Portugal & Spain Beyond the Guidebooks

A Journey Through Wine, Culture & Coastlines

Join a group of fellow women travelers for an unforgettable journey through Portugal and Northern Spain.

Experience the perfect balance of iconic highlights and hidden gems as we explore Lisbon, Porto, and the Douro Valley before venturing off the beaten path to Galicia, one of Spain's most beautiful and least-visited regions. Enjoy boutique accommodations, incredible food and wine, meaningful cultural experiences, coastal wellness, and authentic connections with local communities. From catamaran cruises and vineyard tastings to clam harvesting and seaside sunsets, this thoughtfully curated journey invites you to experience a side of the Iberian Peninsula that most travelers never see.

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MaY 14-22, 2027
6-14 Travelers

9-days, 8-nights
Portugal & Northern Spain

pricing starts at $5,795
Only a $500 deposit to reserve your spot.

trip highlights

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Who is the trip for

all the details

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Trip Highlights

• Fully planned and guided journey through Portugal and Northern Spain

• Travel with a small group of inspiring women

• Explore the vibrant cities of Lisbon and Porto alongside trusted local guides

• Discover the storybook towns of Sintra and Óbidos, two of Portugal's most beloved destinations

• Cruise along the Tagus River and the Douro River while taking in stunning coastal and vineyard landscapes

• Taste your way through Portugal with wine tastings, market experiences, traditional cuisine, and local specialties

• Venture beyond the typical tourist route into Galicia, one of Spain's most authentic and least-visited regions

• Experience local traditions firsthand through a unique clam harvesting excursion

• Visit Santiago de Compostela, the final destination of the world-famous Camino de Santiago pilgrimage route

• Stay at a boutique coastal wellness retreat designed for rest, reflection, and connection

• Learn from local women preserving cultural traditions, hospitality, food, and wine across Portugal and Spain

• Support local and women-owned businesses simply by traveling with Cherish

• Simply show up, the rest is taken care of for you!

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WHO IS THIS TRIP FOR?

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THOUGHTFUL WANDERER

WINE & FOOD
LOVER

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COASTAL
ROMANTIC

HIDDEN GEM SEEKER

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PURPOSEFUL TRAVELERS

CLICK TO BROWSE

the ITINERARY

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day one | May 14th

Arrive in Portugal

Bem-vinda a Portugal!

Upon arrival in Lisbon, you'll be welcomed and transferred to our boutique hotel in the heart of the city. Portugal's vibrant capital is known for its colorful tiled buildings, historic neighborhoods, incredible food scene, and warm hospitality.

Take time to settle in, rest after your travels, or head out for a short stroll through the surrounding streets before meeting your fellow travelers.

This evening, we'll gather for a special welcome dinner at a local restaurant, where you'll enjoy your first taste of Portuguese cuisine while getting to know the incredible women who will be sharing this journey with you.

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day two | May 15th

Lisbon & the Tagus river

Today offers the perfect blend of exploration and ease.

To start the morning, you can choose to explore Lisbon’s streets at your leisure or join a local woman guide for an insider's look at Lisbon. Together, you'll wander through historic neighborhoods, discover hidden corners of the city, and gain a deeper understanding of Lisbon's culture and everyday life through the eyes of someone who calls it home.

Later, rejoin the group to board a private catamaran for a cruise along the Tagus River. As we sail past some of Lisbon's most recognizable landmarks, enjoy drinks, beautiful scenery, and a unique perspective of the city from the water.

The remainder of the evening is yours to enjoy. Find a cozy restaurant, stroll through Lisbon's lively streets, or simply relax and soak in the atmosphere of one of Europe's most captivating cities.

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day three | May 16th

Castles, Coastal Views & Porto

Depart Lisbon for a unique road trip to Porto. Along the way, we'll stop in Sintra, a magical town known for its colorful palaces, lush hillsides, and fairytale charm. Frequently considered one of Portugal's most beautiful destinations. We'll also visit the medieval village of Óbidos, a beautifully preserved walled town filled with cobblestone streets, whitewashed buildings, and colorful flowers.

By the early evening, we'll arrive in Porto, Portugal's beloved northern city known for its riverside setting, rich history, and world-famous wine culture.

After checking into our hotel, enjoy a relaxing evening settling into your new surroundings and preparing for the adventures ahead.

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day FOUR | May 17th

Porto through flavor & local traditions

This morning is another opportunity to choose how you want to explore this iconic city. Explore on your own with curated recommendations or join a local female guide for an insider’s experience of her hometown.

In the afternoon, we'll come together for one of the culinary highlights of the trip. Alongside a private chef, we'll explore the vibrant Mercado do Bolhão, Porto's beloved market filled with flowers, seasonal produce, fresh seafood, and local specialties. As we wander through the market, we'll enjoy tastings that celebrate the region's rich culinary traditions, including fresh oysters, seafood, and local wines.

Later on, you have another opportunity to enhance your trip by participating in an optional Portuguese tile workshop.

To end the day, we'll gather for dinner accompanied by traditional Fado music. Through soulful songs and heartfelt storytelling, you'll experience one of Portugal's most treasured cultural traditions.

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day FIVE | May 18th

The Douro Valley

Today we'll venture into one of the world's most beautiful wine regions.

Our first stop is the Douro Valley's most celebrated woman-led wineries. Surrounded by terraced vineyards overlooking the river, we'll enjoy a guided wine tasting and lunch while learning about the family's history and the women helping shape the future of this iconic estate.

After lunch, we'll board a traditional boat for a private journey along the Douro River. As we glide past vineyards, historic wine estates, and dramatic hillsides, you'll gain a deeper appreciation for the landscape that has defined this region for centuries.

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day six | May 19th

From Portugal to Spain

After breakfast, we'll say goodbye to Portugal and begin our journey into Northern Spain. Traveling through beautiful coastal landscapes, we'll make a stop for lunch before continuing toward Galicia, a region many international travelers never experience. Known for its rugged coastline, incredible seafood, strong cultural traditions, and slower pace of life, Galicia offers a side of Spain that feels authentic, welcoming, and refreshingly undiscovered.

Be greeted at our next getaway along the coast by a local woman wellness practitioner who will guide us through a gentle yoga or meditation session designed to help us slow down, reconnect, and fully embrace the next chapter of our journey.

We'll end the day with dinner at our retreat home and a relaxing evening together.

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Day 7 | May 20th

Women of the sea

Today offers one of the most unique cultural experiences of our journey. Along Galicia's coastline, shellfish harvesting has historically been a profession led by women. This morning, we'll join a local woman on her clam farm to learn about her work, the region's traditions, and the important role women have played in sustaining these coastal communities for generations.

Following our time on the water, we'll return to Terranam for a light snack and time to refresh. In the afternoon, you can choose between having a relaxing afternoon or continuing to explore by heading to Santiago de Compostela.

Known as the final destination of the world-famous Camino de Santiago pilgrimage route, Santiago is filled with history, beauty, and emotion. We'll explore its charming streets and lively atmosphere before enjoying a tapas dinner that showcases the flavors of Galicia.

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day 8 | May 21st

Time to Unwind

Today offers the perfect blend of exploration and relaxation. Choose between a visit to Isla de Arousa, where you'll enjoy scenic coastal views, beach time, and a generous local snack by the sea, or upgrade your experience with a visit to Pazo de Rubianes, one of Galicia's most celebrated wine estates, for an exclusive Albariño wine tasting.

Enjoy a free afternoon to relax, book an optional massage, explore the property, or simply soak in the peaceful surroundings.

This evening, we'll gather for a traditional Galician Fest Dinner before ending the night with a special fire ceremony, a meaningful opportunity to reflect on the experiences, connections, and memories made throughout our journey.

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Day 9 | May 22nd

Departures

Enjoy one final breakfast at your retreat home away from home before beginning your onward journey. Cherish will provide a group transfer back to Portugal, with drop-offs available at both Porto Airport and Porto's city center. Flights are recommended after 1:00 PM to allow for a comfortable and stress-free transfer.

For guests who choose to extend their time in Porto, the city center drop-off offers the opportunity for one last stroll along the riverfront, a leisurely lunch, or a final taste of Portugal before heading home.

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Women this trip supports

Throughout our journey through Portugal and Spain, we intentionally seek out opportunities to support local communities, women entrepreneurs, and small businesses that help preserve the culture and traditions of the places we visit. From sharing a meal prepared by a local woman chef in Lisbon to learning from women guides, wellness practitioners, winemakers, and shellfish harvesters, this trip offers meaningful opportunities to connect with the women shaping their communities.

Guests will have the opportunity to connect with the people preserving the traditions, food culture, wine heritage, and coastal livelihoods that make these regions so special.