DAY 1: SOAR TO THE LAND OF CASTLES, COASTLINE AND COBBLESTONES Start dreaming of your first glass of port wine on your overnight flight to Porto, Portugal's second-largest city.

DAY 2: IT'S NEVER TOO EARLY TO POUR YOURSELF A GLASS OF PORT Olá e bem-vindo! Touch down in Porto, where a Go Ahead representative greets you at the airport and escorts you to your hotel in the heart of this 2,000-year-old UNESCO World Heritage-listed city. After taking some time to relax and explore, greet your fellow travelers at your welcome dinner.

DAY 3: UNCOVER OLD-WORLD NEIGHBORHOODS IN A WHOLE NEW LIGHT Stock Exchange Palace Get to know Porto like a true tripeiro (Porto resident) as you follow a local through the meandering medieval lanes of the Old-World Ribeira District and along the boat-lined Douro riverfront. Together, you'll pass citywide icons, such as the Baroque-style Clérigos Tower, a lofty landmark that can be spotted from nearly anywhere in Porto, the Gothic Sáo Francisco Church and the wrought-iron Dona Maria Pia Bridge. You'll also step inside the city's famed neoclassical Stock Exchange Palace. Afterward, you'll be free to continue exploring as you like, perhaps delving into Porto's burgeoning art scene or gaining an inside look at the region's most popular export: port wine. Choose to join our optional afternoon cruise down the Douro River, followed by visits to two of the region's most prestigious wine cellars: Offley and Sandeman. At each cellar, you'll have the opportunity to sample world-famous labels and learn about the history and production of port wine.

Port Wine Cellars and Douro River Cruise: Float along the Douro, the Iberian Peninsula's third-longest river, and take in scenes of Porto's vibrant waterfront and historic Villa Nova de Gaia, home to the region's centuries-old port wine warehouses. As you cruise, you'll drift under five of the river's most iconic Old-World bridges, passing colorful hillside villas and traditional rabelos (flat-bottomed boats) along the way. Back on shore, pay visits to two of Porto's most prestigious port wine cellars: Offley and Sandeman. During guided tours, learn the long-standing history of port wine, as well as the ins and outs of port production and warehousing before being treated to a tasting of each cellar's world-famous labels.

DAY 4: STUDY UP ON GOTHIC ARCHITECTURE NEAR THE "OXFORD" OF PORTUGAL Coimbra University, Old Cathedral of Coimbra Drive south toward évora, and stop en route to explore Coimbra. Home to the country's first university, the Universidade de Coimbra, this vibrant college town is known as the "Oxford" of Portugal. Follow a local guide on a tour of the university and uncover Coimbra's striking Gothic architecture on a walk through its medieval old town and riverfront. After free time for lunch, continue on to the UNESCO World Heritage-listed city of évora, where you'll settle in for the night.

DAY 5: EXPLORE THE ANCIENT CITY THAT LURED ROMANS AND ROYALTY St. Francis Church and Gardens Begin your day with a walk through the streets of évora, one of Europe's oldest continuously inhabited cities. This ancient city has deep Roman roots, and was once home to Portuguese royalty. As you stroll, take in the region's distinctive whitewashed homes decorated with intricate tilework, pass the remains of the Roman temple and enter into the eerie "Chapel of Bones." This afternoon, continue to the sun-soaked Algarve region, southern Portugal's resort hot spot and home to some of Europe's most beautiful beaches. After arriving, sample authentic local fare at your group dinner.

DAY 6: LOOK OUT TO OPEN OCEAN FROM THE END OF THE EARTH Sagres Fortress Discover the Algarve's stunning white-sand beaches and breathtaking coastline during visits to the seafaring towns of Lagos and Sagres, as well as Cape St. Vincent. Roam the mostly walled-in town of Lagos, with its sandy shoreline, picturesque churches and quaint medieval fairs. Later, take in views of the sea from Sagres Fortress on Cape St. Vincent, which was considered to be the westernmost point in the world before the Age of Discovery.

DAY 7: BEHOLD BELÉM AND CENTURIES OF PORTUGUESE PRIDE Jeronimos Monastery Make your way back north to Lisbon, Portugal's colorful capital city. Set against the Atlantic, Lisbon boasts an incredible maritime history and served as home to legendary world explorer Vasco da Gama during the Age of Exploration. With a local guide, take in the city's tribute to these explorers at the Maritime Monument and iconic Belém Tower, followed by visits to the Jerónimos Monastery and the culturally rich Alfama District. Tonight, join our optional excursion and sway to the melancholic melodies of Portugal's traditional fado music while enjoying dinner.

Fado Dinner & Show: Spend your evening at Lisbon tavern listening to fado. Derived from the Latin word fatum-meaning "prophecy" or "fate"-fado" is Portugal's national musical treasure. Fado's traditional theme is "saudade," a word that doesn't quite translate to English but conveys an overwhelming sense of longing for something lost. Dinner is included during this memorable musical evening.

DAY 8: CALDEIRADA TO BACALHAU-GET A TASTE FOR LISBON'S LOCAL FLAVORS Stroll through Lisbon's charming backstreets; roam along the treelined lanes of its old quarters; taste fresh pastry from a small cafe; or order up a cup of caldeirada or a plateful of salty bacalhau-Portugal's unofficial national dish. You may also opt to spend your free day venturing outside of the city to the UNESCO World Heritage-listed town of Sintra and the traditional fishing village of Cascais. Later in the evening, come together with your fellow travelers for your farewell dinner.

Sintra & the Portuguese Riviera: Journey to the UNESCO World Heritage-listed town of Sintra and learn why the Poet Lord Byron once called it a "glorious Eden." Having served as the stomping grounds for Portugal's kings and queens, Sintra is home to the only surviving royal palace from the Middle Ages, which you'll explore on a guided tour. Afterward, you'll have free time to stroll through Sintra, viewing its colorful villas, small shops and impeccably manicured gardens before finding a quiet eatery for lunch. On your way back to Lisbon, take in the coastal scenery of the Portuguese Riviera. Stop en route in the old fishing village of Cascais to discover the town's winding, narrow streets, pastel-colored buildings and bustling fish market before continuing back to Lisbon.