Quick Stats

• Duration: 10 Days / 9 Nights
• Trip Type: Private Luxury Tour, Romantic Cultural Escape
• Best Time To Go: April–June & September–October
• Pricing Range: From $7,800 per person (varies by customization)
• Who It’s For: Couples, culture lovers, culinary travelers, honeymooners
• Destinations: Lisbon, Sintra, Cascais, Alentejo wine region, Évora

Day-by-Day Itinerary

Day 1: Arrival in Lisbon – Tiles, Tram Rides & Toasts Arrive in Lisbon to a warm welcome and private transfer to your boutique hotel in the elegant Chiado district. After settling in, enjoy a walking orientation with a local guide – riding the iconic Tram 28, wandering cobbled lanes, and stopping at a hidden miradouro for your first glimpse over the Tagus. Cap the evening with a rooftop welcome drink and a chef’s tasting menu spotlighting Portuguese seafood traditions.

Day 2: Old Lisbon – Alfama’s Soul & Fado’s Serenade Wake to the scent of fresh bread and espresso. Today is all about discovery in Alfama, the oldest part of Lisbon. Meander past tiled houses and secret courtyards with a historian guide, then enjoy a private azulejo tile-painting workshop. Evening brings a romantic dinner followed by an intimate live fado performance in a candlelit tavern.

Day 3: Belém & Maritime Grandeur Travel through time with a visit to Belém. Explore Jerónimos Monastery, marvel at the Discoveries Monument, and taste the original pastéis de Belém. Then, board a private sailboat for a golden-hour cruise on the Tagus River, complete with sparkling wine and panoramic city views.

Day 4: Sintra’s Palatial Dreams Your private driver takes you to Sintra’s lush hills. Visit the whimsical Pena Palace, then descend to the mysterious Quinta da Regaleira with its spiraling wells and forest paths. Enjoy lunch in a Michelin Bib Gourmand spot, then check into a charming heritage hotel nestled among gardens. End with a wine-paired dinner at a 19th-century estate.

Day 5: Cascais Coastal Bliss After a leisurely breakfast, follow the coastal road to Cascais. Stroll along seaside promenades, visit Boca do Inferno’s dramatic cliffs, and explore charming boutiques. Opt for a beachside lunch, then unwind at your ocean-view hotel. Evening suggestion: a sunset drink at a chic terrace bar followed by seafood dinner steps from the surf.

Day 6: Lisbon Free Day or Add-On Experience Return to Lisbon or opt for an add-on (see Strip 8). Enjoy this day at your pace – shop in the Bairro Alto, visit the Calouste Gulbenkian Museum, or take a cooking class with a local chef. Optional upgrade: vintage sidecar tour through hidden neighborhoods.

Day 7: Into Alentejo – Vineyard Roads & Slow Travel Head east toward the Alentejo region, a patchwork of golden plains and sleepy villages. Stop en route for a wine tasting at a renowned estate, then continue to a countryside boutique hotel with olive groves and private terraces. Dine under the stars with a farm-to-table feast and local red wine.

Day 8: Évora – History in Every Stone Explore the UNESCO city of Évora with a private guide. Visit the Roman Temple, the haunting Chapel of Bones, and lively town squares. After lunch, return to your estate for an afternoon by the pool or spa treatment. Evening suggestion: sunset yoga or a countryside horseback ride.

Day 9: Return to Lisbon – Farewell Moments Make your way back to Lisbon with stops along the way for photos or a last winery visit. Return to the city in the late afternoon for your final night in a luxury riverside hotel. Celebrate your journey with a farewell dinner at a chef’s table experience.

Day 10: Departure Day After a relaxed breakfast, enjoy a private transfer to the airport. You leave with curated keepsakes, full hearts, and new favorites to share.

Add-On Experiences

• Three Nights in the Douro Valley: Wine lovers can extend north to Portugal’s famed wine region for boat rides, vineyard stays, and scenic rail journeys.
• Private Azores Getaway: Add a 4-day island retreat to São Miguel – think volcanic lakes, geothermal spas, and coastal hikes.
• Lisbon Photography Day: Capture memories with a pro photographer leading you through iconic and hidden spots.
• Gourmet Day in Setúbal: Visit the market, tour oyster farms, and enjoy a seaside tasting lunch in this foodie haven.

Pro Tips

• Dress the Part: Lisbon’s streets are cobbled and steep – pack chic but comfortable shoes. Evenings can get breezy, so bring a stylish layer.
• Book in Advance: Sintra palaces and fado shows fill up quickly – we’ll secure skip-the-line access and preferred seating.
• Dining Culture: Dinner starts late in Portugal – embrace the local rhythm with aperitifs and tapas around 8 PM.
• Hidden Lisbon: For a quieter moment, visit Jardim do Torel – a garden with panoramic views and few tourists.
• Seasons Matter: June sees Lisbon’s lively Santo António Festival – book early for music, grilled sardines, and celebrations.

   

What to Pack

• Weather Prep: Expect sunny, mild days in spring/fall. Pack layers – linen shirts, light sweaters, and a rain jacket just in case.
• Footwear: Stylish walking shoes for city days; sandals or espadrilles for coastal stops.
• Essentials: Sunscreen, sunglasses, universal adapter, offline maps app, travel journal.
• Cultural Stops: For religious sites like Évora’s churches, pack a modest outfit covering shoulders and knees.
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