Key Takeaways

Our whirlwind trip through Portugal, Italy, and Greece was equal parts breathtaking and chaotic—exactly what you want from a friends’ getaway. We mastered public transport (mostly), ate until we regretted it (always), and collected stories that’ll outlast any hangover. Here’s the unfiltered version of how we conquered three countries in two weeks without losing anyone (permanently).

Portugal – Where We Fell in Love with Custard Tarts & Each Other’s Patience

Day 1: Lisbon – Lost Luggage & Life-Changing Pastries

Our red-eye from JFK left Sarah snoring on my shoulder while Mike scrolled TikToks of New Costco products in store. By the time we stumbled into Lisbon’s golden morning light, we were equal parts exhausted and exhilarated.

Breakfast at Pastéis de Belém was our first stop. “They’re just tiny tarts,” Jake scoffed—until he ate six. The crispy crust gave way to creamy custard that made us all go silent (a miracle). Belém Tower was next, where we immediately underestimated the Portuguese sun. Note: SPF 15 is NOT sufficient, and yes, we all peeled for days.

The afternoon brought us to LX Factory, where Sarah befriended a shopkeeper who gave us free ginjinha (cherry liquor) shots “for energy.” This explained our questionable purchases later. Then came Tram 28, where we played sardines with 50 sweaty tourists. Worth it for the Alfama views, but next time? Uber.

Dinner at Time Out Market turned into a spectacle when Mike challenged a local to a spicy piri-piri eating contest. He lost. Badly. We ended the night at Miradouro de Santa Luzia, where a silver-haired man playing guitar taught us the chorus to a Fado song. We butchered it, but he applauded anyway.

Day 2: Sintra – Fairytales & Near-Death Hiking

The train ride was peaceful…until Jake’s backpack spilled protein bars everywhere. The Portuguese grandma across from us tsk-tsked while handing out wet wipes.

Pena Palace’s iconic yellow tower required climbing stairs that nearly ended our friendship. The view? Absolutely worth the wheezing. Then came Quinta da Regaleira, where we got lost in the initiation wells for 45 minutes. Dave swears he saw a ghost.

Lunch at Tascantiga was a highlight—the waiter took pity on our sunburned faces and brought extra bread “for your suffering.” Octopus salad and vinho verde restored our spirits. Back in Lisbon, we accidentally walked into a locals-only Fado spot. Instead of kicking us out, they pulled up chairs and fed us queijo da serra.

Day 3-4: Porto – Wine, Bridges & The Sandwich That Changed Us

The train ride featured Mike losing at Uno, Sarah flirting with the snack cart guy for free pastries, and collective awe at the Douro Valley views.

Livraria Lello made Jake (our resident Potterhead) cry actual tears in the Hogwarts-esque bookstore. The €5 entry fee includes a book credit, which he immediately used on Portuguese poetry (unread, but it looked smart). Graham’s Lodge tasting turned into a comedy show—our “mmmm” noises grew increasingly sophisticated with each tawny port.

Then came the Francesinha Incident. Imagine a croque-monsieur on steroids. Dave’s face when the cheese sauce cascaded everywhere? Priceless.

Italy – Where We Ate Our Weight in Pasta & Regretted Nothing

Day 5-6: Rome – Gladiator Ghosts & Gelato-Induced Joy

Our Ryanair flight was…an experience. Note: “Priority boarding” means nothing when Sarah’s carry-on contains 17 Portuguese ceramics.

The Colosseum combo ticket (€16) was a steal, unlike the shady guy outside selling “skip-the-line” passes. Roscioli’s cacio e pepe made Mike whisper “holy shit” with his first bite. The waiter nodded like “I know.”

At the Trevi Fountain, Jake threw €5 into the water “just to be safe.” Giolitti’s pistachio gelato was so good Sarah licked her cup. A local nonna applauded.

Trastevere at night was magic. Freni e Frizioni’s €10 aperitivo (cocktail + endless snacks) turned us into regulars in one night.

Day 7-8: Amalfi Coast – Lemons, Luxury & Near-Death Bus Rides

The Circumvesuviana train to Sorrento was an adventure. Note: Do NOT put your bag on the seat unless you want Italian grandmas to shame you.

Da Adolfo’s lunch arrived via a tiny boat with a red fish flag. The mussels made us swear off American seafood forever. The Path of the Gods hike offered breathtaking views, though the stray goat that followed us for 2km stole Sarah’s sandwich.

SITA buses were a horror show—imagine a clown car, but vertical. We learned locals PUSH to get off. Survival skills acquired.

Day 9: Florence – Steak So Good We Cried

The Frecciarossa train spoiled us with free wine. Dangerous.

Botticelli’s Venus was stunning, but the real star was the elderly guard who called Mike “carino” and pinched his cheeks. Trattoria Mario’s Fiorentina steak (1.2kg of perfection) had Dave trying to propose to the chef.

Greece – Ouzo, Octopus & Other Poor Decisions

Day 10-11: Athens – Where We Yelled “OPA!” Unironically

Our Airbnb host met us with ouzo shots “for the road.” This set the tone.

We arrived at the Acropolis at 7:30am to beat crowds. Worth it for Parthenon selfies without 500 strangers. Ta Karamanlidika’s owner force-fed us baklava “for energy.” We didn’t resist.

Day 12-14: Santorini – Sunset Chasers

The 45-minute flight was just enough time for Sarah to panic about our tiny plane.

We found a secret sunset spot behind Atlantis Books (shh!). A local artist shared his flask of rakomelo when we complimented his work. Dinner at Amoudi Bay featured octopus so fresh we saw the fisherman bring it in.

Renting ATVs (€25/day) was our best decision—even when Mike almost drove us into the caldera.

Final Thoughts: How We Survived (& Why You Should Go)

This trip tested our friendships in the best ways. Jake still owes me €20 from that Lisbon Uber. Sarah’s ceramic collection required its own plane seat. We all gained 5lbs and zero regrets.

Local Wisdom We Collected:

1. Always accept free food from grandmothers.

2. “Just one more drink” leads to the best stories.

3. Getting lost is mandatory.