The Thought Card: Smart Travel Tips & Vacation Planning For Financially Savvy Travelers

Should you book now or wait for a better travel deal?

Today, we’re pulling back the curtain with Susan Catto, Head of Publishing, Canada at Travelzoo, to uncover how travel insiders evaluate vacation deals, avoid costly booking mistakes, and find the best value in today's travel landscape.

Drawing on insights from millions of travelers and years of experience covering the travel industry, Susan shares practical tips to help you...

After losing her job, Kelly Peeler made a bold decision: she bought and renovated a home on the Greek island of Milos—with no prior experience—and transformed it into an art residency designed for women to rest, create, and connect.

Kelly shares how burnout and years of living nomadically across Europe led her to Greece, why she chose Milos, and the vision behind building a global ecosystem for female artists.

We also div...

Is travel blogging dead or does it just look different today? Michelle Jensen of Travel HerStory shares what it actually takes to make money as a travel blogger. From earning her first $100 to building sustainable income streams through ads and affiliate marketing, Michelle highlights the realities behind turning a blog into a profitable side hustle or full-time business.

If you’ve ever wondered whether travel blogging is stil...

Some of the best travel experiences happen when you explore the places closest to you. Today I’m joined by Jenn Neilson from Will Save For Travel to talk about all things staycations and micro-adventures.

We dive into how to make the most of where you live, especially in a world of rising costs and limited vacation time.

Jenn also shares how she plans meaningful staycations that feel like real vacations, where she looks for hid...

Quitting your job to travel the world sounds unrealistic… maybe even irresponsible. But what if it’s actually one of the most intentional financial decisions you can make?

Kesi Irvin walked away from a high-powered finance career in New York City after saving for two years to fund her dream of traveling the world.

What started as a round-the-world trip turned into more than a decade of long-term travel across 84 countrie...

Today, we’re heading to the rugged and breathtaking coastline of Newfoundland and Labrador, Canada, one of the best places in the world to experience whale watching up close.

Joining us is Shawna Prince, environmental scientist and co-owner of Sea of Whales Adventures. With decades of experience studying marine wildlife and guiding whale watching tours, Shawna shares what makes this region so special for first-time visitors.

Re...

Ever dreamed of packing your bags and moving abroad but worried about how you’d make a living?

Kiersten Brown did just that. At 27, she left California to move to Panama. She later found a program to teach in Spain, expecting to teach English. But when she found herself struggling financially, she pivoted—building a successful freelance writing career from scratch.

Kiersten shares what life in Spain is really like, the bi...

Most people think savings challenges are designed to help you save money.

But what if the real benefit isn’t the money at all?

Savings challenges can spark something even more powerful. Because when you successfully complete a savings challenge, you begin to see yourself differently: as someone who follows through, saves consistently, and plans for the future.

Today, Deahna Joi from BudgetsByJoi.com joins us for a rich co...

There are so many incredible places to visit on a honeymoon.

Sara Margulis, CEO and co-founder of Honeyfund, shares trending honeymoon destinations worldwide, including countries in Europe, Asia, and even the United States.

Listen to the full episode here: https://thoughtcard.com/crowdfund-dream-honeymoon-honeyfund/

In Episode 187, Sara Margulis shares why more newlyweds are favoring cash gifts over traditional wedding gifts and ho...

Looking for the best NYC photo spots for your next trip?

➡️ Book a NYC Photo Journeys tour and use the promo code ‘SAVVY10’ to get $10 off any photo tour or photoshoot.

New York City moves fast and it’s easy to spend your trip running from Times Square to Central Park, checking off landmarks without truly taking it in.

I’m joined by Jessie Festa, founder of NYC Photo Journeys, to share the best photo loc...

Looking for the best things to do in Puerto Rico beyond the typical tourist attractions?

From the historic streets of Old San Juan to lesser-known beaches and Afro-Caribbean cultural experiences, add these must-see attractions and activities to your Puerto Rico travel itinerary.

Read blog post: https://thoughtcard.com/things-to-do-puerto-rico/

Other Episodes You'll Enjoy

1. Pros and Cons of Moving to Puerto Rico...

One of the things I love about travel is finding small ways to reconnect with a destination after returning home, especially through food and drinks you can find locally.

If you’re wondering what Icelandic food, snacks, and drinks you can buy at your local grocery store, here are some easy favorites to try.

Icelandic Shop ships authentic Icelandic products worldwide, including duties and fees. Find Icelandic orange soda, lava c...

Throughout history, women played a powerful role in shaping the city we know today.

I’m joined by Beth Santos and Nikki Padilla Rivera, passionate storytellers from She Shapes History NYC, who are leading walking tours exploring the hidden stories of women who challenged power, rewrote laws, organized communities, and built lasting change across New York City.

Read blog post: https://thoughtcard.com/she-shapes-history-nyc-tours...

I'm hosting a small-group trip to Iceland in mid-August 2026, designed for travelers who want a thoughtfully planned experience rooted in nature, culture, and soft adventure.

Today, I'm sharing why hosting a group trip to Iceland feels like the right next step and how years of repeated visits have shaped the small-group trip I'm hosting.

👉🏾 If Iceland is on your bucket list, now is the time to plan. Let me help you build a custom I...

Iceland travel advice isn't one-size-fits-all. These unpopular opinions from 10 years of visits may change how you plan your trip to Iceland.

➡️ Here's something most Iceland travel guides won't tell you: you don't have to rent a car to have an incredible trip. I've done it, I've planned it, and I can build you a car-free Iceland itinerary that actually works.

Visit thoughtcard.com/iceland-trip-planning to get started.

Connect With D...

Iceland has my heart, and now I want to share it with you. I'm hosting my first small-group trip to Iceland in August 2026.

We'll explore unforgettable natural wonders and charming small towns:

• Reykjavík, the northernmost capital in the world
• The Ring Road, with erupting geysers and shifting tectonic plates
• The South Coast, home to waterfalls, glaciers, and black sand beaches

If you've ever dreamed of experiencing the midni...

What if travel were less transactional—less about booking flights and checking off destinations—and more about seeking clarity, growth, and transformation?

Sahara Rose DeVore, founder of the Travel Coach Network and a pioneer in the travel coaching space, challenges us to think about travel, not just as an escape, but as a meaningful experience that can support our well-being and life goals.

We dive into:

What if you could make progress on your financial goals without thinking about it every day?

I'm sharing simple ways to automate your finances, from direct deposit and auto-saving to dollar-cost averaging.

These automations have helped me save for travel, buy a house, invest in retirement, and make headway on dozens of goals.

➡️ Sign up for a high-yield savings account with All...

🎄Planning a holiday trip to New York City? NYC Christmas markets are one of the most magical ways to experience the holiday season, but they can also be crowded and overwhelming if you don't know what to expect.

I'm sharing our best NYC Christmas market tips to help you shop smarter and make the most of your time.

Read 'NYC Christmas Markets' blog post: https://thoughtcard.com/christmas-markets-nyc/

🎒Shop Rachel Bloom Anti-Theft Bag...