Cascais in 48 hrs — Beachy days, lively nights (for friends)
A fun, vibrant 2-day weekend in Cascais for a group of friends: fresh seafood, active ocean time, coastal views, lively bars and a sunset sail. Built for groups (4–6), easy split costs and energetic pacing.
Highlights
- Boca do Inferno cliff views
- Stand-up paddle (SUP) on Cascais bay
- Casa da Guia sunset drinks
- Praia do Guincho surf session
- Sunset boat cruise from Marina de Cascais
Itinerary
Day 1
Coastal strolling, a watersport session, seaside dinner and optional Casino night.
Meet at Estação de Cascais (Cascais train station) — group rendezvous
Easy central meetup to sync arrival times, drop bags in lockers and plan the day. The station is a 5–10 minute walk from the marina and the historic center.
Tips from local experts:
- If arriving by train from Lisbon, buy a round-trip Viva Viagem at the machine and keep it for the return — easier to split the fare between friends.
- There are benches and short-term lockers nearby; use a small locker for valuables so you can explore luggage-free.
- Grab a local SIM/shop map from the tourist kiosk at the station if someone needs directions or wants to split rides later.
Breakfast & gelato pick-me-up at Santini (classic Portuguese gelateria & coffee)
Start with a pastel or coffee and a Santini scoop — a local favorite for creamy gelato and quick pastries. Good for groups that want a light, social start.
Tips from local experts:
- Santini gets busy on sunny mornings — order a few scoops and share tasting spoons so everyone tries multiple flavors.
- There are small terraces and standing tables ideal for chatting; if you need a seat for 4–6, ask staff early — they often rotate seats quickly.
- Combine a coffee/gelato order with a to-go snack for the walk toward the seafront to save time and keep costs split evenly.
Wander Cascais town center & Mercado da Vila for local bites and shopping
Explore the pedestrian streets, browse boutiques and the Mercado da Vila for small plates and snacks — perfect for grazing and group sharing.
Tips from local experts:
- At Mercado da Vila, pick several small plates and create a shared platter — cheaper and social for groups of friends.
- Wear comfortable shoes — cobbles and narrow lanes are charming but uneven; leave heavy bags at the station.
- If someone wants souvenirs, look for locally made ceramics and canned fish — small and easy to share between friends.
Boca do Inferno cliff viewpoint — dramatic coast photos
Short walk to this dramatic sea-carved cliff opening — a must-see and an excellent group photo spot. Spend time watching waves and listening to the swell.
Tips from local experts:
- The cliff is windy in June; bring a light windbreaker so jackets don't blow away during photos.
- Best photo angle is toward the carved arch — get there early to avoid crowds and ask a passerby to take a group shot.
- Be mindful of the edges with a lively group; keep a 1–2m buffer from the cliff lip for safety.
Seafood lunch at Mar do Inferno — family-style plates
Classic Cascais seafood (grilled fish, clams and shared platters). The restaurant is group-friendly and perfect for splitting seafood dishes.
Tips from local experts:
- Reserve a table for 4–6 in advance for a weekend June lunch; ask for a round table to share plates easily.
- Order a few mixed fish and one shellfish platter to keep costs balanced — seafood portions are generous and naturally shareable.
- Ask for tap water (água) and bring a card to split the bill; the staff are used to groups and will happily provide separate checks if asked early.
Stand-up paddle (SUP) session on Cascais Bay — shared lesson & rental
A 1.5-hour SUP session suitable for beginners — great active, playful time on the water with easy instruction and plenty of group photo moments.
Tips from local experts:
- Book a group SUP lesson in advance for a June weekend slot; shops often give small group discounts.
- Wear a swimsuit with a lightweight top you don't mind getting salty; bring a disposable bag for phones or use a waterproof case.
- Rotate turns with a GoPro or phone on a floating strap so everyone gets a turn on camera — perfect for social media and memories.
Beach break at Praia da Rainha — chill, photos and quick swim
A small, sheltered beach right by the old town — ideal for a relaxed post-SUP cooldown and casual beach games with friends.
Tips from local experts:
- Bring a small towel and a picnic blanket — seating is limited; lying out is the most comfortable option for groups.
- Try a quick dip; the water is usually warm enough in June. Keep valuables in a group bag and rotate a 'watcher' every 10–15 minutes.
- Buy slices or snacks from a nearby kiosk and share — perfect for low-cost, social snacking while watching the sunset build.
Casa da Guia — sunset drinks and dinner in a seaside terrace complex
A cluster of terraces, bars and restaurants carved into the cliffs. Great for groups who want multiple dining options and sunset views.
Tips from local experts:
- Reserve a table at your preferred Casa da Guia restaurant for 19:00 — terraces fill fast in June; ask for an outdoor table to catch the sunset.
- Split appetizer platters among the table and mix drinks from different bars; many spots here are relaxed about sharing between groups.
- Walk the cliffside promenade for photos before dinner — the lighting 30 minutes before sunset is perfect for group shots.
Optional: Casino Estoril — late-night live music, drinks and games
For a lively end to night one, try the Casino Estoril: bar, occasional live acts and a social gambling floor. Good for friends who want music and a bit of nightlife.
Tips from local experts:
- Check the casino event calendar before you go — there are occasional concerts or DJ nights that are perfect for groups.
- If you plan to play table games, set a shared 'fun budget' so the group can enjoy without surprises.
- Dress smart-casual for a smoother entry; the casino can be busier on summer weekends so arrive around 22:00.
Day 2
Active morning at Guincho, relaxed central afternoon with culture and a sunset boat cruise to cap the trip.
Surf lesson at Praia do Guincho with a local surf school
Group surf lesson for beginners at Guincho — famous waves and a fun, active morning. Instructor-led sessions include boards, wetsuits and beach safety.
Tips from local experts:
- June has consistent surf — book a morning lesson to avoid the stronger afternoon winds common at Guincho.
- Bring sunscreen and a warm layer for after the session; the Atlantic breeze cools you down quickly once you stop moving.
- Ask the school about group discounts and whether they can split equipment costs up front so payment is simple between friends.
Brunch at House of Wonders — rooftop vegetarian/mediterranean
Bright rooftop spot with sharing plates, great for groups and story-worthy brunch photos. Relaxed vibe and good for dietary variety.
Tips from local experts:
- House of Wonders is popular for brunch — reserve a table for your full group; ask for a corner table if you want to be lively without crowding neighbors.
- Order a few mezze-style plates to share so everyone can taste a variety without individual bills.
- The rooftop can be sun-drenched in June — request shade if you’ll be lingering over mimosas or board games.
Parque Marechal Carmona — picnic, quick games and chill time
A leafy park with benches, large lawns and a relaxed vibe — ideal for an afternoon picnic, frisbee or people-watching with coffee.
Tips from local experts:
- Pick up cheese, bread and wine from nearby shops and split costs — park picnic is cheaper and more social than a sit-down lunch.
- Look for shaded bench clusters or under the big trees if you want quieter conversation away from the touristy spots.
- Bring a compact speaker for background music but keep volume polite — the park is popular with families and groups.
Museu Condes de Castro Guimarães — quick cultural stop and gardens
Small museum with interesting interiors and a seaside garden — a calm indoor cultural break that’s easy to enjoy in an hour.
Tips from local experts:
- Buy combined tickets early if you want a guided explanation; otherwise the garden and the manor room photos are highlights.
- Keep the visit to ~45–60 minutes — it's compact and perfect as a light cultural interlude between outdoor activities.
- The museum garden is a great spot for group photos; look for the sculpture terrace that frames the sea.
Stroll Marina de Cascais — gelato, shops and pre-sail meetup
Marina walk to browse boats, grab a light snack and meet the boat crew for a sunset cruise. Relaxed, photogenic and group-friendly.
Tips from local experts:
- Pick up light snacks or extra drinks at the marina kiosks to enjoy on the boat; splitting costs for a shared cooler keeps things simple.
- Plan to arrive 15–20 minutes before the sailing meetup so everyone can check-in together and store belongings.
- If anyone gets seasick easily, grab ginger candies from a nearby shop and sit toward the middle of the boat on the cruise.
Sunset boat cruise from Marina de Cascais — 90-minute coastal sail
A relaxed sunset sail around Cascais bay — perfect for group toasts, skyline photos and spotting the coastline from the water.
Tips from local experts:
- Bring a small, marked bottle of bubbly to share and a reusable cup so you can toast at sunset without extra waste.
- Choose a seat on the windward side for unobstructed views of the coast; take jackets — it gets cooler on the water after sunset.
- Confirm a single group booking so the operator will keep you together; ask about a private music playlist to set a fun vibe.
Farewell dinner in Cascais old town — group-friendly shared plates
Finish with an upbeat restaurant that welcomes groups; order several plates to share and celebrate the trip.
Tips from local experts:
- Book a larger table in advance and request a shared-platter-friendly server so bill-splitting is easier at the end.
- Ask the restaurant for ‘tapas’ style options or a chef’s sharing menu — it keeps the mood social and costs even.
- End with a walk along the marina or an ice cream from Santini for a casual nightcap photo-op with the group.
