8-Day Luxury Portugal Journey
8 Days | 2 Nights Lisbon | 2 Nights Sintra & Cascais | 3 Nights Algarve
Starting from $3,100 per person | Land Only*
Pena Palace, the Atlantic coast & the golden Algarve cliffs
Inquire About This JourneyBegin with two days in Lisbon. End on the golden Algarve coast.
This is the Portugal journey travelers dream about: two nights among Lisbon's tiled hills for trams, miradouros and Belém—then into the romantic Sintra hills and the elegant bay town of Cascais, and three nights of golden cliffs and turquoise coves on the Algarve.
Your journey ends where it began, back in Lisbon for your departure flight, so there is no wasted travel day—just a seamless circle through Portugal's greatest hits, designed and booked end to end by Jamie Leigh.
The journey
The City of Seven Hills Welcomes You
Land in Lisbon and let everything be waiting: your private transfer from the airport, your hotel confirmed and ready, your first evening unhurried.
Settle in, then step out for a ginjinha or a glass of Vinho Verde as the tiled façades catch the last light.
Jamie Leigh plans this arrival around your flight so the very first hours feel effortless, not rushed.
Alfama, Belém & the Tiled Hills
Your full day in Lisbon is designed around what you love—the tram-tight lanes of Alfama, the monastery and monument at Belém, the miradouros, elegant Chiado boutiques or a little of everything.
Timing matters: Jamie Leigh sequences your visits so you see the icons when the crowds are thinnest and linger where the light is best.
In the evening, choose from a shortlist of restaurants reserved with you in mind, from family-run tascas to a quietly celebrated chef's table.
Palaces, Forests & Romantic Fantasy
A short private drive carries you out of the city and into the misty hills of Sintra, where romantic palaces hide in the forest above the Atlantic.
Settle into your Sintra or Cascais home base, chosen with Jamie Leigh for the way you like to travel.
Begin with Pena Palace, the Quinta da Regaleira's winding wells, or whichever of Sintra's wonders calls to you first.
Cabo da Roca, Marinas & Seafood
Your second hillside day is yours to shape: the western cliffs of Cabo da Roca, the elegant bay town of Cascais, the surf-fringed beaches of Guincho, or a slow morning with no plan at all.
Lunch on the water—a plate of fresh fish and a cold white wine as the Atlantic rolls in.
Return through the hills for one more golden Sintra evening.
Golden Cliffs & Turquoise Water
Travel south to the Algarve, where golden cliffs, hidden coves and calm turquoise water define Portugal's southern coast.
Settle into your Algarve home base—whether you prefer the polished marina life, a clifftop resort or a quiet fishing-village hideaway, Jamie Leigh has options for each.
Toast your arrival with sunset over the sea.
Grottoes, Cliffs & the Benagil Caves
Cruise to the Benagil sea caves by private boat, walk the cliff-top trails above secluded beaches, or play one of Europe's most scenic seaside golf courses.
Timing matters here too: Jamie Leigh sequences your days so the famous coves belong to you and not to the crowds.
In the evening, dinner in an old town square or at your hotel's terrace, the water glittering below.
Beach Days & One Last Sunset
Spend your final full day in the south as you wish: a long beach day, a market morning, a spa afternoon, or one more boat out to the caves.
This is the day travelers remember most—the one with nothing urgent on it and everything beautiful around it.
Enjoy a special farewell dinner before your journey home.
Adeus • Until Next Time, Portugal
Your private transfer carries you back to Lisbon for your flight home—no backtracking, no wasted day.
Or extend: more time in Lisbon, the Douro Valley wine country or the island of Madeira can be added to your design.
Until next time, Portugal. Jamie Leigh is already ready to plan the next one.
How it works
Your hotels in Lisbon, Sintra or Cascais and the Algarve, your private transfers and drivers between all three, your palace tickets in Sintra, your boat to the Benagil caves, your guides through Alfama and the old towns—reserved, confirmed and sequenced before you ever pack a bag.
Jamie Leigh handpicks the hotels, times the visits, and builds in the free afternoons that make a luxury trip feel like a luxury trip rather than a checklist.
And because you are in touch with a real person a phone call away—not a call center—if anything changes while you travel, she is the one who fixes it.
Personally designed
The route is the beginning.
Jamie Leigh designs the experience.
Add a private fado evening in Lisbon, a port wine tasting before you head south, a day trip to the Douro Valley, or extra days on the Algarve—or slow the whole journey down a full day.
Whether this is your honeymoon, a couples' escape or a girls' getaway, the journey is tailored to the way you want to travel. No two Follow Your Bliss journeys are exactly alike.
Plan your journey
Selected departures are available April through early November 2027.
Starting from $3,100 per person*
8-day journey, 2 nights Lisbon, 2 nights Sintra/Cascais and 3 nights Algarve, land arrangements only. Airfare is additional. Your journey is privately planned around the departure dates you choose—no fixed group departures, no tour buses.
*Starting price is per person for land arrangements only; airfare is additional. Final pricing is confirmed in your personalized proposal, based on your dates, your hotels and your experiences, and is subject to availability and change until confirmed. Tell Jamie Leigh when you hope to travel and she will design the journey and its pricing around you.
Start My JourneyFollow Your Bliss Travel
Tell Jamie Leigh when you hope to travel and how you'd like to make Lisbon, Sintra & the Algarve your own. This is an inquiry, not a confirmed reservation.