There’s a special kind of glow to Portugal in summer, the tiled terraces, the panoramic sunsets and the salt-soft breeze off the Atlantic.
If you're dreaming of a trip that blends city culture, seaside ease, and island adventure, Kate's recent family journey through Lisbon, Algarve, and Madeira is a blueprint for exactly that. Below, we share where to stay, what to do, and how KJ Travel strings it all together, especially in Madeira, where the magic truly unfolds.
Lisbon: Classic City, Fresh Energy
Where we stayed: Four Seasons Hotel Ritz Lisbon
Set high on one of the city's seven hills, the Four Seasons is an urban resort with oversized rooms (most with balconies), a spa and indoor lap pool, and a new outdoor pool and garden terrace that feel like a private club in the middle of the city. From the rooftop, Eduardo VII Park spreads below like a green carpet, with São Jorge Castle perched on the opposite hill, a view that shifts as evening falls. Kate was able to stop by and check the newly renovated rooms as well.
Kate's stay Three nights in Lisbon gave time to settle into the city's rhythm and explore, Kate recommends stopping by one of José Alvarez restaurants, definitely a favorite.
How we’d shape your days
Private guiding through Lisbon’s neighborhoods and time in Belém’s monuments, with a hands-on tile-making workshop for a meaningful keepsake (Kate’s family loved bringing home their own pieces).
A half-day to Sintra (approx. 40 minutes from town) for palaces and misty hilltops, then back to the hotel for a sunset swim on the new pool terrace.
Advisor tip: Make sure to check Google Maps, so it can tell you about incline and elevation changes through its "Terrain" view and the elevation profile for walking and cycling directions…Trust us, we've hiked those hills.
Algarve: Sun-Drenched Coast, Lazy-Day Rhythm
Where we stayed: VILA VITA Parc
Perched above the Atlantic in Porches, VILA VITA Parc is a lush, 54-acre cliffside oasis with 12 restaurants (including two-Michelin-star Ocean), a Sisley spa, family-friendly spaces, and direct beach access. It’s classic Algarve, golden sand coves, grottoes and caves, and warm hospitality.
Kate's stay
Three easy, summer-slow days (beach, spa, pool, kids’ club) plus dinners at Whale and Arte Náutica. The highlight: a private catamaran along the Lagos coastline, gliding past the famous golden cliffs and sea grottoes. Kate's family also explored the caves around Carvoeiro.
How we’d shape your days
Day at leisure on property (spa, beach, pool repeat).
Private catamaran to explore Benagil-area sea caves; swim stops where the water is clearest.
Driver-guided outing to whitewashed towns for tiles, ceramics, and gelato on the praça.
Madeira: Adventure, Gardens & Old-World Glamour
Where we stayed: Reid’s Palace, A Belmond Hotel
A legend since 1891, Reid’s sits on a promontory above Funchal with terraced gardens, sea-view pools (including a tidal pool down by the waves), tennis, and the island’s first Michelin-starred dining at William. It’s the grand dame with a playful soul, afternoon tea, sunset cocktails, and front-row views of the Atlantic.
Kate’s stay
Three nights was the sweet spot for a first look at the island. Her family loved the 1891 Bar for sunset petiscos (small savory dish, very similar to spanish tapas) and a proper Porto Tónico, a fun local twist on the classic spritz.
What Madeira looks like when we plan it
Day 1 – Hills & Gardens
Gondola to Monte for cinematic island views.
Monte Palace Botanical Garden wander with our favorite guide for the best paths and photo angles.
Aperitivo at 1891 Bar on Reid’s terrace
Day 2 – Sea Cliffs by Boat
Private boat day along Cabo Girão, among Europe’s highest sea cliffs; swim in glass-clear water that’s often warmer than the Algarve in midsummer (Kate noticed the difference).
Fresh lunch and a lazy sail back toward Funchal as the sun drops.
Day 3 – Levadas, Toboggans & Wine
Morning levada walk (scenic irrigation-channel trails) tailored to your pace, then the iconic Carro de Cesto wicker toboggan ride down the steep lanes of Monte, equal parts history and thrill.
Madeira flavors: espetada (grilled beef on bay-leaf skewers), bolo do caco (garlic-buttered sweet bread), and a tasting of Madeira’s fortified wines.
Why Reid’s is perfect for families
Garden-level rooms with terraces, multiple pools, kid-approved dining, and space to roam, plus Belmond’s famously warm service. We layer in curated experiences (dolphin/whale-spotting, jeep tours, garden tours) so everyone gets their version of adventure.
Logistics made easy
Fly into Funchal (FNC); it’s a short drive to the hotel. Seasonal nonstop routes from Newark have recently made access even smoother. We handle transfers, boat charters, and dining so your time is pure play.
How We Stitch It Together
Kate’s Portugal flow—Algarve - Lisbon - Madeira—works beautifully for families: start with beach-day ease, shift to city culture, and end on an island high note. On her trip we reserved VILA VITA Parc for three nights, then Four Seasons Hotel Ritz Lisbon for three, and finally Reid’s Palace for three—an elegant cadence that balances rest and discovery.
VIP treatment
As a KJ Travel client, you’ll receive our preferred-partner perks (think: upgrades when available, daily breakfast, resort credits, welcome amenities) and priority wait-lists at in-demand restaurants and kids’ clubs. At these properties, those little advantages add up to a noticeably smoother stay.
Are you ready to visit Portugal?
Tell us what you want this trip to be: Easy, adventurous, celebratory? KJT advisors will design the version that fits you best. Click here to fill out our form and let's start planning today!