Taking a Career Break or Life Transition: A Transformative Chile Sample Itinerary

Alison’s dream was to see and explore Chile, using the three themes: quiet, water, and adventure. Luxury Travel Advisor Theresa Jackson created for her a custom travel itinerary that brought her to the Atacama Desert, the island of Chiloe, and Patagonia. Please read below about the adventures she experienced there.


The Custom Travel Itinerary We Created for Alison’s Adventure in Chile.


The Traveler:

Alison, 45, a NYC designer in a creative field at the top of her game.


Alison’s Journey Dream:


Combining Quietness and Excitement

To take almost 3 weeks to decompress from and leave behind her 20-year career with a creative company. Her life plan was to take a break to figure out exactly what she wanted to do in her next chapter and to create the life and business she wanted. She hoped to gain both a quietness within after a hectic wrapping up of her turnover process and the excitement of inspiration in a place this world traveler hadn’t been before, Chile.


Alison’s Travel Problems:


One Must-Be Destination with a Lot of Time

  • Alison had one must-be destination, Patagonia, and even a specific must-have accommodation but with a lot of time, didn’t know what else or where to incorporate in her journey.
  • She needed to know what else there could be for her and wanted expert destination advice and to “learn what I don’t know”.
  • She wished to be inspired in the outdoors with relaxation and nourishing at the end of the day.

Since it was my job to inform her about places she didn’t know, we decided to steer away from any city touring and wine area stays. She was quick on her responses to suggestions which helped narrow my focus for her. She also was incredibly sharing about where she was in life and where she wanted to be in her emotional wellbeing and mindset. Even though she was not familiar with the places I suggested for her inner journey, she was so open to the idea!

Her last requirement was a seamless transition from place to place, and to have a slow pace, only with a maximum of three locations.


Alison’s Tailor-Made Round the World Adventure Travel Itinerary:


There were 3 themes to Alison’s journey: quiet, water and adventure.

I took these as my cue to structure an itinerary where she could quiet her mind and busy energy, be washed of the old to leave it behind, and be inspired by new creative juices in magnificent nature – and to be pampered throughout.

Her carefully chosen locations and accommodations also came with the clue she first gave me: her dream property in Patagonia.


Terrific Rates and Inclusions for Solo Travelers

I matched that experience she dreamed of throughout her itinerary so that there were no dips or disappointments. Luckily, I could get terrific rates and inclusions for her!

As a solo traveler, it's important to know where you are going next, and how you get there. Click To Tweet

As a solo traveler, it was important to her to know where she was going next, and how she was going to get there. I left no room for error or doubt.


First, it was important to have quiet in her mind and soul.

She began her journey in the Atacama Desert, a beautiful expanse of wilderness where the night sky is as spectacular as the landscape.

Her luxury accommodations throughout included excursions and all meals, so each day she could decide what she felt like doing.

She consulted with the guides there who got to know her interests and physical activity level, helping to create a bespoke journey unique to her. In addition to the activities she did and the expansiveness of the landscapes, she took time at the spa facilities and quiet locations around the property to reflect, decompress, and meditate.

Patagonia, Chile, Chile Dream Adventure | Tailor Made Travel Itinerary Sample

Photo by Jake Peacock on Unsplash


Next, adventure. Marine life, sailing, and kayaking on the island of Chiloe

Next, it was time to feel washed of her past career demands and the corporate “box” she built her career in.

Alison loved water – particularly the ocean. The Chilean coastline is dotted by islands and fjords, so from the top of Chile, she went down to northern Patagonia along the coast to the island of Chiloe. Besides encountering fantastic marine mammal wildlife – sea lions, otter, penguins and dolphins – on adventure expeditions on sailing and kayaking excursions, Alison explored small fishing communities and the waters around its national park archipelago. And at the end of each day there awaited delectable dining and delicious relaxation and pampering.


Finally, her dream destination, Patagonia.

Finally, she was ready for her dream destination and to be filled with adventure, beautiful landscapes and the confidence and creative inspiration to set her mind to her next chapter.

From Chiloe Island, Jenny was transported to Patagonia and the Torres del Paine National Park. Her accommodation here was the one she had built this travel dream around, and by this time she was ready simply to absorb the experience.

Her days were again filled as she wished with curated activities when she wanted them, and her evenings with pampering and delicious food.

To complete her travel desires, she had seamless and easy transitions from one destination to the other.


A solo traveler with a solid idea and a dream …

As a solo traveler with a solid idea of what would be good for her, it was important to her to not disrupt the inner journey with any outer stress.

Alison had private transfers to and from airports, well-timed flights to take full advantage of her time in each location. She had the experience of ease of movement, safety, and an in-country host contact (as well as me as full support throughout her trip) should anything go astray.


Her Experience:

Alison returned to New York City completely energized for her new adventure designing her next chapter.

“I achieved an unforgettable journey by partnering with Theresa on my vacation planning.  Ultimately, it a transformative experience that I will never forget. Overall, I found Theresa to be both professional and personally insightful. She cared about the higher purpose of the trip for me personally and worked to ensure that it was filled with not only the activities I wanted but that those activities were true experiences that would build into meaningful memories.  I felt like the trip was crafted around my needs and goals and unique to me.  I love great design, nature, authentic experiences, and environmentally responsible resources.  When I learned of a hotel that seemed to suit those needs she vetted the resource locally and didn’t just add it to the trip, but really built the entire itinerary around those values that would bring me such comfort and joy. I would not have been able to achieve this type of trip if I attempted to plan on my own.” ~Alison



Every client is different.

When taking the break between careers or between one career and a life change, like our other clients Sam on his mini sabbatical in Sri Lanka, Bernie and Barbara’s Morocco adventure, and Georgia in the Peruvian Jungle, inspiration can come from many sources in travel. But the important element is giving yourself the opportunity to get back to your SELF – your core, the values you want to express, the space to dream big again.

Some clients enjoy immersing history and culture and art, others nature and human experiential discoveries. A custom travel itinerary gives you the opportunity to create your own dream journey and the experiences that come with it.


Are you ready for your next journey? Contact me!

Let experienced Luxury Travel Advisor Theresa Jackson and her team help you to create your own dream journey today!

If you’d like to have more ease in your travel planning, I’d love to help!

You can stay informed and inspired in planning your travel in 2018 by reading more of my blogs. You can also follow me on Facebook. Twitter @enlitndjrntrvl, and Instagram @enlightenedjourneystravel. Sign up to receive the blogs and a newsletter filled with more insights and offers so you don’t miss a thing.

luxury travel advisor Theresa Jackson on one of her adventures journeys

At Enlightened Journeys Travel, we design handcrafted travel itineraries for your immersive journeys of a lifetime.

Keep exploring – Life’s an adventure!

I look forward to opening hidden doors in exclusive travel for you!