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Italy, Spain & Portugal: 2-Week Itinerary of Culture & Charm
15 Days
5 Stops
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Trip curated by Roman Karin
ExpertToledo earns a full day when you reverse the standard route. Cathedral treasury and El Greco museum before the coaches arrive, then the Jewish quarter in the afternoon when the light on the Tagus below is at its best. Driving the Chiantigiana through Greve and Radda before reaching Siena places the Renaissance indoors into the agricultural landscape that funded it; that's the spatial argument this day trip is actually making. For Rome as the final stop, Trastevere on an evening walk and Palatine Hill at closing time deliver a city the headline monuments alone don't reach.
Toledo earns a full day when you reverse the standard route. Cathedral treasury and El Greco museum before the coaches arrive, then the Jewish quarter in the afternoon when the light on the Tagus below is at its best. Driving the Chiantigiana through Greve and Radda before reaching Siena places the Renaissance indoors into the agricultural landscape that funded it; that's the spatial argument this day trip is actually making. For Rome as the final stop, Trastevere on an evening walk and Palatine Hill at closing time deliver a city the headline monuments alone don't reach.
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Lisbon
Day 1 - 3
Lisbon, Portugal's hilly capital on the Tagus estuary, where the river meets the Atlantic Ocean, combines historic neighbourhoods, grand squares and waterfront districts with a lively contemporary atmosphere. A vibrant European capital, it is known for its distinctive yellow trams, tiled facades, winding streets and viewpoints overlooking the Tagus River. Travellers can explore the UNESCO-listed Jerónimos Monastery and Belém Tower, wander through the atmospheric lanes of Alfama, or ride Tram 28 through the city's historic quarters. Praça do Comércio and Rossio serve as lively gathering places, while the waterfront offers opportunities for dining and leisurely strolls. Lisbon also makes an excellent base for exploring nearby coastal scenery and cultural attractions, including Sintra. With its mild climate, rich maritime heritage and relaxed café culture, Lisbon offers a varied city break with plenty of character.
Portugal Boutique Hotel
With a stay at Portugal Boutique Hotel, you'll be centrally located in Lisbon, just a 3-minute walk from Rossio Square and 8 minutes by foot from Avenida da Liberdade. This hotel is 0.3 mi (0.5 km) from Santa Justa Elevator and 0.5 mi (0.8 km) from Commerce Square.
Enjoy recreation amenities such as an attached winery or take in the view from a rooftop terrace. This hotel also features complimentary wireless internet access and concierge services.
Make yourself at home in one of the 53 guestrooms featuring minibars and LCD televisions. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Bathrooms feature bathtubs, complimentary toiletries, and bidets. Conveniences include safes and desks, and housekeeping is provided daily.
Your activity
Sintra, Cabo da Roca & Cascais Tour
Discover the charming town of Sintra, where the royal family once had their summer residence, with an experienced guide. Enjoy typical local pastries and immerse yourself in the historic atmosphere of this unique region.
The tour continues to the spectacular Cabo da Roca viewpoint, the westernmost point of Europe, and the impressive Boca do Inferno rock cliff. Afterward, explore the sophisticated town of Cascais and the elegant gardens surrounding the famous Estoril Casino.
An unforgettable trip along Portugal's most beautiful coastal towns – rich in nature, culture, and history.
Highlights
- Sintra National Palace - visit
- Sintra Village - free time
- Cabo da Roca* or Hell’s Mouth** free time
- Guincho - panoramic
- Cascais - free time
- Estoril - panoramic
Madrid
Day 4 - 6
Spain’s enormous central capital, Madrid, lies on the River Manzanares and is a city of contrasts. Historical monuments like the impressive Royal Palace stand in stark contrast to state-of-the-art skyscrapers; masterpieces by Picasso, Dali and Velazquez adorn the walls of the city’s world-class galleries alongside contemporary modern works; local chefs display a passion for Spanish food at traditional eateries while chic fusion restaurants operate next door. Madrid’s real attraction lies in the seductive lifestyle of its hedonistic inhabitants; indulging in tapas, hunting for treasures at the El Rastro flea market or partying the night away in one of the many lively nightclubs. Make sure to soak up the vibrant street life of the grand, historic Plaza Mayor, Madrid's central square, and spend a leisurely afternoon on the landscaped lawns at the Parque del Buen Retiro.
Hotel Villa Real
Hotel Villa Real invites you to enjoy a luxurious stay in the heart of Madrid. Located in the historic and cultural center of the city, this elegant hotel offers an exceptional base for exploring iconic attractions such as the Prado Museum, Plaza del Sol, and the bustling Gran Vía.
Your room at Hotel Villa Real is designed to provide comfort and sophistication, featuring classic decor and a range of modern amenities. Enjoy complimentary Wi-Fi, flat-screen TVs, and plush bedding, ensuring a relaxing and indulgent experience. Many rooms also offer private balconies with stunning city views.
Start your day with a delightful breakfast featuring fresh, local ingredients. The hotel's restaurant serves exquisite Mediterranean cuisine, allowing you to savor the authentic flavors of the region. After a day of sightseeing, unwind with a cocktail at the stylish bar, where you can relax in a chic and inviting atmosphere.
With its prime location, Hotel Villa Real offers easy access to the city's vibrant shopping districts, theaters, and cultural hotspots. Coupled with attentive service and timeless elegance, your stay promises to be a memorable experience in one of Europe’s most captivating capitals.
Your activity
Flamenco Show with drink
Flamenco, a lively mixture of dance, song and guitar, is the heart and soul of Spain. It has developed alongside the contrasting historical influences of Arab, Jewish and gypsy cultures. Ava Gardner or Hemingway, they all loved flamenco. In this show you will enjoy the best pure flamenco in a mythical place in Madrid. Experience how heart, soul and the artists' total dedication to their craft is what it's all about.
Barcelona
Day 7 - 8
Set on Spain’s gorgeous southeastern coast, the capital and largest city of the Catalonia region, Barcelona, is an exquisite, seaside metropolis. With its dizzying array of architecture and its world-class galleries and museums, artistic delights abound at every corner (most strikingly in the astonishingly whimsical structures designed by the prolific modernist architect Antoni Gaudi). Explore the winding alleys of the picturesque Gothic Quarter, take in the boisterous carnival atmosphere of the world famous, tree-lined La Rambla boulevard, or go on a gastronomical adventure through the city's restaurants. Head to one of the gorgeous white sandy beaches and when the sun sets, join the eclectic all-night party scene. Don’t miss the opportunity to see the phenomenal Sagrada Familia, take in an opera at the sublime Palau de la Musica Catalana, and watch a game at the famous Camp Nou stadium.
Claris Hotel & Spa
Claris Hotel & Spa Barcelona is a luxurious haven located in the heart of the city, offering a perfect blend of elegance, comfort, and art. Situated just steps away from the renowned Passeig de Gràcia, the hotel provides easy access to Barcelona’s top attractions, including Gaudí’s masterpieces and exclusive shopping destinations.
The hotel boasts exquisitely decorated rooms and suites, each adorned with unique artworks and modern amenities to ensure a sophisticated and comfortable stay. Whether you choose a room with a view of the city or the tranquil inner courtyard, each space promises a restful retreat.
Indulge in a diverse culinary experience at the hotel’s award-winning restaurants, where you can savor Mediterranean flavors and innovative dishes. The rooftop terrace is a highlight, offering breathtaking views of Barcelona’s skyline and serving as a perfect spot for a relaxing evening drink.
For those seeking relaxation and rejuvenation, the Claris Hotel features a luxurious spa that offers a range of treatments designed to soothe and invigorate. Additionally, the hotel's central location provides excellent access to public transportation, making it easy to explore all that Barcelona has to offer.
Your activity
Skip the Line Park
Join an English-speaking guided tour to discover two of Antoni Gaudí’s most iconic works: the Sagrada Familia and Park Güell.
Begin at Park Güell, located in a unique area with stunning views over the city. Declared a UNESCO World Heritage Site in 1984, the park was originally conceived as a residential project before becoming a public space. Explore the monumental area with your guide and admire Gaudí’s mastery. See how he blended architecture and nature through his organic, naturalistic style.
At the appointed time, a transfer will take you to the Sagrada Familia. Enter this breathtaking monument and discover why it’s the ultimate must-see landmark in Barcelona. Learn about its history and symbolism with your local guide, and marvel at the interior—richly inspired by natural forms and spiritual meaning.
Florence
Day 9 - 11
Florence, the beautiful capital of the Italian region Tuscany, lies in the center of the country. A small city with a big heart, and an even bigger offering of artistic and historical treasures. For centuries, travelers have journeyed to the birthplace of the Renaissance era to marvel at the many masterpieces of architecture and art: Michelangelo's iconic David, the impressive works of Botticelli, the Uffizi Gallery (packed with works by Caravaggio and Da Vinci), and of course, Brunelleschi's remarkable dome — the religious centerpiece of Florence that dominates the skyline. All are absolute must-sees on any itinerary. Once you've ticked off these renowned attractions, you can take a stroll through the vast Boboli Gardens or climb the hill to the church of San Miniato al Monte for a breathtaking view of this beautiful, enchanting city.
Tivoli Palazzo Gaddi Florence Hotel
Tivoli Palazzo Gaddi Florence Hotel is located in a historical palace in the heart of Florence, the birthplace of the Renaissance. It is only 400 meters from the magnificent Florence Cathedral, and its rooftop terrace offers stunning city views. The hotel features 86 elegant rooms equipped with air-conditioning, flat-screen TV, rain effect shower or bathtub, complimentary Wi-Fi and a comfortable bed with pillows. The hotel has a restaurant serving Tuscan and Mediterranean specialities and a spacious bar next to the hall.
Your activity
Siena, San Gimignano, Chianti
Your memorable journey starts with the charming San Gimignano, world famous walled town located on a hilltop, which remained intact through the centuries, renowned for its tall towers, wonderful frescoes and many other valuable works of art: here the tour leader will lead you to the historical center, where you will have around 2 hours of free time for a fascinating discovery. A short distance from San Gimignano, crossing the gently Chianti rolling hills, a short ride will take you to a cozy Winery, where you can relax and enjoy the fantastic world of Chianti with its wine and typical products: tasting of three fine wines and balsamic vinegar followed by a Chianti style lunch: 3 course with “zero food miles” products which ends with "cantucci e vin santo". Later on, getting to Siena, you will have 3 hours of free time to end your perfect day enjoying the unique atmosphere of this amazing city, before the return to Florence in the evening.
Meeting Point: 07:45 AM Piazzale Montelungo at the end of the ramp connecting with the railway station. An Assistant waits wearing blue clothing with Gray line logos
Start time: 08:00 AM
Group size: Min 1 to max 55 pax
Rome
Day 12 - 15
Experience Rome, the bustling capital of Italy. This city, rich with exciting history and culture, offers an unparalled mix of ancient explorations and modern living. Immerse yourself in the past and explore the Colosseum, the Roman Forum, and the Vatican. Wander through other must-see destinations like The Spanish Steps, Trevi Fountain, and Pantheon. Experiencing the culinary scene is a delight, from traditional pasta to world-renowned Italian gelati. You can explore daily markets such as Campo de' Fiori for local ingredients and fresh food. A stay in Rome promises great experiences all year round, but it is advisable to take seasonality into account. While spring (April–May) and fall (September–October) offer pleasant weather and less crowds, summer (June–August) has a lively, spirited atmosphere — but can also be hot. No matter when you go, visiting Rome promises an unforgettable journey through the centuries. The unique combination of a rich historical past mixed into a thriving and vibrant modern community makes Italy's Eternal City one of the world's most intriguing and inspiring tourist destinations.
Grand Hotel Palace Rome
Centrally located in Rome, Italy, the five-star Grand Hotel Palace Rome is an ideal accommodation option for leisure and business travellers. The guest rooms are equipped with workspaces, Wi-Fi, and bathrooms; upgraded rooms feature minibars and terraces, and some suites feature Nespresso machines and sitting rooms. Enjoy meals and drinks at the on-site restaurant and bar. Amenities include a gym and a spa.
Your activity
Sorrento and Ancient Pompeii Tour
Start your adventure with a comfortable transfer from Rome to Sorrento aboard an air-conditioned coach. Marvel at the breathtaking scenery of the Italian countryside and the Amalfi Coast, where crystal-clear waters meet hills dotted with citrus groves and charming villages. Arrive in Sorrento, the jewel of the Amalfi Coast, renowned for its picturesque streets, ceramic workshops, and historic churches. Soak in the unique atmosphere of this coastal gem, and begin your visit with a limoncello tasting at a local producer, where you’ll uncover the secrets behind this famous elixir. Continue your journey to Pompeii, a UNESCO World Heritage Site and one of the world’s most extraordinary archaeological treasures. Buried under a thick layer of volcanic ash during Mount Vesuvius’ catastrophic eruption in 79 AD, Pompeii offers a rare and vivid glimpse into everyday life in Ancient Rome. Accompanied by a professional archaeologist guide, stroll along perfectly preserved streets, exploring homes, shops, and bakeries that bring the past to life. Admire the frescoes, squares, and temples that tell the story of this remarkable city frozen in time for over 1,500 years. Your guide will share captivating insights into the eruption that destroyed Pompeii and the incredible discoveries that have brought this ancient city back to light. At the end of the day, you’ll carry with you unforgettable memories of Sorrento’s charm, the stunning Amalfi Coast, and the timeless ruins of Pompeii - an inspiring journey blending breathtaking landscapes and history.
Meeting Point: Pick up starting at 6:30 am from centrally-located hotels
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Why plan with an expert?
200+
Plan with professionals who are explorers themselves.
38+ hours of time saved
Our experts plan and book for you.
16+ Bookings managed
Everything is bundled in one place and perfectly planned.
8+ Transfers coordinated
For optimal transport and comfort.
Excellent
Itinerary inspiration
Lisbon to Madrid to Barcelona, then Florence and Rome — fifteen days moving from the Atlantic coast of Portugal to the heart of ancient Italy. The trip builds in historical density as it goes. Lisbon is lyrical and maritime. Madrid is grand and formally Spanish. Barcelona is inventive and Mediterranean. Florence is precise and Renaissance. Rome is everything at once, and arriving there at the end is the right order.
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A detail worth knowing about the Toledo day trip from Madrid: the city is best explored before noon. The medieval streets and the Gothic cathedral draw organized tours from the capital through the mid-morning, and the quietest version of Toledo — which is also the best version — belongs to the early arrivals.
Day 1–3: Lisbon
Hotel: Portugal Boutique City Hotel
Three nights gives you Alfama and Belém on one day, the Sintra, Cabo da Roca, and Cascais day trip on another, and a fado evening in the Chiado. Book the venue before you travel — the good ones fill up on weekends.
Day 4–6: Madrid
Hotel: Hotel Villa Real
Three nights covers the museum visits, the tapas evenings, the flamenco show, and the Toledo day trip. The Prado rewards more time than most visitors give it — the permanent collection alone justifies an unhurried morning.
Day 7–8: Barcelona
Hotel: Claris Hotel & Spa
Two nights means keeping things focused. The Sagrada Familia and Park Güell on the first full day, the Gothic Quarter and the Born neighborhood in the evening. The Claris sits well for both the Eixample architecture and the Gaudí landmarks.
Day 9–11: Florence
Hotel: Tivoli Palazzo Gaddi Florence Hotel
The Accademia Gallery, the Siena, San Gimignano, and Chianti day trip, and the walking tour in the right order — the gallery first, the countryside second, the tour third when you know the city well enough to go deeper. What I always tell people: arrive at the Accademia at opening on a weekday and you will have David to yourself for the first twenty minutes.
Day 12–15: Rome
Hotel: Grand Hotel Palace Rome
Three nights gives the Colosseum and Roman Forum a proper morning, the Vatican complex another full day, and still an evening free for the piazzas and neighborhoods that don't appear on any organized itinerary. The area around Campo de' Fiori and Trastevere are the most rewarding parts of Rome for a slow, unplanned evening.
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Tips for your 2-week Portugal, Spain, and Italy trip
The best time to travel for this multi-country trip is during the shoulder seasons of spring and fall. These seasons offer a perfect balance of pleasant weather, ideal for exploring cities like Lisbon and Madrid, while avoiding the intense heat and heavy crowds of the peak summer months.
➔ Best time to travel Portugal | Best time to travel Spain | Best time to travel Italy
The cost for this multi-country trip can be tailored to various budgets. On a mid-range budget, a week in Portugal starts at about $1,000 per person, a week in Spain at around $1,400, and a week in Italy at around $1,700, excluding flights. A budget-friendly trip starts at approximately $55 per day in Portugal, $80 per day in Spain, and $115 per day in Italy.
➔ Travel cost Portugal | Travel cost Spain | Travel cost Italy
This trip is a rich blend of history, culture, and coastal landscapes. Highlights include the royal palaces of Madrid, the architectural wonders of Valencia, and the art and history of Milan. For activities, you can take a culinary walk in Lisbon, a cooking class in Barcelona, or a sailing tour in Sardinia.
➔ Things to see Portugal | Things to see Spain | Things to see Italy
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