Ehm, from where to where are you traveling exactly? Overseas can mean a lot of destinations depending on where you travel from.

if this is your first time doing a big trip together, honestly, forget about it being prefect. it won’t be, and that’s ok. trips don’t need to be perfect to be meaningful, in fact, i’ve found the opposite to be true. the more wild and unexpected the adventure is, the more memorable and important it becomes to me.

so I’d say it’s best to keep an idea of things you’d like to see or do, but also be flexible and willing to adapt. traveling with someone that forces everyone to stick to a rigid itinerary is never fun and is a good way to ruin the trip. all it takes is one lost bag or one missed train to throw all your careful planning out the window. better to roll with the punches than self destruct when that happens.

Above EVERYTHING ELSE!!!!

DON'T EXPECT IT TO GO PERFECTLY!!

No matter what you plan and budget, something will probably go wonky. Hopefully, it's nothing major, but no matter what, IT WON'T RUIN YOUR TRIP. HOW THE TWO OF YOU DEAL WITH IT, DETERMINES IF YOU'LL HAVE A GREAT TIME.

sorry for the yelling. I just thought it was a very important perspective to share.

Where are you from? Where are you going? Can't really give you advice without knowing those things.

As a general rule: don't expect perfection. Some things will suck, and if you go in expecting everything to be perfect you'll be disappointed. Also, wherever you go is still a normal place, filled with normal people, living normal lives. Don't be a nuisance to the locals, and don't expect/demand anyone not working in hospitality to go out of their way on your behalf (and even people working in hospitality, the "the customer is always right" mentality isn't a thing everywhere).

"I want to make it perfect, memorable, and the best trip of our lives"

Lower your expectations and just focus on having a good time and getting closer to each other. If that means spending more time in bed relaxing, that's ok.

Wikipedia has a sister site which is full of travel information: http://wikivoyage.org/

Cities and towns big and small are on there. Usually with helpful info about how to get around a the destination and how to access its attractions, as well as any local customs. It was a godsend for us on my recent trip to France with my dad

Bring earplugs. Multiple pairs.

There's always more noise than there should be.

Make sure you will have internet access. You may need to buy a SIM card at the airport, or buy a plan/package from your provider that supports the country you will be visiting. It may be costly but it will be worth it.

My #1 tip is wear a mask on the plane if you're flying. You don't want to get sick, it's an instant end to the holiday.

The other tip would be to pack relatively light, you won't need a lot of things you might want to bring, just keep it simple.

We always just pick some key places, get transport (usually a hire van) and just go explore. Best thing is to go into small local places and ask them about cool stuff around. People are always friendly and love hearing about where you're from and what you're into, and the local suggestions are always stellar. Lots of times we've had people tell us a popular place is pretty shit and another lesser known place is way better. Most of the trip is unplanned apart from the key locations and expected travel route. But we'll skip stuff if we find something cooler or get advised to check out another place a day out of the way. We've diverted from plans lots of times, and because that's loosely the plan, it's super fun and rewarding.

It's also important to go do your own things and get out of each other's faces. Im into a lot of stuff she isn't and vice versa. So some days we go check out our own stuff and do our own things, then at the end of the day we share our adventures and anything cool we found we think we should check out later. I also tend to make friends easy, so it's not unusual for her to meet me and some fellow travellers at a bar and we exchange how our trips are going, what's cool, what's not, and suggestions on where to go next. Locals and other travellers are always friendly like that and it's obviously super interesting learning more and sharing about yourself and home country, where they should go if they ever visited it.

Lastly, don't stay in one place too long unless there's a reason like you're snowboarding for a few days, or something like that. Things can get real boring when you've seen enough but are still stuck there for a couple more days. That's why we usually opt for a 5 person van over hotels, little hotel room on wheels and costs about the same. It's also frustrating getting to a new place and it's awesome, but you're meant to fly out soon and you wish you didn't waste that extra day or two at the place you weren't having much fun.

It's important to remember, everything is just another town or city like where you came from. It's the culture and experiences you're chasing there which you can't get back at home. "Can I do this at home? Yeah." move on.

Relax and don't worry about itineraries. You will get to a place and love it, and get somewhere else and hate it. Be flexible.

From experience: chill out. Do your homework in the background to ensure you understand train stations, airports, city centers. I'm that guy, I try to memorize maps for weeks before a trip. (I enjoy this).

Then when you are there just go with the vibe. Try to make things seem casual and carefree.

If the attraction is too crowded: oh well. Let's just get coffee and stroll the city center.

If the rental car gets a flat: oh well. Let's just have a picnic while we handle this little tire thing. (Safety off the road of course)

A little slow at a train station waiting for a connection? Let's review our photos and pick some favorites.

You can see my thread is: have a plan of how things should go, but then be ready to have a "zero-speed" alternative in your head that boils down to: "I'm spending time with my gf in a new place, and that's enough"

I've done a lot of this.

One thing to remember is that the things you look back on fondly will be the most frustrating and painful in the moment. Try to keep that in mind when things go sideways. Nobody remembers the times when everything went perfectly.

That said, my fiancee and I have developed a set of travel ideals to keep us both from feeling like hobos.

Two nights, minimum. We try not to spend single nights anywhere. It isn't worth it. We don't end up with enough time to see anything. The big exception can be first and last-day hotels.

Four nights after three shorter stops. We need the extra day to crash and/or do laundry, etc.

Try to spend (at least) a full week somewhere. We both really enjoy the simple process of learning to live somewhere. Learning the transportation system, buying groceries, etc.

No Airbnb for less than a week. The hassle and uncertainty of getting situated isn't worth the trouble.

Depending on distance and timing, it can be worth it to double-book the last night at an airport hotel. The last mad rush to get checked out of an apartment, and get to the airport on time isn't ever fun, especially somewhere like CDG in Paris. It can be really nice to just remove that stress from the equation.

I hope you have a fantastic trip!

I can buy a lot of travel staff in this sport shop!

Don't fly Boeing!