How To Plan The Perfect Trip

How To Plan The Perfect Trip | jumpseatjenny | Travel and Lifestyle Blogger | Lisbon Portugal

Planning a trip can quickly become overwhelming – years of research have lead me to a compilation of largely unorganized notes. Scheduling changes can mean that I’ve got to formulate a new itinerary with no time to spare.

To say that I am a thorough planner is an understatement. Being the type of traveller who will drive far and wide for a milkshake I saw on the Internet means that at times my “itinerary” is a touch overwhelming. I have learnt the hard way not to create unreasonable expectations. Picking a few key “can’t miss” spots in each destination is key.

As a rule of thumb I always keep a notebook on me at all times. You never know when you’ll stumble upon someone with a thorough knowledge of an area that you’ll soon be visiting. This is especially true in the flight attendant world where almost everyone you come in contact with has/is/will travel. I take no shame in whipping out my little pink book with its destination categorized pages. However, often I am heading to destinations for which I haven’t gotten any recommendations, in that case I turn to the following resources;


A fantastic way to gather “Must-Do” and “Top 10” lists for any location. There are endless suggestions at the ready, which may even lead you to blogs that become a daily read. This is the first place I go to gather information and select articles to read based on title and the image chosen to reflect the link. (Talk about judging a book by its cover)


Next up I always check the location tag on Instagram, if a place is worth checking out it’s likely that people have – and that they’ve wanted to share it! I’ve discovered interesting restaurants, shops and galleries this way. Generally speaking they will have hashtagged the location or mentioned it in their description. If you find an Instagram account that seems to frequent interesting places in their area they are worth a follow!


There are a couple blogs and websites that I compulsively check every time I am ready to explore a new area;

Hand Luggage Only 

is an excellent blog which couples incredible photography with an extensive list of destinations and recommendations.

Messy Messy Chic

is described as a cabinet of curiosities, which couldn’t be more accurate. It’s a fun collection of articles showcasing vintage finds, offbeat locations and truly interesting bits of history.

Atlas Obscura 

is neat user submitted community where fellow explorers can submit “hidden gem” type attractions. Offbeat and mysterious locations that are difficult to find elsewhere are often mentioned on Atlas Obscura. I have used this website for areas abroad and to discover interesting destinations right in my back yard.


is somewhere I always turn if I am looking to explore locally, for their fun local bucket lists and local escape suggestions. It is geared towards GTA (or Canadian depending on which city you choose) readers and I am always pleasantly surprised by their suggestions.

After having compiled a long list of things I would like to do and see I will organize all of the landmarks by type; see, eat, drink, shop and nightlife. Destinations can be as small as a graffiti mural and don’t necessarily need to take a load of time even some of the larger attractions can take as little as 5 minutes to see. It depends on which kind of traveller you are – I enjoy seeing beautiful things for myself, capturing a picture, enjoying the sight then moving on.

Once categorized I will use Google maps to pin point all of the attractions I have picked relative to the hotel or AirBnb I intend to be staying at. I rearrange and eliminate stops according to walking time and logical order. For example, if two restaurants I have picked are right next to each other I will obviously only pick one. The other I could return to another time or stop into for just a coffee. Or if one of the landmarks is much further than the others it is clear that I either have to make it a priority or leave it off the list this time around until I choose to explore the area its in.

Once everything is mapped out nicely I jot down the landmarks in the order that I will visit them. I like doing this on a small piece of paper that is easy to toss into a purse and dispose of when I am finished, this way its not a hassle to pull it out on the go. Also, it is always a good idea to write down a couple alternatives that did not make the list (especially with restaurants) there is no guarantee that where you want to go will be open or have space so always keep some desired backups on hand!

This “method” of planning is something I’ve developed purely through experience and time. Hopefully some of these resources could help you plan your next perfect getaway!

Happy Hunting!