How to Make Your Dream Bucket List Trip a Reality

This image was taken at the romantic and luxurious Ladera Resort while Scott and I were traveling in St. Lucia several years ago. For me, this island was definitely on my list of dream bucket list destinations and it did not disappoint. For some people, a dream destination pops easily into mind and they know exactly where they would go in a heartbeat if there were no obstacles. For others, it’s a bit more ambiguous. You might have an idea about what you’d like, but you might not be entirely certain where you’d have your passport stamped if the opportunity came up tomorrow.

We all know that the best way to make something happen is to start intentionally giving it shape — something to look at, imagine, talk about, and (most importantly!) plan for. With that in mind, here are a few questions to ask yourself so you can get started working out the details of that trip you fantasize about during those hectic workweeks.

What’s your “happy place” when you have bad days? Again, for some, this might be a specific place — Bora Bora or the Alps or Johannesburg. But more than that — what’s the feeling you go to when you’re stressed out or stuck in traffic? Do you imagine the lazy perfection of pristine beaches? The thrill of craggy mountains? The rush and sensory feast of busy marketplaces? The smells of spicy foods? Make a quick list: 10 things that come to mind on the most fun, free, relaxed, no-obligations, open day you can imagine.
What do you crave? Think of what you say you wish you had more of — free time, adventure, romance, time to learn a new skill, sunshine, purpose. What are you truly, deep down, just plain hungry for? What do you long for? When you imagine being your best self — what are you doing? And who is with you? Jot down 10 things you are longing for in your life right now.
What season suits you best? Do you love to soak in the sweltering heat in your swimsuit? Or the crisp crunch of autumn leaves underfoot? Or the intense blue quiet of a mountain snowfall? When do you feel most at home in your body and most in love with your environment? Your perfect vacation doesn’t have to be the most popular! It’s your perfect vacation, remember?
What’s one crazy luxurious thing you secretly wish for? For some people, it’s as simple as a pile of books and no emails to answer for three weeks. For others, it’s endless room service or all-day spa treatments or king-size feather beds and huge whirlpool tubs. No matter how big or small — go ahead. Write down five luxuries that would make you feel like you’d won the lottery if someone handed them to you right now.
When you scroll through magazines, which images grab you the most? What colors draw your eye? Spicy and exotic? Cool and laid back? Misty and mysterious? Go to a bookstore, and pick up four or five travel magazines — and just notice which images you keep going back to, the ones that make your heart skip a little. You might be surprised. Some people assume that their “dream” trip is an all-inclusive resort somewhere. But if you keep coming back to the pictures of a bike tour through Tuscany — well, that’s worth paying attention to. That experience might feed something in you that an all-you-can-eat buffet might not even begin to touch. Cut out the images that speak to you the most and look for common themes, even (and especially) in images that seem to be opposites.

When you’ve had time to assemble your thoughts — and if you’re working on this with your partner or friends or family members — look for overlaps, recurring themes, those quiet nudges you can’t seem to shake. Listen to your gut. And start to dream big.

You can set a goal, start saving if you need to and start giving shape to your plan. Put your images and any accompanying words or phrases up on a cork board, or glue them to a big piece of tag board, or make a digital collage that can be your screensaver on your computer at work — anyplace where you’ll see it multiple times a day — and let those images inspire you as you get closer and closer to making your bucket list trip a reality.

The best part? I can help you design this trip down to the last customized detail. Send me an email or give me a call and let’s get started!

Yours in wanderlust!

Heather

Curated Travel