Sip & Cycle in Portugal

Sip & Cycle in Portugal

The confluence of Portugal’s wine is truly unique. Their wine-making roots emerged out of ancient civilizations, and, due to centuries of economic isolation preventing trade with other European countries, Portuguese growers were forced to perfect their own grape varieties. In a world long dominated by France, Spain, and Italy, Portugal's wines seem finally to have emerged from the shadows. The country is home to famous wine regions such as the picturesque Douro Valley, which produces the famous Port wine, and the Alentejo region, known for its red wines made from the Touriga Nacional grape. Portugal is also home to the Cork Oak tree and contributes roughly one third of global cork production.

So raise a glass to one of Europe's most underrated wine destinations and discover with us the quality and diversity of Portuguese wines. There is a wealth to explore beyond great ports.

Why Into The Vineyard

Why Into The Vineyard

Commitment to Service

We believe life is most enriched when time is spent meaningfully, and the people around us are well cared for. We offer tailored travel that is effortless and designed to inspire discovery, foster connections, and build community.

Private & Customizable Journeys

Travel preferences are as unique as an individual’s fingerprint. Our expertise lies in designing bespoke journeys to the wine regions of the world. Using our global networks, we craft your trip to suit your own style.

Regional Expertise

Discover the world alongside passionate locals who bring each destination to life. Garner authentic insights and connection. Our Sales and Planning teams have explored at length the destinations they specialize in. We continuously revisit regions, inspect accommodations, and experience wineries, so we can deliver the quality and service you expect.

Extraordinary Experiences

We design immersive experiences with excellence. Whatever your request - a private Mendoza vineyard lunch, truffle hunting in Piedmont, or a First Growth in Bordeaux - you will enjoy exclusive access to unparalleled encounters.

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Plan and travel at ease with the support of expert travel professionals. Headquartered in Canada and with staff around the world, we ensure you are supported from initial planning discussions to full on-trip coverage.

Responsible Travel

Our aim is to provide travel that inspires both the traveler and the communities we visit. We prioritize privately-operated accommodations, locally-owned restaurants and generational wineries, and encourage low-carbon private transportation where viable.

Quick Summary

Itinerary Detail

Day 1: Introduction to Lisbon

Daily Summary

Welcome to Portugal! Upon arrival into Lisbon Airport, you will be greeted by your private driver and transferred to your accommodation in the city to check in.

Introduction to Lisbon

You’ll meet your local guide at your hotel this afternoon and set out on an introductory walking touring of Lisbon, known as the City of the 7 Hills. From afar these hills look like a montage of traditional white painted houses and stone walled churches each taking up the little space left between them, so typical of a southern European country.

Within these 7 hills there are innumerous “treasures” to discover. You'll begin in downtown Lisbon, with a visit to the Saint Jorge Castle for scenic views of the city and stroll through the historic quarters. With your guide explore the popular neighborhoods of Lisbon such as Alfama and Mouraria, where the sound of Fado emulates through the narrow streets coming from small taverns. Coming down to the “Baixa” with its imponent squares, traditional shops and electric trams going up and down the century old cobbled streets. Chiado and Bairro Alto are the trendy quarters, with designer shops, lively night-time bars or roof top sunset cocktails.

During your visit this afternoon, stop for a tasting of local products such as cured ham, Azores cheese, bread and round it out with a glass of Port wine.

Day 2: E-Bike Tour to Belem

Daily Summary
  • Tour: E-Bike Tour to Belem
  • Experience: Fado Show with Traditional Dinner
  • Accommodation: PortoBay Marques Hotel
  • Meals: B, D

E-Bike Tour to Belem

Make your way to a central meeting point where you will be greeted by the local bike team. After introductions, together set out on a private E-bike tour of Lisbon. During the 2-hour visit, you will pass by the riverside and typical quarters of Lisbon on the way to the UNESCO area of Belém to visit the Jeronimos Monastery church and surrounding area, a mix of historical buildings and vanguard new architectural buildings such as the MAAT.

Here, learn about the importance of this location to the Portuguese people and have the opportunity to taste the famous “Pastel de Belém”, a delicious custard tart and an essential Portuguese treat.

You'll be back to Lisbon for an afternoon at leisure.

Fado Show with Traditional Dinner

This evening, make your way to a special dinner with Fado show in the historic neighborhood of Alfama.

A symbol of identity, Fado music is widely sung in Lisbon and represents a distinctly Portuguese multicultural synthesis of Afro-Brazilian music, local genres of song and dance, rural music, and urban song patterns of the early nineteenth century. Fado is typically performed by a solo male or female singer, accompanied by an acoustic guitar and the Portuguese guitarra, a pear-shaped twelve-stringed lute. It is performed professionally and informally in grass-root associations and often transmitted over successive generations within the same families. Fado is inscribed by Unesco as a cultural intangible heritage since 2011.

Your special dinner will include a traditional menu with house wines from the restaurant, all while you attend to a very intimate Fado performance from well-known local artists.

Return at leisure to your hotel this evening.

Day 3: Lisbon to Dão

Daily Summary

Lisbon to Dão

After checking out, join your guide this morning and set out towards Dão. Along the way you will enjoy a tasting in the Ribatejo wine region.

Start the day with a private visit and tasting at a wine estate such as Quinta de São Sebastião in the Ribatejo wine region. Here you’ll have the chance to learn about the estate’s history, and embark on a trip through time to appreciate the architecture of the 18th century building. Visit the chapel, the cellar, the vineyard, discover the mine and the horseriding ring. Following the visit, sample some of winemaker Antonio Parente’s four ranges, Grande Escolha, Reserva, Vinho Branco and Mina Velha.

Lunch will be enjoyed at the Lagoalva Wine Estate, a working farmhouse.

After lunch, continue on the scenic route north, where your guide will bring you to your accommodation in the Dão.

Day 4: Transfer to Duoro Valley

Daily Summary

Transfer to Duoro Valley

This morning, after checking out of your hotel, your private guide will pick you up for your journey towards the Douro Valley. En route, you’ll visit one final winery here in the Dão Wine region.

Your first destination today is the Quinta do Soito Wine Estate where you’ll be treated to a privately guided visit with premium wine tasting and picnic lunch overlooking the vineyards. Soito Wines, created in 2013, is one of Dão’s youngest and most promising projects. At Quinta do Soito, with an already long wine tradition, two teachers gave wings to the dream of transforming the family farm into a reference producer, with wines of exceptional quality.

Departing the estate, you’ll continue to the Douro Valley, where you’ll check into your hotel and enjoy the evening at leisure.

Day 5: Explore Douro Valley by E-bike

Explore Douro Valley by E-bike
Explore Douro Valley by E-bike
Explore Douro Valley by E-bike
Explore Douro Valley by E-bike
Explore Douro Valley by E-bike
Explore Douro Valley by E-bike
Daily Summary
  • Tour: Douro Valley Exploration
  • Activity: Evening Cooking Class
  • Accommodation: Casa Relogio de Sol
  • Meals: B, L, D

Douro Valley Exploration

After breakfast this morning, you’ll be rejoined by your private guide as we set out for a charming day in the vineyards and rolling hills of the Douro Valley.

Begin the day with an active start with a private E-bike ride through the Douro Valley. On this 25km bike ride (2hrs30mins) along the back roads of the Douro, amongst vineyards and small villages, take in the beautiful views and the river as your backdrop on the way down the valley hills.

Next, you will be welcomed at Quinta do Crasto wine estate, considered to be one of the top wine producers in Portugal.

A member of the famous Quinta do Crasto will be pleased to receive you for a visit to the vineyards and wine cellars, followed by a taste of its red Douro wines and Ports (Late Bottle Vintage and Vintage). This ancestral Quinta with 130 hectares is located in the Cima Corgo area of the Demarcated Region of Douro in the right bank of the Douro River. It is planted with 60 hectares of excellent vineyards, some almost eighty years old. This special visit will allow you to discover one of the mythical wine estates of the Douro Valley, considered to be one of the 3 top Portuguese wine producers.

A private lunch will be set outside by their house and vineyards, with an astonishing view of the river and valley. The main dish is the famous country duck rice with Crasto wines.

Continue with a transfer in a classic Bedford farm truck from the estate, down to the river dock. On arrival, embark on a private cruise on the Douro river aboard a typical “Rabelo” boat (50min). One of the most interesting ways to discover the Douro Valley is in an enchanting cruise. The boat is a replica of a traditional Rabelo boat that, for centuries, carried casks of young wine from the Douro Valley downriver to the lodges in Vila Nova de Gaia.

Disembarking from your cruise, you will be have some time to explore the charming village of Pinhão and its historical train station. The Pinhão train station dates back to the early 20th century, a time when the Douro railway was used in good part to transport wines down to Porto, and no longer by river boats. It is craftfully decorated with Portuguese Azulejo tiles, in total 3047 tiles compose 24 panels that illustrate “Scenes of life in the Douro”.

After the visit, your guide will return you to the hotel.

Evening Cooking Class

This evening, walk to a neighboring wine estate where you'll enjoy a private cooking lesson with the estate's owner. You'll enjoy the fruits of your labor for dinner this evening, along with some of the estate's delectable wines. Afterwards, return at leisure to your hotel.

Day 6: Douro Valley to Porto

Daily Summary

Douro Valley to Porto

This morning, after checking out, transfer with your driver guide towards Porto.

Arriving in Porto mid-morning, meet your local guide in Porto's UNESCO listed city center for a walking tour of Porto and its delightful squares, monuments and traditional shops. During this tour, enjoy stopping to taste the delicious local produce on offer including gourmet canned fish, Portuguese sparkling wine, bread, cheese, olives, cured meats and red wine from the local markets in town.

As the tour comes to an end, you'll reach your hotel for check-in and lunch and most of the afternoon at leisure.

This evening, around 5pm, make your way to the other side of the Douro River, to the town of Gaia and its Port Wine Cellars District. Here, enjoy a small-group visit of Graham's Port Wine Cellar, a local institution, for a tasting of three of their Premium Tawny Ports. Following this tasting, you'll be treated to a delicious three course meal and wine at their Vinum Restaurant before returning to your hotel at leisure after dinner.

Day 7: Porto

Daily Summary


Capital and gateway to the North of Portugal, Porto is both the city that provided a nation with a name and a fortified wine famous world-wide: Port Wine. With its splendid geographical location on the mouth of the river Douro and an architectural heritage of exceptional quality, the historic centre of Porto is a World Heritage Property declared by UNESCO. Its hard-working inhabitants are noted for their commercial enterprise, always standing firm against outside impositions and foreign invaders, which explains why Porto has become known as the “unvanquished” city. When discovering Porto, you will find a traditional welcoming and conservative environment, but also a contemporary and artistic city. This is shown in the streets, in the architecture, monuments and museums, and in the lively terraces, restaurants and leisure areas.

Porto at Leisure

The day is yours to discover at your own pace. We suggest visiting the Serralves Museum of Contemporary Art and their current exhibits.
Alternatively, venture to the nearby fishing town of Matosinhos and visit the local market in the morning, followed by a fresh seafood lunch.

The beach of Porto and the extensive boardwalks also make for an enjoyable and calm day. Rental bikes can be arranged from many shops around town should you wish to set out on two wheels.

Day 8: Departure

Daily Summary
  • Transfer: Hotel to Porto Airport
  • Meals: B

Your driver will meet you at your accommodation and bring you to Porto airport for your onward flight. Obrigado!


PortoBay Marques Hotel
PortoBay Marques Hotel
PortoBay Marques Hotel

PortoBay Marques Hotel

This four-star hotel in Lisbon, located on Rua Duque de Palmela, is right around the corner from Marquês de Pombal square and just a few steps away from Avenida da Liberdade, a pleasant walk from the city’s main attractions. The industrial chic design restaurant is open for lunch and dinner, and breakfast can be enjoyed from 7:00. The rooftop bar offers city views, and the lounge bar and terrace invites guests to relax. After a day exploring Lisbon, guests can unwind at PortoBay’s indoor and outdoor gyms.

Parador Casa da Insua
Parador Casa da Insua
Parador Casa da Insua

Parador Casa da Insua

The Parador Casa da Ínsua is the only Portuguese Hotel which belongs to the prestigious Spanish Parador de Turismo chain. Located in Penalva do Castelo, about 30kms from the city of Viseu and 1h30m from the city of Porto, Parador Casa da Ínsua combines the location and the surrounding nature to its history, comprising Quinta da Ínsua and the Dão wine route, with connection to the Serra da Estrela natural park. The atmosphere and sophistication of the 18th century are always present in this boutique hotel. Combined with the wine tasting cellar, the regional cuisine and the outdoor swimming pools, make Casa da Ínsua a perfect destination for a perfect stay or event any time of the year.

Casa Relogio de Sol
Casa Relogio de Sol
Casa Relogio de Sol

Casa Relogio de Sol

Casa Relógio de Sol is a charming family house located in the enchanting Douro Valley region of Portugal. Situated amidst rolling vineyards and scenic landscapes, this traditional Portuguese house offers a peaceful and authentic experience for guests. The rooms at Casa Relógio de Sol are thoughtfully designed, combining rustic elegance with modern comforts. Wooden floors, light fabrics and warm colors give each spacious room at Casa Relógio de Sol an elegant touch. The guesthouse provides a perfect base for exploring the renowned wine estates and picturesque villages of the Douro Valley and a seasonal outdoor pool is the perfect spot to relax after a day exploring the region.

Hotel Carris Porto Ribeira
Hotel Carris Porto Ribeira
Hotel Carris Porto Ribeira
Hotel Carris Porto Ribeira

Hotel Carris Porto Ribeira

Charm and historical environment, outstanding World Heritage location, riverside quarter. Five historic buildings located in the central World Heritage zone of the city, have been converted into this 4-star hotel offering 90 elegant guestrooms. Hotel Carris Porto Ribeira offers accommodation in double and superior double rooms as well as double rooms for single use to suit al needs. All these rooms are stylish and very comfortable. They have a modern décor and they are equipped with a full range of amenities. Around the hotel you will find at 1 min walking the amazing Douro River with lively terraces, bars and restaurants, several monuments and shops, all this in the famous Ribeira quarter at the best centre of the World Heritage classified area.



Price Includes

Bespoke organization of the trip

Bilingual guide with expert regional knowledge

Regional restaurant recommendations

Accommodation as per the daily summary

Meals as per the daily summary

All transfers on private basis as per the daily summary

All tours on private basis as per the daily summary (unless otherwise stated)

Wine tasting fees

Price Excludes

International and domestic airfares

Any entrance tickets not mentioned in the itinerary

All meals and beverages not included in the daily summary

Dinner restaurant reservations (available for a supplement)

Gratuity (at your discretion)

Travel insurance

Items of a personal nature

Rental vehicle hire (if applicable)

Your Dedicated Into the Vineyard Team


Trip Designer 

Madison currently resides in Colorado where she was born and raised – loving to live near the mountains and sunshine. With a background in tourism management and spending a great deal of time traveling around the world, she is very passionate about learning about other cultures, cuisines, and of course, wine.

One of her fondest travel memories was watching the sun rise over Machu Picchu with a cup of hot tea atop Huayana Picchu. She has loved learning about French wines and enjoying the cuisine components to travel. She is excited to share her travel experiences and use that knowledge gained to help curate memorable, unique, custom trips.