• Guillaume Cachia

How to Plan a Trip Like an Expert: 15 Tips

Planning a trip—especially an international trip to a new country with language and cultural barriers—can be daunting. After all, there is so much to think about and much of the information and photography found online can be misleading or outdated.


As the world slowly overcomes the recent global health crisis, travelers are anxious to get back out to exploring as well! In fact, 41% of frequent travelers have already booked or plan to book their next trip before the end of summer 2020 according to a survey conducted by WandrHop in May 2020.


41% of frequent travelers have already booked or plan to book their next trip before the end of summer 2020.

If you are looking to experience what locals do and capture stories worth telling, use this article as a guide to help you plan a personal trip like an expert with these 15 tips.

Biggest takeaways from a WandrHop survey of 189 frequent travelers in the U.S.

Tip 1: Dedicate the Time to Create a Memorable Trip


For most of us, traveling is a substantial investment. And as all investments go, a substantial return is to be expected. A well-constructed itinerary requires true dedication with lots of research, communications with locals, benchmarking vendors, negotiations, and dealing with the unnerving logistics options. On average frequent travelers in the U.S. spend 18 hours planning for a trip, but for a top-notch itinerary that will make the most of your investment, you should plan for at least double that.


Frequent travelers in the U.S. spend 18 hours on average planning a personal trip.

Tip 2: Book Flights and Hotels on Points


With the incredible offers and credit card deals available nowadays, you are doing something wrong if you are not spending at least one week abroad a year completely paid for with points (airlines and hotels).


Make the most out of every dollar you spend and redeem them for a trip of a lifetime! It feels good to get paid to spend money—you’ll see. Depending on your current purchasing and spending behaviors, you may select one or several credit cards to open. Our top four recommendations in this area include:

  • CHASE® Sapphire Reserve®: With a great sign-up bonus, points worth 1.5 for travel redemptions, and the potential to earn 5 points on travel-related expenses, this card is great for frequent travelers. It also gives you access to the Priority Pass lounges. We believe this card is the #1 in terms of value for the annual fees you spend.

  • American Express Platinum Card®: In addition to being a great add-on to your wallet, this card has two luxury must-have perks for travel-lovers. First, it gives you access to the Centurion Lounges, which caters to AMEX Platinum card holders. With its infamous cuisine, showers, and complimentary massages and manicures, these lounges are the best way to wait for your flight at the airport. Second, should you book a hotel that is part of the Fine Hotels and Resorts list, you will immediately receive early check-in, late check-out, room upgrades and a gift to use during your stay. Typically the gift is nothing less than $100 in value to be used for a variety of amenities on-site.

  • Choose an Airline Loyalty Program: And stick to it! When determining your airline-of-choice, consider their international partners. For instance, Delta is a partner with Air France, KLM and many other renowned airlines. Once you obtain status with Delta, you get it with the other partner airlines as well and it opens the door to a lot of perks. Sticking to one airline will allow you to gather more miles into one account instead of spreading them across several and rendering them useless.

  • Choose a Hotel Brand: And stick to it also! Similar to airlines, loyalty pays off in hotel brands (and when you get their credit cards too). Bonvoy (Marriott) is my go-to as it has a range of hotels that can accommodate any budget. If you get their credit cards, you will get a nice signing bonus and a lifetime “gold” status, which means more perks and more points every time you book.

Tip 3: Pay Attention to Local Maps and Distances


When planning a trip abroad, getting acquainted with the layout of the country and cities you will visit is very important. Some cities may appear very walkable from the few photos you’ve seen on Instagram or travel books or very easy to get from one point to another, but reality may be different. Here are the main things to watch out for:

  • Walkability: I always recommend using Google Maps to get an idea on the distance between two sites and using Google Street View to get an idea of the walk or drive. For many major cities in Western Europe (Paris, London, Barcelona, Brussels etc.) and some of the major U.S. cities (New York, Boston, San Francisco), it is easy to get a hotel anywhere in the ‘city center’ and cover everything by foot but that is not always an option in other cities such as New Delhi, Kathmandu, Sydney, Los Angeles and Rio De Janeiro.

  • Optimized Routes: Having a good idea of all the sites you wish to visit/see laid out on a map is very helpful to determine your route and agenda for the day based on the walkability. That way you are not doing a zig-zag through town for no reason.

  • Danger Zones: Outside of those large ‘self-contained’ cities such as Paris or New York, you will find not-so-safe areas mixed together with the safe areas in a patchwork of streets. You need to be familiar with them in order to minimize the chances of something unfortunate happening.

Overall, there is something oddly satisfying about walking into a new city already being able to ‘go with the flow’ and understanding the layout and directions. That extra effort ahead of your trip will save you countless hours looking at Google Maps while on-the-go. That way you can spend more time appreciating the city, wandering and being a traveler instead of one of the many tourists.


Tip 4: Don’t Always Rely on “Top 10” Lists


Whichever city or country you are going to, there are probably hundreds of Top 10 or Top 20 to-do lists that exist (with the occasional Top-12 odd ball). Most of them cover the exact same obvious sites one must visit while there, such as the Eiffel Tower in Paris or Machu Picchu in Peru.


But they all lack the true wonders of those destinations, the ‘off-the-beaten-path’ sights, and experiences that only a handful of travelers and locals know about. Those lists should give you the bare minimum to include in your itinerary but those are rarely experiences that create stories worth telling.


58% of frequent travelers have missed out on an experience simply because they didn't know about it until they returned home.

According to the WandrHop survey, 58% of frequent travelers have missed out on an experience simply because they didn’t know about it until it was too late. This is where making local connections can come in handy!


Tip 5: Know What You Want and Leverage Local Resources


We are all different and therefore our travel expectations and needs are too—that means that the trip your neighbors organized for themselves last year in Indonesia may not be what’s best for you.


Take the time to think about what would make the trip memorable. Would a local cuisine cooking class be of interest? Would you rather book an overnight hike in the mountains? Would you prefer to splurge on local delicacies at renowned-chef restaurants or eat where locals eat and splurge on art?


Once you know what works for you and your traveler partner(s), use it to craft the perfect itinerary. Take advantage of locals. Do you know anyone who lives there or has lived there? The best tips and experiences always come from them! We know the value of local expertise at WandrHop as we strive to gather and collect updated knowledge on local experiences to share with our customers.


Tip 6: Hotel Location Matters Big Time


Choosing a hotel especially in large cities is daunting. A lot of travelers end up choosing the hotel solely based on price (obviously) and pictures of the room, common areas and from inside the hotel. This is fine and dandy if you are traveling to a self-sufficient resort.


60% of frequent travelers express regret in their hotel choice after check-in (due to location, amenities, or value).

But 60% of frequent travelers express regret in their hotel choice after check-in, according to WandrHop survey. This means the process to book a hotel needs to be different!

  • Know your Budget: If you don’t know what to expect, take a look at all the hotels on a travel aggregator site to get a feel for what the average nightly price is for the type of room you are looking for.

  • Get the Location Right: You can probably find quite some literature online, usually with a title starting like this: ‘best place to stay at in […]’. But again, it should be based on your preferences and needs, the best place to stay at for a 22-year-old bachelor may not be right for a 38-year-old couple with two kids.

  • Use a Travel Aggregator Map tool: This tip is valid for any city. First get an overview of all the hotels and their prices (can be done on Expedia, Google and any other trip aggregators), this way you can visually measure the clusters of hotels (sign that it is a sought-after area).

For example, if you want to stay in Cusco and within the Centro Historico district (highly recommended) you will have to choose the district in which you would like to settle. Based on the clusters of hotels, the Northern part seems like a better bet. Judging by the prices, the North-Eastern part is the winning combination. These locations are indeed very close to the Plaza de Armas of the Historic Cusco and offer the most convenience to anything you’ll be doing. This section of the district is fairly flat, which will be a much-appreciated perk!


Tip 7: Use Excursion Resellers Only for Ideas


I like to go on Viator and similar websites to get ideas and see what’s out there. But I would not nor would recommend booking directly through them. There is always a large mark-up, understandably so since there is a middle man for activities or experiences you could book yourself for cheaper and negotiate directly with the owner of the local business.


Go to the source, negotiate the prices and have a direct line of communication with the people that will show you around once abroad. It requires time, patience, and travel planning skills but it pays off in the end.


This is especially important for those ‘full-day tours’ that tend to be very appealing to the travelers who like to be catered to! Those tours not only could be negotiated for a lot less with the actual local business providing the tours but you could also arrange a different path, add or remove stops based on your needs and wants, which you can’t through Viator and others.


Tip 8: Figure Out the Logistics Within a City and Between Cities


Chances are, you will be traveling between cities during your trip abroad and planning the logistics aspect is imperative to a good trip. You need to find the train/buses timetables and figure out what is possible or not for your itinerary ahead of time. Be mindful of the seasonal schedule changes and if it is obligatory to book in advance.

Some trains in Europe or Asia require an assigned seat and booking in advance. You do not want to get to the train station excited about an imminent departure to a new city, only to be told the next available train is tomorrow night.


Tip 9: Create a Travel Itinerary Journal


I always recommend having a travel journal with the printed-out itinerary with as many details as you can! You will never follow your itinerary exactly as it is written because life happens and because not everything will always go according to plan. But that is why you want to have a travel journal.


Should anything change or move around, you will have the advantage to have an overview of the trip and all there is to do. If you come across an amazing shopping street and want to spend the rest of the afternoon there instead of the museum and park visit you had planned, it won’t be a problem. All you have to do is to check the itinerary and figure out how to make them fit in the remaining days there. Make the decision to edit the itinerary based on what you think is best for you. So you don’t have any regrets once you get home!


If creating your own travel itinerary journal seems like too much effort, you can hire a company like WandrHop to build your individual itinerary with custom recommendations—all based on your needs and wants. These types of digital itineraries are accessible on-the-go and give you all the details you need for a safe and memorable trip.


Tip 10: Always Pick a Travel Engineer Over a Travel Agent


Let the travel agents be a thing of the past! Own your travel and what you do—don’t be limited by the hotels, flights, and activities because of what the agents have to sell to get larger commissions.


The biggest difference between a travel engineer and a travel agent is that the engineers work for you and you only! If you want to use points or miles to pay for your flights and hotels or if you want to stay in AirBnb’s for the duration of your stay, travel engineers can organize it all for you. You tell them your preferences, budget, and interests, and travel engineers make your dream vacation a reality. Travel agents give you pre-packaged trips, whereas travel engineers build a custom experience just for you!


According to the WandrHop survey, when planning their trips through travel agents, the most common complaint frequent travelers have is that the trip wasn’t personalized enough or was a cookie-cutter experience that was pushed onto them.


Tip 11: Determine Sunrise and Sunset Times


Make sure you check and write down the sunrise and sunset times in the destinations you will be visiting. Chances are they are different from where you came from and you need to use that for your planning for two major reasons:

  • When to Start and End Your Day: If you are going to a country where the sun rises earlier in the day vs. where you are from (5am vs. 7am) but also sets earlier (4:30pm vs. 7pm), you will need to adjust your sleeping hours and plan accordingly. Instead of going to bed at midnight and waking up at 8am, you may want to take more advantage of the daylight hours to be out and about rather than spending a large portion of it in your hotel room.

  • Watching the Sunrise/Sunset: If you are an aficionado of watching sunrises and sunsets when on vacation, knowing the exact times will be useful to add in your itinerary and build your day around that.

Tip 12: Know Your Transportation Options


Make sure to Google if ride-sharing (such as Uber or Lyft) is available where you are going. This is a great lifesaver at home but even more so abroad. If Uber is not available, also check the times taxis operate—for instance, in many cities in Japan (outside of Tokyo), taxis do not start roaming the streets until 8am at the earliest which may be inconvenient if you are trying to get somewhere for sunrise around 6am. You will need to organize a pick-up the evening prior via phone with the taxi company, not knowing that fact may mean a missed opportunity due to poor planning!


Tip 13: Portable Wi-Fi can be a Great Friend


In this day and age, having access to the internet constantly is primordial and vital for some. While most operators will charge you $10 or more per day of data usage while abroad (per phone), I do highly recommend getting a Wi-Fi Hotspot as it will save you money.


You can order your hotspot online, ahead of your trip. They typically go for approximately $8 a day per usage and you can connect several devices to it. This is a great deal for couples and families to save some money when traveling.


Tip 14: Plan Time to Do Nothing or to “Get Lost”


Getting lost is a great part of any trip, those precious hours where you don’t need to worry about going from point A to point B or rush to the museum before it closes etc. Some people laugh at me when I say I plan for those ‘getting lost’ moments, but there is a lot of value in planning for them!


For instance, Paris is an amazing city for getting lost, and there are especially three or four specific areas that are great for that (and nothing else). Instead of hoping for the best and stumbling upon those areas between point A and point B, I usually plan to spend a good chunk of the day just wandering around in those areas on purpose.

The issue with not planning those wandering moments is that you will have to have tradeoffs! Yes, you will get to one of those areas that are perfect for wandering and feel in your bones that you want to walk around more and enter all the boutiques, take pictures etc. – which means that whatever else you had planned during the following 2 or 3 hours now is on the back-burner. Depending on the itinerary and your must-dos, some things will have to be removed. In those moments, proceed at your own risk!


Another way, which I have tested while in Egypt is to keep a full day to a day and a half at the end of the trip with no set plans – that way you can go back to places you wanted to see more of or places you had to trade in for changes in plans earlier on.


Tip 15: Be Mindful of How Much You Pack On Daily Schedule


How much can you do in a day? Well that will depend on your traveling party and your style.


I like to pack my days with a lot, usually a mix of learning (museums, visits) and relaxation (parks, views, eateries). Others may prefer one big thing a day and keep the rest as TBD or spending half the day at the hotel pool and afternoons visiting.


One thing for sure though is that travelers often overestimate the time they will spend at specific areas, so make sure to think twice about the time stamp you attach to each activity. How many times have you made it to a place, viewpoint, museum thinking you would spend two hours there, only to be done after 20 minutes and wondering what to do next? That used to happen to me a lot!


This can become problematic if it happens at each activity planned for the day, although a great way to remedy this gap is to find the nearest café and mingle with the locals.

Planning a trip is hard work unless you are amenable to being ripped off by travel agents or aggregators such as Viator.


46% of frequent travelers admit overspending on their personal trips due to poor planning.

Considering that 46% of frequent travelers admit to overspending due to poor planning and three out of four worry about their daily itineraries at least twice during the trip, everyone can use some help planning their next international trip.


If you want to skip the hassle of planning the details of your own trip, save time and money, plus get a crafted itinerary just for you, get started with WandrHop to plan your personal trip!


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