After collecting your hire car at Faro Airport, take a gentle coastal drive to Praia de Faro for a refreshing stroll along the sand and seabird-watching; there's a small café nearby offering naturally gluten-free options like grilled fish and salads. Continue west to charming Fuzeta where you can board a short Ria Formosa boat trip to explore salt pans and estuary islands, then browse the local market for regional olives and almond sweets (ask vendors for gluten-free choices) before heading inland toward Évora later in the day.
Drive a short distance west to the picturesque fishing village of Olhão and wander the whitewashed streets before hopping onto a small boat for a guided Ria Formosa birdwatching and salt-pan tour that often includes local shellfish tastings (ask for gluten-free preparations). Later, continue to the historic maritime town of Cacela Velha to enjoy panoramic views from the clifftop church and relax with a seaside gluten-free meal at a terrace restaurant while watching the tide come in over the sheltered lagoon.
As the sun softens, drive to the clifftop village of Santa Bárbara de Nexe for a relaxed stroll through orange groves and a sunset viewpoint over the hills, then descend to the nearby fishing cove of Praia da Salema for beachside aperitifs. Finish with a leisurely gluten-free dinner at Vila do Bispo's local tavern (ask for fresh grilled seafood and salads) or a cozy wine bar in Burgau where you can sample regional Alentejo wines and chat with locals about tomorrow's inland drive.
Set off inland on quiet country roads toward Évora, pausing at the medieval hilltop village of Monsaraz for a sunrise walk along the castle walls and sweeping views over the Alentejo plains and Alqueva Reservoir; browse artisan shops for local ceramics and cured olives (ask vendors for GF items). Continue to Herdade do Esporão for a mid-morning cellar tour and a guided tasting of regional wines paired with gluten-free almond paste and cheeses in their shaded courtyard, then arrive in Évora in time for a relaxed stroll through the whitewashed streets toward Praça do Giraldo to soak in town life before lunch.
Take a leisurely drive along quiet backroads to the fortified hill village of Estremoz, where you can explore its marble-filled castle and weekly market stalls selling local cheeses and GF almond sweets; climb the castle tower for panoramic views of the Alentejo plains. Continue through cork oak countryside to the frescoed chapel of São Bento do Mato for a short, peaceful visit, then arrive in Évora midafternoon to tour the atmospheric Roman Temple of Évora and settle into a gluten-free friendly café near Praça do Giraldo for coffee and a light salad before evening plans.
As golden hour arrives, take a short scenic drive to the hilltop hamlet of Arraiolos to wander its tiled streets and visit the Arraiolos Castle, then browse workshops where traditional embroidered rugs are made-many artisans sell small, gluten-free almond confections nearby. Afterward return toward Évora for a relaxed wine-focused evening at Adega do Alentejano, a low-key cellar bar offering local reds and a small gluten-free tapas menu; finish with a slow stroll past the illuminated façade of Sé de Évora (Évora Cathedral) to soak in the town's night-time atmosphere.
Leave Évora before breakfast for a peaceful backroad drive to Quinta do Mouro, where a small-family tasting introduces you to low-intervention reds and a platter of locally produced cheeses and GF almond breads beneath an olive grove; ask to join the short vineyard walk to learn their organic practices. From there, continue to the boutique Herdade da Malhadinha Nova estate for a cellar tour of their older barrels and a courtyard tasting paired with naturally gluten-free migas-style local dishes or grilled seasonal vegetables, offering a relaxed, authentic Alentejo morning before lunch.
After a morning of estate tastings, take a leisurely backroad drive to Herdade do Grous, where a small, family-run tasting focuses on estate whites and an outdoor pairing of local goat cheeses and gluten-free almond biscuits under carob trees. Continue to the intimate, low-intervention project Quinta da Planície for an afternoon tour of their clay amphora cellar and a guided tasting of skin-contact whites and micro-batch reds paired with grilled seasonal vegetables and discuss biodynamic practices with the winemaker while watching the light sweep across the cork oak hills.
As the light softens, take a slow drive to Vila Viçosa to wander its marble-paved streets and visit the twin courtyards of Paço Ducal, then sip a twilight glass at the intimate cellar bar of Herdade do Sobroso, where staff will pair local Alentejo reds with gluten-free almond sweets and artisanal sheep cheeses. Finish the night in the village of Redondo with a relaxed dinner at Taberna do Arco, known for grilled seasonal vegetables and naturally gluten-free fish dishes, followed by a short stargazing pause among the cork oaks before returning to your Évora base.
Leave Évora early on scenic, toll-free backroads toward the Atlantic and stop for a seaside coffee and a short walk along the dramatic cliffs at Praia da Comporta, then meander through rice fields and pine woodlands to the charming fishing village of Setúbal where you can explore the bustling Mercado do Livramento for fresh fish, citrus and GF snacks. Continue north along the coast, pausing at the quiet estuary hamlet of Costa da Caparica for a beachside stroll and a relaxed gluten-free brunch at a café overlooking the sea before driving the final stretch into Lisbon and checking into your central hotel.
After arriving in Lisbon, head to the riverside neighborhood of Cais do Sodré for a relaxed walk along the Tagus and a visit to the revamped Time Out Market's gluten-free stalls where you can sample regional cheeses, fresh seafood and GF pastries. From there wander through the nearby maritime quarter of Mouraria, discover its narrow lanes and street art, then pause at the intimate Miradouro de Santa Luzia for panoramic views before settling into an early evening wine tasting at By the Wine - José Maria da Fonseca, which offers a thoughtful selection of Portuguese wines paired with gluten-free bites.
As dusk falls, wander the lively streets of Bairro Alto, dropping into a small fado house like A Baiuca for an intimate acoustic set while you sip local wine and nibble on gluten-free petiscos arranged on request. Afterwards, stroll down to the riverfront and enjoy a nightcap at Topo Chiado with sweeping views of the Tagus, or head to the cozy, GF-friendly wine bar TABERNA DO ROMEU in Chiado for a relaxed tasting of Portuguese reds and regional cheeses before returning to your hotel.
Begin with a gentle ascent through the winding lanes of Graça to catch sunrise views from the Miradouro da Senhora do Monte, then stroll down into the historic streets to visit the small, atmospheric Igreja de São Vicente de Fora and its rooftop vistas. Continue to the nearby Feira da Ladra flea market to hunt for vintage finds and artisanal crafts, followed by a gluten-free friendly coffee and pastry at Fábrica das Verdades in Campo de Santa Clara, where the staff can point you to a midday gluten-free food tour meeting point.
Wander the mosaic-lined streets of Alfama heading down toward the river, pausing at the sunlit terrace of Museu do Fado for a short exhibition and then slipping into Miradouro das Portas do Sol for postcard views of terracotta roofs and the Tagus. From there take a short tram or walk to Belém to stroll the riverside promenade, sample certified gluten-free pastries at Pastéis de Belém (GF counter/ordering options available) and visit the ornate Mosteiro dos Jerónimos gardens before joining an early-evening gluten-free tasting at a nearby specialist deli that pairs artisanal cheeses, conserves and local Arrábida wines.
As twilight deepens, drift to the riverside district of Docas de Santo Amaro for dinner at a waterside restaurant offering clear gluten-free menus and views of the illuminated 25 de Abril bridge; linger over grilled fish and a chilled Vinho Verde. After dinner, take a short cobbled walk to the intimate concert venue Café Teatro do Bairro for live acoustic music, then finish the night with digestifs and a late stroll through the lit-up lane of Rua do Alecrim, popping into a small wine shop for a tasting of Portuguese fortified wines to round off your Lisbon evening.
Depart Lisbon after breakfast for a calm drive through pine-scented hills to Serra da Arrábida Natural Park, where you'll stretch your legs on a short cliff-top walk to the lesser-known viewpoint at Cabo Espichel for dramatic sea views and seabird sightings. Continue to the village of Azeitão for a private morning tasting at José Maria da Fonseca (visitor cellar in Azeitão) focused on traditional Moscatel and artisanal table wines paired with locally produced, clearly labelled gluten-free cheeses and jams, then browse the family-run Queijaria da Azeitão to sample and buy GF sheep cheeses before a relaxed seaside coffee in the nearby fishing cove of Portinho da Arrábida.
After a morning in Azeitão, drive along quiet coastal lanes to the sheltered coves of Portinho da Arrábida and take a short glass-bottom boat trip to spot coastal seabeds and marine life, followed by a relaxed picnic of locally sourced gluten-free cheeses and charcuterie from Queijaria da Azeitão at the pebble shore. Later, wander the whitewashed streets of Sesimbra Velha, climb to the panoramic terrace by Castelo de Sesimbra for sweeping bay views, then finish the afternoon with a tasting at the small, family-owned Casa Ermelinda Freitas cellar in nearby Palmela that offers a clear GF tasting menu and a tour of their old-vine parcels.
As the sun lowers, drive along quiet lanes to the hilltop village of Palmela to explore its castle terraces and sip a sunset glass on the ramparts while watching fishing boats cross the Sado estuary; pair this with a small plate of gluten-free smoked tuna and local cheeses at Restaurante O Barradas's terrace. Afterwards descend to the sheltered marina at Setúbal's Troia ferry terminal for a short sunset stroll along the marina promenade, then finish with an intimate tasting of regional Moscatel and fortified wines at the family-run Adega Luis Pato (arranged in advance for GF pairings), before a calm night drive back to Lisbon.
On your final morning, take a gentle pre-dawn stroll along the salt flats at Ria Formosa Natural Park near Faro for birdwatching and soft sunrise light, then return to town for a relaxed, gluten-free breakfast at Café Aliança, which can prepare fresh omelettes and fruit plates to go. Leave time to drop the car at the airport branch and visit the small local Museu Marítimo Almirante Ramalho Ortigão for a brief overview of Algarve seafaring history before checking in for your early flight.
Spend a relaxed afternoon exploring the quieter side of the Algarve: stroll the shaded lanes and craft shops of Old Town Faro (Cidade Velha), then visit the intimate Museu Municipal de Faro for local archaeology and maritime exhibits. Follow this with a calming riverside picnic at Jardim Manuel Bivar using gluten-free treats from a nearby deli, and finish by tasting regional Algarve wines and light GF plates at the cozy cellar bar Wine & Food Faro before an early evening check-in near the airport.
For a calm final evening, head to the peaceful marina at Marina de Faro for a waterside stroll and watch the last boats return while enjoying a gluten-free tapas plate at Restaurante Ria Formosa (they clearly label GF options). Afterwards, unwind with a relaxed glass of Algarve wine at the nearby intimate bar O Castelo in the old quarter, or take a short walk to the atmospheric Igreja do Carmo's lit façade for a gentle last-night photo stop before returning to your airport-area accommodation for an early check-in and car drop-off prep.