Portugal ~ Signature Collection

PORTUGAL ~ Signature Collection

This journey brings together the sophistication of Lisbon with the stillness and sun-washed beauty of the Alentejo countryside. It’s a week of warm hospitality, thoughtful experiences, with time to wander, taste, learn, rest, and simply be.

We begin in Lisbon, staying at a 5-star hotel in the heart of the city. With our local guide, we’ll explore historic neighborhoods and share meals that reflect the city’s culinary style — from casual, shared-plate dinners to an unforgettable evening at a Michelin-starred restaurant. One night, we’ll take to the water for a private sunset sail along the Tagus — the city glowing gold as we drift past Belém Tower and under the 25 de Abril bridge.

Midweek, we travel inland to Évora, a UNESCO World Heritage town of golden stone streets, Roman history, and quiet plazas. From there, we settle into our countryside retreat — surrounded by olive groves, vineyards, and big, open sky. Here, the pace shifts. Mornings are gentle. Afternoons are free to wander, nap, enjoy the spa or the pool, read, or simply look out at the landscape.

During our days in the Alentejo, we’ll enjoy a hands-on cooking experience that highlights regional flavors, visit a family-run olive oil estate for tasting and lunch, and take optional morning walks through the countryside. One evening, we’ll shuttle into Évora for dinner on your own — the town especially lovely in the evening light.

And after dinner at the retreat one night, we’ll step outside to look up: the Alentejo is a Dark Sky Reserve, where the stars are bright enough to feel close. Constellations are easy to see, and it’s one of the most moving moments of the trip.

We end with a farewell dinner shared at the table — unhurried, seasonal, generous — a celebration of new memories, new friendships, and the beauty of Portugal.

PORTUGAL Highlights

  • Three nights at 5-star PortoBay Liberdade in Lisbon city center
  • Three nights at Convento do Espinheiro in the countryside of Alentejo
  • Private ground transportation from Lisbon to Alentejo
  • Private ground transfer from Alentejo to Lisbon Airport on departure day
  • All breakfasts
  • 3 Lunches
  • 5 dinners — from casual shared dishes to an evening at a Michelin-starred restaurant
  • Guided walk through Lisbon’s historic neighborhoods and viewpoints
  • Sunset sail on the Tagus River
  • Excursion to seaside Cascais
  • Guided walking tour of historic Évora, including the Roman Temple, cathedral, and main square
  • Olive oil & wine tasting experience
  • Star gazing in the Alentejo
  • Hands-on cooking lesson featuring local specialties
  • Comfortable pacing with time to rest, explore, swim, or enjoy a spa experience

ITINERARY

DAY 1, Monday, May 3: Welcome to Lisbon

  • Highlights: Arrival + River Walk + Welcome Dinner

Arrive in Lisbon and settle into our 5-star hotel in the center of the city. In the afternoon, we’ll meet for a leisurely walk along the riverfront — a comfortable way to stretch after travel and get our bearings.

Before dinner, we’ll gather for a welcome aperitivo and toast to kick off our week together. Then we’ll enjoy an elegant dinner at one of our favorite Lisbon restaurants — good food, friendly atmosphere, and a relaxed chance to get to know one another.

Included: Aperitivo + welcome dinner

DAY 2, Tuesday, May 4: Experiencing Lisbon

  • Highlights: Lisbon with a Local + River Cruise + Casual Tapas Dinner

This morning, we’ll set out on a relaxed walking tour through Lisbon, offering a gentle introduction to the city’s historic heart and time to absorb the rhythm of the city while learning about Lisbon’s history, culture, and everyday life. With our local guide, we’ll wander through some of its most iconic neighborhoods—Baixa, Chiado, and Alfama—taking in charming streets, traditional architecture, and scenic viewpoints along the way.

Following our walk, we’ll enjoy a casual lunch at a local spot, featuring a selection of small dishes inspired by traditional flavors—the best way experience the local cuisine.

If you’d like to continue exploring, São Jorge Castle is a wonderful option, offering sweeping views over the city and the Tagus River. It’s easily reached by taxi or tuk-tuk from the hotel.

In the late afternoon, we’ll set out on a  sunset cruise along the Tagus River, offering a beautifully serene perspective of Lisbon from the water. As we glide past the city’s most iconic landmarks—including Belém Tower, the Monument to the Discoveries, and the 25th of April Bridge—you’ll see them softly illuminated in the golden light of day’s end.

With a welcome drink in hand, this becomes a moment to slow down and take it all in—the gentle movement of the river, the shifting light across the city, and the quiet elegance of Lisbon at sunset.

After we dock, we’ll enjoy a casual, tapa-style dinner with shared plates and simple, flavorful regional dishes — the kind of meal that feels warm, friendly, and very Lisbon.

Included: Breakfast, Guided City Walk, Casual Dinner

DAY 3, Wednesday, May 5: Coastal Cascais

  • Highlights: Excursion to Cascais  + Michelin Dinner

This morning, we’ll set out on a scenic drive along the coast to Cascais, a former fishing village that has evolved into one of Portugal’s most charming seaside destinations.

With our private guide, we’ll take a relaxed walk through the historic center, where narrow streets, sun-washed houses, and lively squares reflect the town’s maritime roots. You’ll then have time to enjoy Cascais at your own pace—perhaps exploring the boutiques, lingering along the marina, or simply soaking in the fresh ocean air and coastal ambiance.

In the afternoon, we’ll return to Lisbon, where you’ll have time to enjoy a bit more of the city at your own pace. Perhaps revisit a favorite corner, browse the shops along Avenida da Liberdade, or simply wander and take in the atmosphere one last time.

Later in the evening, we’ll come together for a truly special experience—a Michelin-star dinner, thoughtfully chosen to bring a memorable close to our time in Lisbon.

Included: Breakfast, Excursion, Michelin Dinner with Pairings

DAY 4, Thursday, May 6: From Evora to the Alentejo 

  • Highlights: UNESCO Évora + Into the Alentejo + Slow Dinner

After breakfast we’ll journey into the Alentejo, stopping in the town of Évora for an immersive journey into one of Portugal’s most historic and beautifully preserved cities, and a UNESCO World Heritage Site. Our visit begins with a guided walk through the charming old town, where highlights include the Roman Temple, the Cathedral of Évora, and narrow streets lined with whitewashed houses that reflect the city’s layered past.

A visit to the Chapel of Bones—one of Évora’s most striking and thought-provoking monuments—offers a powerful reflection on the transience of life. As we continue through the historic center, there will be time to take in the unique atmosphere of this ancient city, where Roman, medieval, and Renaissance influences come together seamlessly.

From there, we continue into the countryside to our retreat surrounded by vineyards and olive groves. The afternoon is yours to settle in — wander the grounds, take a swim, enjoy a glass of local wine, or simply breathe in the quiet. There’s no rush here — this is the Alentejo at its most restorative.

This evening, we’ll gather for a slow, seasonal dinner — regional dishes prepared with simplicity and care, shared at the table in true Alentejo style.

Included: Breakfast, Évora Guided Tour, Dinner

DAY 5, Friday, May 7: Alentejo Experiences

  • Highlights: Countryside Walk + Winery Visit + Star Gazing

This morning, you’re welcome to join an optional guided walk in the countryside — a gentle route through olive groves and open fields, with time to enjoy the quiet rhythm of the landscape. Or, simply take the morning slowly with coffee or a spa experience.

In late morning we’re off to visit to one of the Alentejo’s most renowned estates offers a relaxed and immersive experience, bringing together tradition, gastronomy, and the beauty of the surrounding landscape. The experience begins with a guided visit to the olive oil mill, where you’ll learn about the production process and enjoy a tasting of three distinct oils, each with its own character and aroma.

We’ll then continue to the winery, exploring the production and aging areas before a tasting of four carefully selected wines that reflect the depth and quality of the region.

To conclude, we’ll sit down to a leisurely lunch at the estate, featuring seasonal local ingredients and enjoyed in a warm, welcoming setting overlooking the vineyards.

In the afternoon we return to our hotel where you might rest by the pool, stroll the grounds, nap, read, or simply enjoy the peace of the countryside. For those who wish, we can even arrange transport into Evora to browse local shops.

This evening we’re in for a treat as we experience one of the great gifts of this region: the night sky.

Set just outside Évora, our stargazing experience takes place in a region known for its exceptionally clear skies and minimal light pollution—ideal conditions for observing the night sky. In a quiet, natural setting far from urban distractions, we’ll enjoy a guided session with an experienced astronomer, who brings the night sky to life in an engaging and accessible way.

Using a professional telescope, you’ll have the opportunity to observe celestial highlights such as the Moon’s craters in remarkable detail, distant planets like Saturn and its rings, and a vast expanse of stars and constellations. Throughout the evening, the experience is enriched with insights into astronomy, mythology, and the stories written across the night sky.

Included: Breakfast, Wine & Olive Oil Tasting with Lunch, Star Gazing Experience

DAY 6, Saturday, May 8: Flavors of Alentejo

  • Highlights: Cooking Experience + Optional Spa Time + Farewell Dinner

This morning we’ll take our time and enjoy a slow breakfast and perhaps a leisurely walk.

In late morning we’ll be transported to a location just outside Évora for a hands-on culinary experience dedicated to discovering the authentic flavors of the Alentejo region. In a warm and welcoming setting, a local chef will guide us through the preparation of traditional Portuguese and regional dishes, using fresh, seasonal, and locally sourced ingredients.

The experience begins with an introduction to the region’s rich culinary traditions, followed by the preparation of a full menu—typically including a starter, main course, and a traditional dessert. Along the way, you’ll learn techniques, cultural insights, and the stories behind each dish, making the experience both engaging and memorable.

Once everything is prepared, we’ll sit down together to enjoy the meal, accompanied by carefully selected regional wines—a relaxed and convivial moment that reflects the generous spirit and hospitality of the Alentejo.

In the afternoon, we’ll return to our countryside retreat, where the rest of the day is yours to enjoy as you wish. Take advantage of the spa, stretch out by the pool, wander the grounds, or simply settle into the quiet rhythms of the Alentejo.

This evening, we’ll gather for a farewell dinner at our hotel — unhurried, seasonal, and shared together, marking the close of our spectacular journey in Portugal.

Included: Breakfast, Cooking Experience, Lunch, Farewell Dinner

DAY 7, Sunday, May 9: Departure 

Early morning private transfer to Lisbon or Lisbon Airport.

ACCOMMODATIONS

Lisbon ~ PortoBay Liberdade  ⭐️⭐️⭐️⭐️⭐️

PortoBay Liberdade is a refined five-star boutique hotel tucked just off Lisbon’s elegant Avenida da Liberdade, offering the feel of a private urban retreat in the heart of the city. Housed behind a restored historic façade, the interiors blend contemporary comfort with understated sophistication, creating a calm and beautifully designed space to return to after a day of exploring. Thoughtful amenities—including a serene spa, indoor pool, and inviting restaurant—give it the ease of a small resort, while its central yet quiet location makes it an ideal base for experiencing Lisbon at a relaxed, unhurried pace..

Alentejo ~ Convento do Espinheiro ⭐️⭐️⭐️⭐️⭐️

Convento do Espinheiro is a truly special five-star retreat set just outside Évora, where centuries of history and quiet luxury come together in a beautifully restored 15th-century convent. The property retains a deep sense of place, with soaring cloisters, a serene chapel, and expansive grounds that invite you to slow down and take it all in. Guest rooms blend contemporary comfort with historic character, while the atmosphere throughout feels peaceful, refined, and distinctly Portuguese. With its spa, indoor and outdoor pools, and exceptional dining, it offers a restorative countryside escape that feels both elegant and deeply rooted in its surroundings.

INCLUSIONS

  • 6 nights: 3 nights 5-star PortoBay Liberdade and 3 night 5-star Convento do Espinheiro
  • Private group driving service on all excursions and transfers
  • Private group transportation to Lisbon Airport on departure day
  • All breakfasts
  • 3 lunches
  • 5 dinners (including a Michelin-starred dinner with wine pairings)
  • Guided walking tour in historic Lisbon
  • Visit to Palácio Nacional da Ajuda
  • Excursion to seaside Cascais
  • Guided walking tour of UNESCO-listed Évora
  • Visit and tasting at a winery & olive oil estate
  • Cooking lesson featuring regional Alentejo dishes
  • Star gazing experience in a designated Dark Sky Reserve
  • Optional spa visits and treatments
  • Entrances to all sites included in the trip itinerary
  • Daily accompaniment with Pamela Haack
  • Daily opportunities for rest, wandering, swimming, exploring, and time to yourself

Not included: Airfare, transportation and meals outside of that which is specifically listed in the trip package, gratuities for hotel staff and drivers.

Note: Because we’re planning well in advance, some details of the itinerary may shift as we get closer — whether due to seasonal schedules, local events, or special opportunities that arise. Any adjustments will always be thoughtful and in the spirit of creating the most beautiful experience for our group.

DATES & DETAILS

✴️ This trip is part of our Signature Collection, a series of boutique, small-group journeys designed around intimacy, place, and presence. We choose hotels with character, meals that feel connected to the land, and experiences that are grounded, generous, and unhurried.

  • Dates:
    • May 3-9, 2027 – SOLD OUT
  • Couples, friends and solo travelers are all welcome
  • Room Description: Rooms throughout the trip are elegantly decorated and comfortably appointed, each with an ensuite bath, air conditioning, hair dryer, room safe, and high-quality toiletries. Every space is designed to feel both luxurious and inviting, offering a quiet, restful place to unwind at the end of each day.
  • Trip Price: 
    • $5,295 USD per person. Twin/Double Occupancy, Queen or 2 Twin Beds with Ensuite Bath
    • $6,495 USD. Single Occupancy, Queen Bed and Ensuite Bath
  • Trip Insurance ➡️  We highly recommend obtaining travel insurance. Your policy should include coverage for trip interruption, cancellation and medical needs. While this itinerary is designed to be comfortable and not overly strenuous, we want all guests to travel with peace of mind, knowing they’re protected should the unexpected occur. Please note: Travel insurance is not included in the tour price and must be purchased separately.
  • Luggage: We suggest traveling with no more than one medium-size checked bag and one carry-on bag. No oversized baggage, please.
  • Walking: We explore towns and landscapes on foot, and you can expect daily walking on streets and pathways that may include cobblestones, uneven surfaces, slopes, and stairs. Guests should be comfortable walking and standing for extended periods and moving at a steady group pace. For your comfort and enjoyment, guests who find this level of mobility difficult may wish to consider a different itinerary.
  • $700 deposit is required to book your space on this tour
  • Terms and Conditions

SOLD OUT