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How we choose our vacation destinations + travel planning tips

Mar 1, 2022

How we choose our vacation destination

How do you choose your next vacation destination? 

Back with another travel post today! This is a question that came up recently in an Ask Jess, and I feel like it really deserves it’s own blog post! With the world opening up again, I know everyone is itching to start traveling and starting to think about their next vacation! Our list of “must visits” is miles long, as I’m sure yours is too! How to choose!? The decision fatigue is real!

To help you plan out your next trip, here are some things we consider when narrowing down a vacation destination.

How long of a vacation do we want to take?

This narrows down destinations by how long it takes to get to and from and how long we need in a given location and how expensive that is to get there.

As a general rule, if we’re doing a longer trip (say, a Europe trip) we don’t like to move around a whole lot, because you lose so much time traveling between locations. We usually aim for a 3 night minimum in any city we’re in. Any less than that feels like you don’t really have enough time to get a feel of/enjoy the city, and it puts a LOT of pressure on you to pack a lot into a small amount of days and it becomes stressful instead of relaxing. Direct flights are also very important to us, as connections eat up a lot of precious time, as is how much we want to do when we get there.

How much are we wanting to spend?

Not just dollar amount but considering–is this a romantic splurge trip? Or a fun adventure trip? A mix of both? With June or without June? Is this a budget-friendly AirBnB type of trip, or are we wanting a splurgey 5 star hotel? (Note: A 5 star hotel is never worth the splurge with kids in tow IMO)

What kind of experience do we want to have?

Do we want warm weather or do we care about weather? Do we want to be outdoorsy in that we go camping/hiking or outdoorsy in that we drink rosé on terraces? Do we want to go somewhere we’ve never been, or return to somewhere we love already?

Consider high/low seasons:

I am a huge fan of planning big trips during shoulder seasons. For example, September is an AMAZING time to travel to Europe because it’s not as busy, but it’s still warm. We did Barcelona and Mallorca in early September and it was lovely and much less busy (and not so stifling hot) than it would’ve been in say, July. Not to mention, rates and flights were much more affordable.

Consider alternatives to more touristy destinations:

For example–Are you considering an Italy trip? (Say, Rome, Florence, Tuscany, Amalfi coast?) Wanting a combo of a bustling European city, small, ancient and romantic towns, and gorgeous beaches–but you don’t want to pay high season prices? With a little research, you can find places that are just as beautiful without the high prices. For example–Puglia is gaining popularity because it offers so much at a less expensive price. Or you could do Portugal for example–which is just as beautiful and offers all of the same things (bustling city of Lisbon, beautiful charming smaller towns like Porto, and tons of gorgeous beach towns) at a much cheaper price (and a lot less tourists!) Use google to your advantage!

Are there any really cool places we’ve seen on social media that have caught our eye lately?

A specific place we’ve been dying to go? Is there a hotel/experience that is sealing the deal for us? (For example, we narrowed down Mallorca as our winning beach destination for our Spain trip after lots of Instagram stalking–and I found Cap Rocat after seeing Julia’s trip! It looked SO cool–that sealed the deal!)

How easy is this to plan?

How much time do we have to dedicate to it? (Or are we willing to hire someone to help us plan it?) Do we want somewhere new, or are we craving to go back to somewhere familiar? For example, maybe we want to go to Europe, but we only have 5 days and we want a leisurely trip–we might choose to just go to Paris, as that’s somewhere we’ve been, we love, it’s easy to get to relatively quickly from Chicago, and it’s a really easy city to just “be” in. We don’t feel like we have to pack in the itinerary or plan much. Vs. if we were going to a brand new city, that would require a lot more leg work to plan and would feel like more pressure to “pack things in.”

How to choose a vacation destination

Once you’ve found your destination, some tips on planning your trip further:

Consider hiring a travel agent/planner:

If I was planning a really big trip to a place I’d never been and/or I just didn’t have the time to plan it properly, I would consider hiring a travel planner. We did this on our trip to Italy and it was 100% worth it, especially those with decision fatigue!

Since then, I’ve become friends with Whitney who is basically a travel planner for millennials who want a more local, non-touristy experience. Not only will you save hours and hours of time researching, booking, etc, but you’ll also get access to perks that you wouldn’t get otherwise–like free upgrades, free champagne, and more! She’s WONDERFUL and will plan the trip of a lifetime for you!

If you want to DIY your planning, here are more tips: 

Download the Out Of Office app

Have you heard of the Out Of Office app? Anna turned me onto it (two of her best friends are the founders!) and it’s so cool! It’s kind of like Yelp and Google meets Trip Advisor but for a very specific target audience–us! While I’ve found some gems on Trip Advisor, I’ve also been lead to some pretty awful tourist traps, so this app is curated specifically to those who want travel recommendations from the bloggers and friends they know and trust!

You can sync with your contacts and see all the places they’ve been and recommend, add in your own recommendations, create wishlists for future travel, and more! This way, you know you’re getting reccos that are in your wheelhouse, vs random strangers on Trip Advisor who may or may not have the same interests and travel style as you!

The app is still fairly new and people are adding more and more content every day, but I think it’s so helpful–I just added all my reccos for Napa, so follow me over there to see them all! (I also added in what I wore to each place, in case that’s also helpful!) I also have reccos for Amalfi Coast and Barcelona on there too!

(Note OOO sponsored a series of Instagram stories but this mention is not sponsored. I just really love the app and think it’s an amazing tool and would be remiss not to include it here!) 

Search geotagged locations on Instagram: 

For example, if I want to spend a few days in Lagos, Portugal, I will search “Lagos, Portgual” in “Places” on Instagram and scroll through the photos that pop up! Within a few minutes I can have a list of beautiful restaurants to visit, beaches to hit, and a short list of hotels to investigate!

Search flights on Hopper and sign up for Scott’s Cheap Flights: 

Have you heard of Hopper? They’re an awesome app that allows you to search your dates and see how expensive flights are to different cities during certain time periods. It’s an amazing way to save some major $$ on your flights if your dates are flexible and/or you aren’t loyal to one specific airline. They have recently added hotels, cars, and house rentals as well, although I can’t vouch for those!

You can also sign up for Scotts Cheap Flights, which sends out free emails alerting you to different deals to specific cities! Also helpful if you have a handful of places you’d like to go, are fairly flexible, and would like to let the best flight deal choose your next destination!

Consider booking through your credit card: 

If you have a travel rewards credit card (between us we have the Chase Sapphire and the Capital One Venture card) look into booking your travel through them and see if you are eligible for any special rates or perks, even if you aren’t using your points to book. I’ve scored some good deals and founds great hotels this way before!

Pack accordingly: 

If you’re traveling anywhere that requires moving around, I’m usually a fan of “less is more” as it becomes a big pain to lug a ton of stuff!  I do my best to bring items that do double duty and plan out a lot of my outfits in advance. You don’t want to waste time hemming and hawing over what to where when you can be out exploring the city! Comfort and versatility are key–but also, I want to love what I’m wearing, too!

Here are some oldie but goodie packing posts that might be helpful! 

How to pack for long trips: my best hacks and packing essentials 

My Europe in the Shoulder Seasons Packing List (Good for Fall + Spring!) 

My Barcelona Packing List (Helpful for any warm weather!) 

Don’t over-schedule:

Have a list of things you *want* to do, but don’t schedule SO much that you don’t have any free time to just soak up the beautiful place you’re in! My favorite memories made on trips aren’t ever at museums or waiting in lines at touristy spots–they’re the long leisurely lunches, the random conversation we struck up with a shop owner, the hidden gem pub we stumbled upon when we took a wrong turn, the drinks we had with new friends made on a food tour. If you pack your schedule too much, you don’t leave room for the magic to happen!

2022 Travel tips

I hope these tips were helpful in planning your next trip!

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