How Paul & I Plan Our Vacations--flights, hotels, restaurants, & more!

How I Plan Vacations

When I started drafting this post Paul was PISSED. Realistically, he plans all of our vacations. He has agreed to share some insight, though, since I’m pretty worthless when it comes to booking just about anything. I get super overwhelmed with the options and when websites look like something from the 90’s (ie: Ferry booking websites) there’s just no hope. The best I can do is pick the destination, and even sometimes that’s a struggle. Things that factor into this decision range from: How far is it? How many planes will I have to get on? What type of hotels are available? How expensive is it? What’s the time difference (my jetlag is gnarly!)? When is the best time of year to go for good weather? If all the answers align with good / acceptable answers, then we are good! But if not, then we have a problem. Can you see how it can be tricky picking a place?

Something you should know about me, if you didn’t already know this, is I’m VERRRRRRY lazy on vacation. I don’t like to “travel” per se. I like to vacation. Big difference. I like to lay on a beach, read my book, drink a cocktail, eat, and basically keep doing that every day of the trip. I’m not very active when I vacation–fuck the gym! Like I’d waste space in my luggage with workout shit?! No thanks. Vacation time is for relaxing and being worthless, not for being productive and healthy. No judgement if you’re the complete opposite, but just know I’ll be waving at you from the beach with my cocktail at 9:40AM while you run on the treadmill….that’s all.

Anyway, Paul has is down to a science at this point. He knows in order for us BOTH to have a good vacation, it needs to revolve around the beach. I enjoy city trips sometimes, but it has to be something that will allow for frequent food and cocktail breaks (aka Italy). I’m slightly ashamed to admit this, but I’m not a big history person. Museums, churches, historic landmarks, etc. just don’t excite me. There’s usually a line involved, and even worse, they are usually indoors. I like spending my every waking moment on vacation outside. I want sunshine, fresh air, sand on my bare feet, a TAN! If we are on the same page so far, I think my / our tips will be helpful to you. Otherwise, you might want to Google a different travel guide for booking trips LOL.

Tips For Planning Your Vacation: (P is Paul, S is Sivan)

P: First decide on the type of trip: tropical, city, island hopping, active, road trip, etc.

S: Google weather reports and trends for your destination. There is NOTHING worse than arriving to Positano and seeing all thunder storms on the forecast. I will say this, I’m either cursed with bad weather when I travel, OR tropical / beachy destinations are just THAT unpredictable. Literally anytime I’ve gone on a beachy vacation (ie: Fiji, Bora Bora, Hawaii, Amalafi Coast, Cabo) and made sure to go during the best weather periods I’ve encountered rain and clouds at some point. No joke, EVERY. SINGLE. TIME. without fail. SUCH a buzzkill but that’s what you risk in beachy destinations.

P: I like to look at US News to see the highs and lows (temperatures) to determine when “shoulder season” is. That’s our preferred time to travel since it’s right before high season, aka less busy and less expensive. I also look at local advisories to know what’s happening in the city.

P: Keep an eye on the flights. Check well in advance first (start 6 months before the trip) and check rates daily. Make sure to check from different devices since airlines are sneaky and can raise the price if they see you checking from the same device often. We typically book flights between 2-3 months before a trip. It can get risky, but if you’re watching the rates (Google Flights & Kayak are our fave sites to check) you should know if you’re getting a good deal or not. Kayak has a tool that will let you know if flight prices are expected to go up, so pay attention to that.

P: Some things we always look at when booking flights: flight time, layovers, stops, etc. We try to fly direct as often as possible, but if that’s not an option pay attention to your arrival times and how long you have between flights (too short is cutting it close, but you don’t want to sit around for hours, either). Once you’ve picked a flight, book through the airline. They will treat you better.

P: Use to look up which seats on a plane are the best. They will tell you things like which seats are worth the $, more leg room, arm rests don’t work, etc. We don’t fly business so I do everything in my power to make it as enjoyable as possible without having to shell out all the $$$$.

S: Once the destination is selected, I start making a list of the things I want to do. Based on the distance of each thing / activity, we decide on how many days is appropriate. If it’s just a laying-on-the-beach type of trip then 5-6-7 days is plenty. If there are actual activities involved, or if it’s Europe, we always factor 2 days for travel. In my head those days don’t count so we will usually do a 12-day trip if the travel is intense.

P: We always look for a hotel with at least 4 stars on Make sure you look at the guests’ photos in addition to the professional hotel ones. Those photos are the real deal. I also like to check out their tagged photos on IG to 1) get ideas for good photo spots & 2) determine if the hotel is what it says it is online. Also, make sure to check the location / distance from all the things you want to do. Sometimes great hotels are inexpensive because their location isn’t ideal.

P: We never book ocean views or pay extra for better rooms (unless it’s hardly an increase in $$) since we will pretty much just be sleeping there and spending all our time outside. However, you can always see if they have an upgrade available when you check in, and sometimes you get lucky and it’s free.

S: I’d say we mostly stay at boutique hotels, but every now & then we like to do a big resort like the Four Seasons if we are in the mood to splurge and enjoy maximum luxury (ie: Bora Bora).

S: Instagram is seriously one of the best resources for finding things to do, see, eat, etc. I find SO many great hotels, restaurants, shops, & beaches just by scrolling through IG. If taking cute pics is important to you, I recommend doing this & “saving” the image into your archive for future reference. Pinterest is also great for inspiration.

P: I like to look up random blogs and forums to find the non cliche things to do and see when we travel. It takes a lot more time than Sivan’s method (Instagram & Pinterest), but it’s worth it.

S: Since eating is truthfully the highlight of my evenings on vacation I always like to go big. No dinner is wasted unless I’m too drunk and need to do room service. But typically I like to find something with good vibes / ambiance and a spectacular menu. Food is a BIG part of the trip for me, so even if it’s $$$ I still do it. Chances are I won’t be back for a long time so YOLO!

P: I use Yelp to narrow down restaurant selections. I know what Sivan likes–cute decor, good drinks, and excellent food. Just like looking up things to do, I read through tons of reviews to really determine if the ratings are legit. You have to be able to read through the B ratings to know if the person is similar to you or just an overreactor.

S: Depending on the type of trip (beach vs city), I start buying my clothes about 1 month in advance. I love the feeling of new stuff on a trip. I load up on bikinis, bring 1 or 2 denim shorts, a cover-up for each day, and a dinner outfit for each day. Obviously there’s a lot more: shoes, hats, toiletries, chargers, Kindle, pills, etc. but the clothing sitch on my type of vacay is VERRRRRY simple. On most tropical vacations I can get away with just a carry-on.

Did we miss anything? Paul & I are answering all your travel questions down below in the comments!