This trip is all about experiencing Portugal from the inside out. It combines time outdoors with culture, food, and wine, moving easily between cities and wine country. You’ll walk through historic neighborhoods, explore vineyard landscapes, and taste wine right where it’s produced, with space for long meals and good conversation along the way.

Get ready to fall in love with the world-renowned Douro Valley and the awe-inspiring city of Porto.

Cindy Vance and Angelique Fish are the co-founders of the Women’s Wine Hiking Society, a 501(c)(7) nonprofit organization built on connection, confidence, and adventure. What started as two friends hitting the trail while their husbands went dirt biking grew into a thriving nonprofit that now helps women across the country build friendships and discover their strength in the outdoors. Their mission is simple: create welcoming, judgment-free spaces where women can explore the outdoors, challenge themselves, and feel fully supported along the way.

Traveling internationally with the Women’s Wine Hiking Society is about so much more than seeing a new destination. It’s about experiencing it in a way that feels intentional, connected, and deeply memorable. 

Co-founders Cindy and Angelique built this community on the belief that adventure is better when shared and that some of life’s most meaningful friendships are formed on the trail, around the dinner table, or over a glass of wine after a full day of exploring. Their trips are designed to take the stress out of planning and replace it with confidence, connection, and unforgettable experiences.

What makes traveling with Cindy and Angelique different is their philosophy: no rushing, no pressure, no getting left behind. Whether you’re hiking through vineyards, walking historic pilgrimage routes, or exploring a new country for the first time, these adventures are created for women who value community as much as the destination itself. 

With small group sizes, thoughtful itineraries, and a judgment-free environment, you’ll return home with more than great photos. You’ll leave with new friendships, renewed confidence, and memories that stay with you long after the journey ends.

Because with the Women's Wine Hiking Society, you don’t just visit a destination, you experience it alongside an incredible group of women who often arrive as strangers and leave as friends.

Welcome to Lisbon, a city full of life and color. Upon arrival, a representative will be there to meet you at the airport and take you straight to the hotel.

Around 6:00 pm, you head out together for dinner and a traditional Portuguese Fado show.

Meals Included: D

Exe Saldanha or similar

After breakfast, a guided walking tour takes you out exploring Lisbon’s historic neighborhoods and hidden corners. From the Alfama to Baixa and Chiado, the tour gives you a clear picture of Lisbon's diverse and vibrant atmosphere.

The rest of the day is free. Don’t miss the chance to taste traditional favorites like pastéis de nata or bacalhau. This afternoon is also a great moment to find a good viewpoint for sunset, and soak in the city’s everyday rhythm.

Meals Included: B

Exe Saldanha or similar

After breakfast, you’ll leave Lisbon behind and head south toward the wide-open landscapes of Alentejo. The day begins with a transfer to Alcácer do Sal, where you’ll stretch your legs on a short hike along the Rota do Senhor dos Mártires, a peaceful trail that winds through rolling hills, river views, and quiet countryside. It’s an easy, scenic introduction to hiking in this region and a great chance to settle into the group rhythm.

Continue on to Évora, a UNESCO World Heritage city, where Roman ruins and medieval streets make you feel like you've travelled back in time. The evening is free to relax and enjoy the slow Alentejo life.

Meals Included: B

Ibis Évora or similar

The day begins with a scenic morning hike along the Rota da Água da Prata, following Évora’s historic aqueduct as it winds through rolling countryside, olive groves, and open farmland. It’s a relaxed, immersive walk that sets the pace for the day.

After the hike, the journey into Alentejo’s wine culture officially begins with a visit to a local winery. There you enjoy local wines, and then it's time to return to Évora for a laid-back afternoon.

Meals Included: B

Ibis Évora or similar

With a scenic transfer you make it to the jaw-dropping Douro Valley, not without stopping at Castelo Branco for a short visit to its historic center and gardens.

Once in the valley, you check in at the hotel and can wander through this famous wine region.

Meals Included: B

Douro Inn or similar

Today is all about walking through some of Portugal’s most iconic landscapes. The morning hike takes you along vineyard trails between São Cristóvão do Douro and Provesende, where terraced hillsides drop toward the river and the Douro Valley unfolds step by step. It’s a scenic, steady walk with sweeping views over the vineyards and the river below — classic Douro at its best.

Midday brings a relaxed picnic lunch paired with a wine tasting at a local Quinta in the Régua/Pinhão area, offering a deeper taste of the region’s wine traditions. This is the perfect day for all our wine-lovers!

Meals Included: B, L

Douro Inn or similar

Get ready to see the Douro from a different angle, cruising down the river from Pinhão or Peso da Régua toward Porto. Vineyard-covered hills rise on both sides as the landscape unfolds at river level, a perspective you don’t get from the trails.. Lunch is served on board, meaning you’re eating while floating through the heart of the Douro Valley, with the quiet rhythm of the water beneath you.

Meals Included: B, L

Premium Porto or similar

A guided walking tour through Porto’s historic areas, including Ribeira, Sé Cathedral, and São Bento Station offers a great introduction into this magnificent city. It’s a practical, well-paced walk that helps bring together Porto’s history, architecture, and everyday life. After the tour, the afternoon is free to explore further, relax by the river, or revisit a favorite spot.

What better way to wrap up the trip than a farewell dinner together? You’ll try local dishes, share memories, and enjoy one last evening as a group.

Meals Included: B, D

Premium Porto or similar

Right after breakfast our trip comes to an end. You can either head back home or continue the adventure by joining us on the Camino walking program! Click here to see the details.

Meals Included: B

Trip Dates: May 6-14th, 2027
Starting City: Lisbon
Finish City: Porto
*You may arrive anytime on day 1, and depart anytime on Day 9. If you require pre or post accommodation to extend your stay, please let us know.

Payment
Twin/Double Rate per person: 4299 USD
For this rate, you will share a room with another traveler in the group.
Single Room Rate per person: 4999 USD
For this rate, you will have your own room throughout the trip.

Deposit: $500 USD due at time of booking
Final Payment Due: 90 days prior to departure date.

Included
Accommodation
Transport throughout the tour
Activities and Meals as Indicated on Itinerary
Transfer in
English-Speaking guide throughout

Not included
International Airfare
Meals not indicated on itinerary
Tips and Gratuities
Travel Insurance

Booking Terms and Conditions
Group Size Minimum: Pricing is based on a minimum of 8 travellers.
Deposit required to confirm: $500 USD per person
Full Payment Due: 90 days prior to departure

Cancellation Penalties
Cancellation 120 Days prior to departure - loss of deposit
Cancellation 119-90 days prior to departure - 50% non refundable
Cancellation 89 days or less prior to departure - 100% non refundable