Luxury 11-Day Relaxed Italy Self-Drive Road Trip Vacation With Itinerary from Florence to Pisa and Rome
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Discover Florence, Pisa, Rome, and Santa Maria degli Angeli on a luxurious, relaxed 11-day road trip in Italy. Immerse yourself in a world of elegance, as Italy stands out as one of the ultimate luxury holiday destinations for travelers seeking an unforgettable adventure.
Italy offers the ultimate luxury holiday experience for anyone up for an unforgettable adventure, including couples, families, solo travelers, and friends.
Your exclusive luxury holiday package will bring you to the country's most popular attractions and restaurants in the best destinations in Italy. With this perfectly planned itinerary, you will stay 3 nights in Florence, 1 night in Pisa, and 6 nights in Rome, experiencing a stress-free luxury vacation in Italy.
Finding the perfect luxury lodging is going to make your vacation in Italy feel truly special. The home for your 11-day luxury holiday will be only the most exclusive 5-star hotels in Italy. You will choose from the best selection of luxury hotels and places to stay, all conveniently located along your carefully planned self-drive route.
Upon arriving in Italy, you will collect the luxury rental vehicle of your choice. We will provide you with the best car rental for the entirety of your 11-day luxury self-drive holiday, including CDW insurance. From there, you will drive off at a relaxed pace to discover some of the best travel destinations in Italy.
Throughout your exclusive vacation in Italy, you will get to experience some of the best attractions and activities offered in the country. Each moment promises to be filled with unforgettable memories and unique experiences.
Between attractions and activities, you will have plenty of time to stroll along the best shopping streets and markets in Italy. We recommend you take the opportunity to explore the shopping experiences available to you in Florence. Here you can find unique souvenirs to preserve the memory of your relaxed luxury holiday in Italy.
This exclusive travel plan is designed to include everything you need to have the best vacation in Italy. By booking this luxury holiday package, you can avoid spending hours researching and planning your 11-day road trip in Italy. Let the experts figure out the details, so you can focus on enjoying.
To deliver the best experience possible, we make it easy for you to customize each day of your luxury holiday in Italy before and after booking. Our flexible trip planning means you will be able to explore Florence, Pisa, Rome, and Santa Maria degli Angeli at your own pace.
Book with us to get access to 24/7 personal travel support throughout your entire journey. Enjoy a step-by-step guide in our easy-to-use mobile app, including all travel documents for your exclusive getaway to Italy.
The best services in Italy fill up quickly, so book your luxury vacation package in advance. Select a date and start planning your relaxing luxury holiday in Italy today!
Itinerary summary
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Day 1 – Florence - arrival day
- Florence - Arrival day
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- piazzale Michelangelo
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Your relaxed luxury holiday in Italy begins as soon as you reach the city of Florence, your home for 2 nights. There, you’ll pick up the luxury rental vehicle of your choice and set off on a relaxed drive to discover Italy.
Florence is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out Piazzale Michelangelo or taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.
Tonight, you will be treated to a stay at one of the best luxury hotels in Florence. We have picked out three of the most exclusive luxury lodging and hotel options for you to choose from.
Exploring new destinations can leave you craving great food and drinks. Satisfy your cravings and unwind by visiting the finest restaurants and bars in Florence.
Make sure to book a table at Ristorante Oliviero 1962, a popular restaurant in Florence. This acclaimed restaurant and its mouthwatering dishes have earned the admiration of countless food lovers. Alternatively, experience a taste of Florence at Di Poneta Novoli, a popular local restaurant. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. Another top-rated restaurant to try is Caffe San Firenze. As a dining spot that gains high praise from guests, it’s an ideal choice to enhance your time to Florence tonight.
Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Manifattura stands out as an excellent choice for a post-dinner cocktail. Alternatively, Se·sto On Arno Rooftop Bar offers an ideal atmosphere to enjoy the pleasures of the night. Il Vinile is also a great option that provides a perfect setting for a relaxing evening.
Raise a toast to the start of your relaxed 11-day luxury vacation in Italy and look forward to more fantastic days to come!
Day 2 – Florence
- Florence
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Drive 4 km, 56 min
- Basilica of Santa Croce in Florence
- Galleria dell'Accademia
- Cathedral of Santa Maria del Fiore
- Basilica of Santa Maria Novella
- Ponte Vecchio
- More
Day 2 of your luxury road trip means another day to soak in the splendor of Italy. At the city of Florence, you will continue your laid-back luxury holiday in the best possible way. Enjoy the best sights, the most exciting activities, and the finest restaurants in the city. You have ample opportunities to make your 1 night in the city more special.
Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most captivating attractions included on the itinerary is Basilica Of Santa Croce In Florence. This inviting church will help you start your sightseeing on top. Then, take a leisurely stroll to Galleria Dell'accademia and learn what makes this noteworthy art gallery unique.
Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the impressive Cathedral Of Santa Maria Del Fiore. After exploring the church, head to Basilica Di Santa Maria Novella, Firenze (fi). This well-known church is a highlight in Florence. Lastly, don’t forget to check out the globally renowned Ponte Vecchio. Enjoy exploring this incredible historical landmark at your own pace.
You can learn more about Florence today by going on a tour. Florence offers many top-rated tours and unique experiences that will inspire you. You can browse and select your favorites below.
After a long day of discovering the unique quirks of Italy, it’s an excellent idea to sit down for a lovely meal or enjoy a refreshing drink. We’ve gathered the most recommended dining and drinking spots in Florence so you can check out the menus and make advance reservations.
Treat yourself to an extraordinary dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an incredible italian contemporary menu. Alternatively, if your taste buds call for something different, Santa Elisabetta is one of the best restaurants for creative and mediterranean cuisine in Florence. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Gucci Osteria da Massimo Bottura. As a top-rated establishment with 1 Michelin star, it is an ideal choice for italian contemporary and international cuisine in the city.
Following your dinner, dive into the local bar culture at Bar 50 Rosso. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bitter Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Archea Brewery provides excellent drinks and a great atmosphere, ensuring a memorable night out.
Go over your photos from the day, raise a toast, and rest your tired legs. A new adventurous day of your relaxed luxury road trip in Italy awaits!
Day 3 – Florence and Pisa
- Florence
- Pisa
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Drive 85 km, 1 hour 43 min
- piazza della Signoria
- Uffizi Gallery
- Ponte Vecchio
- Palazzo Pitti
- The Boboli Gardens
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On day 3 of your relaxed luxury road trip holiday in Italy, you will have the opportunity to experience Florence, 1 of the most vibrant destinations in the country. You’ll stay in Pisa for 1 night.
A blend of a romantic, an awe-inspiring, a visually striking, a respected, a symbolic, and a masterful await you in Florence on today’s itinerary. First up is the extraordinary public square, Piazza Della Signoria. It's a standout spot that offers a memorable visit. Afterward, continue to Uffizi Gallery. A visit to this art gallery is an enriching experience for all.
As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Pitti Palace. This popular palace is an essential stop that should not be missed. Following that, head to The Boboli Gardens, another must-visit site that will enhance your experience.
In Pisa, you will be treated to a stay at one of the most exclusive 5-star luxury hotels the destination has to offer. From the moment you arrive in Pisa, prepare to be pampered with exceptional service, luxurious accommodations, and top-notch amenities that promise to make your stay truly unforgettable.
After a long day of exploring, it’s a great idea to relax with a lovely dinner or a refreshing drink. We’ve gathered the most recommended dining and drinking spots in Pisa for you, so you can check out the menus and make your reservation in advance.
Make sure to book a table at Anima di Grano Pizzeria Napoletana Pisa Italy, a popular restaurant in Pisa. This acclaimed restaurant and its mouthwatering dishes have earned the admiration of countless food lovers. Alternatively, experience a taste of Pisa at il Mercante, a popular local restaurant. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. Another top-rated restaurant to try is La Ghiotteria. As a dining spot that gains high praise from guests, it’s an ideal choice to enhance your time to Pisa tonight.
Round off your dining experience by visiting Jeffer Cocktails & Friends, a prime location for a drink. Alternatively, explore the distinctive characteristics of Le Parisien Wine Bar, a bar catering to every mood and preference. Las Volta Cocktailbar likewise offers a unique atmosphere, perfect for a memorable night out.
Raise your glass and toast to another unforgettable day of your relaxed luxury holiday in Italy!
Day 4 – Pisa and Rome
- Pisa
- Rome
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Drive 347 km, 4 hours 6 min
- Knights' Square
- Leaning Tower of Pisa
- Piazza del Duomo, Pisa
- Pisa Cathedral
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On day 4 of your relaxed luxury holiday in Italy, wonderful attractions await. Today you have the opportunity to discover 1 remarkable destinations — Pisa. You’ll stay in Rome for 6 nights.
Set out on a day brimming with a breathtaking, a photogenic, a standout, a culturally significant, a remarkable, an UNESCO world heritage-designated, and a sacred. Start at the locally appreciated Knights' Square, a breathtaking public square in Pisa. Next, go to Leaning Tower Of Pisa.
After visiting Knights' Square and Leaning Tower Of Pisa, take time to explore Pisa's streets and absorb its charm. Continue your sightseeing by heading to Piazza Del Duomo, Pisa. This stunning public square offers a unique experience. Pisa Cathedral is another noteworthy stop.
For the night, you’ll have the choice of the best luxury hotels and places to stay in the city of Rome. Whether you prefer the grandeur of a luxury hotel or the charm of a boutique stay, you'll find an array of exquisite options to suit your tastes and preferences. Indulge in world-class amenities, impeccable service, and unforgettable experiences as you unwind and create memories in Rome.
After exploring the unique sights of Italy, savor a delicious meal or get refreshed with a drink. We’ve gathered the most recommended restaurants and bars in the city of Rome for you so you can browse their menus in advance and make a reservation.
Begin your culinary exploration in Rome by securing a reservation at La Pergola. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of mediterranean and contemporary cuisine. For another dining delight, visit Il Pagliaccio, celebrated for its delectable creative and innovative menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Enoteca La Torre, a top local spot known for its tantalizing mediterranean and creative menu. With a 2-star Michelin recognition, it guarantees an exceptional dining adventure.
After savoring a delicious meal, step into the vibrant nightlife at La Botticella Of Poggi Giovanni, where the evening is just getting started. In the same way, Almalu Trastevere offers a unique charm perfect for experiencing the local bar scene in Rome. Bar Viminale Di Pepi Maurilio is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.
Raise your glass and toast to another unforgettable day of your relaxed luxury holiday in Italy!
Day 5 – Rome and Vatican City
- Rome
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Drive 11 km, 59 min
- St Peter's Basilica
- Sistine Chapel
- Saint Peter's Square
- Vatican Museums
- Trevi Fountain
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Day 5 of your luxury road trip in Italy is another opportunity to explore what this region has to offer. Start your day with a drive to visit the amazing attractions in the surrounding area of Rome. After a day of sightseeing, return to the city, where you still have 5 nights left to enjoy. End your evening with a fulfilling dinner at one of the finest restaurants in Rome, savoring the local culinary delights.
Set out on a day brimming with a romantic, an awe-inspiring, an instagrammable, a standout, a culturally significant, and a remarkable. Start at the world-famous Trevi Fountain, a romantic monument in Rome.
Continue your road trip and head to your next destination, Vatican City, Vatican City. This car ride takes around 11 min.
One of our top recommendations for your sightseeing is St. Peter's Basilica. Then, head to Sistine Chapel. This famous chapel is a traveler-favorite in the city. Not far away, you’ll also find Saint Peter's Square. Feed your curiosity by learning something new about the square. Next, continue your journey to Vatican Museums, a world-famous art museum.
When you’re done exploring for the day, you’ll return to Rome and your accommodation.
After a long day of discovering the unique quirks of Italy, it’s an excellent idea to sit down for a lovely meal or enjoy a refreshing drink. We’ve gathered the most recommended dining and drinking spots in Rome so you can check out the menus and make advance reservations.
Savor the flavors at RomAntica, a top pick for dinner tonight. Alternatively, Coso Ristorante beckons with its unique menu offerings. Also, consider DEROMA - Farine Romane. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.
Continue the enjoyment post-dinner at Sant' Eustachio Caffè, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Yellowsquare Rome offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Caffè Portofino. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.
Enjoy an amazing evening in Rome, and get ready for more fantastic days to come on your relaxed luxury vacation in Italy!
Day 6 – Rome
- Rome
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Drive 5 km, 52 min
- Castel Sant'Angelo
- Campo de' Fiori
- Piazza Navona
- Pantheon
- largo di Torre Argentina
- Trevi Fountain
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Day 6 of your luxury road trip in Italy brings you another chance to explore the wonders of Rome. Immerse yourself in the best sights and most thrilling activities as you continue your laid-back holiday in style. End your day at one of the top restaurants in Rome, making the most of your 4 nights in this exquisite city.
Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Rome allows for both. Start by heading to Castel Sant'angelo. This astonishing castle provides an insightful glimpse into the city's identity. Next, discover Campo De' Fiori, a history-steeped public square, promising a delightful encounter.
Continue your sightseeing with a visit to Piazza Navona, a wondrous public square. When you’re done, don’t forget to make a stop at the world-famous Pantheon. Round off your day at Largo Di Torre Argentina, another gem in Rome with instagrammable features to discover.
There are plenty of experiences you can choose from in Italy that will add excitement to your vacation. When you’re keen to discover what else Rome has in store for you, use this day to go on a tour.
After a full day of exploring, treat yourself to a delightful dinner or a refreshing drink at the best spots in Rome. Choose from a selection of excellent restaurants and bars and find the perfect place for your evening.
Treat yourself to a delicious dinner at Hotel de Russie, an excellent option for tonight's dining. Looking for something different? La Taverna Italiana offers a tantalizing alternative with its diverse menu. And don’t miss The Parrot Bar. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.
After your delicious meal, get a taste of the vibrant nightlife with a visit to The Apartment Bar Roma, known for its inviting atmosphere. Hotel Hassler Roma is another great option if you’re looking for a place to get the night started.
Reminisce about your day, look through photos, and prepare for another great day to come! Your relaxing luxury vacation in Italy still has more in store for you.
Day 7 – Rome
- Rome
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Drive 4 km, 54 min
- Altare della Patria
- Capitoline Hill
- Roman Forum
- Colosseum
- Circus Maximus
- Trevi Fountain
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Day 7 of your luxury holiday in Italy is another opportunity to leisurely explore the spectacular city of Rome. You still have 3 nights in Rome, which gives you enough time to discover some of the most amazing things to see and do in the city. Start your morning with a hearty breakfast and get ready for an entire day of enjoying Rome to the fullest.
Today’s well-planned self-sightseeing route offers several a breathtaking, a visually striking, a history-steeped, a majestic, a remarkable, a charming, and an UNESCO world heritage-designated. Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Altare Della Patria is the first of them. Spend some time admiring this picture-perfect monument before continuing your journey. Capitoline Hill is your next stop. This well-known public square is one of the best-rated sights in Rome.
Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Roman Forum. This breathtaking archeological site is a sight to behold. To round off your sightseeing experience, visit Colosseum and Circus Maximus.
Your discoveries in Rome do not have to stop there. Check out the fantastic selection of tours and tickets offered in Rome on this day of your trip.
Discover a world of culinary delights in Rome, where top-notch dining experiences await at every corner. Consider whether you need to make a reservation in advance to secure a table at your preferred restaurant.
Dine in style at Sofitel Roma Villa Borghese, a top recommendation for dinner tonight. Or, for a change of pace, Centro boasts a menu that's sure to impress. Also, be sure to check out Ristorante Tema. Known as a local hotspot, it’s a great choice for tonight in Rome.
Enjoy an amazing evening in Rome, and get ready for more fantastic days to come on your relaxed luxury vacation in Italy!
Day 8 – Rome
- Rome
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Drive 18 km, 1 hour 36 min
- Borghese Gallery and Museum
- Villa Borghese
- piazza del Popolo
- Auditorium Parco della Musica
- Foro Italico
- Trevi Fountain
- More
On day 8 of your relaxed luxury holiday across Italy, you'll continue your adventures in the city of Rome. You'll explore Rome, taking breaks from the road for some sightseeing. At the end of day, you'll dine at some of Rome's best restaurants and bars conveniently located close to your accommodation, making the most of your remaining 2 nights in the area.
Rome is brimming with adventures. Today’s wonderful stops include a museum, a park, a public square, a concert hall, a sport complex and much more! Begin your sightseeing adventure at the locally renowned Villa Borghese Pinciana. Just a short distance away is Villa Borghese, a mesmerizing park that draws visitors from far and near.
Continue your journey to Piazza Del Popolo, one of the city’s most astonishing spots that you shouldn’t miss. Another great site to visit is the locally renowned Auditorium Parco Della Musica. Last up on today’s itinerary is a sport complex. Make your way to Foro Italico for some final sightseeing. Each attraction will leave you with lasting memories and a deeper appreciation for the rich heritage of Rome.
If you have an appetite for more adventure, check out the fantastic selection of tours and tickets offered in Rome on this day of your trip. You'll find the most recommended ones below.
Exploring new destinations can leave you craving great food and drinks. Satisfy your cravings and unwind by visiting the finest restaurants and bars in Rome.
Don’t miss out on dining at Ristorante Va. Do. , a top-rated dining destination in Rome. If you're in the mood to try something new, consider Giulia Restaurant, another top spot with a mouthwatering menu. You might also want to secure a reservation at L'Archeologia. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.
Raise your glass and toast to another unforgettable day of your relaxed luxury holiday in Italy!
Day 9 – Rome
- Rome
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Drive 11 km, 57 min
- Spanish Steps
- Piazza di Spagna
- Trevi Fountain
- Basilica di Santa Maria Maggiore
- Archbasilica of St. John Lateran
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Day 9 of your luxury road trip in Italy grants you another day to experience Rome. You will continue your laid-back luxury holiday in the best possible way - by discovering the best sights and most exciting activities. You'll then conclude your adventure at one of finest restaurants in Rome, fully indulging in the 1 night you have in the city.
Immerse yourself in Rome’s rich culture with today's sightseeing itinerary. Start your journey at Spanish Steps. This awe-inspiring public square is sure to ignite your curiosity. Next, dive into the history-steeped features of Piazza Di Spagna, a must-visit public square in the city.
In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Basilica Di Santa Maria Maggiore, a captivating church. For a change of scene, check out Archbasilica Of St. John Lateran, known for its stunning features.
To make your vacation in Rome more special, check out all the available tours and tickets you can add to your itinerary! You’ll find that Rome offers many top-rated and low-priced tours you can try out on this day of your holiday.
In Rome, delicious dining experiences are never far from reach. Take your pick and consider whether you need to book a table in advance.
Treat yourself to a delightful dinner at Caffè Antica Roma, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Maccheroni? It's another excellent option with a diverse menu. Consider reserving a table at In Roma - since 1917 as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.
Raise your glass and toast to another relaxing day of your luxury holiday in Italy!
Day 10 – Rome, Santa Maria degli Angeli, and Florence
- Rome
- Assisi
- Santa Maria degli Angeli
- Florence
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Drive 360 km, 5 hours 12 min
- Basilica of San Francesco d'Assisi
- Rocca Maggiore
- Basilica of Santa Maria degli Angeli
- Trevi Fountain
- More
On day 10 of your relaxed luxury road trip holiday in Italy, you will have the opportunity to experience Santa Maria degli Angeli, 1 of the most vibrant destinations in the country. You’ll stay in Florence for 1 night.
Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Santa Maria degli Angeli. This drive usually takes around 2 hours 25 min, without any stops or traffic disruptions.
Savor the rest of your day by heading to Basilica Of San Francesco D'assisi, an interesting church that draws visitors from near and far. When you're done, continue on to Rocca Maggiore, where you can soak in the grand surroundings.
Fasten your seatbelt and make your way to your next stop. Santa Maria degli Angeli, home to many well-known sights in the region, is a lovely destination on today’s itinerary. Keep in mind that your travel time from Santa Maria degli Angeli to Santa Maria degli Angeli may take around 13 min without traffic disruptions. Upon arrival in Santa Maria degli Angeli, we highly recommend checking out some of the top attractions.
Take your self-guided tour to Basilica Of Santa Maria Degli Angeli, a notable church that everyone visiting Santa Maria degli Angeli should see. Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings.
As the day is coming to an end, it's time to make your way to your home for the night. On this day of your exclusive holiday, you will stay at a luxury hotel in Florence. With a variety of popular luxury lodging options available in the city, you'll have the opportunity to select the perfect retreat to unwind and pamper yourself in style.
Exploring new destinations can leave you craving great food and drinks. Satisfy your cravings and unwind by visiting the finest restaurants and bars in Florence.
Have a fantastic dining experience at Ristorante Buca Mario, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Agricola Toscana offers an enticing alternative with its varied menu. Additionally, Eataly Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.
Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Gosh* stands out as an excellent choice for a post-dinner cocktail. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers an ideal atmosphere to enjoy the pleasures of the night. Quelo Bar is also a great option that provides a perfect setting for a relaxing evening.
Relax and enjoy an amazing evening in Florence, and get ready for more fantastic days to come on your relaxed luxury vacation in Italy!
Day 11 – Florence - departure day
- Florence - Departure day
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- Central Market
- Ponte Vecchio
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Today is the last day of your 11-day relaxed luxury holiday in Italy and it’s soon time to start your journey home. This is your chance to get one last glimpse of Florence before saying goodbye.
Make the most of your final day in Italy by visiting Florence’s iconic markets and shopping establishments. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy.
Make the most of what's left of your luxury vacation and head out to the stunning Central Market. This extraordinary food market and attraction is rated an average of 4.4 out of 5 stars in 43,100 reviews, and is an excellent choice for your last sightseeing in Florence.
Unwind and look back at the past 11 days of your relaxed road trip over a bite to eat. This is your chance to enjoy one last traditional meal in Florence or just grab something light to keep you going.
If you're in the mood for something new, try Djària - American Bar, another premier location with a delectable menu.
You will then say farewell to Florence and begin your journey home. We wish you safe travels and a warm welcome home, with unforgettable memories and incredible photos from your relaxed luxury holiday in Italy in your luggage!
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