Lisbon in May: My Next Adventure 🌸

I believe in speaking dreams into life, so let me tell you about my next one. Just a couple of months after I return from my two-week journey through Italy, I’ll be heading back across the Atlantic for a long holiday weekend in Lisbon, May 21–26. The timing feels perfect: spring in full bloom, long golden evenings, and Portugal waiting to welcome me with tiled streets, storybook castles, and seaside breezes.

Day 1: May 21 – Arrival & First Glimpses

I’ll check into my home base in the heart of the city—a boutique spot in Biarro Alto. After a quick refresh, I’ll wander down to Praça do Comércio and the riverfront. The light will be soft, cafés bustling, and I know I’ll feel that thrill I always get when stepping into a new city alone but ready. As the sun sets, I’ll walk up to Miradouro de Santa Catarina for my first view of the Tagus shimmering in the evening glow. Dinner nearby—something cozy and authentic—will be the perfect start.

Day 2: May 22 – Lisbon’s Soul

The morning will begin with coffee in Rossio Square, then a ride up the Santa Justa Lift to see the city spread out below. From there, I’ll walk to the hauntingly beautiful Carmo Convent ruins—I can already imagine myself lingering in that open-air shell of history.

Lunch at Time Out Market will be fun and lively, and in the afternoon, I’ll lose myself in the winding lanes of Alfama, peeking into the Sé Cathedral and climbing toward the castle if I feel like it. I’ll end the evening with dinner in Alfama, perhaps with fado music humming in the background.

Day 3: May 23 – A Fairytale in Sintra ✨

On this day, I’ll hop on the train from Rossio Station (so easy—no advance booking needed) and head into a dream. Palácio da Pena, with its candy-colored towers, will be my first stop (I’ll buy my ticket online in advance to skip the line). Then I’ll wander the mysterious gardens of Quinta da Regaleira, complete with its spiraling Initiation Well. After lunch in Sintra’s historic center, I’ll take the train back to Lisbon and slip into an easy dinner close to “home.”

Day 4: May 24 – Belém & the River

I’ll set out for Belém to see the Jerónimos Monastery (this one I’ll definitely book online in advance), the Belém Tower, and the Monument to the Discoveries. Of course, no trip to Belém is complete without a warm custard tart from Pastéis de Belém.

Later, I’ll head to the LX Factory for quirky shops, murals, and a great cup of coffee. I plan to end this day with a sunset cruise on the river—or dinner by the waterfront, watching the lights of Lisbon flicker on.

Day 5: May 25 – A Coastal Escape to Cascais

The morning will take me on the train from Cais do Sodré Station to Cascais (another easy ride with no need to book in advance). I’ll stroll the cobbled streets, dip my toes in the Atlantic, and enjoy fresh seafood by the harbor. If the mood strikes, I’ll take the scenic coastal walk toward Estoril before returning to Lisbon for dinner in Príncipe Real, a neighborhood I know I’ll love for its stylish, local charm.

Day 6: May 26 – Sweet Goodbyes

On my last morning, I’ll brunch slowly in Príncipe Real or perhaps wander the botanical gardens. I’ll climb to one more miradouro for a final look at the red rooftops and the sparkling river before making my way home. Trips like this always leave me full—of joy, of gratitude, and of inspiration.

Must-Do’s & Ticket Notes

• Santa Justa Lift, Carmo Convent, Sé Cathedral: Buy tickets on-site.

• Jerónimos Monastery & Palácio da Pena: Book tickets online in advance to avoid lines.

• Trains to Sintra & Cascais: Easy, frequent, and no advance booking needed—just tap your transit card at the station.

• Sunset Cruise: Book online a few days before to secure your spot.

Why I Can’t Wait for Lisbon in May

There’s something magical about Lisbon. It’s not just the tiled streets, pastel facades, or the way the sun paints everything gold. It’s the rhythm—the trams rattling by, the music floating through alleyways, the sea air carried up into the city.

In May, it feels like Lisbon comes alive in the gentlest, most welcoming way. And I’ll be there—walking, wandering, and soaking it all in.

✨ And here’s the part where I lean into manifesting: I don’t just hope I’ll be there—I already see it, already feel it. I see myself sipping coffee in Rossio Square, breathing in the scent of bougainvillea, standing at the edge of the Atlantic in Cascais, and smiling up at Sintra’s fairytale turrets. When I picture it this way, it’s not a wish—it’s a plan, a promise, and a joy waiting to unfold.

Here’s to always having the next adventure on the horizon—booked, planned, and waiting to be savored.

💛 Honey