What to pack
Lisbon is a small city with a lot of hills. Seriously, when you think you couldn't possibly have to climb any higher -BAM!- there's a vertical cobbled hill to climb...With a rickety roller coaster-style tram flying down the hill inches past your shoulders for good measure. Don't try and go stylish in wedges or (heaven forbid) heels, find some trainers. I survived any potential injuries with the support of my Nike winflow shoes - which I was also able to use for runs along the harbour and HIIT workouts in the hotel room (fitness never stops). Also bring comfortable, light clothing as the weather temp is high 20s between May and October - remember, it is not a catwalk, nor will you randomly bump into Anna Wintour, scowling at your frayed denim shorts (so 2008) and hiking shoes. Invest in some decent soled-sandals (FitFlop, Birkenstock): not flimsy plastic strappy things - and importantly, whatever you do, do not, I repeat DO NOT buy Crocs. For the sole reason that they are disgusting. Worth packing a shawl/floaty scarf/pashmina. It might sound 'old lady' but it is great for keeping the sun off your shoulders - particularly as you won't want to be wearing a woollen cardi in 28 degree heat. (And I've been rocking my floaty scarf since the Summer of 2014, free or sunburn.) Also pack sun cream, otherwise you'll be fried alive.
Where to stay
Hotels that appear cheaper or ones that can pay money to appear at the top of your search (such as the Sheraton) are usually miles out. They are a good 5 stops on the metro away from where you actually want to be, which is in the centre, by the sea, by all the tapas and wine bars, by the nightlife, with the canary yellow trams hurtling round corners, and all the typical, traditional Lisbon features. Further out resembles an airport terminal. Aim for a quaint boutique hotel in Baixa/Chiado, and not because I'm biased. I can recommend AlmaLusa Hotel, in Praca do Muncipale, Baixa Chiado - a listed building, gorgeous architectural features, the most invigorating power-shower ever, helpful staff, and a delicious restaurant below/adjacent where breakfast is served, but also really delicious Portuguese meals throughout the day. I stayed there, and I woke up happy every morning. It also meant we could easily return to change clothes, change footwear, or enjoy a siesta.
Hit up all the roof top bars you can fit in. In Lisbon you'll start to crave being up high and getting a good snap of the view. There is a great speakeasy/cocktail bar called Red Frog but this is quite a trek from the centre unfortunately, and not great if you don't fancy sitting underground in a dark room (in hot weather). TOPO is a bar/restaurant on the sixth floor of the Martim Moniz shopping mall with near-panoramic views, and still remains virtually undiscovered apart from young locals. An excellent cocktail list - I had a 'spicy or not' cocktail with absolut citron, orange juice, lemon juice, and some spices (think a Bloody Mary-style kick of chilli at the end) and Ollie had a Mojito.
PARK is a bar on the top floor of a car park in Bairro Alto. It's not very well sign posted but apparently that doesn't matter because it was absolutely rammed. Arrive early to bag a seat, grab a few snaps of the view, and watch the sunset. I went for a frozen lemon daiquiri and Hmm mmmm, think boozy sorbet in a martini glass (and totally Instagramable). There's a DJ, and it's almost a little too cool for me. Hey! I said 'almost'.
Bairro Alto hotel (also nearby) has a sunny, Riviera-style rooftop bar, but worth seeing if you can book in advance or at least get there early/be prepared to wait, as they prioritise hotel guests and if full, ask you to wait in their smoky airport lounge-style bar back on the ground floor. Honestly, it's like a lift descent of total rejection. Views over the red-roofs of Baixa-Chiado and over the sea, and a more relaxed and elegant vibe.
Another great cocktail hub includes Tabik, and 'By the Wine' on Rua do Flores is excellent place for...well... Wine. And cold meats. Ollie had a glass of Armagnac, naturally.
Traditional Portuguese food includes: these weird custard tart pastry things (Pasteis de Nata) which everyone goes crazy for, but I never had one because I had custard/creamy things like that and Ollie was never hungry whenever we were near some (my aunt will be appalled by this fact). They serve a lot of sardines (also you can buy retro tins of sardines as a souvenir), rice, bacalhau (salted dried cod which stinks), and layered stacks containing a cod fillet with corn crumb, a layer of spinach, and a layer of Portuguese potato (sliced finely like lyonnaise) served as a main meal, and really anything else caught from the sea.
Best food places we ate at were:
Taberna Moderna, featuring a bar with 110 gins and great staff. Their menu is totally amazing, and you order 2 or 3 dishes TO SHARE, and the waiter brings them out one at a time. It totally works. I tried a tonic water by 1742 made with quinine handpicked from the inca trail, and it was so smooth and delicious (usually I hate tonic water) and Ollie basically tried all their gins and schmoozed with the bar lady (NB they also stock Sipsmith). We ordered octopus fillets with asparagus and squid ink rice, followers by the iberico pork which Portuguese sausage (chorizo) which kind of resembled a fajita mix (but incredible and so filling). Book in advance to avoid disappointment.
Sea Me has an impressive array of fresh fish displayed with a little tongue-in-cheek - there was a giant stone bass displayed with a red mullet flopping out of its mouth like a tongue. I don't think my Instagram followers saw the funny side. You choose your fish, and they cook it for you with some seasonal vegetables. It's such a great vibe in there - the staff are charismatic, patient, knowledgable, and hilarious, and the food was absolutely mind blowing. Just keep an eye on the price per kilo before you pick your fish - I opted for stone bass and we were a bit surprised when we discovered after the bill had arrived that my portion was €41... But TOTALLY worth it. And I'd even let Ollie try some. He ate octopus which was a more reasonable €17. BOOK IN ADVANCE.
A Cevicheria. This was amazing in its own special way - doing weird and wonderful things with regular dishes. They don't take reservations, so it's a place you need to be prepared to leave your name at the door and then go away and wait, for an hour or more. There're plenty of bars around- including the Chinese Pavillion Bar about two doors down (a blue building), and it the food/experience is certainly worth the wait. It's similar to one of London's oyster bars inside, with white tiles, a chef cooking in front of a c-shaped bar and smaller tables by the wall, and a busy, chatty, 'fast' food atmosphere. There's also a giant (fake) octopus hanging on the ceiling, great for the 'gram. Food wise we had Portuguese ceviche, truly delicious, and I had the seaweed quinoa bowl for main - which a lot of other people were having also. It isn't just me and my mad obsession with quinoa, it is actually amazing and a dish that pops up regularly in tripadvisor reviews. It's an orange quinoa soaked in some tasty liquid with seaweed, served with an oyster broth, more seaweed, and mussels and prawns. It wasn't gross and fishy - it was full of flavour and textures.
I can't not mention Delfina, the restaurant next to our hotel. The food there is fresh and beautifully presented. We ate there on our last day - I had a smoked salmon salad which I had been craving during the whole holiday, and came with fennel and capers and a beautiful dressing (and loads of thick, fresh smoked salmon) and Ollie had Chicken Fracasse - chicken thighs stewed in a light creamy/white wine sauce, with some rice on the side. Decor is quite French-inspired, gorgeous crushed velvet chairs I wish I could have taken home, and a huge menu with really tasty dishes.
Head to Ribadouro (nextdoor to Red Frog speakeasy) if you fancy picking out a live lobster from a tank to eat, and other gruesome fish dishes. My dad would be there in a shot. I also discovered 'Fabulous' whilst searching for health food places in Lisbon, and it's up a small alley way in Chiado. Be sure to request outdoor seating, and you're taken round the labyrinth-like place and out into a sunny, warm, peaceful courtyard, completely out of the way from tourists (and full of locals). I had a vibrant tabouleh salad and Ollie had an silky smooth prawn and coriander risotto. It's not advertised as being a health/fit-food place, but it has a really good selection of fresh 'clean' dishes.
We walked to most places, particularly as we were already in the centre making most things a nice 30 minute wander. Pick up a Viva Viagem metro card to use on the metro (we used this once to go up to Martim Moniz), the tram (a truly terrifying experience but definitely worth a go), the bus (we used the bus to visit Belem), and the overground (returning from Belem, and to the towns and beaches further out, such as Cascais, Carcavelos, or Sintra).
Things to see and do
Lisbon is really the type of holiday where you potter around, eat great food, and overall do absolutely nothing. Like any picturesque city however, you may want to see the things that make it so beautiful and historic. You won't be able to step into anywhere without hearing about the Great Earthquake in 1755, and how it transformed the Baixa/Chiado area by rebuilding it in a grid format, with mosaic tiled pavements.
Where better to spend your first day than at the city's birthplace: Castelo de Sao Jorge, to snap that perfect photo of the a view below (rooftops, the sea, and the 25 de Abril bridge in the distance) and learn the history about Lisbon.
The National Pantheon is in Alfama, and a good opportunity to explore old (steep) streets with cute doorways, tile-fronted houses, and laundry hanging over balconies - giving it a humble, traditional, step-back-in-time feel. Plus, the golden domes in the Pantheon (AKA Santa Engracia) are stunning and picture-perfect - you can skip the €4 entry fee if you just stand in the entrance by the ticket booth and then leave, although the ticket gets you up to the terrace which has jar dropping 360 views of the city.
Next, walk along to the Convento do Carmo (better known as the Archaeological Museum) - a gothic church ruin located at Largo do Carmo, Baixa, with a €3.50 entry fee. The naves and transept were badly destroyed in the great earthquake, followed by a fire caused by lit candle sticks toppling over from the tremors, leaving an impressive shell (before the earthquake it was the largest church in the city). They started restoring it, but a love of ruins in the early 1800s ceased the re-building leaving it open to the Lisbon sky, and the chapel rooms at the back now display an interesting mishmash of artefacts and statuary, gothic tombs, mummies, shrunken heads, and prehistoric objects discovered from an excavation of the site. The square outside offers great food and drinks from surrounding restaurants (totally time for sangria and tapas).
Belem is a good day excursion, and there is a maritime museum if you have a boyfriend/boat fanatic in tow to entertain. The queue to Jeronimos Monastery is huge (and you have to pay) but there are beautiful architectural features (think Hogwarts-style verandas). Head to the Monument to the Discoveries (free to look at), and walk east from that to the tower of Belem which looks like a fairytale castle in the sea. The queue was too huge for us to go up inside, so head early to enjoy the second-level terrace. Grab lunch in the sun, meander about the seaside town, and queue for the Pasteis de Belem - if you're going to try those custard pastry tarts, this is the place to get them from. You can't miss it - there's blue awnings over Rua de Belem, and a humongous queue out the door.