How to Plan Your Dream Vacation

Recently, I wrote a piece about the genius of shopping for swimsuits during the winter. In it, I championed the benefits of buying swimwear now. It’s smart to take advantage of the off-season sales so you’re extra-prepared for summer. Part of what led me to this discovery is my penchant for mood boarding.


The mood-board — aka vision board — is my staple way to express my creativity, exercise my personal style even when winter restricts my fashion sense to thick sweatpants and puffer jackets. It’s time to get excited for activities and celebrations that are months away.

Creating mood-boards to bring summer closer led me to buy my latest swimsuit at a fraction of the price. This simple action sent my imagination soaring. I clearly envisioned the pools I’ll swim in, the oceans and lakes I’ll plunge into, and the boardwalks I’ll strut about on while flaunting my leopard, plunged-neck bikini.

So — six months in advance — I’ve effectively pulled my summer plans together. I’ve always been a planner as it goes a long way to actually achieving whatever I’m meticulously planning, be it a goal or an awesome trip.

However, this summer’s arrangements are more fraught than ever, as my imagined itineraries ride on the hope that there’s not yet another COVID variant looming in the wings. One that cancels my flights and banishes me back to my apartment. But — in the spirit of positive thinking — I'm not going to let logic obscure my vision. I intend to go full-speed-ahead with my dreams.

La Residencia, a Belmond Hotel, Mallorca Currently on my list: La Residencia, a Belmond Hotel, Mallorca

Starting early also means I have clarity about my budget. This provides greater incentive to save money this year. I have more options than ever before. Flights are cheaper, hotels will welcome me with open arms, and my inspiration awaits.

Here are some of my tips for planning your dream vacation:

Dream Big!

Even before I started making concrete plans, I’ve already stockpiled ideas for future vacations for a future self. The pandemic taught me that life is too short to wait on those enjoyments for a future me. So, I’m taking the plunge and setting out on one of my bucket-list vacations rather than settling for a more local trip.

Save-Save-Save

In order to make my biggest dreams happen without falling into credit card debt, I’m putting aside money every month that goes towards my vacation. Before making non-essential purchases, I ask myself: would I prefer another iced coffee from my neighborhood cafe or a croissant and coffee in Paris? Chipotle or a gourmet meal in Mexico? Put that way, the choice is simple.

A app like Meet Cleo makes the money part a little easier and seriously keeps me accountable for my spending. After all, there’s no better way to stop those credit-card-swipes my credit card than depending on an app that keeps it real. Meet Cleo reminds me of my regrettable purchases before I rack up another one.

Plan EVERYTHING

In arranging my itinerary, I don’t just plan hotels and flights, I plan out every single day. Sure, I leave time to explore neighborhoods and wander through museums and stores. But even that time is scheduled. This helps me visualize more clearly what I’m going to do, but it also provides a realistic ballpark budget. When and where will I need to flag a cab? How efficient is public transit? How can I schedule my days most efficiently and cost-effectively?

Shop Smart

Leaving seasonal shopping to the last minute often leads to panic buys, overpaying, and desperately buying forgotten items at the airport. Shop smart, and start shopping today. Taking cues from my swimwear hack, I have price alerts on critical purchases so I’m notified whenever there’s a sale.

That means no more frantic airport shopping for me — my Meet Cleo app will be proud.

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