San Jose, Calgary, Lisbon

Affordable Hotels LA, Life Saving Items

Author

David Rowe
March 25, 2025

“There should be sympathy cards for having to go back to work after vacation.”

In today’s newsletter:

San Jose: Might just be California’s most underrated city, tucked in the heart of Silicon Valley
Calgary: This city is full of big-sky beauty, warm hospitality, and a surprising amount of fun.
Lisbon: With its sun-drenched streets, colorful tiles, and the sweet smell of pastries wafting through the air.

San Jose, California

San Jose might just be California’s most underrated city. Tucked in the heart of Silicon Valley, it’s got all the innovation and energy of a tech capital—with a laid-back vibe, great weather, and a surprisingly rich mix of culture, food, and outdoor fun.

Sure, it’s home to big names like Apple and Google nearby, but you don’t need to be a tech nerd to enjoy it here.

Start your trip with a wander through the San Pedro Square Market, where you can snack on global street food, sip craft beer, and catch live music all in one lively spot.

Then swing by the Rosicrucian Egyptian Museum (yes, in San Jose!) for a dive into ancient history.

Nature lovers can hit the trails in Alum Rock Park or take a scenic drive up to the Santa Cruz Mountains. Art fans?

The San Jose Museum of Art and SoFA District are packed with creativity and cool events year-round.

The city’s diverse culture means amazing food—think Vietnamese pho, Mexican street tacos, and Korean BBQ all on the same block.

And if you're in town during hockey season, catching a Sharks game is a must.

San Jose blends innovation and charm in the best way, and is most certainly an under-appreciated Californian destination.

Calgary, Alberta

Calgary is where cowboy charm meets modern cool. Nestled where the Canadian prairies roll into the Rocky Mountains, this city is full of big-sky beauty, warm hospitality, and a surprising amount of fun.

Start in downtown Calgary, where glass towers share space with historic sandstone buildings and buzzing neighborhoods like the East Village and Kensington.

Grab a coffee, hop on one of the city’s rentable e-scooters, and cruise along the Bow River Pathway—it’s a vibe.

Calgary is famous for the Calgary Stampede—a ten-day celebration of rodeos, concerts, and deep-fried everything.

But even outside Stampede season, there’s a lot going on. Think art galleries, craft breweries, and top-notch food (Alberta beef, anyone?).

Plus, the Calgary Tower offers panoramic views and a glass floor if you're feeling brave.

Nature is never far away. In under two hours, you can be hiking in Banff National Park, soaking in hot springs, or snapping pics of turquoise lakes you’ve only seen on postcards.

It’s easy to get around, the people are friendly, and the vibe is a mix of laid-back and adventurous. Calgary doesn’t try too hard—and that’s what makes it great.

Add it to your list, and don’t forget your cowboy hat (or your hiking boots).

Lisbon, Portugal

Lisbon is a city that instantly charms you—with its sun-drenched streets, colorful tiles, and the sweet smell of pastries wafting through the air. It’s laid-back, beautiful, and buzzing with life, all at once.

Start your day with a creamy pastel de nata (or three), then hop on one of the city’s vintage yellow trams and let it rattle you up and down the hills. Lisbon is built on seven of them, so comfy shoes are a must—but every climb rewards you with jaw-dropping views of red rooftops and the sparkling Tagus River.

Each neighborhood has its own flavor. Alfama is all winding alleys and fado music echoing from tiny taverns. Bairro Alto cranks up the energy at night, and Belém offers a slice of Portugal’s seafaring history—and even more pastries.

Lisbon’s food scene is fire, from fresh-off-the-boat seafood to petisco plates (think Portuguese tapas) and world-class wine without the price tag. And if you’re craving a beach day, the coastline is just a short train ride away.

It’s easygoing, affordable, and filled with soul. Whether you're into history, nightlife, food, or just golden-hour strolls, Lisbon delivers the goods.

Add it to your list—and prepare to fall in love one hilltop sunset at a time.