Winter getaway style + travel tips


Sharing outfit idea + travel tips for your next trip to escape the winter! 

Let me be the first to say that I do not travel often. My work as a blogger and waitress means I spend at lot of my time either working at a restaurant or in front of a computer. However, for the first week of 2020 I got a chance to go away for the week to sunny Jamaica! As such, I wanted to share my winter getaway style + travel tips for you to use for your next trip to escape the cold!

Avoid overpacking by packing only what is necessary

My boyfriend is one of the most incredible minimalists I know. For our week long trip to Jamaica, he only had a carry bag pack. That’s right – one carry on for the entire week! You can follow his example by considering the following when you are packing:

  • Your location: are you going some place warm or cold? If you are going somewhere tropical, pack more bathing suits and cover-ups.
  • Toiletries: are you staying at a resort? A house? Some of your toiletries items you can get there instead of packing in your bag.
  • Chargers: what do you need them for? Your phone, camera, laptop?

Below is a image that you can download for as an easy reference guide!

winter getaway (tropical) (2)

Petite friendly swimsuit options

I did a lot of a last minute packing for this trip. Thanks to Amazon, I was able to get some new swimsuits quickly like the one I am wearing. **IMPORTANT** this suit is a set. Sadly, you cannot switch out a small top for a medium bottom so keep this in mind. In these images I am wearing a size S but I will be exchanging it for a size M.


Swimsuit: Amazon  // Earrings: J.Crew

More petite friendly swimsuits

Traveling in style

When it comes to traveling, it’s important to dress properly. You want to make sure you are comfortable. For me, that is a a warm sweater, a pair of jeans (for me, thats comfort lol) and ankle boots. Under my sweater, I had a camisole shirt so that I could take off my sweater once we arrived to warmer weather (the fans on the plane might also make you cold so keep this in mind). Remember: comfort is key.


Sweater: Karen Kane // Camisole: BP (under $30 & one of 2019’s best sellers during Nordstrom’s Anniversary sale)

I hope you found my winter getaway style + travel tips useful! If you want to learn more about my past trips to Jamaica, you can check them out here!

About the blog

Timeless Optimist is a petite fashion, beauty & lifestyle blog by Cristina Medina. This page focuses on creative storytelling, photography and positivity.

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