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, visit a royal palace and the National Tile Museum, and stand among the ramparts of São Jorge Castle as the city unfolds beneath us — rooftops, river, and the soft curves of Lisbon’s hills. We’ll 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.

On our final full day, there’s even the option to begin the morning floating above the landscape in a hot air balloon — sunrise light over cork forests, vineyards, and rolling fields.

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 in Lisbon at a 5-star hotel in the center of the city
• Three nights in the Alentejo at a 5-star countryside retreat surrounded by vineyards and olive groves
• 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, including São Jorge Castle
• Sunset sail on the Tagus River
• Guided walking tour of historic Évora, including the Roman Temple, cathedral, and main square
• Optional sunrise hot air balloon experience over the Alentejo (weather permitting)
• Olive oil & wine tasting experience
• 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 + Sunset Sail + Casual Tapas Dinner

This morning, we’ll explore Lisbon with our private guide. We begin at the Palácio Nacional da Ajuda, once home to Portugal’s royal family. The grand salons, tapestries and gilded details are beautifully preserved, yet the visit feels quiet and intimate — a glimpse into Portugal’s royal past.

From here, we continue to the National Tile Museum, housed in a former 16th-century convent. This is where Portugal’s love story with azulejos unfolds — from Moorish influences to the blue-and-white panels that define so much of Lisbon’s character. Afterwards we’ll gather for a regional lunch at local restaurant — think olive oil, slow-cooked dishes, and warm bread.

In the early evening, we’ll make our way to the Belém marina and board a private sailboat for a gentle sunset cruise along the Tagus River. As we drift past the 25 de Abril Bridge, the Monument of the Discoveries, and the Belém Tower, the city begins to glow in soft gold. The breeze, the water, the rhythm of the river — it’s one of the most beautiful ways to experience Lisbon.

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, convivial, and very Lisbon.

Included: Breakfast, Guided City Walk, Casual Dinner

DAY 3, Wednesday, May 5: Royal Lisbon

• Highlights: São Jorge Castle + Michelin Dinner

This morning, with our local guide, we’ll begin at São Jorge Castle, a historic fortress overlooking the city. The walk through the ramparts and courtyards gives a quiet view into Lisbon’s past, and the castle’s hilltop location offers some of the best views in the city — rooftops, river, and the old neighborhoods below. From there, we’ll continue through nearby historic streets and public squares, getting a feel for the rhythm of Lisbon and its different neighborhoods.

The afternoon is free — good for wandering, shopping, or a quiet walk along the river.

This evening, we’ll dine at a Michelin-starred restaurant where the menu unfolds like a story — layered flavors, attentive service, and wines chosen with care. A slow, beautiful meal meant to be savored.

Included: Breakfast, Castle Visit, Michelin Dinner with Pairings

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

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

After breakfast, we’ll journey into the Alentejo, stopping in the town of Évora, a UNESCO World Heritage site known for its golden stone streets, Roman ruins, and unhurried rhythm. Together we’ll take a guided walking tour of the historic center — the Roman Temple, the Cathedral, and the network of quiet lanes and small, sun-washed squares that make this town feel timeless.

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 at the retreat — regional dishes prepared with simplicity and care, shared at the table in true Alentejo style.

After dinner, we’ll step outside to experience one of the great gifts of this region: the night sky. The Alentejo is part of a designated Dark Sky Reserve, where there is almost no light pollution — meaning the stars are astonishingly bright.

Included: Breakfast, Évora walking tour, Dinner at countryside retreat, star gazing experience

DAY 5, Friday, May 7: Flavors of Alentejo

• Highlights: Countryside walk + Cooking Lesson + Optional Spa Time + Free Evening

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.

Later in the morning, we’ll come together for a hands-on cooking experience, learning simple, regional dishes that reflect the flavors of the Alentejo — relaxed, welcoming, and unhurried. We’ll then sit down to a shared lunch of what we’ve prepared, accompanied by local wine.

The afternoon is yours — rest by the pool, stroll the grounds, nap, read, or simply enjoy the peace of the countryside.

In late afternoon, we’ll shuttle into Évora for time to explore the historic center, browse local shops, and enjoy dinner on your own. The town is especially lovely in the evening light.

Included: Breakfast, Countryside Walk, Cooking Lesson, Free Evening

DAY 6, Saturday, May 8: Alentejo Experiences

• Highlights: Optional Hot Air Balloon Ride + Olive Oil Tasting + Farewell Dinner

For those who wish, we will arrange a sunrise hot air balloon flight over the Alentejo countryside — drifting above vineyards, olive groves, and golden plains as the light changes across the land. It’s peaceful, quiet, and unforgettable. (Optional; advance reservation will be required.)

Later this morning, we’ll visit a family-run olive oil estate in the Alentejo countryside. We’ll walk the groves and learn how olive oil has been made here for generations, followed by a guided tasting to understand the subtle differences in flavor and aroma. Afterward, we’ll sit down right on the estate for a simple, regional lunch — relaxed, welcoming, and rooted in local tradition.

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 the retreat — unhurried, seasonal, and shared together, marking the close of our spectacular journey in Portugal.

Included: Breakfast, Olive Oil Estate Visit & Tasting, Lunch, Farewell Dinner

DAY 7, Sunday, May 9: Departure 

Early morning private transfer to Lisbon or Lisbon Airport.

ACCOMMODATIONS

Lisbon ~ City Stay

Our stay in Lisbon is at a refined boutique hotel set within one of the city’s historic neighborhoods — elegant, warm, and full of light. Rooms are comfortably sized with soft linens, beautiful textures, and thoughtful details. There are inviting lounges and quiet corners for morning coffee or an afternoon pause, and we’re just steps from viewpoints, cafés, tiled facades, and the rhythm of everyday Lisbon. It feels intimate, well-situated, and welcoming — a gentle landing into the city.

Alentejo ~ Countryside Retreat

In the Alentejo, we’ll settle into a serene countryside retreat surrounded by vineyards, olive groves, and open horizons. The atmosphere is relaxed and unhurried — spacious rooms with natural materials, shaded terraces, gardens, and a pool overlooking the rolling landscape. It’s beautifully simple, soulful, and deeply quiet — a place designed for rest, conversation, and the pleasure of doing things slowly.

INCLUSIONS

• 6 nights: 3 nights Lisbon, 3 nights Alentejo Countryside
• Private group driving service on all excursions and transfers
• Private group transportation to Lisbon Airport on departure day
• All breakfasts
• 3 lunches (including vineyard lunch on Lake Alqueva)
• All dinners (including a Michelin-starred dinner with wine pairings)
• Guided walking tour in historic Lisbon
• Visit to Palácio Nacional da Ajuda
• Visit to the National Tile Museum
• Guided walking tour of UNESCO-listed Évora
• Visit and tasting at a family-run olive oil estate
• Cooking lesson featuring regional Alentejo dishes
• Olive oil & wine tasting
• Star gazing experience in a designated Dark Sky Reserve
• 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 (6 nights)
• 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: 
  • $5,195 USD per person. Classic Room, Twin/Double Occupancy, Queen or 2 Twin Beds with Ensuite Bath
  • $5,595 USD per person. Deluxe Room, Double Occupancy, Queen Bed (no twin) with Ensuite Bath
  • $5,995 USD. Classic Room, Single Occupancy, Queen Bed with Ensuite Bath
  • $6,495 USD. Deluxe Room, Single Occupancy, Queen Bed and Ensuite Bath
• Installment Payments: Would you like to make installment payments towards your trip balance? Just let us know and we’re happy to set it up for you.
• 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

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