Last Updated: October 14, 2025 by Michael Kahn. Published: October 14, 2025.
Whether you’re working away for a few months, a digital nomad, or simply spending time in a place you’ve always wanted to visit doesn’t matter. If you are currently planning for an extended stay in a city, it’s vital that you approach it in style.
Extended breaks do offer incredible opportunities. However, there are some additional challenges to consider too. Here are five top tips to ensure that the trip remains smooth.
1- Confirm Your Eligibility To Stay
If you are only making a domestic move, you probably won’t need to worry too much about this issue. When traveling internationally, though, it’s essential that you check your eligibility to stay in the country. Even when visiting a nation where short stays do not require a Visa, you may find that you’ll need one to stay longer than 90 days. Similarly, if you are planning to work during the extended stay, there may be additional requirements. This could even extend to tax obligations.
Avoiding nasty surprises upon your arrival into the country is essential.
2- Get Your Accommodation Under Control
Accommodation plays a key role in all trips, but carries even greater importance for an extended trip. It’s not just about a suitable location and a little luxury. You actively need essential household comforts that make it a home from home. Opting for apartment-style extended stays in Washington DC will deliver a better outcome than hotel stays in the capital. Aside from boosting your comfort during the stay, it lays the foundation for increased productivity.
Make the wrong accommodation choices and the trip will be far worse.
3- Think About Internal Travel
When taking a short city break, public transport and taxi services will suffice. However, this can become very time consuming and expensive when spending several months in a destination. An extended holiday car rental is the far better solution, especially if your accommodation has parking included. Aside from the financial aspects, it puts you in control of your travel. This covers daily commuting and road trip excursions to explore the local region alike.
It is the safest, cheapest and most comfortable way to travel. Do not ignore it.
4- Plan NatureTrips
Short city breaks often focus on visiting historical landmarks and enjoying manmade venues. You crave frantic excitement. When spending more time in the area, though, you have the freedom to couple this with more relaxed activities. Finding natural attractions like Lake Natoma in California can significantly improve your trip. Aside from the direct benefits of being in nature, you should find that relaxing your mind enhances the fast-paced city activities.
It is one of the most important ways to maintain your health and happiness.
5- Stay In Touch With Home
Finally, spending a long time away from friends and family can be a little challenging. Thankfully, you can use social media and video messaging to stay in touch from around the world. Of course, you will need to plan those interactions if you have moved to a new timezone. As well as missing people, you may begin to miss places. Keeping abreast of the latest local news by following the online news channels can be a very therapeutic feature.
Just be sure to avoid letting it distract you from the trip. As with everything, balance is vital.
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Whether she is researching the latest trends in home decor, life-changing destination getaways, or the best way to maintain your finances, Dewey takes pride in leaving no stone unturned. She is passionate about distilling and delivering high-quality information that you can use to upgrade your life.
