Delve Deep: Spain & Portugal

Today is your day, your way. Spend your free time ticking off those bucket list items AND exploring the backstreets. Beat the crowds and get up early to ride Lisbon's famous yellow 28 tram. Check out the winding medieval maze that is Alfama (Lisbon's oldest neighbourhood). Venture up to São Jorge Castle for epic views and a history lesson on Moorish culture. Check out the colourful street art in Mouraria.

Then grab yourself some pastéis de nata (binge-worthy custard tarts) and relax in the Botanical Gardens. Fact: this place was built by a Portuguese king who wanted one of every type of plant in the world (meaning: boho vibes galore). Tonight, dinner is on you but head to the Time Out Market and you're guaranteed to find something totally drool-worthy. Then: wind things up at a cosy rooftop wine bar in Bairro Alto. This is what you came for.

No guesses on what Porto is famous for. But before your inner wine connoisseur gets too excited – we'll make a stop in the fairytale town of Sintra. You'll have plenty of free time to check out this UNESCO World Heritage-listed town in all its glory – ticking off the likes of the Castle of the Moors and the technicolour Pena Palace (pssst book your tix in advance). Make some time to stop off at Fábrica das Verdadeiras Queijadas da Sapa – they've been serving queijadas (small pastries filled with goodness) since 1756. Then: we'll roll onto Porto, where the evening's yours to get lost in a maze of cobbled streets and fancy blue-tiled buildings. (B)

Time to delve a bit deeper – lace up those Nikes, we're gonna take a look around Porto's medieval streets, quirky alleyways and picture-perfect port on a walking tour. Pass by Porto Cathedral. Gape at Palácio da Bolsa. Count your blessings at San Francisco Church. And check out the hand-painted azulejos (colourful tiles) in San Bento Station.

Then: the rest is up to you – but we reckon an optional cruise down the mighty Douro River is the best way to spend the afternoon. Or you can head to Matosinhos Beach to work on those European tan lines. Later, tickle your taste buds with an included port wine tasting experience before hitting one of the local rooftop bars for allll the views (top tip: ask for white port and tonic *chef's kiss*).

You wanted more time to explore – so here's a free day we prepared earlier. Go get it. Check out the Royal Palace: the home of one of Europe's oldest monarchies. Stroll through the expansive Plaza Mayor. Make eyes at the masterpieces in Museo del Prado (aka Madrid's Louvre). Take in all the views from Palacio de Cibeles.

Grab yourself some churros and take a stroll around El Retiro Park. There's even an optional tapas experience on offer. Then: seek out a buzzing bistro for dinner in the Malasaña district – an über trendy neighbourhood with a unique character and a provocative past. Ready for round two of chocolate-covered churros? No judgement here.

Forget hitting snooze, this Basque hotspot is begging to be explored. Get your bearings on an orientation walk around town. DW, our in-the-know Trip Leader will point out the best pintxos places along the way. Then the rest is up to you. Join the crowd of beachgoers at La Concha. Hit the surf with the locals. Jump on a ride at one the oldest theme parks in the world. Or take a cold beer up Urgull Hill for incredible views over the bay.

Later, choose your pants wisely – if you're embarking on a pintxos-bar-crawl through the Old Town tonight, or heading to Bar Borda Berri for some slow-roasted beef (melt-in-your-mouth good), you're gonna' need a LOT of room.