Watch our Online Travel Show about this tour and earn a $100 credit for your next booking with Holiday Vacations.
Portuguese Culture & Fado Show
Historic Center of Evora
Spanish Culture & Flamenco Dancing
Local Cuisine
Barcelona
Erin Davisson
Erin Davisson
Erin is the former anchor of Local 5 News at 5, 6 and 10 p.m. with Tom Zalaski. She has been at Local 5 News since 1988. Erin has won numerous reporting and anchoring awards and has consistently been voted Best Anchor in newspaper polls in the…
Discover the fascinating history, vibrant cities, and breathtaking beauty of Europe’s Iberian Peninsula, featuring Portugal and Spain’s top highlights with ample time at leisure throughout. Arrive in the charming city of Lisbon for a guided tour and travel to romantic Sintra’s Pena Palace. Explore the well-preserved city of Evora and admire its medieval wall enclosure, then cross the border into Seville, Spain, to marvel at the world’s largest Gothic cathedral. Journey into the foothills of the Sierra Nevada Mountains to experience Moorish culture in Granada while viewing spectacular palaces dating back to the ninth century. Immerse yourself in ancient Toledo’s three distinct cultures and spend two evenings in Spain’s vibrant capital city, Madrid, where we learn about centuries of Spanish history on a guided tour that includes the Royal Palace of Madrid. Embark on a delightful train ride to cosmopolitan Barcelona, the perfect bookend of our unforgettable trip with two full days of visiting the city’s exceptional attractions.
Trip overview may vary by departure.
Highlights
Lisbon
Nestled along the sun-kissed shores of the Tagus River, this capital city boasts a rich blend of culture and captivating attractions that are rooted in Portugal’s heritage. Explore the grandeur of two UNESCO World Heritage Sites, the Tower of Belem and Jeronimos Monastery. During leisure time, savor the flavors of Portuguese cuisine and stroll the cobbled streets of the historic district, lined with pastel-colored houses and quaint Fado bars.
Gaudi’s Masterpieces
Get a glimpse into the mind of one of the world’s most celebrated architects, Antoni Gaudi, as you behold his acclaimed masterpieces in Barcelona. Known for Catalan Modernism, Gaudi’s distinctive and one-of-a-kind designs are often inspired by his three greatest passions: religion, architecture, and nature. Learn how he tells the story of life, death, and faith to evoke wonder by using wood, stained glass, wrought iron, stone, and more. See the way stone is used to create natural features on Casa Mila, marvel at the immaculate mosaics on Casa Batllo, discover Gaudi’s naturalist phase at Park Guell, and explore the fruition of his biggest dream, La Sagrada Familia.
Pena Palace
Travel into the picturesque Sintra Mountains to visit one of the most recognizable palaces due to its brightly colored exterior. This whimsical palace is a beautiful expression of 19th-century Romanticism. Enter through the Door of Alhambra, embellished with ceramic tiles depicting flowers and knights in armor. Wander the gardens and terraces, then step inside to explore the lavish rooms including Noble Hall, where the king threw his parties.
Royal Palace of Madrid
Take a captivating journey into Spanish royalty and history with a tour of this 18th-century palace, the largest in Western Europe. The moment you step into the vast courtyard, you’ll be transported to a bygone era of monarchy. The opulent rooms and chambers, adorned with priceless art, chandeliers, and furnishings, offer a window into the lifestyle of Spain’s royals. Don’t miss seeing an actual throne used by past kings in the Throne Room!
- Day 1: Fly to PortugalOur journey begins with a flight across the Atlantic.
- Day 2: Arrive in LisbonUpon arriving in Portugal’s vibrant capital, we explore the best sights with a local guide. Perched on hilltops, it offers gorgeous coastal views, incredible seafood, and fascinating attractions rooted in the country’s heritage. We see the famous 16th-century Belem Tower and Jeronimos Monastery, as well as the neighborhoods of Baixa, Chaido, Bairro Alto, and Alfama. After checking in to our accommodations, there’s time at leisure to enjoy the city’s charm before gathering for a Welcome Dinner.
Meals Included: Dinner
- Day 3: Sintra & Pena PalaceAfter breakfast, we’re off to discover the royal history and magnificent architecture in Sintra. Now a renowned UNESCO World Heritage Site, this resort town was the first hub of European Romantic architecture. Enjoy a tour of Pena Palace within the Sintra Mountains, one of Europe’s finest palaces, followed by time to explore eateries, quaint shops, and stunning vistas on your own. Later, we return to Lisbon for dinner at an authentic fado restaurant, where we see a moving cultural performance with folkloric music.
Meals Included: Breakfast, Dinner
- Day 4: Roman Temple & Cathedral of EvoraWe depart our hotel this morning and travel to Evora, a UNESCO World Heritage Site partially enclosed by medieval walls. A local guide joins us for a tour of the city, including its well-preserved historic center that consists of an ancient Roman Temple, aqueduct, and 12th-century Gothic cathedral. The afternoon is yours to try savory cuisine and visit more fascinating attractions. We then travel across the Portugal-Spain border, over the Guadiana River, and check in to our accommodations in Seville.
Meals Included: Breakfast
- Day 5: Seville Cathedral & Flamenco ShowOur day kicks off with a city tour of Seville, the capital of Andalusia. Cherish its lively culture as we view the Santa Cruz Quarter, Parque de Maria Louisa, and the world’s largest Gothic cathedral, where great navigator Christopher Columbus was laid to rest. There’s also time at leisure to stroll through orange-scented courtyards, explore the Plaza de Espana, or take a relaxing boat ride down the canal. Tonight, we enjoy an immersive cultural experience at a local restaurant with dinner and a flamenco show, showcasing traditional Spanish music and dancing.
Meals Included: Breakfast, Dinner
- Day 6: Granada & Historic PalacesToday, we journey to Granada, nestled within the foothills of the Sierra Nevada Mountains. Gaze upon the last fortress of the Spanish Moors, Alhambra, and Generalife, a summer escape for Nasrid dynasty rulers. As you explore the city, enjoy its famous free tapas with drinks and admire the ever-present Moorish culture found within the historic Arab quarter. This evening, we get settled at our hotel and gather for dinner. *Entrance to the palaces and gardens is not always guaranteed.
Meals Included: Breakfast, Dinner
- Day 7: Toledo & MadridThis morning, we drive to the ancient hilltop city of Toledo. Known as the City of Three Cultures, it has strong influences from medieval Arab, Hebrew, and Christian occupants dating back to the Middle Ages. Enjoy a guided tour featuring the Toledo Cathedral with its famous gold monstrance and grandiose chapel. Later, our journey continues to Spain’s capital city of Madrid.
Meals Included: Breakfast
- Day 8: Royal Palace of MadridAfter breakfast, we join our local guide for a tour of Madrid to see its distinguished boulevards, impeccable parks, and European art. We also visit the Royal Palace of Madrid, the largest in Western Europe and home to several generations of royal families. Discover centuries of Spanish history within these illustrious walls while visiting its iconic spaces, such as the Throne Room and Hall of Columns. The remainder of the day is yours to explore the unique neighborhoods, food markets, and lively nightlife.
Meals Included: Breakfast
- Day 9: BarcelonaOur morning begins with a high-speed AVE train ride to Barcelona, a destination offering the finest in everything – art, weather, beaches, cuisine, and architecture. Enjoy a guided tour with sights of Las Ramblas Boulevard, Casa Mila, Parc de Montjuic, and the Columbus Monument. Then, spend the rest of the day exploring the city’s spirited atmosphere and attractions.
Meals Included: Breakfast
- Day 10: Gaudi’s MasterpiecesWe continue sightseeing this morning with attractions such as Park Guell, one of Spanish architect Antoni Gaudi’s most expansive and spectacular designs. We also visit the innovative La Sagrada Familia Cathedral, the world’s largest unfinished Catholic church. Our afternoon is free for individual pursuits, like shopping for souvenirs or appreciating masterpieces in world-renowned museums. This evening, we celebrate our adventures at a delicious Farewell Dinner.
Meals Included: Breakfast, Dinner
- Day 11: Fly HomeWe board our flight and return home with treasured memories of our time in Spain and Portugal.
Jun 2-12, 2026
$9,199
per person
$7,999
per person
Feb 27, 2026
What's Included
All Accommodations
- 2 nights in Lisbon
- 2 nights in Seville
- 1 night in Granada
- 2 nights in Barcelona
Attractions & Highlights
- Lisbon guided city tour
- Pena Palace tour
- Evora guided city tour feat. Roman Temple
- Seville guided city tour feat. Seville Cathedral
- Toledo guided city tour feat. Toledo Cathedral
- Madrid guided city tour feat. Royal Palace of Madrid
- Barcelona guided city tour feat. Park Guell & La Sagrada Familia Cathedral
- Rail journey from Madrid to Barcelona
- Time at leisure in Lisbon, Seville, Madrid & Barcelona
13 Excellent Meals
- Welcome Dinner in Lisbon
- Fado dinner & show
- Flamenco dinner & show
- Farewell Dinner in Barcelona
Learn more about what's included with the Holiday Advantage.
Chicago - O'Hare International Airport