Is Repeatedly Visiting Portugal in a Year Too Suspicious?

I am completely smitten with Portugal. I usually set up camp in Lisbon and use it as a home base for exploring other areas. I’ve made trips in October 2024, February, and April 2025, and I’ve already got my next one lined up for mid to late June 2025. My last visit was a bit of a washout because of the incessant rain, which left me cooped up in my rental the whole time. I always worry that immigration might raise an eyebrow at my frequent trips to the same place, even though I’ve visited other countries in between. But Portugal is my sanctuary, especially since I work remotely and need a break from long stretches of work. Anyone else out there who keeps going back to the same destination multiple times in a year? One big reason for my return trips is my fantastic tour guide, as well as needing to finish off the sleeve tattoo I started there. As someone flying in from the US, I’ve never had to go through customs in Portugal since my flights usually have layovers in Frankfurt or Paris. Any thoughts or advice on this?

What are the best seats for comfort on long-haul flights?

Hey there! So, I’m gearing up for my first overseas flight from the US, and I’m feeling a bit unsure about the seating situation. I’ve only ever been on planes with the 3-3 seat configuration, and now I’m facing the wider 3-4-3 layout. With this upcoming 10+ hour flight to Tokyo, I’m eager to find the most comfortable spot to settle into for the journey. Normally, I opt for window seats to avoid the hassle of constantly getting up for fellow passengers, but I’m thinking maybe a seat next to the main row might be a better choice this time around. As a bigger guy at 6ft and 200lbs, I’m worried about feeling cramped and uncomfortable during such a long haul.

I’m also pondering the timing of booking my flight. I’m eyeing a mid-May trip next year, and while airlines are currently only offering flights up to April, I’m wondering if I should jump on those May seats as soon as they become available or hold off for a bit. In the past, I’ve typically left booking my international flights to places like Canada or Mexico until around 6 months before the trip. But is that the best approach for this long-haul adventure to Tokyo? Any advice on this front would be super helpful.

Thanks in advance for any tips or suggestions you might have!

Is Japan’s Digital Nomad Visa Worth the Effort?

Man, let me tell you about my six months in Tokyo. It all started after a wild week in the city back in January. I was struck by the intense cultural shock and organized chaos, which woke me up from my autopilot life in Germany. That’s when I decided I needed more time in Japan. And lucky me, the Digital Nomad Visa came along in April. After some hurdles, my boss agreed to let me work from Japan for six months. Fast forward to August, I landed in Tokyo, ready for the adventure.

Living in a quiet neighborhood in West Tokyo, away from the hustle and bustle, I found peace in the midst of the city. Walking around, especially during cherry blossom season, was pure magic. The food scene was incredible, with delicious and affordable meals at every corner. Despite being introverted, I managed to connect with locals at izakayas and through apps like Timeleft.

While Tokyo stole my heart, I did venture out to Hiroshima and Kyushu but always found myself longing to return to Tokyo. Dealing with the paperwork for the visa and finding housing were challenges, but the kindness and helpfulness of the Japanese people made up for it. Even when I fell ill with a severe flu, the care and support I received from locals made me appreciate Japan even more.

Despite the hurdles, my time in Tokyo was the best of my life. I found peace in the chaos of the city and fell in love with Japanese culture, food, and the warmth of the people. If you’re a digital nomad, I highly recommend spending time in Japan. It was an experience I’ll never forget, and I hope others can have a similar life-changing journey. Feel free to ask me anything about my time in Tokyo.

Are There Social Travel Options for Middle-Aged Solo Explorers?

Hey there! I’m a 48-year-old who recently went through a divorce, has young adult kids, and is taking a break from my career to figure things out after some major life changes. I’ve been doing some solo traveling since last November, but I’ve been feeling a bit lonely and bored during my trips. I try to stay connected with friends and strike up conversations wherever I go, but it’s not quite cutting it. I’m wondering if there’s a travel option like hostels, but geared towards older adults like me. I know the typical hostel scene is more for the younger crowd, and I’m not exactly looking to party like it’s 1999. So, I’m on the lookout for a more ‘elevated’ option where I can connect with people my age who are also not quite ready for the retirement life.

I’m not really into the idea of pricey group tours or retreats right now, so I’m hoping to find some more affordable and laid-back ways to meet new people and have some fun while traveling. If anyone has any suggestions or ideas for me, I would greatly appreciate it. I’m in need of some brainstorming to spice up my trips and make them more fulfilling. Thanks for any help you can offer!

Are You Thriving in the 3:00 AM Economy?

So, have you noticed that my workday starts when everyone else is wrapping up theirs? It’s like there’s a whole new hustle happening between midnight and morning. You know, you’re putting out content at 2 AM to catch those U.S. folks, hopping on calls at 4 AM to sync with Europe, or just staying “online” because, well, FOMO kicks in when you hit the hay. I read about this concept called the 3:00 AM economy the other day, and it really struck a chord with me. It’s not some over-the-top thing, but it perfectly sums up what many of us are quietly going through. Anyone else out there navigating this kind of non-stop schedule? How are you handling sleep and keeping your energy up when the world never seems to hit pause?

As someone who juggles clients in different time zones, I’ve observed this interesting shift in my daily routine. It’s like a whole new world opens up after hours. You find yourself working late into the night to cater to global audiences or setting those early morning alarms to catch up with clients overseas. And let’s not forget the constant need to stay connected, just in case something comes up. It’s a strange feeling, isn’t it? The idea of the 3:00 AM economy captures this phenomenon so well. It’s not just about late nights and early mornings; it’s about adapting to a world that never truly sleeps.

I can’t be the only one feeling this, right? It’s like we’re all part of this unspoken club of night owls and early birds trying to make it work in a world that’s always buzzing. So, how do you strike a balance between work and rest in this around-the-clock cycle? Do you have any tips for managing your energy levels and getting enough sleep when the rest of the world is wide awake? Let me know how you’re navigating this new normal because, hey, we’re all in this together.

Can We Travel Across Europe and Asia on $36k?

Hey, my girlfriend and I are saying goodbye to the 9-5 grind and embarking on a grand adventure across Europe and Southeast Asia. We’ve set aside around $36,000 for our year-long journey, aiming to keep our daily expenses to $50 each. We’re all about the backpacker lifestyle – hostels, Airbnb, camping, couchsurfing, you name it. Our plan is to hit up Europe from Portugal to Istanbul, then jet off to Bangkok for some Banana Pancake action before exploring Indonesia and the Philippines. Finally, we’ll reunite with family in Northern Australia in the summer of 2026.

We’re a bit torn on whether to work remotely part-time or just roll with the punches and use platforms like Workaway to keep within budget. Our setup is coming together, but we’re turning to the awesome folks at r/Shoestring for any tips or tricks. We’re open to all suggestions – from packing hacks and money-saving ideas to must-visit spots and places to steer clear of. Peace and love, H.

What’s the Best Bag for EDC and Travel Post-Injury?

So, yeah, I messed up and broke my collarbone in a dumb accident that was totally on me. Now, I’m stuck with a long road to recovery ahead of me, which means all my cool backpacks are gonna gather dust at home for a while. Since biking and driving are out of the question, I guess it’s gonna be a lot of walking and maybe the occasional bus ride for me in the coming months. I can’t really do any proper workouts either, so I’m gonna need some smart solutions for carrying my stuff around town and for any future travels.

For my everyday carry needs, I picked up this 7L tomtoc laptop sling bag. It’s not bad, but I could definitely use more room for my keyboard, mouse, and other essentials. Plus, a little more sturdiness would be nice to help me handle the weight better. On the bright side, my body’s pretty strong, so I can manage to haul quite a bit with my good shoulder and legs. I just need a bag that’s designed to work with my current physical limitations.

When it comes to traveling, I’ve been rocking the same backpack for ages and steering clear of wheeled luggage. But now, I’m thinking it might be time to switch things up. I could probably handle my Farpoint 40 with its side handle using my uninjured arm, but lugging that thing around the airport might be a real pain, especially when it’s fully loaded and weighs around 20lbs (or 10kg). Plus, I can’t even reach up to stash it in the overhead bin on my own. So, I’m open to suggestions and ideas on what might work best for me in this new situation.

If you’ve got any recommendations or tips on EDC and travel bags that are both safe and easy to carry, I’m all ears. I’m looking for something that can help me stay organized and comfortable while I navigate this unexpected journey of recovery and rediscovery. Let’s make the best out of a not-so-great situation together!

Want to Travel Europe for a Month with New Friends?

Hey folks! So, I’m on the lookout for two sets of couples or solo travelers who don’t mind sharing a room to join me on an exciting adventure in July. My plan is to rent a flat in each of three awesome cities for a whole month, with a total budget of around 1000-1500 euros for each place. That works out to a pretty sweet deal of 30-50 euros per night, which is way cheaper than booking through Airbnb or staying in a hostel for two people. The idea is for each of us to spend about 10 days in each city, soaking up all the sights and sounds they have to offer.

Initially, I put the word out on my Instagram, hoping to gather a cool group of travelers who are up for this unique experience. Despite the interest and excitement, not many folks were ready to commit just yet. But hey, we’re flexible! We’re even considering swapping out Barcelona or Paris for a spot in Italy if that tickles your fancy. And hey, if we find a third couple to join us, we might even add another city to the mix and spend a week in each place—depending on what dates work best for everyone.

Now, I get it, the idea of embarking on this adventure with strangers can be a bit nerve-wracking. We definitely need to chat about how to protect our interests and avoid any potential scams. Safety first, right? But hey, let’s start right here and see if there are any other travel enthusiasts out there who are keen to jump on board. So, has anyone out there ever tried something like this before? Are you intrigued by the idea of exploring multiple cities over a month with a fun group of fellow travelers? If this sounds like your kind of gig, hit me up! Let’s make some unforgettable memories together.

Moving to Portugal for Citizenship: Is it the right choice?

Hey there! I’m an American software engineer with plans to move to Portugal by the end of 2026 or early 2027. My goal is to stay for 5 years and eventually apply for citizenship. Here’s what I’ve gathered so far about the process:

First off, I’ll need to save up more than 10,000 Euros before I can apply for the long-term D8 visa. Currently, I’m on a W2 with my company, but to make this move work, I’ll need to switch to a contractor role. I’m currently making 95k, and I reckon I could make even more as a contractor.

In terms of taxes, it looks like under the NHR 2.0 scheme, I’d be looking at around 31% in taxes (20% income tax plus 11% social security tax). Not too shabby, I suppose.

To eventually apply for citizenship after 5 years, I’ll need to reach at least a Portuguese A2 level in the language. That sounds doable, but I’ll definitely need to put in the effort.

Getting the D8 visa itself takes some time, around 2-4 months. So, I’ll need to plan accordingly and be patient throughout the process.

On a personal note, I’d love to live somewhere in Portugal where I can surf. I’m not much of a partier, but I do enjoy socializing and making new friends. Oh, and I’m also a musician, so finding a community that appreciates music would be a huge plus.

If you’ve gone through the D8 to Citizenship route in Portugal, I’d love to hear about your experience. Any tips or advice you can share would be greatly appreciated. Thanks in advance!

Is Arriving Early to the Gate a Mistake for Travelers?

So, here’s the deal: if you’re like me and tend to push the boundaries with your carry-on or personal item size, you might want to play it smart when it comes to boarding your flight. Let me break it down for you.

Picture this: you’re at the gate, waiting to board your flight, and you’ve got a sneaky feeling that your bag might be pushing the limits of what’s allowed. Well, here’s a little insider tip for you – try not to arrive too early to the gate. Why, you ask? Well, some airlines have this sneaky trick where their gate agents stroll around the gate area before boarding begins, eyeing up bags and sizing them up. I witnessed this firsthand in Lima with LATAM, but trust me, it’s not just them pulling this move. I’ve seen other airlines do the same thing in various airports.

So, what’s the workaround? Simple. Instead of being the early bird, aim to arrive right when boarding starts, or even consider hanging out in a different gate area until the last minute. Keep a close watch on the boarding process, so you know exactly when to make your move and join the line. Why does this work? Well, once the boarding chaos kicks off, the gate agents are in a mad rush to get everyone on the plane pronto. They ain’t got time to be scrutinizing every bag that comes their way.

So, by waiting until the boarding process is in full swing, you significantly reduce the chances of getting busted for your oversized bag. Trust me, this little trick has saved my bacon more times than I can count. Next time you’re cutting it close with your carry-on size, remember this golden rule: timing is everything.