How I plan my solo trips: 9 tried-and-true steps

2020 marks 9 years of solo travel for me. One of my favorite things about traveling by myself is that I get to make all the decisions: where to go; what to eat; when to head back to the hotel early because I’m tired from walking or burned out from too much human contact. In the past 9 years, I have developed a trusted personal trip planning routine that has worked well for me.

1. Research a potential trip on Wikivoyage

Wikivoyage is my favorite resource for getting a high-level but comprehensive overview of what a destination has to offer. I look closely at how easy it is to get around (i.e., how is the public transportation?), the different neighborhoods that comprise the city, and top sites for sightseeing (the “See” section). After reviewing the overview of the destination, I decide whether it’s worth embarking on the trip. This is also where I check for visa requirements.

2. Research travel prices and routes

Since I’m currently based in central Europe, I use Seat61 to look up how long it takes to travel by train from Geneva to my destination, as well as how much I can expect to pay if I book at least a month in advance.

I primarily use two apps to look up train fare. One is SBB, Switzerland’s national railway services. The other is, owned by the French equivalent. Strangely, the cost of the same train trip will sometimes differ depending on which national carrier you purchase the tickets from; sometimes the Swiss one is wildly more expensive, and other times it’s a jaw-droppingly low price. When I’m purchasing international train travel, I always compare the prices on SBB with the carrier of the other country, such as Deutsche Bahn for Germany, ÖBB for Austria and Trenitalia for Italy.

For frequent train travelers in Europe, there’s the Interrail pass (Eurail for tourists). I thought about getting this, but then hesitated as I didn’t think I traveled often enough to justify the cost (I was averaging about one international train trip per month). Then COVID hit, so I guess that was a prescient financial decision.

3. Pin bucket list places on a map

Screen Shot 2020-07-13 at 6.37.22 PM
The map I made for my April 2019 work trip to New York. I even color-coded it: blue was essential locations like the hotel and UNHQ, yellow was food, and red was touristy sites.

For every trip, I create a personal map on Google Maps, using the “See” section from Wikivoyage as a reference for dropping pins on the places I’d most like to visit. I also pin my hotel and the central train station. Once I finish dropping the pins and zoom out of the map to look at the city from a macro level, it immediately gives me a clearer sense of where my activities are going to be clustered and how I should arrange my day-to-day itinerary.

Hotel Relax 5 in Taiwan, one of my favorite hotels that I’ve ever stayed at. It’s a 5-minute walk from Taipei Central Station and the staff is heartbreakingly nice.

4. Book my hotel

Once I’ve completed the mapping activity above, that’s how I know where to book my hotel. There are two possibilities: either the central train station in the city is going to be situated in a prime downtown location, with easy access to tons of touristy sites (e.g., New York City; Paris; Tokyo), or the train station is going to be a bit of a trek from the actual downtown area (e.g., Milan; Brussels; Tel Aviv). I use the map to determine where most of my tourist activities will take place, and I book my hotel in that area.

I use to book all of my hotels. No particular reason really; I just find the website to be pretty user-friendly, most hotels are on there, and now that I’ve been using them for 3+ years, I have ‘genius’ status which gives me a small discount at some hotels.

I only book hotel rooms that are fully cancellable up until a couple of days before the stay, even if that means it’s more expensive. I don’t consider switching to non-refundable rooms until I’ve booked my travel itself.

5. Book my travel

After doing the due diligence in Step 2 and booking my hotel, I finally book travel.

I never use intermediary sites like Expedia or Kiwi to book trains or flights, having always heard that it can be a nightmare to get assistance or your money back through a third-party should something go wrong. We certainly saw this over and over again during the early days of the pandemic.

For flights, I use Google Flights to look up the most cost-effective routes and carriers, but then head straight to the carrier website itself to book the plane tickets directly. For code-sharing flights, it’s also worth looking up the cost on different carrier websites. For my trip back from Bangkok to Zurich, for example, the same journey was $400 on Thai Airways and $600 on Swiss Air.

Te Anau, New Zealand
Pit stop at an alpaca farm in Te Anau during our van tour in South Island, New Zealand.

6. Research and book any group tours

Even though I prefer to travel solo most of the time, I also love taking part in short educational tours. Some of my favorite tour experiences from the last few years include taking a boat ride through the canals of Amsterdam; a full day van tour from Queenstown to Milford Sound in New Zealand’s South Island; and doing a food tour of Seattle’s famous Pike Market.

Some of these experiences sell out way in advance, like the Anne Frank House in Amsterdam. Others are intended to be casual gatherings that you can join on the day of, like most ‘free walking tours’. (Note: most of these free tours are great and run by guides who truly love doing this, but ‘free’ is a bit misleading; they absolutely do expect you to tip at the end, and I usually see people giving $10 to $20.)

7. Get a sense of the local culture and learn some basic phrases

I stumbled upon the Cultural Atlas website a few years ago and found it to be a generally accurate and objective resource for providing insight into local cultures and traditions. It’s written from an Australian perspective, which makes it extra fun to read the entry on the United States. (“Americans are very direct communicators. They tend to convey their entire message verbally, paying less attention to body language. People are expected to ‘get to the point’.” Yes! Literally me!)

For travel to countries where I don’t know the local language(s), I think it’s enough to master the following phrases:

  • Hello
  • Thank you
  • Sorry, do you speak English?
  • Goodbye

8. Finalize my itinerary

I use the free website Trip30 to keep track of travel logistics. I had used Tripit previously, but found the UI too hideous to continue using. In Trip30, you can create an overview of your trip, like this.

Screen Shot 2020-07-13 at 6.40.22 PM

With that, you’ll also generate a nice-looking itinerary that is print-ready. I actually don’t print most of my itineraries; I only do it for trips that have multiple legs and can be quite messy to keep track of, such as my trip from Geneva to Paris to Urumqi to Thailand last December.

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9. Final pre-trip preparations

Before, when I lived in the US, I would purchase travel insurance from Geoblue before each trip and print out the temporary insurance card. It was super affordable — around $14 for a whole week. I never ended up using it, but that’s the goal.

Now, travel insurance is covered by my regular insurance, but I still have to pay for medical expenses out of pocket until I reach my CHF 2,500 annual deductible.

I also register my trips with STEP, a service by the U.S. State Department. They send travel warnings via email, mostly about issues such as political protests near the U.S. embassy and natural disasters. Since I’m also registered with them as an expat, I’ve also been receiving weekly COVID-related updates from the U.S. Embassy in Switzerland.

Prior to leaving for an international trip, I print or make copies of the following:

  • Passport bio page
  • Swiss resident card
  • Address and phone numbers of the local U.S. embassy
  • Itinerary
  • Visa, if applicable

And that’s it! 9 easy steps to planning a trip that is as free of stress and surprises as possible.

I’ve purposefully left out budgeting as a step. The truth is, I don’t budget. I’ve tried to do it in the past, but it’s a habit that doesn’t stick. Luckily, I was raised poor (lol), so I am generally pretty frugal and don’t spend outlandishly, only splurging on something when I really feel it’s worth it.

I do have some mental guidelines when I’m spending on travel. For instance, I am not willing to spend more than $150 per night on hotels unless there are no other decent options. Unless it’s an insanely expensive market like NYC or Amsterdam, I can usually find something at or under $100. As for flights, I usually fly economy, but I will allow myself one business class flight a year if I can keep it under $2,000. I don’t go to fancy restaurants, and I only order alcohol occasionally. I also don’t usually do resorts, spas, massages, that sort of thing. Another huge cost saver: instead of taxis, I always take public transportation or walk everywhere. You get 30,000 steps in, and you’ve saved a boatload of money and also potentially avoided a serial killer masquerading as a taxi driver. Sounds like a win-win to me.

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