A Gay Travel Hiking Tour to Portugal

This once in a lifetime adventure is designed for men who want to spend a week in the spectacular Douro Valley wine country of Portugal, lodge in 4 and 5-star restored manor houses, venture out each day for leisurely hikes amid the vineyards during the harvest, sample the wines at numerous vineyards, and enjoy an awesome Portuguese cuisine.  We also visit Porto, a medieval city with old world charm, lodge in a 4-star historic hotel, sample port wines, stroll along the riverfront promenade, and visit historic buildings.

On this adventure we explore the wine region of the Douro River Valley and the medieval city of Porto. The Douro Valley, the birthplace of Port wine, is one of the oldest and most beautiful of the historic European wine regions and it is a World Heritage Site. Wine has been made in the Duoro Valley for over two thousand years. Steep terraced vineyards carved into mountain slopes, granite bluffs along meandering rivers, whitewashed quintas (farms) estates with 18th century wine cellars, winding country roads, and postcard-pretty villages characterize this region. We take short hikes in the wine country during the wine harvest, visit medieval villages with historical buildings and churches, sample wine in numerous vineyards, lodge in 4 and 5-star restored manor houses, and enjoy the Portuguese cuisine.
Porto, a coastal city in northwest Portugal, was first settled by the Romans. The city is known for its Old World Charm and famous for its port wine production. The old part of the city, the Ribeira (riverside), is a World Heritage Site. This medieval area has narrow twisting streets with mosaic patterned stones which wind past merchants’ houses, residential homes, cafes and small shops all with red-tiled roofs. Spectacular palaces, churches and cathedrals with lavish Baroque interiors, and historical buildings dot the skyline, and ancient bridges cross the river. The nearby Vila Nova de Gaia, the village where port wine is aged and stored, has over 50 port wine lodges. In Porto we lodge in a 4-star hotel and with our cultural guide explore the medieval city, visit a Port lodge and have time to relax at the riverfront promenade.


  • Spectacular walks through colorful vineyards in the fall when locals are harvesting the grapes  
  • Visits to numerous local wine estates to learn about growing grapes and wine production, and for wine tastings
  • Relax in a boat with a glass of port as we cruise along the Douro River and enjoy views of the spectacular wine country
  • Visits to quiet medieval villages in the countryside to see magnificent churches, monasteries and old mansions
  • Lodge in restored 18th century 4 and 5-star manor houses in the wine country and enjoy the Portuguese cuisine and local wines


  • Depart from USA
    Saturday, September 21
  • Arrive in Porto
    Sunday, September 22
    Arrive in Porto
    Arrive at the airport in Porto, clear customs and take a taxi to the Carris Hotel, a restored historical building designed for luxury and comfort, located in the historic Ribeira district of the city. The Ribeira is a maze of medieval alleys that zigzag down to the picturesque waterfront promenade, which has trendy bars, outdoor cafes and small shops. Our 4-star hotel has a bar, restaurant, and free WiFi. Tonight we have a welcome dinner and enjoy traditional Portuguese cuisine and local wines. 1 x Dinner
  • Travel to Douro Valley Wine Country
    Monday, September 23
    Travel to Douro Valley Wine Country
    After breakfast at our hotel, we travel by private van with our cultural guide to the Douro Valley wine country and along the way visit two historical towns. We first stop at Amarante, a sleepy village along the scenic Tamego River, home to 17th century mansions with brightly painted balconies along the narrow streets and restaurants on terraces overlooking the river. The village is dominated by a medieval bridge and the impressive Igreja de Sao Goncalo Church and monastery built in 1620. We tour the town with our Portuguese guide and then stop for lunch at a riverfront café. We next travel to Lamego, an attractive town located amid the vineyards and fruit orchids in the Douro Valley. We visit the Nossa dos Remedios, a hilltop chapel originally dedicated in 1391 to Saint Stephen and one of Portugal’s most important pilgrimage sites. We also visit the Se, a Gothic cathedral dating back to the 12th century. Later in the afternoon we arrive at the Vilarinho de Sao Romeo, a beautifully restored 17th century manor house in the country in the quiet hills above the Douro River. All rooms have their own character and there is a pleasant lounge, a beautiful shady wisteria-engulfed veranda, attractive gardens, a restaurant where we dine each night, and free WiFi. We lodge here for two nights. 1 x Breakfast
    1 x Dinner
  • Vineyard Walk (8.7 miles)
    Tuesday, September 24
    Vineyard Walk (8.7 miles)
    Our walk today takes us into the working wine estates located on terraces laced with vines with ripening grapes and workers busy harvesting the grapes. We walk through several small vineyards, cross the river twice and wind our way through forests and back to our hotel. We have lunch along the way in the village of Celeros. In the afternoon we have the option of visiting the nearby Quinta do Portal, a family winemaking company, for a guided tour and wine tasting. We enjoy dinner at our hotel. 1 x Breakfast
    1 x Dinner
  • Walk to Pinhao & Winery Visit (7 miles)
    Wednesday, September 25
    Walk to Pinhao & Winery Visit (7 miles)
    In the morning we walk to the village of Pinhao and our next lodge. The first part of the walk is through woods, pine, heather, eucalyptus, and thyme on the hills of the Serra de Alem. We descend to the attractive village of Provesende and then through wine country until we reach the Pinhao River, and follow it to the Douro River and to the Vintage House Hotel, a 5-star facility with breathtaking views of the surrounding vineyards and Douro River. It has an outdoor pool, a tennis court, tranquil gardens, a restaurant, bar, and free WiFi. After lunch in the village, we visit the Quinta da Roeda, a short walk from the hotel, to discover the secrets of the vineyards on a guided walking tour followed by a wine tasting. 1 x Breakfast
    1 x Dinner
  • Hike, Wine Tour & Lunch (2.5 miles)
    Thursday, September 26
    Hike, Wine Tour & Lunch (2.5 miles)
    In the morning we visit the Quinta Nova, a luxury wine estate located on a stunning ridge surrounded by luscious ancient vineyards, overlooking the Douro River with views of mountains. We have a tour of the winery and the opportunity to hike on trails throughout the vineyard. The longest trail is 2.5 miles in length. After the tour and hike we have lunch and enjoy an exceptional cuisine and wonderful wines from their vineyard. 1 x Breakfast
    1 x Lunch
    1 x Dinner
  • Douro River Cruise & Train to Porto
    Friday, September 27
    Douro River Cruise & Train to Porto
    In the morning we board a traditional Rabelo boat which has open and closed areas for a two hour river cruise. We travel upriver to the village of Tua, famous for its oranges and figs, and along the way have fantastic views of the surrounding terraced wine country. We can listen to an audio guide in English that explains what we see and enjoy a complimentary glass of port. We return to Pinhao for lunch and then take a scenic two hour train ride to Porto and check in at the Carris Hotel. 1 x Breakfast
  • Tour Porto
    Saturday, September 28
    Tour Porto
    In the morning with our cultural guide we stroll down the Avenida dos Aliados to view the grand buildings and then visit the 12th Century Romanesque Se Cathedral where Prince Henry the Navigator was baptized in 1394, see the tile art work at the San Bento train station, visit the Palacio da Bolsa with its lavishly decorated rooms, and climb the 240 steps of the Clerigos Church and Tower, built in the 18th Century on a hill, for views of the city and the river. After the tour we next walk across the historic Ponte de Dom Luis Bridge on our way to Vila Nova de Gaia, the village where port is aged and stored. It has over 50 port lodges. We visit Taylor’s, a lodge founded in 1692, for a tour to learn about the history of port and then sample some of the wines. After the tour we have lunch at an outdoor restaurant on the postcard-perfect waterfront promenade. Tonight we have a farewell dinner at a local restaurant. 1 x Breakfast
    1 x Dinner
  • Depart for Home
    Sunday, September 29 After breakfast we can take a taxi to the airport for our flights home. 1 x Breakfast
  • Important Notes
  • Included

Important Notes

Note: Details File
Land Cost

$2,350 per person based on double room occupancy. Single Supplement: $444. Please note, a single supplement is available for all dates of travel except for Days 3 and 4. Twin beds are available for these nights.


We hike on well-maintained trails distances of 8.7 and 7.0 miles, respectively, on Days 4 and 5, and up to 2.5 miles at a vineyard on Day 6. All hikes are rated as moderate.

What’s Included

Lodging, all breakfasts, lunch and dinner where noted, wine tasting on Days 4, 5, 6 and 8, Douro River boat tour, train from Pinhao to Porto, taxi to wine estates, local cultural tour guide on Day 3, American tour guide throughout tour, and hotel luggage transfer on Day 4.

What’s NOT Included

Airfare to and from Portugal, hotel-airport transfer in Porto, drinks or alcoholic beverages not noted in the itinerary.

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