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Our 12-Day Portugal Itinerary at a Glance

• Days 1–3: Areias do Seixo Villas (Silver Coast)
  Wild Atlantic beaches, family-friendly seaside vibes, and the perfect place to ease into holiday mode.
  👉 Read more: A Family‑Friendly and Eco‑Conscious Stay on the Coast of Portugal
• Days 4–6: Craveiral Farmhouse, Alentejo
  Sustainable luxury with farm animals, pools, and slow living among cork trees.
  👉 Read more: Planning a Family Holiday in Portugal? Why We Loved Craveiral Farmhouse
• Days 7–8: Ride Surf Resort, Peniche
  Surf lessons for the kids, a surf-skate class, and a short but sweet beachside stay.
• Days 9–11: Look Living, Lisbon
  Boutique apartment hotel on the flat part of town, café breakfasts, and a magical sunset boat ride on the Tagus.
  👉 Read more: **7 Things to Do on a Weekend in Lisbon | A Warm Welcome in Lisbon: Our Family Stay at Look Living
• Day 12: Departure from Lisbon

I love planning a holiday. I’ve blogged before about how I usually do it (How to Plan an Epic Holiday), but this time I tried something a little different. I wrote a script for ChatGPT. Into it, I fed examples of hotels we’ve enjoyed around the world, the kind of vibes we like (eco, off-the-beaten-track, luxe but not wallet-busting), and activities that would work for the kids.

I didn’t want a regimented kids’ club type of holiday. Instead, I was after places with surfing, skateboarding, animals, things they could dip in and out of. Originally, I was torn between Sicily and Portugal, but eventually narrowed it down to Portugal.

I also asked ChatGPT to plot all the suggested hotels on a map so I could see potential routes. Then it was over to me to check prices and availability.

We did discover our trip overlapped with a Portuguese bank holiday (next time I’ll add that into the script to avoid!), which meant our route zig-zagged more than ideal, north of Lisbon, then back down, then up again. But we booked just a few weeks out, and we’re used to the quirks that come with last-minute holidays.

Transport & Travel Logistics

We used airmiles to snag flights from Heathrow to Lisbon. For once, we flew on a Sunday morning at a reasonable hour instead of the usual Friday night or early Saturday start. With school holidays and work schedules, that extra Saturday to pack was a sanity-saver this time.

At Lisbon airport, we hired a car with Hertz. Pickup was smooth, though drop-off was a little dramatic, a staff member accidentally hit reverse and almost backed into us (thankfully missing by a hair!).

Note on Lisbon Airport: Security and passport control were intense. Lines took around 1.5 hours, and many people missed their flights. Passport control is after the food hall, which caught some people out.

We also learned a lesson on tax refunds: you need to have the purchased items with you at the airport, not in checked baggage. We call this a “tourist tax” in our family its the inevitable mistakes you make the first time you visit somewhere.

Stop 1: Areias do Seixo Villas – 3 Nights

We began our trip on the Silver Coast with three nights near Santa Cruz, staying in a villa that felt like the perfect mix of modern comfort and seaside charm. The beaches here were wild and beautiful, with huge Atlantic waves crashing onto long stretches of sand, a playground for surfers and the perfect place for windswept post breakfast walks.

Santa Cruz itself is relaxed and family-friendly, with plenty of cafés, beach bars, and restaurants. It was a great base to slow down, adjust to holiday mode, and let the kids burn off energy by the sea. You can read more about this part of our stay in my post: A Family‑Friendly and Eco‑Conscious Stay on the Coast of Portugal.

Stop 2: Craveiral Farmhouse, Alentejo – 3 Nights

Next, we drove down and inland to Craveiral Farmhouse in the Alentejo region, a stay that turned out to be one of the highlights of our holiday. Set among rolling fields and cork trees, Craveiral is all about sustainable luxury, modern farmhouse apartments with a focus on nature and community.

The kids loved the animals on-site (donkeys, goats, and chickens), while we enjoyed the farm-to-table dining and relaxed pace. There were swimming pools, wide-open spaces for running around, and a real sense of calm. It felt like the kind of place where you instantly breathe deeper. Full details are in my blog post: Planning a Family Holiday in Portugal? Why We Loved Craveiral Farmhouse.

Stop 3: Ride Surf Resort, Peniche – Planned 4 Nights (Stayed 2)

This was the stop where our last-minute planning didn’t quite go to plan. We had expected a lively surf and skate hub in Peniche, with yoga classes and a buzzing rooftop bar, but it turned out much quieter than the website suggested. The area itself also had limited dining options.

That said, there were highlights. The kids loved their surf lessons, and I joined my son for a surf-skate class, fun, even if my thighs complained the next day! We also found a couple of beach bars we loved (Bar da Praia and By Norte Cervejaria). In the end, we cut our stay short and moved on after two nights, which turned out to be a good decision.

Stop 4: Look Living, Lisbon – 3 Nights

Our final stop wasn’t planned with ChatGPT but booked through Booking.com, and it was the perfect way to end our trip. We stayed in a boutique-style apartment hotel close to the river and, most importantly, on flat ground (a blessing in a city built on seven hills!). Check-in began with a complimentary glass of wine, and the team were so warm and welcoming that we felt at home straight away.

Our apartment had high ceilings, beautiful wooden stairs worn smooth by more than a century of use, and what may genuinely be the most comfortable sofa in the world (that also doubled as a bed). With crisp bedlinen, fluffy towels, and plenty of space, it felt like a cosy retreat in the middle of the city. Breakfast was served downstairs in the hotel’s café, and while service was a little slow, it was more than enough to set us up for a day in Lisbon.

One evening, the staff helped us book a last-minute sunset boat ride on the Tagus River, which turned out to be one of the highlights of our trip. Watching the city’s skyline, the 25 de Abril Bridge, and the Monument to the Discoveries glow in the evening light was magical. Lisbon was the perfect finale to our 12 days in Portugal. You can read more in my posts: 7 Things to Do on a Weekend in Lisbon and A Warm Welcome in Lisbon: Our Family Stay at Look Living.

Would I Use ChatGPT to Plan a Holiday Again?

Absolutely. It introduced us to hidden gems that weren’t on Booking.com or Agoda, places I might never have found without a friend’s tip or a travel agent.

Apart from one stop that didn’t quite suit us (which I’ll refine in my script next time by including more about the local area), it was spot-on. Every other place hit the mark for our mix of eco, luxe, and family-friendly.

I’d definitely use ChatGPT again for future adventures.