The best things to do in Cascais in May

An afternoon and night of electronic music, downtempo and organic sounds once again take over Parque Marechal Carmona with the 2026 edition of OUT///FEST. The line-up brings together names like Rui Vargas, Arutani and Just Emma, in a setting that shifts from the central garden to the amphitheatre as the day rolls on. The festival leans into a continuous experience between nature and music, with a focus on sonic immersion and the meeting point between urban culture and natural landscape.

Spring, summer, autumn, winter: there’s no season Maria Guedes misses.Four times a year, you’ll find her (and her curated selection of favourite fashion, home and lifestyle brands,  over 100 of them  and almost all Portuguese) at FIARTIL. What also never goes missing is a lively atmosphere, plus food and drink.

Coala Festival Portugal returns to Cascais for its third edition as a celebration of Portuguese-language music, connecting Brazil, Portugal and Africa. Already confirmed on the line-up are Caetano Veloso, João Gomes, Slow J, Bonga and Lulu Santos, a meeting of generations and styles that blends hip-hop, semba, pop-rock and Brazilian songwriting.

In May, the film cycle at Cinema Cruzeiro turns its focus to war, bringing together four landmark films about conflict, trauma and survival. At the Auditório Carlos Avilez in Estoril, screenings include Fixed Bayonets!, The Deer Hunter, Apocalypse Now and The Hurt Locker, a selection that spans different eras and perspectives on war cinema. Admission is free.

The musician born in Luanda and raised in Portugal is best known as one half of D’Alva, a project that helped redefine Portugal’s indie pop scene with a blend of global influences and a strong generational identity. With a career rooted in songwriting and composition, he has collaborated with several Portuguese artists and taken part in projects beyond the band, while keeping a direct, pop-driven language throughout. This concert takes place at FNAC CascaiShopping and is free to attend.

Daniela Salles first began sharing her day-to-day life on the Cascais Line through the Instagram page Oi Cascais, but her community of more than 50,000 followers soon leapt from the phone screen into the real world. Following its debut last year, Oi Cascais Kids is back for a second edition. On May 16 and 17, the FIARTIL site in Estoril will host this “mega event” for families. The big banner for the 2026 edition is inclusion: the festival wants to be a safe space for atypical children, with psychologists and other professionals on hand to ensure specific activities for kids with ADHD and autism. Tickets cost €7, but entry is free for children up to 13.

Cascais Ópera - Concurso Internacional de Canto takes over Cascais from 29 May to 7 June, spreading across some of the municipality’s most emblematic cultural venues, from the Centro Cultural de Cascais to Casa das Histórias Paula Rego and the Museu Conde Castro Guimarães. Created to discover and support young lyrical voices, the competition brings together participants from several countries in front of an international jury, reinforcing its role as both a meeting point of cultures and a launchpad for new names in the operatic scene.

At the Exhibition Gallery of the Palácio da Cidadela de Cascais, the show "Abeng – Sinal de Resistência: O Arquivo de Tony Russell" brings together the archive of Jamaican photographer Tony Russell, now based in Figueira da Foz. With more than 70 photographs organised into thematic sections, the exhibition explores Russell’s work in Jamaica during independence and the Cold War, as well as in Venezuela’s Andean region, while also tracing the journey of his archive to Portugal. The body of work, which includes portraits of historical figures such as Bob Marley, Elizabeth II and Fidel Castro, is the result of decades of work shaped by radical choices and often challenging circumstances.

The seafront promenade, parks and waves of the Cascais Line are turning into open-air gyms. The municipal Cascais Ativo programme is back and, in May, it comes packed with dozens of free activities, from fitness classes with a view over Tamariz beach (May 2, 9, 16, 23 and 30) or Carcavelos (May 3, 10, 17 and 24) to yoga sessions in Parque Marechal Carmona (May 3, 10, 13 and 24) or on Conceição beach (May 16). There will also be personalised training sessions at Fitness Park Guia de Cascais (May 3 and 17), beginner bodyboarding at Carcavelos beach (May 17, €10), stand-up paddleboarding at Conceição beach (May 23) and caving in the Alvide Caves (May 16).

The Distinguished Gentleman’s Ride returns on 17 May with a twist: this year, the charity parade of classic motorbikes leaves the Hipódromo Manuel Possolo and sets up at the Jardins do Casino Estoril. The event once again brings together hundreds of riders dressed to the nines, raising funds and awareness for prostate cancer and men’s mental health, while keeping its signature mix of socialising, vintage style and a cruise through the streets of Cascais.