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Algar do Carvão volcanic chimney on Terceira island, Azores
Twin-towered church and white houses of Lajes do Pico on Pico island, Azores
Two riders on horseback along a crater lake in the Azores
Steep green cliffs and hydrangeas above the sea on São Jorge island, Azores

Portugal · Private and tailor-made

Lisbon and Five Azores Islands

Sail out of Angra do Heroísmo with a whale-watching crew and their marine biologist.

Suggested length

14 days

Price guide

From $13,972 per person, excl. flights, based on two sharing

Includes hotels, private guiding, experiences and transfers

When

June to September, and spring for whales

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American precision with local expertise · Planned from Europe since 2002 · Nearly 17,000 American travelers · Never cancelled a journey

Lisbon is only the gateway to this 14-day private tour of Lisbon and the Azores, which belongs to five islands in the mid-Atlantic. On Terceira you walk the UNESCO-listed old port of Angra do Heroísmo, then sail out of its harbor with a whale-watching crew and their marine biologist. From Faial you look into the Caldeira and cross to Pico, where vines grow inside black basalt walls, and to São Jorge. On São Miguel you finish among the green and blue lakes of Sete Cidades, the Gorreana tea gardens and Furnas, where cozido, a meat and vegetable stew, cooks for hours in the volcanic ground. Private guides and drivers are with you on every island. Island by island, the days move to your pace.

Walk the lanes of Alfama up to São Jorge Castle with Luisa, Lisbon.

Walk the grid streets of the UNESCO-listed old port, Angra do Heroísmo, Terceira.

Walk through Gruta do Natal, a lava tube nearly 700 meters long, Terceira.

Sail out of Angra with a whale-watching crew and its biologist, Terceira.

Taste wine grown inside black basalt walls, Pico.

Visit the green and blue lakes of Sete Cidades, São Miguel.

14-Day Lisbon and Azores Private Tour: Five Islands from Three Island Bases

“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.

14-Day Lisbon and Azores Private Tour: Five Islands from Three Island Bases

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.

What do our American travelers say?

Elizabeth on her private 30th anniversary trip through Portugal.

The 14-day Lisbon and Azores itinerary at a glance

The route uses four bases and thirteen nights: two in Lisbon, four on Terceira, three on Faial and four on São Miguel. A direct flight of about two hours links Lisbon to Terceira, whose Lajes airport sits about 15 kilometers northeast of Angra do Heroísmo. From Terceira a flight of about 40 minutes reaches Horta on Faial, and from Horta a flight of about 55 minutes reaches Ponta Delgada on São Miguel. Pico and São Jorge need no hotel change. The Atlânticoline ferry crosses from Horta to Madalena on Pico in about 30 minutes, and from Horta to Velas on São Jorge in about two hours.

The route covers the central group of the Azores, then São Miguel in the eastern group. Each island day returns to the same hotel, so you pack only on flight days.

June to September suits the route best. IPMA, Portugal’s weather institute, gives Angra do Heroísmo a mean daily high of 21.1°C (about 70°F) in June, 25.1°C (about 77°F) in August and 24.0°C (about 75°F) in September, on its 1981 to 2010 averages. July is the driest month there, with about 29 millimeters of rain against about 155 in December. Lisbon runs warmer, with a mean daily high of 25.7°C (about 78°F) in June and 26.6°C (about 80°F) in September.

Licensed guides we work with on this route include Luisa and Anabela in Lisbon. 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 Lisbon to São Miguel

The route starts in Lisbon because its airport, the main hub of TAP Air Portugal, sits about 7 kilometers from the historic center, and both TAP and Azores Airlines fly direct from Lisbon to Terceira. Two nights in Lisbon give you a full day in the city to settle the time change before the islands. From Terceira the route moves west to Faial, the nearest base for Pico and São Jorge, then flies east to São Miguel for the final four nights.

The angle is five islands from three island bases. Many Azores trips stay on São Miguel alone, and island-hopping trips often change hotel every night or two. Here Terceira and São Miguel each get four nights, and Faial gets three, because Pico and São Jorge sit within ferry range of Horta.

View Full Itinerary

Journey at a glance

Length
14 days

From
$13,972 per person, double occupancy

Route
Lisbon, Terceira Island, Island of Faial, São Jorge, São Miguel

Your planner adjusts every day to your dates.

A woman in a white hat and tank top holds someone's hand while facing a large plaza with a statue and an arched monument under a bright blue sky.

Day One

Arrival in Lisbon: Alfama, the Castle and Belém

Your licensed driver meets you at Lisbon airport, about 7 kilometers from the historic center. In the afternoon, where your dates allow, Luisa, one of our licensed guides in Lisbon and Sintra, leads you up through Alfama, whose name comes from the Arabic al-hamma, hot springs, to São Jorge Castle. Afonso Henriques took the castle from the Moors in 1147, and King Denis turned it into a royal palace around 1300. From its walls the view runs across the red roofs to the Tagus. The afternoon ends in Belém, where King Manuel I began the Jerónimos Monastery in 1502 and Francisco de Arruda built the Belém Tower between about 1514 and 1519. UNESCO listed both in 1983. A welcome dinner reservation follows on request. Logistics: Lisbon airport to your hotel by private vehicle with a licensed driver, then an afternoon with Luisa and the driver.

People sit at a restaurant table enjoying various dishes and drinks, engaged in conversation and eating in a casual dining setting.

Day Two

Lisbon's Food and an Evening of Fado

Today's booked activity is a guided food walk through the old center with Luisa, where your dates allow, so a light breakfast suits the day. In Belém, the bakery beside the Jerónimos Monastery has sold pastéis de nata, warm and dusted with cinnamon, since 1837. On the Largo de São Domingos, ginjinha, a liqueur of sour cherries and aguardente, comes as a small shot with a cherry at the bottom of the glass. In the evening, where it suits your party, our team reserves a table at a fado house. UNESCO inscribed fado on its list of intangible heritage in 2011, and a solo voice sings it over the Portuguese guitar, a pear-shaped instrument with twelve wire strings. Logistics: a full day in Lisbon on foot with Luisa and a licensed driver, no hotel change.

Twin-towered church and white houses of Lajes do Pico on Pico island, Azores

Day Three

Fly to Terceira: Angra do Heroísmo

A direct flight of about two hours carries you west over the Atlantic to Terceira. From the fifteenth century until the steamships of the nineteenth, fleets sailing between Europe, Africa and the Indies called at Angra, and its builders angled the grid of the streets against the prevailing winds. UNESCO inscribed the center in 1983. Queen Maria II added Heroísmo to the name to honor the island's defense against the Miguelist landing at Praia da Vitória in 1829. Your licensed driver-guide walks you past the Palácio dos Capitães-Generais, the Jesuit College of Saint Ignatius until 1759, and the seventeenth-century Palácio Bettencourt, now the public library and regional archive. Late in the day, the old wharf of Silveira below Monte Brasil offers a swim in the bay, beside the Caracol tower where lookouts once watched for ships arriving to load citrus. Logistics: Lisbon to Terceira by direct flight, about 2 hours, and a licensed driver-guide meets you at Lajes airport, about 15 kilometers from Angra.

Algar do Carvão volcanic chimney on Terceira island, Azores

Day Four

Terceira: Monte Brasil and the East Coast

The day starts on Monte Brasil, the extinct volcano beside Angra. Builders laid the first stone of its fortress in 1583 under Philip II of Spain, and the Portuguese took it in 1642 after a siege begun in March 1641, renaming it for Saint John the Baptist. Your licensed driver-guide then follows the coast east through Ribeirinha and Porto Judeu to the bays of Salga, Porto Martins and Cabo da Praia, with time for a swim. From the Serra do Cume, 545 meters high, the view takes in Praia da Vitória and its bay on one side and, on the other, an interior plain where volcanic stone walls divide the fields into a patchwork. Lunch brings alcatra, Terceira's beef stew, spiced and slow-cooked in a clay pot. Logistics: a full-day loop by road from Angra with your licensed driver-guide, no hotel change.

A volcanic cone rises above green hills, reflected in a calm lake under a blue sky with scattered clouds.

Day Five

Terceira: Gruta do Natal, Furnas do Enxofre and Biscoitos

The morning starts on the north coast, where the Museu do Vinho dos Biscoitos opened in 1990 to mark a century of the Brum family's wine house. Five generations have made Verdelho dos Biscoitos from vines in stone-walled plots on the lava, and where available, a tasting closes the visit. Inland, a path leads to the fumarole field of Furnas do Enxofre, a natural monument, where the ground steams and the air smells of sulfur. In the afternoon, when the cave opens, you go inside the island. Gruta do Natal is a lava tube 697 meters long with high ceilings, and its loop circuit means you never retrace your steps. Logistics: Angra to the north coast at Biscoitos and back through the volcanic interior by road, licensed driver-guide, back in Angra by evening.

Several dolphins swim and leap above the surface of deep blue ocean water under daylight.

Day Six

Terceira: Whales and Dolphins from Angra

Where it suits your party, the morning goes to sea. A whale-watching crew sails from Angra on a half-day trip of about three hours, with a skipper, a biologist and lookouts on the coast who track the animals from the cliffs. More than twenty cetacean species appear in Azores waters, and sperm whales and common, bottlenose and Risso's dolphins live here all year, with blue, fin and sei whales passing through, most often in spring. The afternoon is yours in Angra, with a bolo Dona Amélia, the island's small spiced cake, at a café in the old town. Logistics: a half-day boat trip from Angra with the operator's crew, about 3 hours, then a free afternoon, no hotel change.

Concrete steps lead down to a natural swimming pool surrounded by dark volcanic rocks, with a green cliff and blue sky in the background.

Day Seven

Fly to Faial: The Caldeira and Capelinhos

A short flight takes you to Horta, whose marina walls carry paintings left by visiting yacht crews with their boats' names and years. Your licensed driver-guide heads up to the Caldeira, a crater about 2 kilometers wide and 400 meters deep, by four-wheel drive where it suits your party. On the western tip, Capelinhos erupted from the sea on 27 September 1957 and kept going until 24 October 1958. Ash filled the ground between the new shore and the old lighthouse, and the eruption added about 2.4 square kilometers of land. John O. Pastore and John F. Kennedy sponsored the Azorean Refugee Act of 1958, which let 1,500 people from the islands emigrate to the United States. The visitor center at Capelinhos tells the story, and the Varadouro natural pools, in black basalt rock on the west coast, offer a swim. Back in Horta, Peter Café Sport has faced the marina since 1918, with the gin and tonic sailors know it for. Logistics: Terceira to Horta by direct flight, about 40 minutes, and a licensed driver-guide meets you at the airport.

Steep green cliffs and hydrangeas above the sea on São Jorge island, Azores

Day Eight

Pico by Ferry: Vineyards inside Black Basalt Walls

The ferry crosses the channel to Madalena with Mount Pico ahead of you, at 2,351 meters the highest mountain in Portugal. UNESCO inscribed the vineyard culture of Pico in 2004, covering 987 hectares of currais, small plots inside walls of black basalt, which shield the vines from wind and sea spray. Portuguese settlers, Franciscan and Carmelite friars among them, planted the first vines in the late fifteenth century, and Pico's Verdelho had an international name by the nineteenth. In Madalena, the Wine Museum fills the old Carmelite convent house, with dragon trees in its garden and the old vineyards beyond. Your licensed driver-guide continues along the coast to Lajido de Santa Luzia, home to the interpretation center for the island's vineyard culture, and lunch follows at a local restaurant. Logistics: Horta to Madalena by Atlânticoline ferry, about 30 minutes each way, and a licensed driver-guide meets you at the pier on Pico.

Aerial view of a coastal area with terraced green fields, a lagoon, rocky shoreline, and dense green hills meeting the blue ocean.

Day Nine

São Jorge by Ferry: Fajãs, Coffee and Cheese

Day nine is a long sea day, about two hours each way on the ferry from Horta to Velas. São Jorge runs about 53 kilometers long and about 8 kilometers wide, and most of its villages sit on fajãs, flat deltas of lava and rock at the foot of the cliffs. Your licensed driver-guide follows the island from Velas along the south coast toward Calheta. At Fajã dos Vimes, the Nunes family grows arabica coffee from seeds an ancestor brought back from Brazil in the early 1800s, roasts it on the home stove and serves it in the family café, with quilts on a wooden loom upstairs. São Jorge cheese, a raw cow's milk cheese aged for at least three months, has had its own protected region since 1986, and a tasting comes with lunch. Logistics: Horta to Velas by Atlânticoline ferry, about 2 hours each way, and a licensed driver-guide meets you at the pier on São Jorge.

A scenic lake with clear blue and green water surrounded by lush green hills, small villages, and dense forests under a partly cloudy sky.

Day Ten

Fly to São Miguel: Ponta Delgada

A flight carries you east from Horta to Ponta Delgada on São Miguel, the largest of the nine islands, about 65 kilometers from end to end. The airport sits about 2 kilometers west of the city center. The rest of the day is at your own pace, and dinner often brings lapas, limpets grilled with garlic and butter, and locally caught tuna. Logistics: Horta to Ponta Delgada by direct flight, about 55 minutes, and a licensed driver-guide meets you at the airport.

Two hikers stand on a grassy hillside overlooking a blue lake surrounded by green mountains and a forested peninsula.

Day Eleven

São Miguel: Sete Cidades and Lagoa do Fogo

Your licensed driver-guide heads west to the caldera of Sete Cidades. Inside it lie Lagoa Verde and Lagoa Azul, one lake in two colors joined by a narrow strait with a bridge across it. Local legend says the tears of a princess and a shepherd filled them, green for her eyes and blue for his. Where it suits your party, a kayak on the water gives a view of the crater walls from below, and lunch follows in the village of Sete Cidades. In the afternoon the road climbs to Lagoa do Fogo, about 575 meters above the sea in the youngest volcano on the island, which last erupted in 1563. No village sits inside the crater, and a nature reserve has protected it since 1982, so the view from the rim holds only water and native laurel and juniper. Logistics: Ponta Delgada to Sete Cidades and Lagoa do Fogo by road, licensed driver-guide, back in Ponta Delgada by evening.

Two riders on horseback along a crater lake in the Azores

Day Twelve

São Miguel: A Morning Ride and Gorreana Tea

Where it suits your party, the morning starts on horseback, with a ride for beginners or experienced riders through pasture, valleys and flowering hedges toward the sea. Your licensed driver-guide then takes you to the north coast and the Gorreana tea estate. Ermelinda Gago da Câmara founded the plantation in 1883, and it ranks as the oldest surviving tea plantation in Europe. Rows of tea bushes cover the slopes above the north coast, with the Atlantic beyond them. The tasting covers the estate's own black teas, such as Orange Pekoe, and green teas, such as Hysson. Logistics: Ponta Delgada to the riding stables and the north coast by road, licensed driver-guide, back in Ponta Delgada by evening.

A stone church stands by a lush lakeshore, with dense trees in the background and a small boat floating on the water in the foreground.

Day Thirteen

São Miguel: Furnas and Terra Nostra

Furnas lies about 40 minutes east of Ponta Delgada in a valley of hot springs. On the shore of Lagoa das Furnas, cooks wrap pots of cozido, pork, beef, chicken, sweet potato and cabbage, in cloth and bury them in the hot ground for almost seven hours at about 80 to 90°C, and lunch is the cozido straight from the ground. In the village, Thomas Hickling, the American consul on São Miguel, built a summer house in 1775, the start of the Terra Nostra garden, now about 12.5 hectares of trees from North America, Australia, New Zealand, China and South Africa. Its pool of brown, iron-rich thermal water stays at about 37°C, and bathers float under araucaria trees. Logistics: Ponta Delgada to Furnas by road, about 40 minutes each way, licensed driver-guide.

Three women standing close together outdoors, smiling and talking. One woman wears a hat, another wears glasses, and the third has a blanket draped over her shoulders.

Day Fourteen

Departure from Ponta Delgada

The airport lies about 2 kilometers west of the center, so the morning stays free for a last coffee by the harbor in Ponta Delgada. Your licensed driver-guide collects you from the hotel at an hour set to your flight and brings you to the terminal. Logistics: hotel to Ponta Delgada airport by private vehicle with your licensed driver-guide, about 2 kilometers.

What does a 14-day Lisbon and Azores itinerary look like?

A 14-day Lisbon and Azores itinerary gives Lisbon two nights and the islands eleven, split across three island bases. This one opens with Alfama, the castle and Belém, then a day of Lisbon’s food and fado. Terceira follows for four nights, with Angra, the east coast, the volcanic interior and a morning at sea with whales. Faial gets three nights, with the Caldeira and Capelinhos and ferry day trips to Pico and São Jorge. São Miguel closes the trip with four nights for Sete Cidades, Lagoa do Fogo, the Gorreana tea estate and Furnas. Three flights and two ferries, three island hotels.

Which Azores islands should you visit in two weeks?

In two weeks, Terceira, Faial, Pico, São Jorge and São Miguel give the widest range without long hops. Terceira holds the UNESCO-listed port of Angra and the lava tube of Gruta do Natal. Faial, Pico and São Jorge sit close together in the central group, so one base in Horta reaches all three. São Miguel, the largest island, has the crater lakes, the thermal ground of Furnas and the tea estates. Flores and Corvo, the remote western group, need extra flights and days of their own, and our team adds them on request.

How many days in Lisbon before the Azores?

Two nights in Lisbon suit this route, with one full day in the city between the arrival and the flight to Terceira. The first afternoon covers Alfama, São Jorge Castle and Belém, and the second day goes to Lisbon’s food and a fado evening. American travelers who want Sintra or Cascais as well add a third Lisbon night, and our team shortens an island stay or lengthens the trip to fit.

Lisbon and the Azores, or a mainland Portugal route?

This journey suits travelers who want the Azores as the heart of the trip, with Lisbon as the gateway. A different route serves you better in four cases.

If you want mainland Portugal and one Azores island, the 21-day Grand Tour of Portugal with the Azores runs from Porto and the Douro through Coimbra, the Alentejo, the Algarve and Lisbon, and ends with São Miguel. It covers the whole country but only one island.

If you prefer Madeira to the Azores, the 14-day Portugal tour with Madeira gives the same two weeks to Porto, the Douro, Lisbon, Sintra, the Alentejo, the Algarve and Funchal.

If this is your first trip to Portugal and the mainland comes first, the 12-day Portugal private tour covers Porto, the Douro, Lisbon, Évora and the Algarve, and the 10-day Portugal private tour and 10-day Portugal luxury tour fit Porto, the Douro, Lisbon and the Algarve into ten days.

With one week, the 7-day Portugal private tour keeps to Lisbon, Sintra, Évora, Coimbra, Porto and the Douro. Every Portugal route sits on our Portugal destination page.

Who this journey suits

Returning visitors to Portugal who know Lisbon and Porto and want the islands in depth.

Couples who prefer coastlines, crater lakes and small towns to big-city sightseeing, with a fado evening and a thermal pool as options.

Families with teenage or adult children, since the days mix boats, caves, horses and swimming, and each island base has three or four nights.

Walkers and nature travelers, with crater rims, fumarole fields and coastal paths on four islands.

Food and wine travelers, with alcatra on Terceira, Verdelho on Terceira and Pico, cheese and coffee on São Jorge, tea at Gorreana and cozido at Furnas.

The people behind the route

Luisa, one of our licensed guides in Lisbon and Sintra, leads the two Lisbon days where your dates allow. She works alongside a licensed driver, so the walks through Alfama and up to the castle start where the car drops you, and she shapes the food walk around the season and your tastes. On Terceira, Faial, Pico, São Jorge and São Miguel, a licensed driver-guide on each island meets you at the airport or the pier, drives the touring days and leads the visits.

What the 14-day journey costs and what it includes

This 14-day journey starts from $13,972 per person, double occupancy. The from-price covers thirteen nights in deluxe four-star properties selected for comfort, location and service. Five-star luxury properties are available by request. It also covers a licensed guide and a licensed driver in Lisbon, licensed driver-guides on the islands, 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 fado evening in Lisbon, the whale-watching trip, the four-wheel-drive trip on Faial, the horseback ride or kayak on São Miguel, or extra nights on Pico or in Lisbon. VIP assistance at the Lisbon airport is available by request, and our note on VIP airport services in Portugal explains how it works. Our team prices each journey to your dates and party.

When five islands and a Lisbon prelude sound like the trip you have in mind, speak with our team about your dates, your party and the pace you want.

Questions about the 14-day Lisbon and Azores itinerary

How many Azores islands fit into two weeks?

Five islands fit comfortably into the eleven island nights of this route, from three hotel bases. Terceira and São Miguel each get four nights, and Faial gets three, because Pico and São Jorge sit within ferry range of Horta and work as day trips. A single-island stay on São Miguel suits a short trip, and two islands suit a week. With two weeks, five islands from three bases keeps the hotel changes to three while covering the history of Angra, the volcanic interior of Terceira, the vineyards of Pico, the fajãs of São Jorge and the crater lakes of São Miguel.

How do you get from Lisbon to the Azores?

A direct flight links Lisbon to Terceira in about two hours, and both TAP Air Portugal and Azores Airlines fly the route. Lajes airport sits about 15 kilometers northeast of Angra do Heroísmo, and a licensed driver-guide meets you on arrival and drives you to your hotel in the old town. TAP and Azores Airlines also fly direct from Lisbon to Ponta Delgada on São Miguel, so the route reverses easily, starting on São Miguel and ending on Terceira. Our team discusses flights with each client while planning the journey, and the schedule we send before you leave lists every flight, ferry and transfer.

How do you travel between the Azores islands on this route?

Three short flights and two ferry crossings link the islands. Terceira to Horta on Faial takes about 40 minutes by air, and Horta to Ponta Delgada on São Miguel about 55 minutes, both on SATA Air Açores, the inter-island airline. From Horta, the Atlânticoline ferry crosses to Madalena on Pico in about 30 minutes and to Velas on São Jorge in about two hours. On each island a licensed driver-guide meets you at the airport or the pier, so luggage and timing stay in our team’s hands. Ferry and flight timetables change with the season, and our team sets the order of the Pico and São Jorge days to fit them.

What is the best time of year for Lisbon and the Azores?

June to September suits this route best. IPMA, Portugal’s weather institute, gives Angra do Heroísmo on Terceira a mean daily high of 21.1°C (about 70°F) in June, 25.1°C (about 77°F) in August and 24.0°C (about 75°F) in September, on its 1981 to 2010 averages. July is the driest month in Angra, with about 29 millimeters of rain, against about 155 in December. Spring brings the most sightings of passing blue, fin and sei whales, and sperm whales and several dolphin species stay all year. Summer warms the sea for the natural pools at Silveira and Varadouro. Lisbon runs warmer than the islands, with a mean daily high of 25.7°C (about 78°F) in June.

Why stay on Terceira, Faial and São Miguel rather than Pico?

Each base answers a different need. Angra on Terceira has the UNESCO-listed old town, the harbor and the restaurants, and four nights there cover the island at an easy pace. Horta on Faial sits in the middle of the central group, with the airport, the marina and the ferry pier for both Pico and São Jorge, so three nights there reach three islands. Ponta Delgada on São Miguel puts Sete Cidades, Lagoa do Fogo, Gorreana and Furnas all within a day’s drive. Travelers who want to climb Mount Pico or spend more time among the vineyards add a night or two on Pico, and our team rebuilds the Faial stay to fit.

What does the whale-watching morning on Terceira involve?

The whale-watching morning is an option, and where it suits your party our team books a half-day trip of about three hours from Angra. The crew includes a skipper and a biologist, and lookouts on the coast track the animals from the cliffs. Before boarding, the crew briefs you on the species, the spotting methods and the rules for approaching the animals at sea. More than twenty cetacean species appear in Azores waters. Sperm whales and common, bottlenose and Risso’s dolphins live here all year, and blue, fin and sei whales pass through, most often in spring. Whale-watching boats also sail from Pico and São Miguel, so the trip moves to another island on request.

Who guides and drives us on the 14-day tour?

In Lisbon, where your dates allow, Luisa, one of our licensed guides, leads both touring days and works alongside a licensed driver, two separate people. On Terceira, Faial, Pico, São Jorge and São Miguel, a licensed driver-guide looks after you, one person holding both licenses who drives the car and leads the visits. On boat days the operator’s skipper and crew take over at sea. Every road transfer runs by private vehicle for your own party, from the Lisbon airport pickup to the Ponta Delgada drop-off. Our team plans the whole route, books the site entries and stays in contact through the trip. Our note on driver-guides in Portugal explains how the role works.

How active is the Azores itinerary?

The days mix short walks, viewpoints and optional activities, and you choose how much to add. Gruta do Natal is a walk of about 700 meters on a loop through the lava tube, on a floor that is uneven in places. The Caldeira on Faial and the rim of Lagoa do Fogo have short walks from the car to the viewpoints. The kayak at Sete Cidades, the horseback ride on São Miguel and the four-wheel-drive trip on Faial are all options, and your licensed driver-guide sets the pace to your party. The ferry to São Jorge takes about two hours each way, with time to read on deck. Your guide is glad to advise on suitability before booking.

Is the 14-day route fixed?

The route as written shows one balanced order of islands, and our team shortens, extends or reorders it around your dates, interests and pace. Common changes include running it from São Miguel to Terceira, adding a night on Pico for the vineyards or the mountain, adding Sintra and a third night in Lisbon, or replacing São Jorge with Flores in the western group. Guides, drivers and site entries all move with the change, and 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.

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.

Terceira, Azores

Boutique: Pousada Forte de Angra do Heroísmo. Inside the 16th-century São Sebastião fort on a cliff above Angra’s bay, in a UNESCO-listed town.

Also consider: Quinta da Nasce Água. A renovated 16th-century mansion 3 km from Angra, with a 19th-century garden lake.

Faial, Azores

Four-star: Azoris Faial Garden, Resort Hotel. A garden resort on the edge of Horta, with an infinity pool and views of Mount Pico.

Also consider: Hotel do Canal. A harborfront hotel with Pico-view rooms, a few steps from Peter Café Sport.

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

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Our Unforgettable Trips Are Tailored Just For You

Hi from Spain & Portugal,

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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