After collecting your hire car at Faro Airport, stretch your legs with a relaxed coastal breakfast at Faro Marina before heading west along scenic N125 (no tolls) toward the Algarve cliffs. Stop for a detour to stroll the boardwalk at Praia de Faro and wander the whitewashed lanes of Fuseta village where you can sample fresh seafood (gluten-free options available) and pick up picnic supplies for the drive north.
Drive north along the scenic N125 and pause for a late lunch at Tavira's Mercado da Ribeira where stalls offer gluten-free regional dishes and fresh produce for a picnic. Continue inland to explore the hilltop charm of Castro Marim - wander the castle ruins and salt pans at golden hour, then enjoy an early evening tasting of Algarve wines at the family-run Quinta do Francês (book ahead), keeping you on a relaxed, toll-free route toward the Alentejo.
As dusk falls, wind inland on the N125-free route to the tranquil village of Moncarapacho for a relaxed stroll through its orange-tree lined streets and a coffee at the cozy, gluten-free-friendly Pastelaria Serrão. Finish the night with a sunset aperitivo and small-plate tasting of regional wines at the family-run Quinta do Barranco Longo (book ahead), enjoying hilltop views that set the tone for your northward Alentejo drive tomorrow.
Leave the Algarve behind on quiet, toll-free country roads toward the Alentejo and begin your morning with breakfast in the sun-soaked square of Mértola, followed by a gentle wander through the hilltop castle quarter and riverfront lanes. Continue north to the tucked-away Quinta da Ervamoira for a private morning tasting (book ahead) and a tour of their organic vineyards, then stretch your legs on a short olive-grove walk near Monsaraz with panoramic views over the Alqueva reservoir before a countryside lunch at a gluten-free-friendly local tasca.
After a countryside lunch, follow quiet secondary roads to the hilltop hamlet of Arraiolos to admire its famous embroidered rugs at a local atelier and enjoy a coffee in the shade of the Igreja Matriz. Continue to Herdade do Esporão for an afternoon cellar tour and a guided tasting of Alentejo reds (book ahead) and finish with a slow drive through cork-oak landscapes to the peaceful riverside village of Vila Viçosa for a late stroll among marble palaces and a gluten-free pastry at a neighbourhood Pão & Companhia.
As the light softens, head to the tranquil hilltop village of Reguengos de Monsaraz for a gentle stroll through its whitewashed streets and sweeping views over the Alqueva plains, then settle on a terrace at Restaurante Divinus for a focused gluten-free tasting menu of regional dishes paired with local wines. Finish the night with an intimate sunset tasting at the nearby boutique Quinta do Quetzal (book ahead) where small-batch reds and a cellar tour offer a quiet, atmospheric close to a day of off-the-beaten-track discoveries.
Begin your Lisbon morning with coffee and a gluten-free pastel at Café Janis before a relaxed tram-free walk through the mosaic-paved lanes of Alfama, exploring the maze of viewpoints and peeking into small fado houses. Continue uphill to the airy terraces of Miradouro da Senhora do Monte for panoramic city and river views, then descend toward the riverside to browse the artisanal stalls at LX Factory where you can sample allergy-aware bakeries and shop for local cork souvenirs.
Wander the elegant terraces of Chiado and pop into independent shops for Portuguese ceramics before heading to the lesser-known gardens of Jardim do Príncipe Real to relax under jacarandas and sample gluten-free treats from the nearby Naked bakery. Later, stroll down to the riverside district of Cais do Sodré to browse the Mercado da Ribeira's quieter stalls for allergy-friendly bites, then take a short walk to the atmospheric Docas de Santo Amaro for an early evening glass of Portuguese wine by the boats, keeping your pace gentle as you transition from morning viewpoints to Lisbon's lively waterfront.
As twilight deepens, wander the lantern-lit alleys of Bairro Alto to catch live fado in an intimate setting at Tasca do Chico (arrive early or reserve), then drift down to the riverside for a serene sunset stroll along Praça do Comércio with views across the Tagus. For dinner, enjoy a relaxed gluten-free tasting at Prado Mercearia Moderna-ask for the chef's locally sourced menu paired with Portuguese wines-and finish with a nightcap at the rooftop bar of PARK for sweeping city panoramas that set you up for tomorrow's winery day trip.
Head south along toll-free coastal roads to the Arrábida foothills for a morning tasting and vineyard walk at José Maria da Fonseca (Azeitão) where you can sample the famed Moscatel and ask for gluten-free pairing options; follow this with a quiet stroll through the shaded lanes of Azeitão village to visit a local cheese shop for gluten-free-friendly regional cheeses. Next, drive the scenic backroad to the seaside hamlet of Portinho da Arrábida for a short cliff-top walk and lookout over the turquoise bay, finishing with coffee and gluten-free pastries at the seaside café by Praia do Creiro before heading back toward Lisbon for your afternoon viewpoint explorations.
After returning from Arrábida, wind inland along quiet country lanes to the hilltop village of Palmela for a relaxed lunch on the castle terrace at Castelo de Palmela where the castle restaurant can accommodate gluten-free requests while you enjoy sweeping views over the Setúbal peninsula. In the later afternoon, take a calm, toll-free drive to the peaceful estate of Quinta de Alcube for a guided vineyard walk and small-group tasting of native varieties (book ahead), then pause at the scenic overlook near Miradouro da Serra do Louro to watch golden light spill across the Sado estuary before a short return to Lisbon to freshen up for the evening.
As dusk falls, take a short, toll-free drive to the quiet coastal village of Sesimbra for a seafood-focused aperitivo on the harbor terrace at O Marisco Feliz (ask for gluten-free small plates), then stroll the cliffside promenade toward the ruined Castelo de Sesimbra to watch the sunset over the Arrábida headland. Finish with a relaxed dinner at the family-run A Cascata where the chef prepares naturally gluten-free fish dishes and regional wines, and linger over a nightcap at the low-lit beachfront bar Bar do Peixe while listening to the sea - a gentle close that links today's vineyard walks to Lisbon's coastal mood.
Set off along quiet coastal backroads toward the historic fishing town of Figueira da Foz for a breezy breakfast on the promenade and a walk across its vast sandy Praia da Claridade, then follow coastal lanes north to explore the tidal estuary and birdlife at Parque Natural da Ria de Aveiro with a short boat glide through salt pans and reedbeds. Mid-morning, peel inland to visit the family-run Quinta do Valdoeiro for an intimate cellar tour and tasting of regional whites and light reds (book ahead), then stretch your legs with a vineyard-side picnic of locally sourced gluten-free cheeses and bread while enjoying views of the rolling Coimbra foothills as you continue your gentle push north toward Porto.
After your morning vineyard picnic, take a tranquil, toll-free drive toward the seaside village of Buarcos for a relaxed lunch on the promenade with fresh fish and gluten-free options at A Tasquinha do Saloio, then stroll the pier to watch local fishermen mend nets. In the later afternoon, head inland to the family-run Quinta do Encontro for a guided tour of their organic plots and an intimate tasting of lesser-known Dão varietals (book ahead), finishing with golden-hour views from the hilltop chapel of Nossa Senhora da Lapa before continuing north toward Coimbra's outskirts and Porto the next day.
As the day cools, follow quiet country lanes to the riverside village of Conímbriga to wander the dramatic Roman ruins lit by late light and then sip regional wines at the nearby boutique Quinta do Pôpa (book ahead) where small-batch reds and a wood-fired tapas-style plate of naturally gluten-free charcuterie showcase local producers. Finish with a relaxed twilight drive to the hilltop hamlet of Penacova for dinner at Casa do Adro-ask for their gluten-free specialties-and a riverside stroll along the Mondego as stars begin to appear, setting a calm, rural tone before your final push toward Porto tomorrow.
Start your day with a riverside stroll through Ribeira do Porto, then cross the elegant Dom Luís I Bridge on foot to reach the hillside Vila Nova de Gaia lodges for a morning cellar tour at Caves Calém where a guided tasting focuses on dry vintages and gluten-free pairings (book ahead). Continue to the quieter, terraced gardens of Jardins do Morro for sweeping Douro views and a coffee at the nearby gluten-free-friendly café Mimi Café, then wander down to the artisan food stalls at Mercado de Gaia to sample local preserves and cheeses before lunch.
After lunch, wander the colourful lanes of Rua das Flores to discover independent craft shops before taking a short tram ride to the leafy Jardim de São Lázaro for a relaxed people-watch under plane trees. Continue to the riverside district of Foz do Douro where you can walk the promenade to Farolim do Felgueiras lighthouse, pause for a gluten-free seafood plate at the harbour-side Casa de Pasto da Palmeira, then finish the afternoon with a tasting of boutique Douro whites at the intimate Quinta do Noval Tasting Room in Vila Nova de Gaia (book ahead) to bridge today's cellar visits with tomorrow's deeper exploration of the Douro valley.
As twilight settles, wander the cobbled lanes of Miragaia to discover hidden tile-clad churches and stop for an aperitivo on the terrace of Vinum Terrace & Wine Bar where you can request gluten-free small plates paired with boutique Douro wines. Afterward, take a short stroll to Capela das Almas to admire its azulejo facade in the evening light, then cross back toward the river for a relaxed dinner at Taberna dos Mercadores (reserve ahead and ask for their gluten-free menu) followed by a leisurely riverside digestif while listening to fado drifting from nearby tavernas.
Rise before dawn for a swift, toll-free drive to the airport, stopping for a final coffee and gluten-free pastry to-go at Café Progresso near the city centre before handing in the hire car at Aeroporto Francisco Sá Carneiro. If time allows, take a brisk 20-minute riverside walk along the quieter stretch of Marginal da Errégua for a last glimpse of the Douro light and a calm moment with a portable espresso before you check in and board your early flight.
With your early departure already arranged, use the afternoon for a slow, toll-free coastal detour if your schedule allows before overnighting near the airport: wander the peaceful gardens of Jardim do Passeio Alegre and sit for a late-afternoon riverside coffee at the nearby gluten-free-aware Confeitaria do Bolhão outlet, then drive the scenic N13 along the coast to the tranquil fishing cove of Aguda Beach to watch nets being hauled in and breathe the sea air. Finish by checking into a comfortable airport-area guesthouse such as Hotel Star Inn Porto, drop off luggage, and enjoy a quiet gluten-free dinner at their on-site restaurant to rest well before your pre-dawn transfer.
After a calm final afternoon, enjoy a lingering early-evening meal at Ode Porto Wine House's terrace where the chef can prepare a thoughtful gluten-free plate paired with a final glass of Douro red, then wander the nearby lantern-lit quay of Cais da Ribeira Nova for one last riverside view. Finish with a relaxed nightcap at the cosy jazz bar Hot Five Jazz & Blues Club-a low-key stop to savour Porto's evening atmosphere before your pre-dawn transfer and car return.