Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options

Post originally Published November 15, 2023 || Last Updated November 16, 2023

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Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options - Lisbon - A City of Hills, History, and Hidden Gems


Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options

Lisbon enchants visitors with its hills, history, and hidden gems tucked away in its medieval alleys and vibrant neighborhoods. As the capital of Portugal overlooking the Tagus River, Lisbon has been an important port city for centuries. Earthquakes have shaken the city, but Lisbon has persevered and rebuilt into an architectural wonder mixing Gothic, Manueline, Baroque, Modern, and Postmodern styles.

Wandering the hilly streets, you'll discover charming miradouros (viewpoints) overlooking red rooftops, padrões (elaborate stone monuments), and the iconic Santa Justa Lift linking downtown Baixa with the historic Alfama district spread across the slopes. Ride iconic tram 28 through Alfama’s labyrinth of streets where Fado singers once lamented lost love. Feel the melancholic longing in their voices at small Fado houses and restaurants.

Beyond Alfama sprawls the atmospheric neighborhood of Belém, home to Manueline masterpieces like the ornate Monastery of Jerónimos and the UNESCO-listed Belém Tower standing guard where Portuguese explorers set sail long ago. Don't miss the sublime custard tarts at Pastéis de Belém cafe, still baking the treat according to the original secret recipe since 1837.
Wander beyond the old town to see how Lisbon has transformed into a progressive European capital while preserving its heritage. Head to modern Parque das Nações with cutting-edge architecture, lively riverfront promenades, and Europe's largest aquarium. Take in panoramic city vistas from the hot tubs at Rooftop Pool & Bar or miradouro atop the 25 de Abril Bridge.

What else is in this post?

  1. Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options - Lisbon - A City of Hills, History, and Hidden Gems
  2. Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options - Porto - Charming River Views and Port Wine
  3. Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options - Algarve - Picturesque Beaches and Coastal Towns
  4. Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options - Évora - Wandering Through a Museum City
  5. Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options - Sintra - Fairytale Palaces and Mountainscapes
  6. Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options - Coimbra - Youthful Energy and Ancient Traditions
  7. Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options - Alentejo - Rolling Hills and Sleepy Villages
  8. Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options - Azores - Dramatic Volcanic Landscapes

Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options - Porto - Charming River Views and Port Wine


Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options

Beyond the capital awaits Porto, Portugal's second largest city, beckoning travelers with its postcard-perfect panoramas overlooking the Douro River. Wander across the double-decker Dom Luís I Bridge to Gaia's renowned port wine lodges brimming with barrels of ruby riches. Savor a port tasting and toast to stellar views of Porto's historic Ribeira district from Vila Nova de Gaia’s riverside promenade.
Ribeira's cobblestone streets besiege you with irresistible Instagram ops, from candy-colored houses to wide river vistas to the photogenic São Francisco Church where rococo carvings dance across the gilded interior. But Porto charms with more than just looks. It serenades with soulful Fado, wows with contemporary art, and tempts with comfort food classics like francesinha sandwiches oozing melted cheese.

Beyond the scenic riverbank, Porto's hilly streets invite aimless wandering past Baroque churches, art nouveau cafés, and bustling Bolhão Market where friendly fishmongers hawk the catch of the day. The iconic Café Majestic transports you back to Belle Époque glamor inside its lavishly ornate interior, though Majestic's sidewalk tables prove equally alluring for people watching. Nearby Livraria Lello exudes Harry Potter vibes with its neo-Gothic bookstore staircase that allegedly inspired J.K. Rowling.
No visit to Porto is complete without riding the Funicular dos Guindais, an atmospheric cable car offering breathaking views over Ribeira and the Dom Luís Bridge. Or lose yourself in the past wandering through ancient Palácio da Bolsa, the stock exchange palace lavished with magnificent Moorish-inspired courtyards. When night falls, join locals pub-crawling through nightlife-hotspot Galerias Paris.

Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options - Algarve - Picturesque Beaches and Coastal Towns


With over 150 miles of coastline, it's no wonder the Algarve is synonymous with sun-soaked beaches. This southernmost region tantalizes travelers with its photogenic fusion of sea, sand, and cliffs. Beyond bustling beach resorts, authentic charms await in the Algarve's colorful coastal towns.

The Algarve coastline flaunts sheer cliff faces, secluded coves, and endless golden sand beaches lapped by the Atlantic Ocean and Mediterranean Sea. Whether you're seeking family-friendly beaches with waterparks and restaurants or remote, rugged expanses far from crowds, the Algarve delivers.

Must-visit beaches include Praia da Marinha with its picturesque scenery of steep, striated sea cliffs amid emerald waters that illuminate sea caves. Photographers flock to snap the iconic stone arch emerging offshore. Neighboring Praia da Falésia awes with six miles of ochre cliffs towering above sandy shores dotted with traditional fishing boats.

For remote island vibes, hop a ferry to car-free Culatra Island. Its west coast boasts deserted white sand beaches with prime conditions for swimming and snorkeling. On Barreta Island, walk between the island’s tranquil sides - the calm Rio Formosa lagoon on one shore and crashing waves on the ocean side.

Beyond lounging beachside, base yourself in the Algarve’s alluring small towns to experience authentic local life. The historic coastal settlement of Lagos charms with its well-preserved city walls and picturesque marina flanked by restaurants and bars. Wander quaint, pedestrian-only streets like Rua Cândido dos Reis signposted with colorful ceramic tiles.

In the tranquil western Algarve, Sagres attracts surfers and nature lovers. Watch waves pound the cape’s massive sea cliffs from Fortress of Sagres, a coastal defense fortification offering sweeping views. The cape’s west coast tempts with isolated beaches and coves. At laidback Tonel Beach, beach shacks dish up fresh seafood like grilled sardines.
Picturesque Tavira spans the Gilão River, its seven-arched Roman bridge leading to the historic center's pastel-hued houses with wrought-iron balconies. A Moorish castle and ruins of Tavira's hilltop walls remain from medieval days. Time slows on the Ilha de Tavira, a pristine nature reserve and beach reachable by miniature railway.

Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options - Évora - Wandering Through a Museum City


With over 2000 years of history spanning Roman, Visigothic, Moorish, and Portuguese influences, Évora resembles an open-air museum whispering of ages past. Enc ircled by medieval walls with Roman foundations, Évora's historical core enchants as a UNESCO World Heritage Site studded with architectural wonders testifying to the town’s rich history.

Beyond the arched medieval Gates of Aurélia and Alconchel, lose yourself wandering Évora’s labyrinthine narrow lanes lined with whitewashed houses decorated with azulejos tiles in vivid blues. At relaxed sidewalk cafés shaded by leafy trees, sip strong Portuguese coffee as locals debate football or politics. Follow their gaze to the Roman aqueduct stretching majestically towards the horizon, its two tiers of massive granite arches having served Évora for over a millennia and counting.
Évora Cathedral looms majestically over lively Praça do Giraldo, its soaring Gothic arches dating to 1204 flanked by the city’s turrets. But Évora saves its most dazzling sights for indoors. The Chapel of Bones chillingly confronts mortality with walls and columns decorated with thousands of human skulls and bones exhumed from crypts to make room for the newly deceased. Contemplate the afterlife surrounded by carefully curated remains.
For an enriching glimpse into Portuguese history, the Museum of Évora in a converted 15th-century palace displays everything from Stone Age tools to 16th-century Flemish art to antique Portuguese furniture. Kids delight at spotting dinosaurs along with Portuguese royals and poets in the imaginative tableaus of the Portugal Dos Pequenitos theme park.
Beyond museums and monuments, Évora connects visitors to its ancient soul. At the Roman Temple dating to the first century A.D., channel the ancients who once gathered at this Corinthian columned temple whose original dedication remains shrouded in mystery. Feel a poignant longing singing from within whitewashed walls during performances of mournful Fado music, the Portuguese blues lamenting lost loves.
With student life pulsing through the University of Évora just down the street from the Roman remnants, a lively energy infuses Évora's historic core. Students and professors alike congregate at sidewalk cafés for leisurely lunches followed by coffee paired with pastel de nata custard tarts, the ideal recharge before afternoon classes. In the evenings, university crowds spill into tapas bars pairing Alentejo wines with classic petiscos snacks like grilled chouriço sausage, ham, cheese, and olives.

Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options - Sintra - Fairytale Palaces and Mountainscapes


Beyond Lisbon's hills awaits Sintra, the storybook escape where Portuguese royals once summered to escape the capital's heat. Lord Byron called this mountain town and UNESCO site a "glorious Eden" for its magical palaces and lush landscapes. Sintra feels fantastical, a fairy tale village come to life. Moorish and Manueline architectural marvels crown misty hilltops with candy-colored turrets gazing down on the picturesque village below.
Even arriving by train seems otherworldly as the route winds through dense foliage with only glimpses of distant palaces. Walking Sintra's hilly streets reveals one postcard vista after another with ornate fountains, horse-drawn carriages, and vine-covered estates. At the 19th century Seteais Palace, the neoclassical façade gives way to sprawling manicured gardens with palace views framed by the Sintra Mountains rising in the distance. Or escape the crowds with a woodland hike to Moorish Castle ruins towering over the village.
But Sintra's dazzling whimsy culminates inside its lavish palaces. Romantic Pena Palace perches atop the highest peak, its vibrant terraces and mythic mash-up of architectural styles encapsulating 19th century Portuguese nostalgia for its long-lost Empire. Lush greenery creeps up the castle walls in fairytale fashion. Inside, opulent staterooms fuse Moorish and Manueline influences with vividly painted trompe l'oeil walls and intricately carved wood ceilings in geometric starburst patterns.

Nearby Monserrate Palace embraces an amalgam of Gothic, Moorish, and Indian architectural motifs in a flamboyant fantasy. The lush botanical gardens surrounding the estate offered the ideal setting for 19th century romanticism. Exotic trees mingle with grottoes and follies like the mock ruins of a Gothic chapel consumed by vegetation.
But Sintra's most stunning interior awaits within Quinta da Regaleira. This eccentric estate merged Neo-Gothic, Neo-Manueline, and Renaissance themes with mystical symbols. The property's showstopper is an enigmatic Initiation Well descending 27 meters in a mesmerizing spiral staircase past mystical grottoes with Knights Templar symbolism. The Initiation Well exemplifies how Sintra blends opulence, mythology, and nature into an experience that feeds the soul's longing for magic.

Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options - Coimbra - Youthful Energy and Ancient Traditions


Coimbra enchants with its seamless fusion of tradition and modernity. As home to Portugal’s oldest university, a youthful energy infuses Coimbra’s historic streets with the dynamism of young students chatting beneath ancient arches or grabbing lunch between classes. But Coimbra equally impresses with its wealth of medieval architecture spanning Romanesque cathedrals, Portugal’s oldest university, and a hilltop castle with sweeping views.

Wandering Coimbra delivers Instagram-worthy scenes at every turn. The postcard-perfect centerpiece remains the 18th century Joanina Library, its elaborate Baroque interior brimming with hundreds of thousands of volumes. Ornate dusty rose walls ascend three stories beneath intricately painted ceilings and massive floor-to-ceiling windows that bathe the library in ethereal light. Since visits are limited to small groups at scheduled times, arrive early to avoid queues.

Nearby on the Mondego River, students and locals alike gravitate towards Parque Verde do Mondego, a sprawling park perfect for picnicking beside the river or enjoying outdoor concerts. Follow the riverbank pathway to the architecturally innovative Pedro e Inês footbridge, its pair of asymmetrical arches dramatically framing Coimbra’s skyline.

But the heart of Coimbra is found uphill in the university district surrounding the 12th century old cathedral Sé Velha, one of Portugal’s finest examples of Romanesque architecture marked by Moorish and Byzantine influences. Its weathered façade overlooks an impressive Grand Plateau lined with majestic university buildings.

The streets surrounding the university come alive each summer for Coimbra’s Queima das Fitas festival when students celebrate finishing exams in raucous fashion bedecked in traditional capes and ribbons. Locals join graduating university students parading through the streets led by triumphant brass bands. Celebratory concerts, dances, fado music and fireworks carry on late into the balmy June nights for a weeklong festival infusing Coimbra with youthful revelry.

Beyond the university, Coimbra’s steep winding lanes lined with painted houses in muted yellows and ochres lead uphill to the crenellated walls of the Royal Palace. Converted into a luxury hotel, visitors can still glimpse Coimbra’s long history as the capital of Portugal for over a century before Lisbon. The royal palace foundations date to Moorish rule in the 8th century.

From palace ramparts or miradouro viewpoints, absorb panoramic vistas over Coimbra’s red-roofed historic houses draped across hillsides flanking the Mondego. Come evening, lively student hangouts and fado houses echo late into the night with acoustic Portuguese guitar and soulful singing.

Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options - Alentejo - Rolling Hills and Sleepy Villages


Beyond Portugal's bustling cities awaits the rural tranquility of Alentejo, a region of undulating hills and sleepy villages where life unfolds at an unhurried pace. With cork trees and olive groves blanketing the countryside, Alentejo offers the perfect antidote to urban chaos. Pause and listen to the pace of nature.

Base yourself at a countryside hotel or agroturismo farmstay to experience authentic Alentejo. As the morning sun peeks through shutters, breathe in the fresh country air on your balcony before starting the day with local honey, cheeses, and breads. At boutique 7 Quintas in Évora countryside, creative daily breakfasts feature farm-to-table fare like mimosa eggs with fried kale and seasonal organic fruits plucked from the garden.

Under moss-draped cork oaks, explore picturesque hill towns lost in time. In medieval Marvão, winding lanes lined with whitewashed houses with flower boxes lead up to a 13th century castle with sweeping Alentejo vistas. The walled town of Monsaraz perches on a hilltop overlooking the Alqueva Reservoir, its slumbering streets awakening for a lively medieval festival each July.

In Vila Viçosa, tour the sprawling 16th century Palace of the Dukes of Braganza with its royal apartments preserved in period style. But some of Alentejo's most authentic charms are the simplest. In sleepy Redondo, locals sip espresso in the sleepy main square surrounded by pastel-hued buildings and 18th century Paço dos Henriques manor house.

Beyond its fortified hill towns, Alentejo tempts with more than 150 miles of coastline. Sleepy Vila Nova de Milfontes remains a low-key fishing village and surfing haven fringed by three unspoiled beaches. For off-the-beaten-path adventures, hike fisherman’s trails along Alentejo’s rugged western coastline, tracing cliffs and secluded coves.
Inland, Alentejo's rolling plains burst into color each spring when wildflowers bloom vibrant hues across grasslands. Picnic amid the vivid meadows of flowers near Castelo de Vide. Birdwatchers flock to wetlands, dams and rice paddies to spot herons, flamingos and rare species. Alentejo’s star outdoor attraction remains its Dark Sky Alqueva Reserve, certified for stargazing with minimal light pollution.

Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options - Azores - Dramatic Volcanic Landscapes


Portugal Calling: Crafting the Perfect Itinerary for First-Timers Overwhelmed by Options

The remote Azores archipelago tantalizes adventurous travelers with its dramatic volcanic landscapes scattered across nine islands in the middle of the Atlantic. Formed from ancient volcanic eruptions and still dotted with hydrothermal springs and fumaroles emitting plumes of gas, the Azores bring the power of untamed nature to the surface.

Get a first glimpse during your island-hopper flight, swooping low over black sand beaches framed by steep cliffs and cone-shaped stratovolcanoes jutting dramatically upwards. On São Miguel island, hike through the geo-park around Sete Cidades lake inside a volcanic crater to witness the forces that shaped the Azores. Follow a trail circling the emerald green lake, pausing at overlooks to absorb the sharp contrast between the verdant crater interior and distant vistas of the blue Atlantic. From bonding with baby whales to soaking in thermal ocean pools, the energy of the Azores enthralls.
On Terceira island, underground lava tube caves formed by ancient flows allow close-up exploration of volcanic features. Don a helmet, grab a flashlight, and delve into Algar do Carvão cave’s intricate chambers formed from past eruptions. Winding walkways lead through the caves surrounded by lava stalactites and otherworldly rock formations.

At Furnas valley on São Miguel island, volcanic heat fuels diverse attractions from cooking traditional cozido stew in underground geothermal pits to soaking in rejuvenating hot springs. Witness the Earth's raw power watching a fumarole billowing gas or bubbling mud pots. Nearby Lagoa das Furnas offers a peaceful interlude with its placid waters reflecting the valley's sloping hills.
But São Miguel's volcano highlight awaits at Lagoa do Fogo (Fire Lake) where trails circumnavigate the idyllic crater lake with views of the surrounding caldera formed by immense volcanic eruptions. Stop for snapshots of the panoramic vistas across the island’s patchwork fields to the cobalt-blue Atlantic Ocean in the distance.

On Faial island, hike across the Capelinhos volcano's rugged landscapes emerged after a 1957 eruption created the westernmost point of land in Europe. The eerie ash fields and fossilized lava flows contrast with the island's verdant interior dotted with blue hydrangea blossoms. Neighboring Pico island looms with the imposing volcanic peak of Pico Mountain dominating the horizon, Portugal's highest point.
Beyond exploring volcano remnants, the Azores islands have harnessed geothermal activity for creative endeavors. On São Miguel, tour a pineapple plantation heated by geothermal greenhouses that allow growing the tropical fruit far from the equator. Take a cooking workshop using Azorean pineapple or other local ingredients enhanced with the volcanic island flavors.

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