It’s been over a week since I’ve been back and between jetlag and Holidaying (Thanksgiving, Black Friday sales, Xmas Prep) I’ve been all over the place. My plan now is to properly document a few things:

  1. How I plan for my trip: booking tickets, choosing hotels etc
  2. How I manage trips with a full time career
  3. Hotels I stayed at and reviews
  4. Trip highlights and photos galore.

With this first post, I’ll share how I choose a destination and how I plan for the trip. This will somewhat encompass aspects of #2- how I manage trip with a full time career.

For most of my travel, I plan well ahead, always 6months ahead of time if not more. It usually starts with Google Maps- yes, seriously. I literally pull up the map and look at the lay of the land. Well, let me rewind a little. It actually often starts with the calendar- not just the calendar but all the national (bank) holidays in the year.  I mark off MLK, Columbus, Labor, Memorial, Veterans, Thanksgiving, every single day that I have off. I look to see how I could max those days. Is Columbus on a Monday or Friday- Can I turn it into a 3 day getaway or better yet, a 5 day trip. I’m willing to travel 5-10hours for a 5 day trip. Longer travel time means more days away. I mark off the dates in my calendar and then I check out my office calendar. What’s happening at the office, what’s on my boss’ calendar, my peers, and what’s going on with staff that report to me. I literally map it all out, taking all of above into consideration. If more than one person in my core team is going to be out, then that’s not the best time to go away. On average each year, I take off 15-20days, even though many people think I take way more. Just a reminder- social media and Instagram magnify/amplify each trip.

So, where was I? – Ok, calendar set, now on to Google maps. The goal is to have one long trip and 3-4 shorter trips, not counting weekend getaways that don’t require time out of the office. For every 4-5 day window I have on calendar, I look to see where I can get to in under 10hrs (under 8hrs is preferred) of travel time. Being based in NYC this usually translates to the Caribbean, Canada, quite a bit of Europe, some parts of Central America.

Trips I have taken during a 5 day window have included going to Barcelona in November, Panama in October, Bermuda earlier this year, Montreal almost every summer, Curacao in August (this was more about my sisters wedding), New Orleans, to name a few. These kinds of trips are really the best kind when it comes to maximizing your days off.  I always make sure to book a late flight on my workday- that way I actually go in to work, then take a late flight out, this reduces numbers of physical days out of the office.

Now, longer trips are a little trickier not only for scheduling but also because they tend to cost more. So planning for this requires thinking about the other variables – best time of year to visit, shoulder season vs. peak season, flight deals and prices. I am avid consumer of travel mags and blogs- so even before I look at the map, I have ideas in the back of my head from mags such as AFAR, Travel &Leisure, CN Traveler, NY Times travel section or Travel Noire and more recently instagram feeds which the travel industry better credit for increasing the appetite for travel. So while I look at map, I’m thinking about places I would love to see, where I would get the most for my money, the kinds of cultural and educational experience I’m seeking. It was by looking at Google maps 2 years ago that I realized I had seen so little of Asia and the Middle East and decided to fit trips to both on my calendar. So far I’ve been able to visit Thailand, Cambodia, United Arab Emirates (Dubai and Abu Dhabi), and just now Indonesia, Singapore and a quick teaser of a visit (1 night and day) in Hong Kong.

Looking at the map, also reminds me of how big the world is and I pin places of interest that go into my “maybe soon” list. With dream destinations noted, I turn to my most favorite tool- Tripadvisor and look up 2 things. (1) Things to do and (2) Places to stay. I’ve shared here before that I like nice hotels and it may sound so superficial, but I hate it when a destination has limited accommodation- I actually have 2 destinations that have been on my list for a few years now, I’m hoping someone would open a decent hotel at both of them before I go.

I bookmark things and hotels of interest and then I set fare reminders using Kayak while also checking out sites like the flightdeal desperately hoping for a crazy deal or a travel match with my list. And then the waiting and watching game begins, fingers crossed it all lines up- dates, prices etc. And right at that moment when it does, I start the process all over again- thinking and planning for the next one, like every travel junkie does.

Pictured Above:

Hotel Room Stay at Katamama, Seminyak Bali. more on this location later.
Brief review: LOVED IT, LOVED THEM!!! Their Tripadvisor page doesn’t lie.

Having Kynd Coconut at Kynd Seminyak Bali– Vegans reunite (sshh I eat meat, but appreciate clean eating)

Sandals: Abercrombie seen here.
Shirt and bag- purchased in Bali





  1. Jessie

    December 17, 2017 at 5:24 pm Reply

    You’re such an inspiration! Thank you for this post. It was so informative. 🙂

    1. simplycyn

      December 19, 2017 at 12:18 am Reply

      Oh, thanks a ton. Means alot.

  2. Alexia

    November 29, 2017 at 10:25 pm Reply

    Hi there! How do you manage traveling to countries where you don’t speak the language? I’ve traveled in South America because I’m comfortable speaking Spanish but I’m a bit nervous to venture where I don’t know the language.

    1. simplycyn

      November 29, 2017 at 11:30 pm Reply

      I speak English and French and honestly those 2 have taken me very far. As English speakers we are so lucky cos most people have minimal familiarity with the language. For those places where english has been an absolute no go, I use language apps and smile alot. I’m so serious I have had conversations with people just with a series of smiles and hand gestures. Don’t let language stop you- it’ll just force you to be more creative with your communication and thats a good thing.

  3. Linda

    November 29, 2017 at 5:08 pm Reply

    Thank you for this detailed post. I have a question but it’s about your Instagram travel videos. I must say I look forward to watching your travel videos. They are well edited and always make me want to hop on the next flight. If you don’t mind me asking, what do you use to shoot your videos and how do you edit them?

    1. simplycyn

      November 29, 2017 at 11:28 pm Reply

      HI Linda, means alot that you like them. I use iphone to shoot all video, just easier and I edit them using either quik app, flipagram app or imovie. please let me now if you need more detail

      1. Linda

        December 3, 2017 at 4:16 pm Reply

        Thank you for responding 🙂
        I have few more questions. How do you edit your Instagram photos? What photo edit apps do you use? And do you take photos with your iPhone as well or only with your DSLR camera?

        1. simplycyn

          December 4, 2017 at 6:53 am Reply

          I use Lightroom to edit every single pic on blog. On Instagram, I use Snapseed to edit pictures. I take instagram photos on iphone sometimes but rarely would I use an Iphone pic on the blog.

  4. KaKa

    November 28, 2017 at 11:03 am Reply

    If you don’t mind my asking, please what do you work as? And what did you study?

    1. simplycyn

      November 28, 2017 at 10:34 pm Reply

      I’m an attorney currently doing Compliance work. Went to law school.

  5. Kay

    November 28, 2017 at 8:46 am Reply

    Hey Cyn! Love how detailed you are in this post. Just wondering, do you usually take these trips alone? I’m asking because I will love to go to most of these places you mentioned but don’t know if they are safe for me (I’m a woman and 24 years old btw)

    1. simplycyn

      November 28, 2017 at 10:33 pm Reply

      I often travel with my camera shy hubby. I have taken some trips alone (Paris, London, South Africa to an extent). Almost everywhere I’ve been is safe and sometimes even though I travel as a couple, we split up as we may have different interests. I would say, the more likely you are to blend, the more appropriate it is for solo travel. For plafes where you may stick out, you can still travel solo, but I’d recommend that you have a point of contact as well & limit night time activities until you’re comfortable in a location. I have tons of solo travel girlfriends.

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