A Romantic 2-Day Escape in Cascais
An intimate, unhurried two-day itinerary for couples that balances seaside scenery, art and culture, slow meals, and two memorable special moments (a sunset boat cruise and a spa for two). Planned for May (spring) when evenings are golden and gardens bloom.
Highlights
- Private sunset cruise from Marina de Cascais
- Dramatic cliffs at Boca do Inferno
- Relaxing couples' spa at The Oitavos
- Historic Casa das Histórias Paula Rego and Cidadela promenade
- Fresh seafood dinner by the sea
Itinerary
Day 1
Slow-paced introduction to Cascais: local market breakfast, gardens, a light museum visit, dramatic coastline, and a private sunset boat before a seaside dinner.
Breakfast & local flavors at Mercado da Vila
Start with a relaxed breakfast at the covered market — try a fresh pastry and a café or sit by a window stall with a coffee. Great spot to taste local cheese, jamón, and seasonal fruit for a light, romantic start.
Tips from local experts:
- Arrive early (by 09:00) for quieter seating and the best pastries; stalls restock in the morning.
- Ask a vendor for a small tasting plate to share — perfect for couples who want variety without ordering too much.
- Market has limited seating; grab takeaway and find a bench in Parque Marechal Carmona if the market is full.
Stroll and slow-down in Parque Marechal Carmona
A shaded garden just off the center with old trees, ponds and quiet paths — perfect for a languid morning walk and a few candid photos together.
Tips from local experts:
- Follow the shaded paths toward the small pond for the most peaceful benches and photo opportunities.
- Bring a lightweight wrap for early-May mornings; the breeze under trees can be cool.
- If mobility is a concern, take the main paved paths — they’re flat and stroller- / wheelchair-friendly.
Casa das Histórias Paula Rego — intimate art visit
A small, atmospheric museum devoted to Paula Rego’s work. Rooms are intimate and contemplative — a nice cultural pause without the bustle.
Tips from local experts:
- Book tickets in advance to avoid queues and choose quieter mid-morning slots.
- The museum has compact galleries — move slowly to appreciate the narrative detail in her works.
- There’s a calm terrace area outside ideal for a quiet conversation after the visit.
Leisurely lunch at Mercado stalls / light seafood tasting
Return to Mercado da Vila for a flexible, intimate lunch — share a seafood tapa and a glass of local vinho verde or a chilled white.
Tips from local experts:
- Ask vendors for small plates to share rather than full entrees — it keeps the meal light and intimate.
- Request a recommended local wine by the glass for a relaxed, romantic pairing.
- If the market is busy, take your plates to a nearby quiet bench by the sea for a picnic-style moment.
Boca do Inferno — dramatic cliffside viewpoint
Walk to the famous sea-gouged cliffs and watch waves crash into the cavity — a natural, elemental moment that’s very romantic at golden hour.
Tips from local experts:
- Wear low-profile shoes for the uneven stone paths and arrive earlier in the afternoon to avoid larger tour groups.
- Stand a little back from the railing for privacy and the best photo angles of the crashing surf.
- Bring a light windbreaker — the spray from the blowhole can be surprisingly cool even in May.
Sweet pause: gelato at Santini + Praia da Rainha
Pick up a famous Santini gelato and walk down to the small, sheltered Praia da Rainha for a quiet seaside sit — perfect for people-watching and shared desserts.
Tips from local experts:
- Santini is an iconic stop — order 1 scoop each and share to sample more flavors together.
- Sit on the low stone walls near Praia da Rainha for privacy and the best view of the little bay.
- If you want shade, head to the eastern end of the beach where there are small trees and less direct sun in late afternoon.
Leisurely old-town walk and Museu Condes de Castro Guimarães (castle)
Wander the historic lanes toward the small castle-museum overlooking the bay — its terrace and gardens are quiet and intimate.
Tips from local experts:
- The museum terrace has lovely sea views for photos; plan to be there for soft-afternoon light.
- Combine museum entry with a slow walk along the seafront promenade for a romantic route back toward the marina.
- If you prefer a shorter visit, stick to the exterior gardens and terrace for atmosphere without a full tour.
Private sunset boat cruise from Marina de Cascais (special moment)
Board a private or small-group cruise from Marina de Cascais timed for sunset — toast with a glass of bubbly as the coastline turns gold.
Tips from local experts:
- Book a private or very small-group cruise in advance and request a sunset slot (in May sunset is typically ~20:30).
- Bring a light wrap — breezes on the water cool quickly after golden hour; a blanket can make the moment cozier.
- Request a quiet spot on deck and coordinate a moment to exchange a small surprise (song, note, or toast) mid-cruise.
Short transfer to dinner (private taxi/car)
A quick 20–30 minute transfer to the seaside dinner location — pre-book a private ride so you arrive relaxed after the cruise.
Tips from local experts:
- Pre-book a taxi or rideshare to avoid waits after the cruise; ask the boat operator for a recommended local driver.
- Request a calm vehicle and let the driver take the coastal route for scenic views if you want a longer, romantic transfer.
- Keep a small emergency umbrella in the car during spring evenings — a sudden shower can be brief but welcome for two.
Romantic seafood dinner at Mar do Inferno
An intimate, seafood-forward dinner near the cliffs with ocean views — choose a shared seafood platter and a bottle of local white wine.
Tips from local experts:
- Reserve a table in advance and request a window or terrace table for sea views and privacy.
- Share a whole-fish or mixed seafood plate to create a sharing experience rather than individual mains.
- Finish with a citrus-based dessert and a walk along the lit promenade to end the evening gently.
Day 2
Coastal day with beach air, a lovely lunch at Casa da Guia, a deeply relaxing couples' spa at The Oitavos, sunset cocktails and a final intimate dinner.
Leisurely morning transfer to Praia do Guincho and beach walk
Start the day with fresh Atlantic air at Praia do Guincho — long shoreline walks, dune views and quiet moments together away from the town center.
Tips from local experts:
- Park or be dropped off near the main access and walk along the dunes for privacy — the beach is wide and expansive.
- Take light layers; May breezes are refreshing and perfect for a slow hand-in-hand walk.
- Bring a picnic blanket and some snacks from Mercado da Vila for a seaside pause on sheltered dunes.
Brunch / light lunch and terraces at Casa da Guia
Casa da Guia is a charming clifftop complex of terraces, cafes and small restaurants. Choose a sun-facing terrace for panoramic views while you share a relaxed meal.
Tips from local experts:
- Reserve a table on a terrace (many venues in Casa da Guia accept reservations) for uninterrupted sea views.
- Share small plates so you can sample multiple flavors and keep the meal light for an afternoon spa.
- Explore the small shops and quiet corners for a short post-lunch stroll together.
Leisure transfer to The Oitavos for a couples' spa (special moment)
Check in to The Oitavos Spa for a dedicated couples' treatment — thermal circuits, massage for two and a quiet relaxation suite create a restorative, intimate experience.
Tips from local experts:
- Book the 'couples treatment' package and confirm private relaxation time afterward; late-afternoon spa slots are particularly peaceful.
- Arrive a little early to enjoy the spa's thermal areas together and prolong the pampering.
- Ask for adjacent treatment rooms and request the same therapist tempo so you both relax in sync.
Gentle promenade at the Cidadela and quiet espresso pause
Return toward Cascais center for a slow walk around the Citadel area — cobbled lanes, small galleries and a calm espresso make for an understated romantic interlude.
Tips from local experts:
- The Cidadela area is quieter in late afternoon — seek out a bench overlooking the harbor for a restful moment.
- Stop for a small espresso or digestif at a nearby cafe rather than a heavy dessert after the spa.
- If you want a souvenir, pick a small artisan item from the shops inside the Cidadela to remember the trip.
Rooftop cocktails at Farol Hotel — golden-hour drinks
Enjoy a rooftop cocktail or a glass of local wine at the boutique Farol Hotel bar while the light softens — a sentimental, elevated spot for a couple’s toast.
Tips from local experts:
- Reserve a rooftop or terrace table in advance and ask for a corner seat for more privacy and a better view.
- Order a sharing plate or tapas to prolong the moment without committing to a full meal before dinner.
- Check the sunset time and arrive 30–40 minutes early to watch the changing colors together.
Farewell dinner at Fortaleza do Guincho — fine dining by the sea
Cap the trip with a refined, intimate meal at Fortaleza do Guincho (or similar upscale seaside restaurant) — a multi-course tasting menu and excellent wine list make this a memorable final night.
Tips from local experts:
- Book the tasting menu in advance and request a table with a view or in a quieter corner for a truly intimate experience.
- Let the sommelier choose a pairing to complement the tasting menu — it makes the meal effortlessly romantic.
- Consider a pre-dinner coastal walk if time allows; the approach to the restaurant at dusk is particularly atmospheric.
Easy transfer back to central Cascais (taxi/private car)
After dinner, take a comfortable return transfer — a quiet ride back to your hotel rounds off the evening without rush.
Tips from local experts:
- Pre-book your return ride during your dinner reservation to avoid waits after a late meal.
- If you’d like one last romantic stop, ask the driver to pause briefly at a viewpoint on the way back for a night-time city view.
- Keep small change for the driver and consider a local tip for excellent service — many couples appreciate this personal touch.
