How I travel 5x a year with a full time job

I'll be sharing my tips for memorable but budget-friendly travel and balancing vacations with a full-time job. 

Some context: I do not work remotely or travel for work. I have 18 days of annual leave which is enough to travel 4-5 times a year..

I hope this post gives you practical tips on how to balance a full-time job with frequent travel while keeping it affordable.

Why aim for five trips a year? For me, travel is a great way to recharge, and getting away every three months is the ideal rhythm. I try to balance things out with two longer trips and three shorter ones, plus an occasional bonus getaway. In 2024, I managed to take five trips, spread out fairly evenly throughout the year.

Travel style

Whenever possible, I like to visit multiple cities during a single trip to make the most of the experience, as each city offers something different. By using a total of 22 leave days, I was able to enjoy 36 days of vacation time.

In this post, I'll be sharing how I prioritize and organize my time for travel. For me, a trip is truly successful when I return feeling refreshed and recharged, without the usual post-holiday blues, and ready to get back to my routine in Singapore. Although travel planning and research can be time-consuming, I've streamlined the process using my own templates. I hope this post offers you some helpful insights on how to do the same.

First trip of the year

I prefer to kick off my first holiday in March, as I like to use the first two months of the year to focus on work and build momentum. After that, I travel every three months, starting from March, with one slightly shorter getaway that extends over a weekend.

Travel days

The countries I choose to visit are shortlisted based on favorable weather conditions and the timing of public holidays.

When possible, I try to plan my trips around public holidays to minimize the number of leave days I need to take. I always include weekends as well, which is why I organize my vacation days well ahead of time. Weekends are always factored in, which is why I plan my vacation days well in advance.

Insurance

So far, I have been using FWD for an easy claim process.

Flight tickets

Here are my tips for saving on the biggest expense. I have a price range that I’m willing to pay for flights to ensure the cost stays reasonable.

I keep benchmark prices in mind based on typical rates, travel period and duration. This means I usually travel during off-peak seasons or look for good deals during peak times. For example, I purchased a 13-hour flight to the USA in December, a peak period, for $1.5K. Paying $1K for a 6-hour flight to Japan doesn't feel that justified.

Another way I reduce my overall trip expenses is by booking multicity flights. This offers greater value as I get to visit different cities. As a reference, I can get a direct flight to New york for $1500, but a multicity flight covering New york and LA costs $1800.

Price range

When purchasing flights, there are several factors to take into account:

Budget: For trips under 6 hours, it's ideal if the ticket costs less than $500.

Flight Timing: I prefer flight schedules that minimize disruption to my sleep, allowing me to feel rested.

Price: Where to buy tickets depends primarily on price, though there are some situations where third-party travel partners may be preferable.

Agoda, Trip, and Expedia are available for booking flights that involve multiple airlines.

Length of trip

The length of the trip is based on the activities at the holiday destination, which is why I prepared the itinerary first to figure this out.

So far, trips to nearby countries are usually 3-4 days, while destinations that are 6 hours away tend to be 8-11 days.

I usually purchase my flight tickets 6 to 12 months in advance or during sales events to secure a good rate.

I use Google Flights or Skyscanner to choose my preferred flight departure and arrival times and to monitor prices.

Hotel

To secure good hotel rates, I use travel deal websites like Agoda, apps such as Shopback, or credit card rewards programs. Traveling during non-touristy times of the year can save money on both flights and accommodation.

My criteria for hotels cover these five areas, with a typical price range of $100 to $250 per night. My default accommodation choice is a hotel. However, if I can’t find one that meets my expectations, I’ll consider Airbnb. If Airbnb also doesn't work out—like in the case of my New York trip—there are Telegram groups I can explore. During certain times of the year, there are often room vacancies when hosts are out of the country.

Public transport

Generally, I prefer using public transportation to stay active and burn more calories by moving around, or I take a cab. For cities like Jeju, there’s no choice but to hire a private driver.

Activities

The activities and food are the main attractions of my travels; I love to experience things that aren’t available in my country. My travel priorities are hiking and enjoying beautiful views along the journey, discovering local scene, and joining interesting classes. For day trips,I like to do hikes that is within 4 hours, as it is between lunch and dinner.

Food

As a foodie, I love to try the local cuisine during my travels, especially dishes that are unique to the city. I bookmark places and food recommendations I come across on social media on my Google Maps, so I can explore when I travel. The food doesn't need to be pricey. The recommendations are typically great value for money at their given price point.

Shopping

I love shopping, but it had changed so much ever since my concept of spending had evolved. I no longer want to accumulate things in my space. Much of the shopping I do is overseas, especially finding memorable items made locally or products that are much cheaper.

A note on travelling

Travel is fun and it is a powerful form of self-care for myself, offering a break from daily routine. I love the inspiration and experiences that I cannot find in my home country. I hope this post has been useful. For travel deals using insurance and credit cards, you can click on my post here