3-Day Romantic Getaway in Cascais (September)
A slow-paced, intimate 3-day itinerary for couples in Cascais: sea-view walks, mellow culture, golden-hour moments, private experiences and a pampering spa — timed for September's warm evenings and long golden hours.
Highlights
- Sunset at Boca do Inferno
- Private sunset cruise from Marina de Cascais
- Day trip to Sintra with Quinta da Regaleira and Pena Palace
- Spa for two at The Oitavos
- Seaside dinners and cozy, local cafés
Itinerary
Day 1
A gentle arrival day: settle in, wander the historic center, savor coastal views and finish with a sunset at Boca do Inferno and a waterfront dinner.
Check in and settle at a romantic base
Arrival, luggage drop and a few quiet minutes to freshen up. Recommend a room with sea-view or a turret room if available.
Tips from local experts:
- Request a sea-view room or a higher floor when you check in — it pays off for a private evening balcony.
- Ask the concierge for a quiet table for two suggestions for dinner reservations (they can recommend local intimate spots).
- If arriving early, ask about luggage storage so you can start wandering without waiting for official check-in.
Leisurely stroll through Cascais historic center & gelato
Wander cobbled streets to Praia da Rainha and stop for an iconic Santini gelato — unhurried people-watching and intimate corners.
Tips from local experts:
- Choose a bench near Praia da Rainha to share gelato and watch small fishing boats drift in — great for candid photos.
- Look for narrow alleys north of the main square for quieter, shaded spots if you want privacy.
- Sit on the low seawall at sunset if you prefer a bench to standing; bring a light wrap for September breezes.
Museum Conde de Castro Guimarães — a romantic small museum
Explore a compact, atmospheric palace-museum with gardens that are perfect for quiet conversation and photos.
Tips from local experts:
- The small library and decorative rooms make pretty, intimate photo backdrops — arrive early to avoid groups.
- Combine the museum visit with a short walk along the adjacent garden terrace for a private moment.
- Ask staff about quieter rooms or times to enjoy the collection without crowds — late afternoons are usually calmer.
Golden-hour and sunset at Boca do Inferno
Head to the dramatic cliff viewpoint for the classic Cascais sunset — waves crash below and the light is very romantic.
Tips from local experts:
- Arrive 20–30 minutes before sunset to claim a quieter spot on the cliffs; the golden light is best just before the sun dips.
- Wear comfortable shoes — the cliff edges are uneven; keep a safe distance while enjoying the view together.
- Bring a light blanket or shawl for the sea breeze and plan a quiet toast with a small bottle of local vinho verde or rosé.
Intimate dinner at Fortaleza do Guincho
A celebrated coastal restaurant with refined cuisine and sea views — ideal for a memorable, romantic dinner (reservation required).
Tips from local experts:
- Reserve a table well in advance and request a sea-view or terrace table for the most romantic feel.
- Ask for seasonal tasting options and wine pairing to make the evening special and effortless.
- Allow time for the short scenic drive from central Cascais; timing and a taxi or hotel transfer will avoid parking stress.
Day 2
A dreamy day trip into Sintra’s fairytale hills — gardens, a palace, pastry stops and a dramatic sunset at Cabo da Roca before returning for a relaxed seaside dinner.
Morning transfer from Cascais to Sintra (private car/taxi)
Short private transfer — comfortable and scenic; taxi or arranged car is the easiest way to reach the Sintra sites on a relaxed schedule.
Tips from local experts:
- Book a small private transfer for flexibility — it saves time over public routes and lets you stop for views.
- Keep water and a light snack in the car for the short hill climb between attractions.
- Confirm the driver can wait or return at a prearranged pick-up time to avoid hunting for taxis in Sintra's narrow streets.
Quinta da Regaleira — gardens, grottoes and secret corners
Explore mystical gardens, the Initiation Well and secluded paths — perfect for couples who enjoy exploration with a touch of mystery.
Tips from local experts:
- Hire an audio guide or pick up a map at the entrance to spot romantic hidden nooks like the Initiation Well and secluded terraces.
- Wear comfortable shoes — pathways can be uneven and slightly damp in shaded grotto areas.
- Plan a slow walk through the gardens and pause in quiet corners for a private photo or a moment to read an engraved stone.
Midday pastries at Casa Piriquita
Share Sintra’s famous travesseiros (pillowy pastries) and a coffee — a sweet, authentic pause in the town centre.
Tips from local experts:
- Order a couple of different pastries to share so you can sample travesseiros and queijadas together.
- Sit at a small table outside if the weather is pleasant — perfect for people-watching and close conversation.
- If there’s a short queue, use it as a quick photo opportunity on the historic street in front of the pastry shop.
Palácio Nacional da Pena — vivid palace and panoramic views
Visit the colourful palace and its terraces; the sweeping views over Sintra are especially atmospheric in late afternoon light.
Tips from local experts:
- Buy timed tickets in advance to minimize queues and make more of your afternoon together.
- Plan to move slowly between terraces and pause at viewpoints for photos — some of the best vistas are quiet and slightly off the main path.
- Bring a light layer; higher elevation means it can be cooler and breezier than Cascais even in September.
Late-afternoon transfer to Cabo da Roca for sunset
Drive to the westernmost point of continental Europe for a dramatic cliffside sunset — a naturally romantic special moment.
Tips from local experts:
- Arrive at least 20 minutes before sunset to pick a quieter spot on the cliffs and watch the changing light together.
- Bring a small blanket or shawl — evenings at Cabo da Roca can be windier and cooler than inland Sintra.
- Keep to marked paths and cliff barriers for safety; the best photos are often from the safer viewpoint areas.
Return to Cascais and dinner at Casa da Guia
A relaxed dinner at the Casa da Guia complex overlooking the sea — choose a quieter terrace restaurant for candlelight and sound of waves.
Tips from local experts:
- Reserve a terrace table at Casa da Guia in advance and request an outdoor seat with sea view if you prefer intimate alfresco dining.
- Opt for a tasting menu or a couple of shared plates to create a leisurely, close dining experience.
- Take a post-dinner stroll along the Casa da Guia promenade to end the night with the sound of the sea.
Day 3
A relaxed final day: local market browsing, a pampering couples' spa, a dramatic beach walk and a private sunset cruise for one last intimate golden hour, capped with a fresh seafood dinner.
Morning stroll in Parque Marechal Carmona
Start gently with a shaded walk through this elegant park — fountains, palms and quiet corners ideal for couples.
Tips from local experts:
- Bring a small picnic blanket and grab a coffee from a nearby café to enjoy on a park bench together.
- The park has many shaded lanes — perfect for a slower, private walk away from busy streets.
- Look for the small ponds and sculptures which make lovely, secluded photo spots.
Browse Mercado da Vila and enjoy a light market lunch
Taste local cheeses, cured fish, olives and tapas-style stalls — a casual, flavorful experience to share small plates.
Tips from local experts:
- Sample a few small dishes and share them to keep the meal light and social.
- Pick up a bottle of local wine or a small souvenir from a stall to enjoy later during the day.
- Visit earlier in the market hours to avoid lunchtime crowds and to find a quiet corner for two.
Spa for two at The Oitavos — couples' treatment and relaxation
A pampering couples' massage and relaxation time in a tranquil spa setting — the perfect mid-day special moment.
Tips from local experts:
- Book a couples' package in advance and request adjacent treatment rooms for privacy.
- Arrive 20–30 minutes early to enjoy the spa relaxation areas and to extend the calm together.
- Let the spa know of any preferences (pressure, aromatherapy) when booking to tailor the experience.
Beach walk at Praia do Guincho — wind-swept romance
A dramatic shoreline stroll on the fine sands of Guincho; September light makes for evocative photos and quiet stretches of beach.
Tips from local experts:
- Walk toward the dunes for quieter sections of beach and a more private experience away from parking areas.
- Bring a light windbreaker and a blanket — the September breeze can feel cool after a spa afternoon.
- Plan a short stop to watch kitesurfers from a distance — it adds dramatic motion without interrupting your quiet time.
Private sunset cruise from Marina de Cascais
Board a private (or small-group) sunset cruise from the marina for a final golden-hour moment at sea — clink glasses as the sun sets.
Tips from local experts:
- Book a private or small-group cruise in advance and request a late-afternoon departure timed to catch the sunset.
- Bring a light wrap and consider pre-ordering a small picnic or bottle of wine through the operator for a private toast.
- Confirm pick-up location at Marina de Cascais and plan to arrive 15 minutes early for an unhurried boarding.
Final seafood dinner by the sea at Mar do Inferno
A relaxed, intimate seafood dinner known for freshness and local flavors — a warm, authentic last-night meal.
Tips from local experts:
- Reserve a window or terrace table and ask for recommendations of shareable dishes to keep the dinner intimate.
- Try local shellfish or the day's catch and pair with a light white or a local rosé.
- Allow time to walk a short distance after dinner along the waterfront for a quiet final nightcap or photos.
