalist décor places the emphasis on the stunning views framed by the windows, either the rugged beauty of the island or the sparkling blue of the Aegean Sea. This is the place to come to de-stress and reconnect – particularly in the spa where all-embracing therapies and treatments are the path to rejuvenation.
With 75 kilometres of white sandy beaches, Ios is a dream destination. Take a picnic and find a secluded bay to enjoy the sun and swim in the sea or spend hours relaxing by the Liostasi Hotel pool with the bar on hand for thirst-quenching drinks. In the evening, sit by the pool on the decked terrace of Grandma’s Restaurant for a romantic dinner accompanied by a gentle Mediterranean breeze.
Your room: Panoramic Sea View
Designed to offer a relaxed and graceful stay, the cozy Panoramic Sea View Rooms, feature bedrooms with a large double bed in minimal style, that reflect the Cycladic – chic Liostasi philosophy. The Panoramic Sea View Rooms outdoor balconies are an ode to Mediterranean living, boasting panoramic views of the main pool and the Aegean Sea.
Saturday 17th May 2025
Ferry from Ios to Naxos
Ferry from Ios to Naxos
This morning you will catch a fast ferry from Ios Port to Naxos Port. Today's ferry takes around 1 hour.
Departure time: 1 pm
Arrival time: 2:05 pm
Ferry provider: SeaJets
Vessel: Blue Star 1
Seats: Standard
Schedules haven't been released for 2025, but I have estimated the timings based on 2024.
Welcome to Naxos
Welcome to Naxos
The largest of the Cyclades, Naxos offers you the chance to explore golden-sand beaches, whitewashed farming villages and ancient ruins. The island has played a vital role in Greek mythology — this is where Dionysus met and married Ariadne and it’s home to one of the (many) caves said to be where Zeus was born. More historically, this was an important ancient trading hub and you can visit significant archaeological ruins here. During the Middle Ages, the main town was a major stronghold for the Venetians and later the Byzantines, who left behind a rich architectural legacy that you can explore.
Today, Naxos is quieter than its better-known sisters. Boasting a fertile interior, it’s the main agricultural producer for other Cycladic Islands, and you’ll be able to visit small farming villages that have largely disappeared elsewhere in the archipelago.
18 Grapes Hotel for 3 nights
18 Grapes Hotel for 3 nights
18 Grapes Boutique Hotel is the new 5 stars leading hotel in Naxos, faithful to the spirit of a heartwarming hospitality heritage: each one of the hotel’s 18 signature Rooms & Suites, is designed in an atmosphere of unpretentious elegance and soothing minimalism, offering the privilege of the undisturbed sea and sunset gazing, from the comfort of a private Air Jet Tub or pool.
This graceful 18 Grapes universe, is ideal to unwind and tune in the carefree island vibes: the hotel’s impressive two-level swimming pools and outdoor lounge decks, the high-end fitness centre, the wellness spa, the sophisticated roof terrace, the Grape Sunset bar restaurant, are shaping a unique holiday experience that underlines the authentic singularity of Naxos. The 18 Grapes cultured blend of people, services and ambience, is the perfect match for an outstanding stay.
Your room: Comfort Room with Plunge Pool
Your elegant Comfort Room with Private Heated Pool emphasises in indulging leisure, infused with the luxury of a stylish, tastefully decorated space. Ideal for those that love easy-going lavishness and the comfort of privacy.
Sunday 18th May 2025
Jaike's Naxos Recommendations
Jaike's Naxos Recommendations
Naxos is one of my all-time favourite islands, and here are a few of my personal recommendations:
Naxos is often overshadowed by its more well-known and well-Instagrammed neighbours, Santorini and Mykonos. But having been to all three, Naxos has an identity of its own. With its unspoilt and peaceful atmosphere with beautiful landscapes and smaller less built up towns to explore, it can provide a truly authentic experience. And how can you forget the sensational beaches the island has to offer!
Wander the beautiful streets of the old town, Chora
Santorini and Mykonos seem to get all the attention over on Instagram, but like I said above, Naxos’s stunning old town far surpasses them in a lot of ways. Pretty, intimate, winding streets with all the classic Greek tiled floors and blue doors, yet free from other travellers walking through them in their numbers. It’s all entirely pedestrianised, too.
Naxos' old town is a proper wonderland, typically Greek and endlessly intriguing. You think you’ve covered nearly all the flower-lined streets and then you turn a corner and find a whole new warren of them full of tavernas and shops.
Walk up to the Temple of Apollo (Portara)
This lovely walk is one of the top things to do in Naxos and won't leave you disappointed! The Temple of Apollo is the main landmark of Naxos and the first thing that strikes you when you arrive.
The temple stands on top of the hill on the little islet of Palatia, which was once properly part of Naxos but is now only clinging on via a slim causeway. Palatia is tiny and you can walk around its circumference in a few minutes. This means that the Temple of Apollo is stunning from every angle, with a marble doorway to frame either the island or the sea for your viewing pleasure. There are some other ruins around the main frame, too.
This is one of the things to do in Naxos that you can happily do more than once over the course of your stay if you have time. Visiting Portara in full sunshine is great, but as the sun sets you’ll see it in a new light. Literally.
Walk up to the Castle (Kastro)
Looming above Naxos old town is the citadel, kastro, built in the 13th century by a Venetian duke and still partly surrounded by walls. It’s a maze of quiet squares and alleyways leading to various monasteries and museums. It’s also got real houses inside, still very much lived in, and bustling cafés. Because you’re at the highest point of the town, you get some excellent views.
Dine at Outdoor Restaurant with Lampshades
The lampshades of Naxos may well become the next most-photographed thing on Instagram. They’re definitely incredibly picturesque and worth seeking out while you’re in the old town.
Buy a ‘magic’ Pythagorean Cup
Ceramics are a big deal on Naxos. There are shops everywhere, and I am sure you won't be able to resist buying one of the Pythagorean wine cups made on Naxos, complete with a ‘magic’ trick. A Pythagorean cup is a practical joke designed to teach any greedy drinkers who don’t know their limits a lesson.
Pythagoras – yes, he of the theorem that everyone learns in school and then forgets in real life – apparently also invented this cup. If you fill it up beyond a certain point, it creates a siphon effect and all the booze pours out of the bottom, ruining the drinker’s outfit and of course delivering much hilarity for all their mates.
Tuesday 20th May 2025
Ferry from Naxos to Athens
Ferry from Naxos to Athens
This morning you will catch the ferry back from Naxos Port to Athens Piraeus Port. The ferry takes around 3 hours 20 minutes, offering dreamy views of the Aegean along the way.
Departure time: 1:30 pm
Arrival time: 4:50 pm
Ferry provider: SeaJets
Vessel: Worldchampion Jet
Seats: Standard
Schedules haven't been released for 2025, but I have estimated the timings based on 2024.
Private Transfer from Piraeus Port to Sofitel Athens Airport
Private Transfer from Piraeus Port to Sofitel Athens Airport
On arrival into Athens Piraeus Port, you will be picked up and privately transferred to the Sofitel Athens Airport.
Sofitel Athens Airport for 1 night
Sofitel Athens Airport for 1 nights
Sofitel Athens Airport luxury hotel is just 50m away from the arrival and departure terminals of Athens International Airport and only 35 minutes from central Athens by metro. The hotel is the only one to be located within the airport, overlooking the Messoghia Valley.
Your room: Superior Room
Fully renovated rooms of 28 sq.m. combining luxury and comfort. Beautifully appointed superior rooms featuring an open plan bedroom with a queen bed, a lavish bathroom with bathtub and a separate shower. An excellent range of upgraded amenities is offered to meet your needs. A unique, relaxed atmosphere to enjoy every single moment of your stay.
What's Included
Your itinerary includes
- Car rental between 7th – 12th May
- Midsize vehicle with space for 4
- 5 nights at the Villa di Piazzano, Tuscany
- 2x Classic Double Rooms with breakfast
- Flight from Rome to Athens with luggage
- Private transfer from Athens Airport to hotel
- 2 nights at Ergon House, Athens
- 2x Small Rooms with breakfast
- Private tour of Athens
- Private transfer from hotel to Athens Piraeus Port
- Ferry from Athens to Ios
- 3 nights at the Liostasi Hotel & Suites, Ios
- 2x Panoramic Sea View with breakfast
- Ferry from Ios to Naxos
- 3 nights at the 18 Grapes Hotel, Naxos
- 2x Upgraded Comfort Rooms with breakfast
- Ferry from Naxos to Athens
- Private transfer from Athens Piraeus Port to hotel
- 1 night at the Sofitel Athens Airport
- 2x Double Rooms
- 24/7 emergency concierge service
Your itinerary excludes
- International flights – to be added when released
- Transfers in Ios and Naxos – can be added
- Travel insurance
- 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.