Tour begins 5:00 PM. A transfer is included from Francisco Sá Carneiro Airport (Porto Airport) or Porto Campanhã station to your riverboat, ms Andorinha, on the Douro River. Settle in, then join us for a welcome reception followed by dinner and onboard entertainment.

Situated in northwest Portugal where the Douro meets the Atlantic Ocean, Porto has been known around the globe as the city from which authentic Port wine has been shipped throughout the world for nearly three centuries. Rising on staggered hills along the river, this colorful city beckons you to its labyrinthine streets and stairways, medieval alleys, Baroque churches, fountains, and bell towers, Beaux-Arts buildings, and bohemian neighborhoods whose narrow cobblestoned lanes wind their way past centuries-old former merchants' homes and trendy cafés. You have a sightseeing choice today. Discover Porto by land, river and air – starting from the historic riverfront Ribeira district, walking to Vila Nova de Gaia and riding a cable car for panoramic views. Alternatively, join a local guide for a walking tour that begins in the riverside Riberia district, walking uphill to the Cathedral, crossing the top of the Luis I bridge and concluding in Vila Nova de Gaia with a view overlooking Porto. Return to ms Andorinha late morning and begin sailing to the Douro River Valley, bound for the historic port of Peso da Régua. All along the winding river, rugged conical mountains and shale hills carved by concentric vineyard terraces tell of a winemaking history that's thousands of years old. Inhospitable to most other kinds of farming, the terroir is perfect for Portugal's indigenous wine grapes, whose hardy roots can go down 30 feet or more in search of water. And since the latter half of the 17th century, when Portuguese vintners succeeded in creating a sweet fortified wine – now famous around the world as Port, named for the city of Porto – that could make the long sea voyage to Britain and other destinations without spoiling, the Douro Valley has been the only supplier of true Port, the oldest demarcated wine region on Earth.

Dock in the historic town of Peso da Régua, once a busy hub where wooden boats called rabelos, laden with barrels of Port, sailed downriver to Vila Nova de Gaia. Visit the Douro Museum, set within the restored Casa da Companhia Velha building, once part of Real Companhia Velha (Royal Oporto Wine Company), chartered in 1756. On your guided visit to the museum, you'll explore its exhibits chronicling the history, culture and traditions of the Douro River Valley region, from the cultivation of grapes on the vines to the processes involved in the production of Port wine and its distribution around the world. This afternoon, sail through one of the largest locks on the Douro to the idyllic, tranquil village of Pinhão, nestled at a dramatic bend in the river; Pinhão is known as the gateway to the valley's quintas (vineyards) and large wine estates. From here it's a short drive to Quinta do Portal, a family-run estate in the Cima Corgo region where renowned Port and non-fortified wines are made. Your visit includes an introduction to the vineyards and a private dinner with wine pairings.

The Douro River Valley and its unique landscapes of terraced mountains, villages, and wine estates unfolds today on a full day's sail to the small Spanish port town of Vega de Terron, where the Douro forms the border between Spain and Portugal. The landscape, at a confluence of rivers, is tranquil, beautiful and unspoiled, at the edge of Douro International Natural Park.

At the town of Pocinho you have a choice of shore excursions. Your first option visits a local town on the border between Spain and Portugal for a look at the town and region's historical landmarks including its many defensive strongholds. Alternatively, travel to the Museum of Art and Archaeology of the Côa Valley for stunning exhibits of rock art from the valley's Paleolithic era, discovered in the 1990s when excavations began for a Côa River dam; unlike cave art found in other parts of Europe, the thousands of petroglyphs in the Côa region were created in the open air by the valley's earliest inhabitants, and the museum explores their mystery through state-of-the-art multimedia exhibits. Return to the riverboat for lunch and sail back to Pinhão, arriving this evening.

Your choice of excursions this morning includes an opportunity to explore Pinhão and its early-20th century train station, adorned with blue-painted tiles (azulejos); or a vigorous hike in the hilltop vineyards with striking views of the town and river. Sail to Régua, where you'll have two choices; visit 18th-century Mateus Palace, a lavish Baroque residence designed by Nicolau Nasoni that is now a museum with period furnishings and artwork, a heraldic hall, formal gardens, a winery, and a chapel with tombs and reliquaries. Alternatively, join a local guide for a visit to a local wine-making estate called a quinta, rewarding with a port cocktail making class. Begin the return trip to Porto, and dock overnight in this verdant wine country, where some traditional farms grow vines on pergolas and fences so high the grapes must be harvested with ladders.

Today, you have a choice of full day excursions; one option provides an opportunity to explore the medieval town of Guimarães, known as the "Cradle City; the kingdom of Portugal was born here after a famous battle in 1128. The city center, a UNESCO World Heritage site, offers a wealth of architectural treasures, including the ruined Castle of Guimãraes, with its tempestuous history and sweeping views, the opulent Palace of the Dukes of Braganza, lush with 17th-century furnishings and tapestries, and the 13th-century Church of São Miguel do Castelo. Alternatively, take a bicycle ride (for experienced cyclists in good physical condition) through the Vinho Verde region before arriving in the pastoral town of Amarante, famed as being the hometown of São Gonçalo, Portugal's St. Valentine. Enjoy lunch before your late afternoon arrival into Porto where you'll cross the river to Vila Nova de Gaia. Join us this evening for a farewell reception and dinner aboard the ship.

Tour ends: 8:00 AM Porto. Disembark and fly home anytime. A transfer is included from your riverboat to Porto Airport or Porto Campanhã station. Allow at least 3 hours for flight check-in.