Portugal · Private and tailor-made
All of Portugal, Then the Azores
Walk the crater rim above the twin lakes of Sete Cidades, São Miguel, with the Atlantic all around.
Suggested length
21 days
Price guide
From $21,294 per person, excl. flights, based on two sharing
Includes hotels, private guiding, experiences and transfers
When
April to June and September to October
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American precision with local expertise · Planned from Europe since 2002 · Nearly 17,000 American travelers · Never cancelled a journey
On a clear night the Milky Way spreads over the Alqueva lake below the walls of Monsaraz. It is one evening on this 21-day private tour of Portugal, which runs the length of the mainland before heading out to the Azores. Porto starts at the tiled hall of São Bento, with Braga, Guimarães and striped Costa Nova close by. The Douro Valley and Coimbra lead to Évora. On the Algarve a boat takes you along the cliffs past the Benagil sea cave, then Lisbon and Sintra follow. On São Miguel you walk the crater rim above the twin lakes of Sete Cidades, with the Atlantic all around. Private guides and drivers take care of every day. Three weeks leave room to change anything.
Walk from the tiled hall of São Bento station down to the Ribeira waterfront, Porto.
Taste port at a family quinta above the river, Douro Valley.
Watch the Milky Way over the Alqueva lake from Monsaraz, Alentejo.
Sail along the Algarve cliffs past the Benagil sea cave, Lagoa.
Walk the old town of Sintra with Luisa and try a travesseiro at Piriquita, Sintra.
Look down on the twin lakes of Sete Cidades, São Miguel, Azores.
“We love to tailor-make trips you’ll talk about for years, built on our local relationships & story-worthy experiences.” – Magical’s American founder, in Europe since 1998, culinary enthusiast & world traveler.
A Journey Designed Just for You
Our resident experts wrote this itinerary as a starting point, and your planner shapes every day around your interests, pace and travel style.
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The 21-day Portugal itinerary at a glance
The route uses seven bases and 20 nights: five in Porto, two in the Douro Valley, one in Coimbra, three in Évora in the Alentejo, three on the Algarve coast, four in Lisbon and two in Ponta Delgada on São Miguel in the Azores. From Porto, day trips reach Braga and Guimarães, about 45 minutes north, and Aveiro, about an hour south. From Lisbon, Sintra sits about 30 minutes away by road. Thirteen of the 21 days carry no hotel change.
A licensed driver-guide drives every mainland leg by private vehicle. Porto to Peso da Régua in the Douro takes about 1 hour 15 minutes, the Douro to Coimbra about 2 hours, Coimbra to Évora about 3 hours, Évora to the Algarve about 2 hours 30 minutes, and the Algarve to Lisbon about 2 hours 40 minutes. One direct flight, Lisbon to Ponta Delgada, about 2 hours 30 minutes, carries the route out to the Atlantic.
April to June and September to October suit the route best. On IPMA’s 1981 to 2010 averages, Porto reaches a mean daily high of 22.6°C (about 73°F) in June and 23.4°C (about 74°F) in September, Lisbon 25.7°C (about 78°F) and 26.6°C (about 80°F), and Faro on the Algarve 26.4°C (about 80°F) and 26.6°C (about 80°F). Ponta Delgada, on the Instituto de Meteorologia’s 1961 to 1990 averages, runs milder at 21.8°C (about 71°F) in June and 24.7°C (about 76°F) in September. July and August bring about 28 to 29°C (82 to 84°F) on the Algarve, and our team plans summer touring around the cooler hours.
Licensed guides we work with on this route include Susana and Tania in Porto, Bruno in Coimbra, Elsa and Nuno in Évora, Luisa and Anabela in Lisbon, and Isabel in Sintra. Each is a highly educated local expert who cares about the people in their group. We request your guides by name, and your planner confirms who leads each day once your dates are set.
Why the route runs from Porto to the Azores
The route starts in the north because Porto’s airport sits about 11 kilometers from the center, and from there the journey runs south in one line without doubling back: the Minho, the Douro, Coimbra, the Alentejo plains and the Algarve cliffs, then Lisbon. Lisbon has the direct flights to Ponta Delgada, so the capital becomes the springboard to the islands rather than a stop you return to. São Miguel then closes the trip, and Azores Airlines flies nonstop from Ponta Delgada to Boston in about six hours.
The angle is the whole country in one direction, at a pace three weeks allow. Five of the seven bases hold three nights or more, so Braga, Guimarães, Aveiro, Monsaraz, Sagres and Sintra all become day trips from a hotel you already know. Coimbra is the single one-night stop, placed between the Douro and the long drive south. The route as written is a starting point, and our team shapes it around your dates and interests.
Journey at a glance
Length
21 days
From
$21,294 per person, double occupancy
Route
Porto, Braga, Guimaraes, Costa Nova, Douro Valley, Coimbra, Alentejo Region, Algarve, Lisbon, Sintra, Cascais, Ponta Delgada
Your planner adjusts every day to your dates.
Day One
Arrival in Porto: São Bento, Lello and the Ribeira
Your licensed driver-guide meets you at Porto airport, about 11 kilometers northwest of the Clérigos Tower, for the drive to your hotel. UNESCO inscribed the historic center of Porto, with the Dom Luís I Bridge and the Monastery of Serra do Pilar, in 1996. In the afternoon your guide starts at São Bento station, where Jorge Colaço spent eleven years, from 1905 to 1916, covering the hall with about 20,000 painted tiles. Next comes Livraria Lello, which opened in 1906 with a forked staircase up to its gallery, and our team books the entry. The walk drops to the Ribeira waterfront under the iron arch of the Dom Luís I Bridge, which Théophile Seyrig, a former partner of Gustave Eiffel, designed, with the port lodges across the river and rabelo boats moored along the quay. Logistics: Porto airport to your hotel by private vehicle with your licensed driver-guide, then an afternoon walk in the old city.
Day Two
Bolhão Market, a River Boat and the Port Lodges
Correia da Silva designed the Bolhão market in 1914, and the city reopened it in 2022 after years of restoration, with 79 stalls on its ground floor. Your licensed driver-guide starts the morning there, among the calls of the stallholders and the smell of fresh bread. Late in the morning a private boat takes your party along the Douro under the bridges of Porto. In the afternoon you cross to Vila Nova de Gaia for a tasting in one of the port lodges, with a glass of tawny in the cool of the cellar. On request, Serralves takes the afternoon instead: Álvaro Siza's museum of contemporary art, opened in 1999, sits in an 18-hectare park around an Art Deco villa. Logistics: a full day in Porto and Gaia with your licensed driver-guide, no hotel change.
Day Three
Braga and Guimarães
The Romans founded Bracara Augusta, the city beneath Braga, in 16 BC. Bishop Pedro consecrated Braga Cathedral in 1089, decades before Portugal became a country, and its Chapel of the Kings holds the sixteenth-century tombs of Count Henry and Countess Teresa, parents of Portugal's first king. In the afternoon your licensed driver-guide continues to Guimarães. UNESCO inscribed its historic center in 2001 and ties the town to the emergence of Portuguese national identity in the twelfth century. The words Aqui nasceu Portugal, Portugal was born here, stand on a tower of the old wall, and the lanes up to the castle, which Countess Mumadona Dias first fortified in the tenth century, pass houses with granite ground floors and half-timbered stories above. Logistics: Porto to Braga by road, about 45 minutes, then on to Guimarães and back to Porto, licensed driver-guide.
Day Four
A Chef's Table in Porto
Today runs at an easier pace. Where available, a chef cooks for your party in a private demonstration, with Portuguese dishes made in front of you and a long lunch to follow. Porto's own dish is tripas à moda do Porto, a stew of beef tripe, white beans and carrots over rice, and the people of the city still carry the nickname tripeiros, tripe eaters. Local legend says Porto gave its best meat to the ships Henry the Navigator gathered at the Lordelo do Ouro shipyard for the 1415 expedition to Ceuta and kept only the innards for itself. The rest of the day stays open for a walk along the river or a rest before dinner. Logistics: a day in Porto with your licensed driver-guide on hand, no hotel change.
Day Five
Aveiro and the Striped Houses of Costa Nova
Moliceiro boats once raked seaweed from the Ria de Aveiro lagoon to fertilize the sandy fields, carrying up to seven tonnes, and today the painted boats carry visitors along the canals of Aveiro past Art Nouveau façades. Ovos moles, egg yolk and sugar in thin wafer shells in the form of fish, clams and boats, trace back to the nuns of the convents of the area. About 10 kilometers west, Costa Nova sits between the lagoon and the Atlantic. Its palheiros, wooden houses where fishermen once kept their gear, wear bright vertical and horizontal stripes on white. Your licensed driver-guide leaves time for the beach and a seafood lunch with the sea air off the dunes. Logistics: Porto to Aveiro by road, about 1 hour each way, licensed driver-guide, back to Porto for the night.
Day Six
Into the Douro Valley
UNESCO inscribed the Alto Douro Wine Region in 2001, recognizing some 2,000 years of winemaking by traditional landholders. Your licensed driver-guide follows the river east past terraces of schist walls stepping up every slope. At Pinhão station, 24 tile panels from 1937 show grape treading and rabelo boats carrying wine downriver to the cellars of Vila Nova de Gaia. The afternoon belongs to the valley: a walk on a vineyard trail, a bicycle ride on the river roads or a river cruise, where available, with the terraces turning gold in the late light. Logistics: Porto to the Douro Valley by road, about 1 hour 15 minutes to Peso da Régua, licensed driver-guide.
Day Seven
A Quinta Visit and a Long Lunch
Wine from the Douro has followed defined quality rules since 1756, and UNESCO counts the region among the traditional winemaking areas of Europe. Where available, your licensed driver-guide takes you to a family quinta for a walk through the vines, a visit to the lodge where the wine ages in old wooden casks, and a tasting of the estate's ports and table wines. Lunch follows on a terrace above the river with the estate's wines, and the afternoon stays slow, with a vineyard walk or a rest at your hotel. Logistics: a day inside the valley with your licensed driver-guide, no hotel change.
Day Eight
South to Coimbra
The University of Coimbra began as an academy in the late thirteenth century and moved into the royal palace on the hill in 1537, and UNESCO inscribed the university, Alta and Sofia in 2013. Your licensed driver-guide walks you across the palace courtyard to the Biblioteca Joanina, which King John V founded in 1717 and finished in 1728. A colony of bats eats the insects among the gilded shelves at night, and staff cover the tables with leather sheets each evening. Where your dates allow, the evening brings Coimbra fado, male voices with the Coimbra guitar. Logistics: the Douro Valley to Coimbra by road, about 2 hours from Peso da Régua, licensed driver-guide.
Day Nine
Coimbra to Évora and the Alentejo
Day nine is a long road day, about three hours south, with a lunch stop on the way. UNESCO inscribed the historic center of Évora in 1986, and the Roman Temple of Diana still stands at the top of town. Portuguese kings lived here more and more from the fifteenth century, and the lanes keep lime-washed houses with tiles and wrought-iron balconies from the sixteenth to eighteenth centuries. Beside the Church of St. Francis, the Capela dos Ossos lines its walls with the bones of about 5,000 people. Dinner brings Alentejo cooking such as migas, crumbled wheat bread with garlic and olive oil, beside black pork from the Iberian pig. Logistics: Coimbra to Évora by road, about 3 hours, licensed driver-guide.
Day Ten
Standing Stones, Monsaraz and the Night Sky
West of Évora, the Almendres Cromlech gathers about 95 granite standing stones, the largest such group in the Iberian Peninsula, and its builders raised the first of them in the sixth millennium BC. East of town, the walled village of Monsaraz looks over Alqueva, the largest artificial lake in Western Europe at about 250 square kilometers. The Dark Sky Alqueva reserve became the first place in the world to earn certification as a Starlight Tourism Destination, and Monsaraz recorded some of its darkest readings. Your licensed driver-guide spends the afternoon in the village and the cork oak country below, and where available the evening ends with a stargazing session with telescopes, the Milky Way overhead on clear nights. Logistics: Évora to Monsaraz by road, about 50 minutes each way, with a stop at the Almendres Cromlech, licensed driver-guide.
Day Eleven
An Alentejo Estate: Cork, Olive Oil, Wine and Horses
Portugal produces about half the world's cork, and 84 percent of its cork oak forests grow in the Alentejo. Harvesters strip the bark about every nine years once a tree reaches about 25 years, and the tree keeps growing. Where available, your licensed driver-guide takes you to a family estate in the Évora countryside for a walk under the cork oaks, a taste of green, peppery olive oil on bread and the estate's reds from grapes such as Trincadeira, Aragonês and Castelão. A horseback ride or a hike opens the morning where it suits your party, and a long lunch of regional cooking follows. Logistics: a day in the Alentejo countryside with your licensed driver-guide, back to the same hotel in Évora.
Day Twelve
South to the Algarve Cliffs and Benagil
The Seven Hanging Valleys trail runs about 5.6 kilometers along the clifftops between Vale de Centeanes and Praia da Marinha, in the municipality of Lagoa. Below, the Benagil sea cave opens to the sky through a hole in its roof, and sunlight falls onto the sand inside. Where sea conditions suit, a licensed boat trip runs along the coast to the grotto, and your licensed driver-guide sets you on the trail for as long a walk as you like, with the scent of the pines and the water turning green and blue below the cliffs. Logistics: Évora to the Algarve by road, about 2 hours 30 minutes to the Silves and Lagoa area, licensed driver-guide.
Day Thirteen
Sagres and Cape St. Vincent
Cape St. Vincent, about six kilometers from Sagres, marks the southwesternmost point of mainland Europe. Its 24-meter lighthouse dates from 1846, with the Atlantic breaking against the cliffs below. Your licensed driver-guide stops in villages along the coast on the way west, and lunch brings amêijoas na cataplana, clams in the copper cataplana of the Algarve, which closes like two hinged clamshells. Where it suits your party, a private yacht, a coastal trail or a mountain bike route fills the afternoon. Logistics: a coastal day west to Sagres and Cape St. Vincent with your licensed driver-guide, back to the same hotel.
Day Fourteen
Dolphins, Monchique and the Algarve at Your Pace
Licensed boats leave Portimão and Lagos for dolphin watching, with common and bottlenose dolphins among the species of these waters, and a bird-watching trip along the coast suits early risers. Inland, the Serra de Monchique rises to 902 meters at Fóia, and Caldas de Monchique, a spa town on geothermal springs famous since Roman times for its waters, offers a warm, quiet afternoon. Golfers choose a round on one of the courses of the region instead. Your licensed driver-guide shapes the day around the options you choose. Logistics: a day on the Algarve with your licensed driver-guide, no hotel change.
Day Fifteen
North to Lisbon and Belém
Day fifteen is a road day, about 2 hours 40 minutes north to the capital. In the afternoon, where your dates allow, Luisa, one of our licensed guides in Lisbon and Sintra, meets you in Belém. UNESCO listed the Jerónimos Monastery, which King Manuel I began in 1502, and the Belém Tower, which marks the voyage of Vasco da Gama, in 1983. Monks at Jerónimos created the pastel de nata, and the bakery beside the monastery has baked the custard tarts from their recipe since 1837, warm from the oven with a dusting of cinnamon. Logistics: the Algarve to Lisbon by road, about 2 hours 40 minutes from the Portimão area, licensed driver-guide, then an afternoon in Belém with Luisa and a licensed driver.
Day Sixteen
Sintra, Cabo da Roca and Cascais with Luisa
Where your dates allow, Luisa leads the day with a licensed driver alongside her. UNESCO listed Sintra in 1995 and calls it the first center of European Romantic architecture, and King Ferdinand II finished the red and yellow Pena Palace above the town in 1854. In the old town, Piriquita has baked since 1862, and its travesseiros, pillows of puff pastry around an egg and almond cream, date from the 1940s. The road then runs to Azenhas do Mar, a village on a cliff above a beach with a seawater pool, and to Cabo da Roca, the westernmost point of mainland Europe, where a lighthouse has worked since 1772 above cliffs more than 100 meters high. The day ends in Cascais, the summer residence of King Luís I. Logistics: Lisbon to Sintra by road, about 30 minutes, with Luisa and a licensed driver, then along the coast to Cascais and back to Lisbon.
Day Seventeen
Alfama, the Castle and an Evening of Petiscos and Fado
Alfama takes its name from the Arabic al-hamma, hot springs, and its maze of lanes came through the 1755 earthquake. Where your dates allow, Luisa walks you up to São Jorge Castle, which Afonso Henriques took in 1147 and King Denis turned into a royal palace around 1300, then across to the Bairro Alto, which Lisbon laid out on a near-grid plan in the sixteenth century. In the evening a guided petiscos walk brings small plates to share, such as pica-pau, pork or beef in a garlic and wine sauce, and amêijoas à Bulhão Pato, clams with garlic, coriander and white wine. The night ends with fado, which UNESCO added to its list of intangible heritage in 2011, a solo voice with the twelve-string Portuguese guitar. Logistics: a day in Lisbon on foot with Luisa, a licensed driver on hand, no hotel change.
Day Eighteen
The Tile Museum and a Sunset Sail on the Tagus
Queen Leonor founded the Madre de Deus convent in 1509, and today it houses the National Azulejo Museum, five centuries of Portuguese tiles under one roof. The morning stays open for the museum, where your dates allow with Luisa, or another collection of your choice. In the early evening a private boat leaves the Lisbon waterfront and sails under the 25 de Abril Bridge, which opened in 1966 and wears the same International Orange as the Golden Gate Bridge, with the city turning gold in the setting sun. Dinner follows at one of our favorite restaurants. Logistics: a day in Lisbon with Luisa and a licensed driver, with the sail from the Lisbon waterfront, no hotel change.
Day Nineteen
Flight to São Miguel and Sete Cidades
São Miguel, the largest island of the Azores, carries the nickname the Green Island, and Ponta Delgada, its capital, is the largest city of the archipelago. In the afternoon your licensed driver-guide takes you west to the caldera of Sete Cidades, about 6 by 5 kilometers across, where Lagoa Verde and Lagoa Azul share one body of water under a narrow bridge, green on one side and blue on the other. Local legend says a princess and a shepherd wept the two lakes, green for her eyes and blue for his. Dinner brings lapas, limpets sizzling in garlic butter, with a squeeze of lemon. Logistics: Lisbon to Ponta Delgada by direct flight, about 2 hours 30 minutes, and a licensed driver-guide meets you on arrival.
Day Twenty
Lagoa do Fogo and a Free Afternoon
Lagoa do Fogo fills the caldera of the Água de Pau volcano, which last erupted in 1563. Its shore lies about 575 meters above the sea, and the crater rim rises to about 949 meters. Where the weather suits, your licensed driver-guide takes you up in the morning for the view across the lake to the ocean. The afternoon is yours, at the hotel or in Ponta Delgada, where the three arches of the Portas da Cidade, from the eighteenth century, stand on the square by the harbor. Try a slice of São Miguel pineapple, which islanders grow in glass greenhouses, smaller and sweeter than tropical varieties. Logistics: a morning on São Miguel by road with your licensed driver-guide, then a free afternoon, no hotel change.
Day Twenty One
Departure from Ponta Delgada
João Paulo II airport lies about 2 kilometers west of the center of Ponta Delgada, so a midday flight leaves the morning free for a last coffee by the harbor. Azores Airlines flies nonstop from Ponta Delgada to Boston in about six hours, and connections through Lisbon serve other gateways. VIP fast-track assistance at the airport is available by request, and our note on VIP airport services in Portugal explains how it works. Logistics: hotel to Ponta Delgada airport by private vehicle with your licensed driver-guide, at an hour to suit your flight.
What does a 3 week Portugal itinerary look like?
A 3 week Portugal itinerary covers the whole mainland from the Minho to the Algarve and still leaves two nights for an island. This one spends five nights in Porto with day trips to Braga, Guimarães and Aveiro, two in the Douro Valley, one in Coimbra, three in Évora, three on the Algarve and four in Lisbon, then flies to São Miguel in the Azores for two more. Seven bases, 20 nights, one flight, and 13 days with no hotel change.
How do you add the Azores to a Portugal trip?
Add the Azores at the end, from Lisbon, with a direct flight of about 2 hours 30 minutes to Ponta Delgada on São Miguel, and give the island at least two nights. Two nights cover the Sete Cidades caldera and Lagoa do Fogo with time to rest. Ending on the island also shapes the flight home, because Azores Airlines flies nonstop from Ponta Delgada to Boston. American travelers who want several islands choose our 14-day Portugal tour with four Azores islands instead.
Is three weeks enough to see all of Portugal?
Three weeks is enough for every mainland region and one Azores island at an unhurried pace. This route reaches the Minho, the Douro, Coimbra and Aveiro in the center, the Alentejo, the Algarve, Lisbon and Sintra, and São Miguel. It leaves out Madeira, the other Azores islands and the mountains of the far northeast, each of which needs several more days. Our team adds any of them by trading nights rather than adding hotels.
Three weeks with the Azores, or a shorter Portugal route?
Three weeks suits travelers who want the full length of Portugal in one trip and an island at the end. A shorter or different route serves you better in four cases. With under two weeks, the 12-day Portugal private tour keeps the same mainland spine of Porto, the Douro, Lisbon, the Alentejo and the Algarve, and leaves out Braga, Guimarães, Aveiro, Coimbra and the Azores.
If an island matters more than the north, the 14-day Portugal tour with Madeira runs from Porto to the Algarve and ends in Funchal instead of Ponta Delgada. If the Azores are the point of the trip, the 14-day Portugal and Azores tour spends two nights in Lisbon and the rest on Terceira, Faial, São Jorge and São Miguel.
If you want Spain too, the 30-day Spain and Portugal tour starts on São Miguel and runs through Porto, Lisbon and the Algarve into Andalusia, Madrid and Barcelona, and passes by Braga, Guimarães and Coimbra. Every Portugal route sits on our Portugal destination page.
Who this journey suits
Travelers with three weeks of leave who want to see all of Portugal once, properly, and fly home from an island.
Retired couples and returning visitors who already know Lisbon and want the Minho, the Alentejo and the Azores at a slow pace.
Food and wine travelers, with port in Gaia and the Douro, a chef’s table in Porto, Alentejo reds and olive oil, cataplana on the Algarve and petiscos in Lisbon.
Families with teenage or adult children, since the days mix castles, boats, beaches, stargazing and crater lakes, and most bases hold three nights or more.
Active travelers, with vineyard trails in the Douro, a ride or hike in the Alentejo, the clifftop trail above Benagil and the walk up to Lagoa do Fogo.
The people behind the route
Luisa, one of our licensed guides in Lisbon and Sintra, leads the four Lisbon days where your dates allow. She works alongside a licensed driver, so the walks start where the car drops you, from Belém and Alfama to the old town of Sintra and the cliffs of Cabo da Roca. She knows the order of palaces, viewpoints and pastry shops to suit the day and the season. Across the rest of Portugal, from Porto to the Algarve and on São Miguel, a licensed driver-guide looks after you, one person holding both licenses who drives the car and leads the visits.
What the 21-day journey costs and what it includes
This 21-day journey starts from $21,294 per person, double occupancy. The from-price covers 20 nights in deluxe four-star properties selected for comfort, location and service. Five-star luxury properties are available by request. It also covers licensed guides and driver-guides on touring days, private vehicles for every transfer and excursion, and the planning and in-country support of our team.
What moves the price: travel dates and season, hotel category, the size of your party, single rooms, and added private experiences such as the river boat in Porto, the chef’s table, a night at a Douro quinta, the stargazing session at Monsaraz, a private yacht or dolphin trip on the Algarve, a round of golf, the sunset sail on the Tagus, or an extra night or island in the Azores. Our team prices each journey to your dates and party.
When three weeks across Portugal and out to the Azores sounds like the trip you have in mind, speak with our team about your dates, your party and the pace you want.
Questions about the 21-day Portugal and Azores itinerary
How many days do you need for Portugal and the Azores?
Plan at least 14 days for the mainland and two or three nights for one Azores island. This route uses 21 days: five nights in Porto, two in the Douro Valley, one in Coimbra, three in Évora, three on the Algarve, four in Lisbon and two on São Miguel. The mainland portion alone runs 18 days, and the flight from Lisbon to Ponta Delgada takes about 2 hours 30 minutes. With fewer days, the first thing to trim is the Porto stay, which holds three day trips, or the third Algarve night. With more days, a third night on São Miguel adds the Furnas valley on the east of the island, and a second island such as Terceira or Faial adds two or three nights more. Our team builds the island portion around the flights of your dates.
Should the Azores come at the start or the end of the trip?
This route places the Azores at the end, for two reasons. The mainland legs run in one line from Porto to Lisbon, and Lisbon has the direct flights to Ponta Delgada, so the island follows without a backtrack. Ending on São Miguel also suits the flight home, because Azores Airlines flies nonstop from Ponta Delgada to Boston in about six hours, and connections through Lisbon serve other gateways. Starting on the island works too, and our 30-day Spain and Portugal route opens on São Miguel before a flight to Porto. A start in the Azores gives a quiet first two days after the overnight flight, and an ending there gives a slow close after three weeks of touring. Our team matches the direction to your flights.
What is the best time of year for a 21-day Portugal trip?
April to June and September to October suit this route best. On IPMA’s 1981 to 2010 averages, Porto reaches a mean daily high of 17.6°C (about 64°F) in April and 23.4°C (about 74°F) in September, Lisbon 19.8°C (about 68°F) and 26.6°C (about 80°F), and Faro 20.4°C (about 69°F) and 26.6°C (about 80°F). Ponta Delgada runs milder on the Instituto de Meteorologia’s 1961 to 1990 averages, at 18.1°C (about 65°F) in April and 24.7°C (about 76°F) in September. July and August bring 28 to 29°C (82 to 84°F) on the Algarve and in Lisbon, and our team schedules the walking hours early and late in the day. September and early October fall in the Douro harvest, and Ponta Delgada stays mild through September.
Who guides and drives us on the 21-day tour?
Across most of Portugal, from Porto, Braga and the Douro through Coimbra, Évora and the Algarve to São Miguel, a licensed driver-guide looks after you, one person holding both licenses who drives the car and leads the visits. In Lisbon and Sintra, where your dates allow, Luisa, one of our licensed guides, leads the touring days and works alongside a licensed driver, two separate people. Every transfer runs by private vehicle for your own party, from the Porto airport pickup to the Ponta Delgada airport drop-off. Our team plans the whole route, books the site entries such as Livraria Lello, and stays in contact through the three weeks.
Which days involve long drives?
Day nine carries the longest drive, about three hours from Coimbra to Évora, with a lunch stop on the way. Day fifteen runs about 2 hours 40 minutes from the Algarve to Lisbon, and day twelve about 2 hours 30 minutes from Évora to the Algarve. The Douro to Coimbra takes about 2 hours on day eight, and Porto to the Douro about 1 hour 15 minutes on day six. Every other day either stays in one base or makes a day trip of under an hour each way, such as Braga, Aveiro, Monsaraz or Sintra. Your luggage stays in the car on every road day, and the licensed driver-guide sets the stops to suit your party. The only flight inside the trip links Lisbon to Ponta Delgada, about 2 hours 30 minutes.
Why does the route spend only one night in Coimbra?
Coimbra sits between the Douro Valley and the Alentejo, so one night there splits the drive south into two shorter legs: about 2 hours from the Douro on day eight and about 3 hours to Évora on day nine. The single night still gives you an afternoon at the university and the Biblioteca Joanina and an evening of Coimbra fado, where your dates allow. Travelers who want more of central Portugal add a second Coimbra night and a morning at the Roman ruins of Conímbriga or the convent town of Tomar, and our team adjusts the following days to keep the total at 21 or extends the trip by a day.
How do we add a second Azores island?
Add nights. This route gives São Miguel two nights, enough for Sete Cidades, Lagoa do Fogo and a free afternoon in Ponta Delgada. A third night adds the Furnas valley on the east of the island, with its hot springs and gardens. A second island such as Terceira or Faial needs two or three more nights and an inter-island flight. For an island-first trip, our 14-day Portugal and Azores tour spends two nights in Lisbon and then visits Terceira, Faial, São Jorge and São Miguel. Our team times the island legs to the flight schedule of your dates and adjusts the mainland nights to suit.
How much walking does the itinerary involve?
Several quarters on this route sit on hills with cobbled lanes and steps, including the Ribeira in Porto, the upper town of Coimbra, Alfama and the castle hill in Lisbon and the old town of Sintra. Your driver drops you at the top of a quarter where the roads allow, so most walks run downhill, and your guide sets the pace to your party. Some options involve longer walks, such as the 5.6-kilometer Seven Hanging Valleys trail on the Algarve, the vineyard trails of the Douro and the viewpoints above Lagoa do Fogo, and each one stays optional. Boat days in Porto, on the Algarve and on the Tagus involve little walking. Your guide is glad to advise on suitability before booking.
Is the 21-day route fixed?
The route as written shows one balanced order of bases, and our team shortens, extends or reorders it around your dates, interests and pace. Common changes include running it from Lisbon north to Porto, adding a third night on São Miguel, swapping the Azores for Madeira, adding a second Coimbra night, or turning one Algarve day into a free day at the beach. Each change keeps the same principle of few hotel changes and no more than one long road day in a row. Guides, drivers and site entries all move with the change, so you receive a revised day-by-day plan and price before you commit.
We keep a list of vetted four- and five-star hotels, well located and enjoyed by our past travelers and by our own team.
Examples for each overnight stop on this route. Choose a deluxe boutique hotel or a five-star stay, and your travel advisor matches each night to your wishes, the season and availability.
Porto
Boutique: Torel 1884. An 1884 palace near São Bento station, with rooms themed on Portugal’s voyages of discovery.
Five-star: The Yeatman. Terraced into the Gaia hillside among the port lodges, every room with a terrace facing Porto.
Douro Valley
Boutique: Quinta do Vallado Wine Hotel. An 18th-century house once owned by Dona Antónia Ferreira, plus a modern schist building among vineyards.
Five-star: Six Senses Douro Valley. A restored 19th-century manor near Lamego, above Douro vine terraces, with a large spa.
Coimbra
Boutique: Sapientia Boutique Hotel. A boutique hotel on Rua José Falcão, next to the old university, with a rooftop terrace.
Five-star: Quinta das Lágrimas. An 18th-century palace in large gardens tied to the story of Pedro and Inês.
Évora and the Alentejo
Boutique: Albergaria do Calvário. A 16th-century olive-oil mill inside Évora’s old walls, now a 22-room boutique hotel.
Five-star: Convento do Espinheiro. A restored 15th-century convent near Évora, with arched patios and an underground wine cellar.
Algarve
Boutique: Octant Praia Verde. A hotel in the pine woods of the eastern Algarve, with a boardwalk to Praia Verde beach.
Five-star: Vila Vita Parc. A clifftop resort at Porches on more than 50 acres of gardens, with its own beach below.
Lisbon
Boutique: Memmo Alfama. A design hotel on an Alfama lane, with a pool beside its wine-bar terrace over the Tagus.
Five-star: Four Seasons Hotel Ritz Lisbon. A 1959 landmark beside Eduardo VII Park, filled with mid-century Portuguese art and tapestries.
São Miguel, Azores
Boutique: Senhora da Rosa, Tradition & Nature Hotel. An 18th-century farm estate at the edge of Ponta Delgada, with an outdoor pool and spa.
Five-star: Octant Ponta Delgada. A modern seafront hotel near Ponta Delgada’s port, with a seventh-floor pool and bar over the Atlantic.
What's Included
A Very Personalized Itinerary, Just For You and Your Schedule
Hand-Picked Ultra-Luxury & Boutique Hotel Options
Insider Experiences + Inspiring Sightseeing + Magical Upgrades
Private Touring with Your Own Personal Expert Guide
Private Airport & Train Station Luxury Transfers
Full Breakfasts + Food & Wine Tasting Options
Your Choice of Activities on “Design Your Days”®
Expert Advice, Restaurant Ideas & Reservations
24/7 Support & Concierge Service from Spain, Portugal & Morocco
Magical is an award-winning luxury travel agency
Private journeys with soul & stories
Excellent independent reviews
Only five journeys per country, per week
Hidden gems, insider fun & vetted hotels
Your private guide, deluxe vehicle & flexible pace
24/7 concierge-style support
We handle everything — you live the dream
American Precision, Local Soul
Our Unforgettable Trips Are Tailored Just For You
Hi from Europe,
Along with our local partners across Portugal, Spain, Morocco and beyond we believe that our clients deserve the truly tailor-made private luxury trips, not generic "one-size-fits-all" plans.
Get inspired with our sample trips then get in touch about an expert-made personalized custom luxury itinerary, just for you.
Kind regards,
Dan O'Beirne & the MPT team
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