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Day by Day Itinerary

From a Roman colony and centuries of Moorish rule to the great explorers of the Age of Discovery, Spain and Portugal are home to extraordinary beauty and untold remnants of a tumultuous past. We’ll chart our own course for discovery in these ancient lands while staying in intimate Portuguese pousadas and Spanish paradores, restored historic inns—from castles and convents to manor homes and monasteries—that evoke the glory of an earlier era. We'’ll also dine with a Spanish family in their home, tour a Portuguese vineyard and wine estate, and learn about the history of bullfighting at a finca ranch in Ronda, a medieval town perched high above a plunging gorge. Discover royal cities, hilltop citadels, and ancient olive groves—on a journey deep into the lands of conquerors and conquistadores.

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    You depart today on your overnight flight from the U.S. to Lisbon, Portugal.

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    After an overnight flight, arrive at the airport in Lisbon, where an OAT representative will greet you. After a brief orientation walk to gain familiarity with our surroundings, we’ll enjoy a Welcome Drink and a briefing about our upcoming discoveries at our hotel. We’ll also meet those who traveled on our optional Porto: Northern Portugal’s Romanesque Gem extension. This evening, our group will gather for dinner at a local restaurant.

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    After breakfast, we set out for a discovery of Lisbon. Spread out on seven low hills overlooking the Tagus River, the legendary Portuguese capital has lured traders and settlers for more than 20 centuries.

    In the late 15th century, the port of Lisbon was the staging point for Portuguese explorations that would usher in the great Age of Discovery—and make Lisbon the richest European capital until the 19th century. Highlights of our panoramic city tour include Belém, a neighborhood that is home to a variety of cafés, museums, gardens, and parks, as well as two UNESCO World Heritage Sites dating from the early 16th century—Belém Tower and Jerónimos Monastery. At Jerónimos, which was built as a monument to celebrate Portuguese voyages around the world, we'll visit the monastery's church, whose lower choir is the resting place of Vasco da Gama. Jerónimos is considered a jewel of Manueline architecture (named after King Manuel I), a flamboyant building style that glorifies Portugal’s seafaring past. In Belém, we'll also view Lisbon’s iconic Monument to the Discoveries, where Portugal’s intrepid explorers are immortalized in sculpture. Then, we'll drive through Baixa, an area in the heart of Lisbon that was destroyed and completely rebuilt after the Great Earthquake of 1755. Baixa now features broad squares and avenues flanked by shops, cafés, and elegant Neo-Classical buildings.

    Later, we’ll leave the city’s environs to visit Sintra, a village situated within a fairytale landscape of lush forests, turreted palaces, and castle ruins. Our discoveries include Pena Palace, a lavish 19th-century hilltop castle built on the ruins of an ancient monastery. After a walking tour (of approximately 45 minutes) through the palatial gardens of this UNESCO World Heritage Site, we’ll take a horse-drawn carriage ride along Sintra’s romantic streets—adding to the enchantment of this timeless locale. Then, after returning to Lisbon, we’ll head to a local restaurant for dinner and a private performance of Portugal’s traditional melancholic style of music known as fado.

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    Today, we’ll journey south of the city to a region of bucolic farmland and fields and focus on some of Portugal’s popular rural traditions. Our discoveries include a visit to a working windmill where cereal grains are still ground into flour for the production of fresh local bread. We’ll also visit a traditional artisanal cheese producer to learn about Azeitão cheese, a velvety local specialty made from raw sheep’s milk. Then, after lunch at a local restaurant, we’ll learn about another longstanding Portuguese tradition—azulejos. Introduced to Iberia by Moors, the blue or multi-colored ceramic tiles called azulejos decorate everything from church walls and palaces to the façades of most Portuguese homes. We’ll also gain insight into the ancient art form of azulejos by trying our hand at painting some of the tiles.

    After returning to our hotel in Lisbon in the late afternoon, we’ll embark on a brief walking tour, followed by a fun language lesson to learn some popular Portuguese phrases. Dinner is on your own this evening.

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    After breakfast, we depart Lisbon and journey through the unspoiled wine-growing region of Alentejo province on our way to Évora. Our route is through gently rolling terrain, which is dotted with vineyards, cork trees, olive groves—even several prehistoric monuments. To break up our journey, we’ll learn about Portuguese wine at a traditional 18th-century monte (a typical Alentejo farming estate), where we’ll tour the vineyard, winery, and cellars. We’ll also get to sample a few of the estate’s wines and enjoy an included lunch.

    Then, in the afternoon, we’ll stop in Arraiolos, a small village near Évora that is renowned throughout the world for its hand-embroidered wool carpets and tapestries. Here, we’ll learn about the centuries-old rug-making techniques.

    Later this afternoon, we’ll arrive in Évora and enjoy an included dinner at our historic pousada.

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    This morning features a walking tour of Évora, an ancient hilltop town with Roman and Moorish roots that is a UNESCO World Heritage Site. Our stroll within Evora’s medieval walls will reveal a series of whitewashed houses adorned with wrought-iron balconies. We’ll also see the influence of Rome at the ruins of the Temple of Diana, whose 14 exquisite Corinthian columns date back to the second and third centuries. Next to the Roman temple is the equally imposing Évora Cathedral, a rose granite monument blending Romanesque and Gothic architecture, with some of its most ancient sections dating from the beginning of the 13th century.

    Near Évora’s main square is the Church of St. Francis, home to a macabre bone chapel (Capela dos Ossos) which welcomes visitors with the eerie message: “We bones in here wait for yours to join us.” Inside, thousands of skeletons and skulls have been carefully arranged along the chapel walls, ceilings, and columns—put there by three Franciscan monks in the early 16th century who wanted wealthy residents of Évora to reflect on the transience of material things and inevitability of death.

    Our tour also includes a visit to one of the town’s local markets, where you may wish to pick up a regional specialty like smoky paio sausage or Serpa cheese to go along with freshly baked bread for a simple and delicious lunch on your own. The remainder of the afternoon is yours to stroll along the cobbled streets of the town that many of the 15th-century Portuguese kings once called home.

    This evening, we’ll gather together to learn some of the secrets of Portuguese cuisine during a cooking lesson, followed by an included dinner.

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    Crossing into Spain today, we enter Extremadura, an autonomous Spanish province known as the homeland of such famous 16th-century conquistadores as Pizarro and Cortés. As we traverse this vast and sparsely populated farming region we will likely see views of storks nesting in ancient steeples and medieval towns dotting the plain. Although Extremadura once marked the boundary between Moorish and Christian Spain, the capital of the region, Mérida, fell under Moorish, Christian, and even Portuguese control throughout its storied history. It is better known, however, as one of the most famous Roman capitals on the Iberian Peninsula, and it displays this heritage in some of the best-preserved Roman ruins in all of Europe. Today, we’ll explore the UNESCO World Heritage Site of Mérida, including its 6,000-seat Roman theater and the adjoining amphitheater, where gladiators once battled to the death against animals imported from Asia and Africa and confined in the large, cross-shaped pit we’ll see at center stage.

    After lunch on your own, we continue our journey to the charming Andalusian town of Carmona, arriving in time for an included dinner at our lodgings in one of Spain’s historic paradores.

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    Spend the day exploring Carmona on your own, or join an optional tour to Seville, the romantic Spanish city renowned for bullfighting, the flamenco, and Don Juan. This optional tour reveals several of Seville’s highlights, including its picturesque whitewashed homes, 2000-year-old plazas, and maze of cobbled streets in neighborhoods like the Barrio de Santa Cruz. We’ll also explore the Seville Cathedral, one of the largest and most impressive churches in the world. Built in the 15th century at the site of a 12th century mosque, the massive Cathedral is also home to the golden Retablo Mayor, the largest altarpiece in the world—and is the reputed burial place of Christopher Columbus.

    Travelers staying in Carmona will also enjoy exploring this picturesque walled town with its Roman-era streets at their own pace. You’ll want to see the Seville Gate and its double Moorish arch, which leads to the narrow streets, whitewashed walls, and Renaissance mansions of Old Town. Cozy Plaza San Fernando is home to a series of elegant 17th-century homes; and the nearby Roman Necropolis contains the relics of more than 900 families that lived in and around Carmona some 2,000 years ago.

    This evening, our small group will gather for an included dinner featuring authentic tapas—an essential part of Spanish life—at a local restaurant.

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    Today we journey south from Carmona to Ronda, admiring views of several of the region’s famous “white villages” along the way. Nestled into mountainsides or set atop dramatic gorges, Andalusia’s Pueblos Blancos are a series of picturesque whitewashed hill towns and quaint villages that also offer a glimpse of Spanish life and culture during medieval times. Our destination, Ronda, is actually one of Andalusia’s largest—and most spectacular—of Andalusia’s white hill towns. But to Spaniards, Ronda is far more famous as being the birthplace of modern bullfighting. So before our arrival, we’ll stop for an included lunch at an authentic bull ranch owned by a famous bullfighter and learn about this way of life and the breeding of toros.

    We arrive in Ronda in the afternoon, where you will have free time to explore and relax before dinner at our parador, Ronda’s historic town hall.

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    Few places are able to boast a more dramatic setting than Ronda, one of the oldest cities in Spain and a one-time stronghold for legendary Andalusian bandits from the 18th to early 20th centuries. Ronda is divided by a 360-foot-deep ravine—El Tajo—which is spanned by three bridges, including the newer Puente Nuevo, a graceful 18th-century stone structure high above the Guadalevín River. On one side of the 210-foot-wide gorge are the narrow medieval streets of Ronda’s Moorish Old Town, known as La Ciudad; on the other, the more recent El Mercadillo quarter, which was constructed after the Christian Reconquest of 1485. Homes clinging precariously to the cliff faces of El Tajo add even more to Ronda’s dramatic beauty. Our full-day walking tour will focus on Ronda’s walled Old Town, where we’ll wander through its labyrinth of medieval streets, flanked by Moorish whitewashed homes with wrought-iron balconies.

    We’ll pause for an included lunch during our tour, and also enjoy the spectacular views of the canyon from atop the Puente Nuevo Bridge, with the valleys and hills shimmering in the distance. Just don’t get too close—in his novel For Whom the Bell Tolls, Ernest Hemingway describes how prisoners were tossed alive from this very spot into the deep gorge below during the bitter Spanish Civil War. Hemingway also famously wrote about bullfighting, and Ronda is home to one of Spain’s oldest bullrings. Built in 1785, the Plaza de Toros is where cavalry training consisting of spearing bulls from horseback developed into the more “sporting” form of confronting the bull on foot. The father of this modern form of bullfighting was Ronda native Francisco Romero, and his grandson Pedro is widely considered the most famous Spanish bullfighter of all time (the matador is said to have killed almost 6,000 bulls here during his long career). Pedro Romero is also immortalized by Hemingway in his novel The Sun Also Rises.

    Dinner is on your own this evening.

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    After breakfast at our parador, we’ll depart Ronda and journey to Úbeda. En route, we’ll enjoy an included lunch at a local restaurant before a special visit to the Alhambra in Granada, the last of the Moorish capitals. Visually stunning with its commanding hilltop setting above the Darro River, the reddish-gold Alhambra was constructed as a 13th-century fortress palace of the Nasrid kings—along with their harems. We’ll explore several of the lavish rooms, passageways, palaces, towers, fountains, and courtyards of this fantastic citadel complex—widely hailed as the supreme achievement of Moorish art and architecture. We’ll also view the magnificent Generalife Gardens, which were built as a retreat from the splendors of the Alhambra, before continuing on to Úbeda.

    Upon arrival in Úbeda, we’ll enjoy an included dinner at our parador, conveniently situated in the town’s Renaissance-era main square, a UNESCO World Heritage Site. 

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    Situated in Jaén province on a plateau between the Guadalquivir and Guadalimar rivers, Úbeda is bordered on all sides by numerous olive groves that produce some of the world’s best olive oil. After breakfast at our parador, we’ll learn about the olive oil production process—from harvesting to bottling—beginning with a walk through a stand of olive trees. Then we’ll learn about traditional and modern olive-oil production at one of the many local mills where we’ll sample some of the flavorful Esencial Olive extra virgin olive oil. Afterwards, we’ll split into smaller groups to enjoy some authentic Andalusian hospitality during a Home-Hosted Lunch with some local families engaged in the olive-oil industry.

    This afternoon we explore Úbeda, an ancient provincial city often referred to as the “Florence of Andalusia.” At Casco Antiguo (Old Town), we’ll wander the narrow cobblestone streets lined with Renaissance-era palaces, stately mansions, and tile-roofed whitewashed homes, centered around the Gothic church Iglesia de San Pablo. With dinner on your own this evening, you may wish to work up an appetite exploring a few of Úbeda’s famous leather and pottery craft workshops before trying out a local restaurant.

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    Today, we depart Úbeda for Madrid, stopping en route to explore Toledo. After lunch at a local restaurant, we’ll arrive in Toledo, former Spanish capital—still capital of the autonomous province of Castile-La Mancha—and a beautifully preserved medieval gem. Perched on a hill overlooking the Tagus River in the heart of Spain, Toledo was known as the “city of three cultures” for its harmonious blend of Christian, Jewish, and Muslim cultures from the 11th to the 13th centuries.

    We’ll embark on an afternoon walking tour of this 2,000-year-old UNESCO World Heritage Site, which Don Quixote author Miguel Cervantes described as the “glory of Spain and light of her cities.” Perhaps some of the sights will look familiar from the works of artist El Greco—for example, the enormous vaulted Cathedral of Toledo, whose beauty rivals that of Paris’ Notre Dame; and the lovely, 12th-century Synagogue of Santa María La Blanca, which was converted to a Christian church during the 15th century. We’ll also view the Church of St. Tome, where El Greco’s painting The Burial of the Count of Orgaz now hangs; and the walled fortress El Alcázar, the 16th-century Moorish citadel which dominates the city skyline.

    Upon arrival at our hotel in Madrid in the early evening, dinner is on your own.

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    Contrast Spain’s former capital city with its modern one as we explore Madrid this morning. Highlights include stops at bustling Plaza de España; the opulent Palacio Real (Royal Palace), where King Juan Carlos I and Queen Sofia reside; and Templo de Debod, an ancient Egyptian temple given to Spain in 1968.

    Lunch is on your own followed by an afternoon at leisure. Or, you may wish to join our optional tour to the beautiful medieval town of Segovia, a UNESCO World Heritage Site that is home to an ancient Roman aqueduct and the famous hilltop castle of Alcazar.

    Dinner is on your own this evening.

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    After breakfast, enjoy a day at leisure in Madrid. You may wish to join your Trip Leader on a discovery walking tour of the city, or strike out on your own to mingle with the madrileños along the lively boulevards and plazas, browse one of the city’s renowned museums, such as the Prado; or discover why the Spanish say, “De Madrid al cielo” (Madrid is the next best thing to heaven) in one of the city’s lovely parks.

    This evening, our small group will celebrate our two weeks of Iberian discoveries during a festive Farewell Dinner accompanied by a flamenco performance at a local restaurant.

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    • Meals included:

    After breakfast, we depart for the airport for our return flights home, or to begin our post-trip extension to Bilbao & Spain’s Northern Coast.

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Weather & Regional

Before you travel, we encourage you to learn about the region of the world you'll discover on this trip. From weather and currency information to details on population, geography, and local history, you'll find a comprehensive introduction to your destinations below.

Visit our “What to Know” page to find information about the level of activity to expect, vaccination information resources, and visa requirements specific to this vacation.

What to Know

For more detailed information about this trip, download our Travel Handbook below. This document covers a wide range of information on specific areas of your trip, from passport, visa, and medical requirements; to the currencies of the countries you’ll visit and the types of electrical outlets you’ll encounter. This handbook is written expressly for this itinerary. For your convenience, we've highlighted our travelers' most common areas of interest on this page.

Download the Travel Handbook

What to Expect

Pacing

  • 6 locations in 15 days

Physical requirements

  • Not appropriate for travelers using wheelchairs or other mobility aids
  • Must be able to walk 2-3 miles unassisted each day and participate in 3-5 hours of daily physical activities, including walks along cobblestoned streets and up several steps and steep hills

Climate

  • Spain and Portugal enjoy a Mediterranean climate with warm summers and cool winters
  • Daytime temperatures in July and August often reach above 90°F

Terrain

  • Travel over some rugged paths and cobblestoned streets, as well as bumpy, unpaved roads, both by bus and on foot

Transportation

  • Travel via private, air-conditioned bus and horse-drawn carriage
  • Several overland drives of 5-6 hours

Accommodations & Facilities

  • Most nights are in paradores and pousadas, government-owned restored historic inns with comfortable rooms and private baths
  • Lodgings in Lisbon and Madrid are hotel-standard, with a variety of amenities and private baths

Cuisine

  • Meals will be based on the local cuisine

Travel Documents

Passport

Your passport should meet these requirements for this itinerary:

  • It should be valid for at least 6 months after your scheduled return to the U.S.
  • It should have the recommended number of blank pages (refer to the handbook for details).
  • The blank pages must be labeled “Visas” at the top. Pages labeled “Amendments and Endorsements” are not acceptable.

Visas

U.S. citizens do not need a visa for this trip.

If you are not a U.S. citizen, do not travel with a U.S. passport, or will be traveling independently before/after this trip, then you may need a visa. Please check with the appropriate embassy or a visa servicing company. To contact our recommended visa servicing company, PVS International, call toll-free at 1-800-556-9990.

Vaccinations Information

For a detailed and up-to-date list of vaccinations that are recommended for this trip, please visit the CDC’s “Traveler’s Health” website. You can also refer to the handbook for details.

Before Your Trip

Before you leave on your adventure, there are at least four health-related things you should do. Please check the handbook for specifics, but for now, here’s the short list:

Step 1: Check with the CDC for their recommendations for the countries you’ll be visiting.
Step 2: Have a medical checkup with your doctor.
Step 3: Pick up any necessary medications, both prescription and over-the-counter.
Step 4: Have a dental and/or eye checkup. (Recommended, but less important than steps 1-3.)

What to Bring

In an effort to help you bring less, we have included checklists within the handbook, which have been compiled from suggestions by Trip Leaders and former travelers. The lists are only jumping-off points—they offer recommendations based on experience, but not requirements. You might also want to refer to the climate charts in the handbook or online weather forecasts before you pack. Refer to the handbook for details.

Insider Tips

Accommodations

Main Trip

  • Turim Av Liberdade Hotel

    Lisbon, Portugal

    Located along the Avenida Liberdade near Marquês de Pombal Square in central Lisbon, the Turim Av Liberdade Hotel has a restaurant, bar/lounge, coffee shop, and features complimentary wireless Internet. There are 100 air-conditioned rooms at the hotel, each with satellite TV, minibar, and private bath.

  • Pousada de Évora

    Évora, Portugal

    The Pousada de Évora, a former monastery founded in 1487 over the ruins of an ancient castle, is situated in Évora’s historic center, between the Gothic Cathedral and Temple of Diana. Along with a small swimming pool, there is a restaurant located in the old cloisters. The 36 rooms—former monks’ chambers—are uniquely configured, include a cable TV, safe, mini bar, and private bath with hair dryer and bathrobe.

  • Parador de Carmona

    Carmona, Spain

    Parador de Carmona is a restored 14th-century Arabic fortress situated high atop a hill that overlooks the vast plains below. Amenities at the historic castle include a gift shop, swimming pool (seasonal), restaurant, bar, and elegant Mudéjar courtyard with fountain. There are 63 air-conditioned rooms at the parador, each with satellite TV, safe, minibar, and private bath.

  • Parador de Ronda

    Ronda, Spain

    Built in 1761 as Ronda’s Town Hall, the Parador de Ronda is situated next to the Puente Nuevo Bridge about a ten-minute walk to the old quarter and bullring—and features splendid views of the plunging gorge. Amenities include a restaurant specializing in Andalusian cuisine, gift shop, lounge, café, seasonal swimming pool, and complimentary Wi-Fi. The parador’s 78 rooms are air-conditioned in the summer months (June-September), and include balcony, minibar, safe, satellite TV, and private bath.

  • Parador de Úbeda

    Úbeda, Spain

    Originally a 16th-century Moorish palace, then rebuilt in the 17th-century, the Parador de Úbeda is situated next to the chapel of El Salvador in the center of Úbeda’s historic Plaza de Vasquez Molina. Amenities include a lovely inner courtyard, bar, and restaurant. There are 36 high-ceilinged rooms, each with air-conditioning, satellite TV, minibar, safe, and private bath.

  • Hotel Emperador

    Madrid, Spain

    The historic Hotel Emperador is situated along the Gran Vía in the heart of Madrid, with easy access to such sights as Plaza Mayor, Plaza de España, and the Prado Museum. Hotel amenities include a lobby bar and rooftop garden bar and restaurant. There are 232 air-conditioned rooms, each with Wi-Fi Internet access, satellite TV, minibar, safe, and private bath with robe and hair dryer.

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  • Grande Hotel do Porto

    Porto, Portugal

    Situated in the heart of Porto, within walking distance of shops and major monuments, the Grande Hotel do Porto was inaugurated in 1880 and is home to a rich history. Amenities include a restaurant, bar, and fitness center. There are 94 rooms, each with a flat-screen TV with satellite channels, a minibar and a private bathroom with a bathtub and shower.

  • Miró Hotel

    Bilbao, Spain

    Opposite the Guggenheim Museum and within walking distance of the Museum of Fine Arts and shopping, the Miró Hotel is well situated for discovering Bilbao. Each of the 50 rooms offers air-conditioning, private bath, minibar, telephone, satellite TV, and wireless Internet access. Hotel features include a small café and a fitness center.

  • Hotel Hoyuela

    Santander, Spain

    Situated opposite Playa El Sardinero Beach, the Belle Epoque-style Hotel Hoyuela is in the heart of the district which arose in the 19th century as Santander became a resort town. The 55 rooms of the Hotel Hoyuela each offer air-conditioning, private bath, minibar, telephone, satellite TV, and wireless Internet access.

  • Melia Hotel de la Reconquista

    Oviedo, Spain

    Situated in a National Monument-listed 18th-century building, the Meliá Hotel de la Reconquista is conveniently located near Oviedo's Old Quarter. Amenities include a restaurant, bar, and two outdoor patios. There are 142 rooms, each with air-conditioning, TV, safe, minibar, complimentary wireless Internet, and private bath. 

Flight Information

Flight Options to Personalize Your Trip

You can choose to stay longer before or after your trip on your own, or combine two adventures to maximize your value. Here are more ways to create the OAT adventure that’s right for you:

  • Extend your adventure and lower your per day cost with our optional pre- and post-trip extensions
  • Choose our standard air routing, or work with us to select the airline and routing you prefer
  • Make your own international flight arrangements directly with the airline, applying frequent flyer miles if available
  • International airport transfers to and from your hotel, including meet and greet service, are available for purchase
  • Stay overnight in a connecting city before or after your trip
  • Request to arrive a few days early to get a fresh start on your adventure
  • Choose to “break away” before or after your trip, spending additional days or weeks on your own
  • Combine your choice of OAT adventures to maximize your value
  • Upgrade to business or premium economy class
  • Extend your Land Tour-only Travel Protection Plan coverage and protect the air arrangements you make on your own—including your frequent traveler miles

The air options listed above may involve additional airfare costs based on your specific choices.

Or, when you make your reservation, you can choose our standard air routing, for which approximate travel times are shown below.

Standard Air Routing

w/out standard air $3195
w/ standard air $4095
Gateway Travel Time*
Boston, Chicago, Detroit, New York (JFK), Washington, DC (Dulles) 11hrs
Atlanta, Miami 13hrs
Los Angeles, Minneapolis, Phoenix 14hrs
Denver, Philadelphia, San Diego, San Francisco, Seattle 15hrs
Baltimore 16hrs
Portland 17hrs

*Estimated total time, including connection and layover. Actual travel time may vary.

The information above reflects approximate flight times from the gateway cities listed to Lisbon, Portugal. Routing is based on availability and subject to change. You will receive your final air itinerary approximately 14 days prior to departure.