How to Choose (and Plan) a Vacation in 5 Steps

This vacation planning blog post includes some referral links for your convenience, at no cost to you.

how to plan a vacation - ochristine

Do you want to go on holiday, but don't know how to choose and plan a vacation? This is a common issue for many travelers and makes planning a trip abroad seem like one big headache. It doesn't have to be that difficult: here is the 5-step routine I use to streamline the vacation selection and planning process.

Step 1. Decide on a budget 

I am a long-term traveler, so trips and vacations are often birthed from realistic financial decisions. The trips I take are usually a less expensive alternative to my lifestyle in the United States. As a result, I decide on a budget by calculating what "life" would cost if I stayed home (in the USA) and usually choose a trip that would cost significantly less -- unless it is a major bucket list destination, of course. 

In the United States, for example, nomad life can cost $1,500-$2,500 per month as a couple (unless we are housesitting for longer than a month and spending very little on groceries -- which depends on the city), so an international trip that is under $1,500 for the same amount of time is an ideal budget for a one-month adventure.

Step 2. Choose the best flights

While some people may advise you decide on whether you'd prefer beaches, cities, or the countryside before choosing a place to visit, I disregard those categories altogether (because I love them all). Instead, my partner and I claim our deal-breakers (like places with weather below freezing) and head to my favorite website, to browse the cheapest flights from our city.

I love using this website (and have used it for four years now) because it searches the web every 48 hours for some of the best deals over the next 90 days. I never book through their portal but use their information as a starting point before heading over to Google Flights to see which airlines have the best price and schedule. 

To those wondering, yes I still use Skyscanner and Skiplagged to search flights, but Skycanner has failed me a few times with inaccurate pricing and I haven't loved the new changes to Skiplagged (I can't find what were once my favorite features).

Using is how I found my life-changing trip(s) to Costa Rica, Amsterdam flight with an awesome stop-over in Iceland, and now a month-long trip to Taiwan. My Taiwan trip is the latest booking as of this post so I will reference it in my planning examples.

We were able to book a trip to Taipei, Taiwan from SFO (San Francisco International Airport) on a direct flight with United with less than three week's notice for about $450pp. Because we share one of our primary rewards credit cards to collect points for our travel (Chase Sapphire Preferred — update: now we use “Reserve”) we booked both flights with $650 worth of points through the travel portal, paid just $250 out-of-pocket for the flights, and collected more points for our purchase. 

Note: If you are thinking about getting a Chase Sapphire Preferred card, apply here to earn 50,000 bonus points (the equivalent of $625, according to

If this method still didn’t get you the flight price of your dreams, read my other article on the best ways to find flight deals and error fares.

  • Extra note: When you find the flight that meets your budget, PAUSE. Don't book until you've completed step three.

Photo by  Sofia Sforza  on  Unsplash

Step 3. Double check Costs and Tourist Requirements

Don't book that flight yet! Once you find the best price, you have some research to do.

The one thing that hits travelers unexpectedly is booking a cheap flight without double checking the destination's visa and vaccine recommendations, passport requirements, as well as food and accommodation costs.

For example: 

  • Iceland can be reached from NYC for about $500 (or much less if you are doing a free layover) but kicks your butt if you are a human looking for food and shelter (it's SO expensive there).

  • Bolivia was the most stressful visa experience I ever had because we didn’t do our research (and because the rules were always changing)

  • Other countries' vaccine regulations alone can break your budget (yellow fever and typhoid vaccines aren't covered by most health insurances).

  • Many countries require your passport have an expiration date that is six months out or longer (this means if your passport expires in three months, you may not be allowed take that 3-day trip abroad)

In fact, before we booked Taiwan I actually chose to go to Hong Kong. The flights were about the same price but upon further investigation we realized those cheap flights would require two layovers and the accommodation options were a bit out of our budget (and frankly not rated very well).

We knew part of the reason for our slim pickings in Hong Kong was the last minute nature of our trip. Much of our options were booked. So we went back to and noticed Taipei's similar flight prices -- a city we knew nothing about but are now so excited to visit!

With a quick search on,, and we also confirmed there was more housing availability with higher guest ratings, no visa requirements for American tourists visiting under 90 days, and daily expenses that better fit our budget.

Once you've confirmed that the destination of your choice has requirements and costs that meet your timeline and budget, book your flight!

Step 4. Choose where to stay and what to do

This is the most overwhelming part: choosing where to stay and explore, and how to get to it all.

To get a general idea of what to do in an unfamiliar destination, I first search 10-20 websites with the terms "top things to do in X", "things you can't miss in X", "what is X known for", and "# day itinerary for X". I search tour company itineraries, blogs, and tourism websites to build a list of cities / towns, sites, foods, and photo spots to experience on my trip. 


To get organized, I then create a custom Google map and share it with my travel partner. We'll decide on categories that interest us and go on a hunt pinning locations on the map. These pins represent recommended restaurants, places of worship, museums, national parks, and more. We later organize the pins by color according to the schedule.

The above screenshot, for example, is our Taiwan trip map (still mid-planning, so let me know if a must-see item is missing). We use this step to see where the majority of the pins end up so we can decide on where to stay (and for how long). Taiwan is a small island, and while many of these pins can be accessed from Taipei within a few short hours, doing this activity helped us realize that dedicating a few days in other cities and towns outside of Taipei might offer a fresh look at Taiwan beyond Taipei 101.

Another website I recently stumbled upon and love (especially if you don't have the time to plan) is a website called Inspirock. I can't tell how they make their money (probably through booking tours) but they let you plan itineraries for free based on your destination. Simply enter the country and travel dates, and indicate your interests and desired travel pace. They then create a recommended itinerary for your entire trip.

This is a great supplement to double check against your own plans. Here's a screenshot of part of my itinerary they created. It didn't include everything on my Google Map but definitely had more detail (like addresses and local transportation).


Step 5. Get ready to go!

Once your flights are booked, visa and vaccine requirements met (I try to avoid places with strict requirements), and the majority of your hotels are booked, start thinking about the small, but important logistics: 

  • Do most of your hotels require cash payment in person?

  • Are there ATMs around town?

  • Do you have an unlocked phone to purchase a SIM card or an international plan (like Sprint's free global plan)?

  • Have you called your banks to submit your travel alerts?

  • Have you made copies of your passport and sent your travel details to a loved one?

  • Have you checked that your health insurance can be used abroad (or that the medical industry is affordable for tourists)?

  • Do most locations accept credit cards or are they cash only?

When traveling I always make sure I have at least two credit cards available for use in the event of an emergency. In fact, I even go so far as to make sure they are from different banks and credit companies (Bank of America Visa and Citi Mastercard, for example). Lastly, I keep a third credit card in a separate location in case I lose my wallet. 

Planning doesn't have to be exhausting

If you have the budget, you can even book an all-inclusive tour and have someone else plan it for you. But if you don't, planning your vacation in this order will really help!

We like to get on the ground and do the research and planning ourselves -- not just for financial reasons, but also because it helps us remember the details and have freedom when it comes to altering our journey as we meet more people and receive local recommendations.

Remember, here are the 5 steps to planning your vacation

  1. Choose a budget

  2. Research flights BUT pause before booking

  3. Research hotel/food costs and visa/vaccine/passport requirements, THEN book your flight

  4. Choose where to stay and what to do using a custom Google map

  5. Get Ready to Go and confirm logistics


Enjoy your trip! Share this post if you found it useful.

xx, O.

Original Photo by  on  Unsplash

Original Photo by on Unsplash