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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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107: Destination with Intention: Where to Travel Based on Your Life Goals (Ep 2)
Transform With Travel: Trip Planning Made Easy For Busy Professionals Craving Bucket List Adventures
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Where you go matters, but why you go matters even more.
In this episode of Transform With Travel, we dive into the art of destination selection – helping you choose where to travel based on your goals, values, and energy. Whether you’re planning a health reset, a romantic getaway, or a creative sabbatical, Kelly shows you how to pick a destination that truly supports your intention.
From Greece’s healing blue zones to the quiet beauty of Costa Rica’s jungles, this episode explores how to bring more meaning to your adventures and make every trip feel like it was designed just for you.
Inside this episode:
- How to align your destination with your travel intention
- The difference between “destination-first” vs. “intention-first” travel
- How your budget shapes where (and how) you travel
- The truth about “Instagram vs. Reality” tourism
- When to travel for best experiences (low, shoulder, or high season)
- How to avoid travel stress and find destinations that match your season of life
If you’re ready to make your 2026 travels intentional, transformational, and totally aligned with you, this episode is your roadmap.
📍 Watch the full Intentional Travel Planning Series for a step-by-step guide to creating trips that inspire growth, healing, and joy.
We talk about:
- 00:00 Welcome + What This Series Covers
- 01:10 Why Destination Choice Matters
- 02:00 How to Pick Health, Wellness, or Connection Destinations
- 04:00 Budget, Season, and Reality Checks
- 06:00 Avoiding Overtourism and Stress
- 07:10 Timing, Seasons, and Restrictions
- 08:00 How to Align Your Destination With Your Goals
- 08:30 What’s Next: Building a Balanced Itinerary
Resources & Links:
- Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packages
Connect with me
- Follow the Podcast on IG: http://www.instagram.com/transformwithtravel
- Follow Kelly Tolliday on IG: http://www.instagram.com/kelly.tolliday
- Transform With Travel Website: https://www.transformwithtravel.co
108 episodes
