Portugal & Spain

Embark on a 10-day journey through the enchanting castles and historic cities of Portugal and Spain. From Lisbon’s vibrant streets to the fairytale castles of Sintra, explore Segovia’s Roman aqueduct and Madrid’s Habsburg legacy. Enjoy guided tours, scenic drives, coastal adventures, and luxurious stays in top hotels along the way.

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10 Days Food & Drink History Outdoor Tours Wine Tasting Portugal Spain

Lisbon & Belem Tour

Tours History

Depart from your hotel to explore Lisbon. Begin by seeing the April 25th Bridge and the Christ the King Statue. Enjoy a walking tour through Alfama, with a stop at St. George Castle for views over the city, and visit Rossio, Chiado, and Bairro Alto. In the afternoon, head to Belém to tour the Jeronimos Monastery, Belém Tower, and taste the iconic "Pasteis de Belém." Included: Transportation, English-speaking guide, drink & pastry tasting, entry to Belém Tower, Jeronimos Monastery & St. George Castle
Not Included: Lunch
Note: Comfortable walking shoes recommended; cobblestone terrain

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Tour of Sintra & The Coast with Castle Visits

Tours History

Drive along the scenic coast past Estoril and Cascais to reach the UNESCO heritage site of Sintra, considered one of Portugal's most beautiful places. Visit the historic center, the 14th-century Pena Palace, Castelo dos Mouros, Regaleira Palace, Sintra National Palace, and Monserrate Palace. Enjoy free time to explore and have lunch at a local restaurant (at your expense) before returning to Lisbon. If time allows, stop at Cabo da Roca, the westernmost point of mainland Europe. Included: Transportation, English-speaking guide, entry to Pena Palace, Castelo dos Mouros, Regaleira Palace, Sintra National Palace, and Monserrate Palace
Not Included: Lunch

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Fishing Tour from Cascais

Activity Tours

Set off from Cascais with a local skipper and fishing guide to cast your line off the Portuguese coast and reel in a wide variety of Atlantic fish against the backdrop of the Sintra Mountains and Cabo da Roca. Your captain will choose the most promising spots to drop anchor based on the weather and sea conditions, plus offer expert tips and techniques to maximize your chances of a great catch.

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Segovia Walking Tour

Tours History

Explore the UNESCO World Heritage treasures of Segovia, including the iconic Roman aqueduct with its impressive 167 arches, reaching up to 28.5 meters (93 feet). Discover the Alcazar of Segovia, a fairytale-like fortress that served as a royal residence during the Middle Ages, and admire the Gothic Segovia Cathedral with its soaring bell tower, dome, and art-filled chapels. Stroll through the elegant historic center, exploring Romanesque churches and the Jewish quarter.
Included: English-speaking guide, entrance tickets to the Cathedral & Alcazar
Not Included: Lunch

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Castles of Castile Tour

Food & Drink Tours History

Explore the stunning 15th-century castles of Peñafiel, Castillo de la Mota, and Fuensaldaña. Built on a 10th-century fortress, Peñafiel Castle, declared a national monument in 1917, features a long, narrow structure and offers breathtaking views over the Duratón and Botijas valleys. Since 1999, it has housed the Provincial Wine Museum. Castillo de la Mota, one of Castile’s largest towers, served as a strategic military center and royal archive, and even hosted Juana la Loca. The stately Fuensaldaña Castle, built by the Vivero family, later became the seat of the Castilla y León Parliament.
Included: Transportation, English-speaking guide, entrance tickets to Peñafiel, Castillo de la Mota, and Fuensaldaña
Not Included: Lunch

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Madrid of the Habsburg Walking Tour

Tours History Food & Drink

You will be introduced to the Habsburg legacy in Madrid. The Royal Palace, vaulted in stone and brick along the lines of Versailles, was once Carlos III’s residence. The nearby Almudena Cathedral is a late and imposing construction in neo-classical and neo-Gothic style, only completed in 1993, giving the capital its grandest temple. The Austrias’ Quarter, with its monasteries, churches and elegant squares such as Plaza Mayor, recalls Spain’s Golden Age when Madrid was the capital of an empire extending from Latin America to the Philippines. During your tour, you will enjoy a break to taste some delicious chocolate with churros.

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Experience the Allure of Portugal & Spain

Journey through vibrant cities, historic castles, and coastal landscapes where ancient traditions meet modern charm. Discover the cultural richness, world-class cuisine, and stunning architecture that make these destinations unforgettable.

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