How Travel Is a Personal Reinvention, Not Escape as We Age
If you’re an empty nester, nearing retirement, or craving something deeper than another European highlights trip, this episode is for you. I sat down with Lisa Pagotto, founder of Crooked Compass, to talk about travel in retirement, or what I like to call the “what’s next” phase of life, and how this season can be the perfect time to explore beyond the usual bucket list destinations.
Why Retirement Is a Travel Sweet Spot
For many travelers, this season of life offers:
More flexibility with time
Greater financial freedom
Fewer family logistics
A desire for meaning and depth
Lisa shared that the majority of their travelers are empty nesters, recently retired professionals, or simply people scaling back work but not slowing down life.
And while cruises and beach resorts have their place, many retirees are asking a different question: Where can I go that still feels undiscovered?
What’s Next After the “Classic” Destinations?
If you’ve already done London, Paris, Italy, or Japan… what’s beyond that?
Here are destinations Lisa says are booming among well-traveled Americans:
Mongolia
Nomadic culture
Vast, untouched landscapes
Deep cultural immersion
Opportunities to stay in traditional gers
The Silk Road & Central Asia
Uzbekistan
Kazakhstan
Kyrgyzstan
Why now?
Infrastructure has improved dramatically
Boutique hotels are emerging
High-speed rail connects major hubs
It’s no longer just a backpacker route
Papua New Guinea
Remote tribal experiences
Rare cultural encounters
Truly frontier-style travel
Eastern Europe Rising
Romania
Bulgaria
Moldova
Georgia
Azerbaijan
These destinations offer:
Rich history
Fewer crowds
Strong cultural identity
Incredible value compared to Western Europe
If you’ve been craving something different… this is your sign.
Redefining Luxury Travel
Let’s talk about the word “luxury.” For many couples, luxury isn’t about $5,000/night resorts, butler service, or white gloves and marble floors.
Instead, it’s about depth, access, exclusivity, and meaning. Lisa describes luxury as the privilege of experiencing something few others have.
Think:
Stargazing in the Atacama Desert with an astronomer
Meeting a shaman in Mongolia
Tracking endangered wildlife alongside conservationists
Is This Style of Travel Only for the Ultra-Wealthy?
Short answer: no.
Long answer: it depends on destination and design.
Lisa shared that for their style of curated, high-touch travel, budgets typically start around $500 USD per person, per day with Crooked Compass.
That includes:
Expert local guides
Carefully vetted accommodations
Unique access experiences
On-ground logistics and safety planning
Some destinations (like parts of Asia) are more economical. Others (Africa, remote regions, helicopter access) cost more.
But the key is intentional design around your interests, pace, comfort level, and priorities.
Why Expert Planning Matters More in Remote Destinations
You can probably plan a Paris trip yourself.
But what about:
Medical evacuation plans in remote regions?
Safety assessments in post-conflict countries?
Language barriers?
Access to non-touristic communities?
This is where experienced operators make a massive difference. It’s not just about convenience.
It’s about safety, access, cultural sensitivity, and long-standing local relationships.
Travel as Reinvention (Not Escape)
One of my favorite parts of our conversation was this idea: Travel isn’t just about getting away. It’s about perspective shifting.
Many of the destinations Crooked Compass operates in have:
Been misrepresented in media
Recently emerged from conflict
Been overlooked by mainstream tourism
When you visit, you often discover:
Warmth and kindness
Community resilience
Cultural pride
Shared humanity
You realize quickly that we are far more alike than we are different. This kind of travel changes you.
A Reminder for This Season of Life
In Australia, they have a playful term for retirees: SKIs — Spend the Kids’ Inheritance.
And while that might make you laugh, there’s wisdom there.
If you’re in this stage of life:
Stay curious
Follow your interests
Chase the deeper experiences
Don’t wait for “someday”
Whether you love archaeology, wildlife conservation, tribal cultures, history, or spiritual traditions, there is a corner of the world waiting for you.
Where to Learn More
If you’re curious about planning a journey to one of these lesser-known destinations, you can explore more through Crooked Compass.
They offer:
Small group tours (max 12 guests)
Fully customized private journeys
Deep cultural access experiences
And if you’re ready to move beyond the typical bucket list… This might just be your next chapter!