Celebrating
Letty's 50th
Portugal Girls Trip
May 21 – May 30, 2026
Celebrating
Portugal Girls Trip
May 21 – May 30, 2026
Quick Reference
9 Days of Magic
From the cobblestone streets of Alfama to the golden cliffs of Cascais — every day designed for discovery, relaxation, and unforgettable moments.
Lisbon · May 22–26 · Days 1–4
Culture, history, rooftops & fado — grand boulevards, cobblestone streets, and the best miradouros in Europe.
Cascais · May 26–30 · Days 5–8
Coast, spa & day trips — 5-star beachfront with an infinity pool, plus Sintra and the Atlantic coast just 30 min away.
The Birthday Girl & Her Crew
Letty turns 50 and she's celebrating the only way that makes sense — with her sister Dinora and their ride-or-die Gail, on a sun-soaked Portuguese coast.
Cheers to 50!
City lights & good nights
Sisters forever
Always celebrating
Adventure buddies
🎉 🍾 🎉
"Here's to 50 years of being absolutely fabulous"
— and the next 50 in Portugal
Day 0 — Thursday, May 21
The adventure begins. Time to head to Newark and catch the overnight flight to Lisbon.
Redeye to Lisbon — sleep on the plane, arrive fresh.
Evening
Overnight TAP Air Portugal flight out of Newark (TP 204). Sleep on the plane and you'll arrive in Lisbon at 11:00 AM Friday morning, ready to explore.
Day 1 — Friday, May 22
Touch down, drop bags, and ease into Portugal with a stroll down the grand boulevards toward the river.
Arrival + easy Lisbon orientation — boulevards, riverfront, rooftop toast.
Your Stay · 4 Nights
Praça dos Restauradores 78, 1250-188 Lisboa · Check-in 4:00 PM
Late Morning · 11 AM
Land at 11:00 AM. Uber or taxi to the hotel. Drop your bags and grab lunch or coffee nearby — you made it!
Afternoon · 1–4 PM
Walk Lisbon's grand boulevard lined with designer shops and shade trees. Check into the hotel at 4:00 PM and settle in.
Late Afternoon · 5 PM
Get a drink in Rossio Square, then stroll through the elegant Baixa grid down to the majestic Praça do Comércio on the riverfront.
Evening · 7 PM
Dinner near the hotel, then toast your arrival with cocktails at a rooftop bar overlooking the city's terracotta rooftops and the Tagus river.
Seafood · Portuguese · Rossio
Classic Lisbon institution right on Rossio Square. Famous for their prawns and shellfish. Touristy but earned its reputation.
View on Maps →Traditional Portuguese · Seafood
A Lisbon institution since 1974. Incredible seafood rice and aged presunto. Reservations recommended.
View on Maps →Upscale · International · Chic
Glamorous spot right on Avenida da Liberdade. Part restaurant, part concept store. Great for a stylish first-night dinner.
View on Maps →Hidden rooftop on top of a parking garage. Incredible panoramic views, great cocktails, cool crowd.
View on Maps →Swanky rooftop at the Tivoli Hotel. Perfect for a celebratory arrival cocktail with 360° city views.
View on Maps →
Day 2 — Saturday, May 23
Get lost in the soul of old Lisbon — winding alleys, fado echoing off azulejo walls, and miradouros with jaw-dropping views.
Old Lisbon + viewpoints + fado — the city's soul, on foot.
Morning · 9–12 PM
Breakfast at the hotel, then Uber up to Miradouro das Portas do Sol for stunning views. Wander downhill through Lisbon's oldest neighborhood — the Sé Cathedral, narrow medieval streets, colorful doorways, and maybe hop on the iconic Tram 28 as it rattles through.
Afternoon · 2 PM
Walk back to the hotel for a well-deserved nap. You've been on your feet all morning — rest up for the evening ahead.
Evening · 5 PM
Explore the artistic Chiado district and the vibrant Bairro Alto. Dinner in this neighborhood, then stop by the Church of Our Lady of Grace (Igreja da Graça) — beautiful at night.
Modern Portuguese · Petiscos
Tiny, trendy tavern with amazing small plates. The ceviche and pica-pau are incredible. Get there early — it fills up fast.
View on Maps →Rooftop · Portuguese · Views
Hotel rooftop restaurant with gorgeous views over Alfama's rooftops to the river. Great for a relaxed lunch.
View on Maps →Rooftop · Cocktails · International
Stunning panoramic views from the Bairro Alto Hotel rooftop. Great cocktails and small plates.
View on Maps →Food Hall · Everything · Cais do Sodré
Lisbon's legendary food hall. Dozens of stalls from the city's best chefs. Everyone can pick what they want — perfect for a group.
View on Maps →Seafood · Sushi · Raw Bar
Choose your fresh fish and they cook it however you like. Surprisingly great sushi for Lisbon.
View on Maps →Alfama & Chiado neighbourhoods
Walk downhill from the miradouro — all stops within 15 min on foot
Open in Maps →
Day 3 — Sunday, May 24
Where Portugal's Age of Discovery began — grand monuments, the old waterfront, and the world's most famous custard tarts.
Belém waterfront + iconic landmarks — where Portugal's Age of Discovery began.
Morning · 9 AM
Uber or Tram 15E to Belém (~20 min). Start at the stunning Jerónimos Monastery — a UNESCO masterpiece📅 Book ahead with lace-like carved stone cloisters. Then grab Pastéis de Belém (the original since 1837⏰ Arrive early — order at least 2 each). Walk to the iconic Belém Tower along the waterfront.
Afternoon · 2 PM
The Museum of Art, Architecture & Technology has a striking wavy building on the river. Even if you skip the exhibits, walk across the rooftop for incredible views. See the Monument to the Discoveries nearby.
Late Afternoon
Head back to the hotel. Optional: nap, rest, or walk around the neighborhood. Take it easy tonight.
Bakery · Iconic Custard Tarts
Non-negotiable. The secret recipe has never left this bakery since 1837. Dust with cinnamon and powdered sugar.
View on Maps →Casual · Riverside · Brunch
Right on the Belém waterfront with outdoor seating overlooking the marina. Great for a relaxed lunch after sightseeing.
View on Maps →Wine Bar · Portuguese · Tapas
Charming wine bar with excellent Portuguese wines and sharing plates. A hidden gem in the Belém neighborhood.
View on Maps →Belém waterfront cluster
Pastéis de Belém, Belém Tower, MAAT — all within 10 min walk of each other
Open in Maps →Lunch: Enoteca de Belém
5 min walk from the monastery · Uber back to hotel ~€12, 20 min
Open in Maps →
Day 4 — Monday, May 25
Last day in the city — botanical gardens, creative markets, and a sunset ferry ride to dinner across the Tagus.
Lisbon finale — gardens, creative market, and a sunset ferry dinner.
Morning · 9 AM
Breakfast at the hotel, then head to leafy Príncipe Real — Lisbon's hippest neighborhood. Stroll through the Jardim Botânico de Lisboa, a lush tropical oasis. Browse the boutiques and antique shops. Also nearby: the beautiful Jardim de Estrela.
Afternoon · 2 PM
Walk back to the hotel for a rest. Then around 4–5 PM, Uber 10 minutes to LX Factory — a converted industrial complex packed with independent shops, galleries, street art, bookstores, and amazing food. Think Brooklyn meets Lisbon.
Evening · 7 PM
The grand Lisbon finale. Take the 10-minute ferry from Cais do Sodré across the Tagus to Cacilhas. Dinner at Ponto Final — grilled fish, wine, views of the city skyline. Sunset is around 8:50 PM. Chef's kiss.🌅 Best at sunset
Peruvian-Portuguese · Seafood · Trendy
Chef Kiko Martins' famous ceviche spot with the giant octopus hanging from the ceiling. Incredible ceviches and tiraditos. Book ahead!
View on Maps →Steakhouse · Portuguese · Premium
For when you need a break from seafood. Excellent steaks and traditional Portuguese meat dishes.
View on Maps →Riverside · Seafood · Iconic Views
THE spot for your Lisbon farewell dinner. Right on the water in Cacilhas, looking back at the city and the 25 de Abril Bridge at sunset. Fresh catch of the day, amazing wine, unforgettable vibes.
View on Maps →Morning: Príncipe Real & Jardim Botânico
10 min walk from hotel (downhill) or Uber ~€5
Open in Maps →Dinner: Ponto Final, Cacilhas
Walk or Uber to Cais do Sodré · 10-min ferry across the Tagus · ~€1.35
Open in Maps →
Day 5 — Tuesday, May 26
Swap city cobblestones for coastal breezes. Check out of Lisbon, check in to beachfront luxury.
Check into beachfront luxury — swap city cobblestones for coastal air.
Your Stay · 4 Nights
Av. Marginal 8554, 2754-536 Cascais · 5-star beachfront luxury with infinity pool, spa & ocean views · Check-in 4:00 PM
Morning · 9–11 AM
Enjoy a lazy breakfast at the hotel. Get ready to head to the beach. Check out of Blue Liberdad and Uber to Cascais (~30 min).
Afternoon · 1–4 PM
Drop bags at the Miragem. Head into the Centro Histórico — pastel-colored pedestrian streets, local shops, gelato. Hit the beach if the weather's right. Check in at 4:00 PM.
Late Afternoon · 5 PM
Walk the coastal path to Boca do Inferno ("Mouth of Hell") — dramatic sea cave where waves crash through rock arches. Time it for golden hour.🌅 Golden hour
Evening · 7 PM
Drinks at Farol Hotel or Villa Cascais Rooftop with ocean views, then dinner in Cascais.
Seafood · Fresh Fish · Local
Fresh catch right off the boat. Unpretentious and delicious — exactly what you want for your first Cascais meal.
View on Maps →Seafood · Cliffside · Views
Right next to Boca do Inferno with dramatic ocean views. Great seafood in a stunning setting.
View on Maps →Contemporary · Brunch · Healthy
Stylish spot with a great brunch menu and healthy options. Beautiful interior design and chill vibes.
View on Maps →Seafood · Beachfront · Special
Spectacular restaurant built into the cliffs at Guincho Beach. The seafood rice for two is legendary.
View on Maps →Portuguese · Wine · Cozy
Hidden-gem tavern in old town Cascais. Excellent petiscos and curated wine selection in a warm, intimate setting.
View on Maps →Cascais centro histórico
10 min walk from hotel along the waterfront · Fully walkable
Open in Maps →
NYE crew!
Escape artists
Supermom
Date night vibes
Day 6 — Wednesday, May 27
You've earned this. A full day of pure relaxation — pools, saunas, hammam, massages, and poolside mimosas.
Spa reset day — beach, infinity pool, and real relaxation.
Morning · 9 AM
Head straight to the hotel's Water Lounge. Start with the thermal circuit — heated pools, swim, sauna, and hammam. The indoor-outdoor pool overlooks the Atlantic.
Midday · 12 PM
Light lunch on the terrace. Have a drink — maybe a mimosa? You're on vacation. Don't forget to hydrate between thermal circuits.
Afternoon · 2 PM
Book a signature treatment — deep tissue, hot stones, or hammam experience. After: pool, napping at the pool, reading at the pool. Noticing a theme?
Evening · 7 PM
Pre-dinner drinks (don't forget to hydrate!). For dinner: stay in the hotel restaurant, venture into Cascais or Estoril, or take an evening stroll by the beach. Dealer's choice — you're relaxed now.
Day 7 — Thursday, May 28
Step into a fairytale. Colorful palaces on misty mountaintops, hidden tunnels, and pastries that rival Belém.
Sintra highlight day — palaces, mystical gardens, legendary pastries.
Morning · 9 AM
Breakfast at the hotel, then Uber to Sintra. Head straight to Pena Palace — buy tickets in advance!📅 Book ahead A Romanticist palace in wild yellows, reds, and blues perched above the forests. The terraces and views are the showstopper.
Early Afternoon · 1 PM
The most mystical place in Portugal. Gothic palace, hidden grottos, underground tunnels, and the famous Initiation Well — a spiral staircase descending 27 meters into the earth. Like a fantasy novel come to life.👟 Wear good shoes
Afternoon · 3 PM
Reward yourself at Piriquita — Sintra's famous bakery since 1862. Try the travesseiro (almond puff pastry). Get a box to bring back to the hotel.
Optional · 4 PM
If you have energy, detour to Cabo da Roca — the westernmost point of mainland Europe. Dramatic cliffs, crashing waves, edge-of-the-world vibes.
Evening · 5–6 PM
Head back to the hotel to relax. Dinner either at the hotel restaurant or head out into Cascais town.
Portuguese · Wine · Tapas
Cozy spot in Sintra town for a proper lunch. Great local wines and petiscos. Perfect refueling between palaces.
View on Maps →Modern Portuguese · Creative
Upscale but relaxed, with creative takes on Portuguese classics. Beautiful plating and a great wine list.
View on Maps →Bakery · Pastries · Since 1862
The travesseiro (puff pastry with almond cream) is legendary. Also try the queijada. Get a box for the road.
View on Maps →
Day 8 — Friday, May 29
Choose your own adventure. Sail the coast, explore a medieval walled town, or chase the edge of the continent.
Your day, your call — sail, explore, or do absolutely nothing.
Today is wide open. Here are the top picks — do one, do all, or just sleep in. You've earned it.
Half-day catamaran or sailboat along the coast. See dolphins, swim in secluded coves, and sip wine on the water. Most tours leave from Cascais Marina.
🎒 Bring: sunscreen, windbreaker, sunglasses
A fairy-tale medieval walled town about 1.5 hours north. Walk the ancient walls, sip ginjinha from chocolate cups, and wander flower-draped streets.
🎒 Bring: comfy walking shoes, small daypack
Head up the Atlantic coast. Cabo da Roca (westernmost point of Europe), Azenhas do Mar (cliffside village), or just find a beautiful beach and stay.
Day 9 — Saturday, May 30
All good things… One last Portuguese coffee, a final look at the ocean, and then it's time to head home with a full heart (and suitcase).
One last coffee, one last look at the ocean, then home.
Morning
Sleep in, enjoy a leisurely hotel breakfast, and take one last walk along the waterfront. Soak it all in.
Afternoon
Uber to LIS airport (~35 min, €35–45). Arrive at least 3 hours early for the international flight. Grab some port wine and canned fish at duty-free and one last pastel de nata at the airport.
Evening
Depart 5:45 PM · Arrive EWR 9:00 PM (Terminal B). ~8 hour flight. Start planning the return trip on the way home — because you'll definitely want to come back.
Through the Years
From baby showers to boat cruises, paint nights to Dublin pubs — these three have been making memories for decades. Here's to the next chapter in Portugal.
"The best is yet to come" 🇵🇹
Before You Go