Disclosure: I started writing this post a while ago before the COVID-19 pandemic. Having time to spare, I could finally finish it. Although nobody is traveling for pleasure right now, read and save this information for when vacation traveling is possible again.
We have friends who find it stressful to plan a trip. Surely there is a lot to think about, from buying airplane tickets and booking accommodations, to getting a visa and figuring out what to do when you get to your destination. I can see how nerve-racking these tasks can be when you have no idea where to start and which steps to follow. Having been in that position before, I totally sympathize with those who struggle to plan a vacation, especially when you are visiting a different country for the first time.
We still make mistakes. Who doesn’t? However, these days we’re more experienced travelers. Now, our trips begin at home when we start discussing where to go. Each place I research and each activity and hotel I book takes me on an imaginary adventure that is surpassed only by the actual voyage. The lessons we learned along the way through our errors and struggles will be shared with you today. We’ll lay out a step-by-step guide that will ensure you will not only find it easy to execute each point, but also bring you joy and triumph.
The steps listed below don’t necessarily need to be followed in this order. Depending on your kind of trip and destination, you may skip some of these topics. Nevertheless, follow this checklist for guidance and adjust it according to your journey.
Ready to start? Sit back, relax, and enjoy the ride.
1. Choose your destination or let the destination choose you
With so many amazing places on this planet, you either already have your destination in mind or find yourself debating between a few options. Perhaps you are the kind of traveler who just wants to go somewhere, no matter where. If this is your case, start narrowing down what attracts you the most: mountains, beaches, modern cities, or historical sites. The choices are endless.
If you still don’t know where to go, let the destination choose you. Use Google Flights and click on “Explore destinations.” A map of the entire world will pop up, along with prices. You may be surprised by the excellent deals that appear on your screen.
2. Take care of passports and visas
There is nothing more frustrating than finding out days prior to a trip that your passport has expired. It happened to us once when we were flying to Brazil. Ted realized his passport would no longer be valid by the time we would return from our two-week vacation. Things worked out fine at the end, but he had to spend an extra few hundred dollars to get it before our departure.
The same thing goes for visas. As an American citizen, if you are planning to travel abroad, check this detailed list of all visa-free countries as well as the ones that are not. If a visa is enforced, you must apply through that country’s consulate. Alternatively, hire a travel agency to take care of this part for you. A fee applies.
3. Check other papers enforced by the country you are visiting
Remember, the laws of your country don’t follow you while you are in a foreign nation. Familiarize yourself with travel laws and customs of the countries you are visiting. When we traveled to South Africa in 2017, we were at the airport in Amsterdam when we heard for the first time that we needed to present our daughter’s birth certificate in order to board the next flight. Thankfully, we solved the problem, but it was the most stressful situation we have had on a vacation. Read more about it on our Birth Certificate required to fly to South Africa post.
4. Choose your dates
Flexibility is a winner! If your travel schedule is attached to a school calendar (parents with kids at school, we included) or any other restriction, likely you will be traveling during the high season. Travel off-season if you can as the advantages will be endless. You will not only pay less for flights and accommodation but also deal with smaller crowds. Moreover, you will have better chances to absorb the local atmosphere. Last but not least, you will be able to take your photos without big crowds. May and September are ideal because the weather is usually best.
5. Book your flights!
Destination and date chosen; it is time to book your flights. Depending on where we fly, we use different services to get reservations. We plan most of our vacations well ahead, especially when planning long, international trips. Why? Because we can often get better fares and spread out our expenses!
When it comes to visiting multiple locations in another country or region, booking flights can be tricky. In that case, we find it easier to book the international roundtrip first. Then, we book domestic flights one by one inside the country or region we’re exploring. In most cases, we save money and get more flexibility on our schedule.
Unfortunately, there is no website out there that I could recommend as the best to be used all the time. Check as many sites as you can (Skyscanner, Kayak, Justfly, etc.) to ensure that you will get the best deal. Also, sign up for flight alerts. We use Scott’s Cheap Flights and Google Flights. Additionally, as a Houstonian, I followed Escape Houston on Twitter.
Further, here are some of our favorite sites when searching for a flight:
Google.com/flights – favors travelers with specific travel dates as it allows comparing airlines, routes, prices, and times.
Google.com/flights/explore – excellent option if you are flexible with dates and destinations. Updated prices are shown daily for each port of call for the next six months.
Southwest.com – It is our favorite domestic airline. Moreover, it offers some international flights to Mexico, Costa Rica, and the Caribbean. Check their Low Fare Calendar.
EasyJet.com – Not a luxury experience, but a fabulous option if you are flying within Europe. Prices cannot be beaten.
United.com – These days, there are hundreds of travel rewards credit cards to choose from. Although there is no perfect one out there that I could recommend, we have the United Explorer Card. Despite not getting attached to it, we use it when prices are worth it to collect miles.
6. Plan your arrival accordingly
When we visited China in 2016, it was late at night when we arrived at the airport in Zhangjiajie. Although we had planned to take a taxi to our hotel, little did we know that we had to negotiate the price of the ride before hopping in the car. Someone at the airport told us that it would be advisable to avoid getting scammed.
Despite having the hotel address written in Chinese, the negotiation wasn’t easy. I blame myself for it. Knowing China could be challenging regarding communication, I should have put more thought on this matter. For example, we could have landed during the day or hired a transportation company to pick us up. In other words, pre-planning your arrival when traveling is a huge step for avoiding stress.
First of all, always use licensed transportation. Arrive in daytime if you can. Moreover, check your options on how to get to your hotel. Does the hotel have its own shuttle? Will you take a taxi, Uber, or metro?
7. How will you get around
Transportation varies from one country to another, and depending on where you are traveling, you may use different means to get around. When possible, we walk as much as we can because we believe it is one of the best ways to experience a new destination. Nevertheless, if sites are far apart, we check the options available. Are there taxis or Uber? Does the place have a good metro system? Would you need to rent a car? Is the place bike-friendly?
8. Buy travel insurance
Despite so many people still thinking of travel insurance as an additional expense, it should be seen as peace of mind when it comes to traveling. Accidents may happen, problems may arise, and they will definitely bring more stress if you are far from home. Travel insurance will help in case of unexpected matters such as illness, severe weather, delays, interruptions, or cancelation of the trip, lost luggage, delays, injury, and theft.
We have been using Allianz Global Assistance, which eliminates several of my traveling concerns. Coverage can vary from policy to policy, so to know more about how to choose yours, read Money-Saving Strategies for Buying Travel Insurance.
9. Search the sites and activities you want to see and group them by area
Before booking hotels, I search all points of interest in the area we are visiting. I talk to other travelers and friends, read blogs, and check popular websites such as TripAdvisor and Viator to pull out suggestions. List in hand, I use Google Maps to locate and save each site.
To do that, type the name of the location on “search”, swipe the bar on the bottom of the screen, and mark it as “Save” or “Want to go”. Then, I repeat this process for each attraction we want to see. At the end, Google Maps will be dotted by flags or stars of all desired spots. This process facilitates my day-by-day schedule, but first and foremost, will help me to choose the location of my hotel.
10. Book hotels
When choosing a hotel, we take into consideration a series of factors, but more often than not, the location is the first thing on our mind. It must be near sites we want to see on foot. Furthermore, it must be quiet at night. Although we read the hotel website description, I do not ignore customers’ reviews.
We also check the kind of clientele as we prefer family-friendly hotels. Our family is versatile, so we fluctuate from smaller, intimate boutique-hotels to luxury or business-like rooms. It depends on the kind of vacation we are taking and how much time we will be spending in the hotel itself.
Once we have a good grasp on what we’re looking for, we check booking.com. It is our favorite platform because it:
- provides the necessary information (map location, photos, and guest reviews) to track down more details on the respective hotel and area.
- offers clear pricing with no hidden fees.
- has an excellent app that allows you to book hotel rooms on the move.
- holds an incredible inventory. Instead of checking 15 different hotel websites, I can simply search for hotels in one location and compare them. Additionally, it helps me to find hotels that more than likely I wouldn’t find on my own. Very easy process!
11. Book tours and/or tour guides in advance
I often find this topic controversial. Some people would rather wait until the last minute to book a tour wishing for flexibility or a better deal. Others overbook their days. We find a middle ground. There is nothing more frustrating than having our minds set to see something and realize that it won’t be possible because we didn’t plan ahead. Consider booking some activities in advance if there is a chance for them to be sold out. At the same time, do not overbook yourself. Leave space for some flexibility.
We generally book everything directly with the site we will be visiting. Nevertheless, Viator and Get Your Guide (third party bookers) are excellent marketplaces where tours, activities, and attractions providers from all over the world can list their services. I recommend always reading the description and the cancellation policy sections before buying a tour or activity.
12. Look into specific details for certain activities you want to book
Certain attractions require more attention to details. For instance, if you are visiting the Vatican Museums in Rome, all visitors, males and females, should wear clothing that covers both their shoulders and knees. Waiting in line for the Eiffel Tower can cost precious hours of your vacation, so book your ticket in advance. With a reserved ticket, you will be in a much shorter line and spend those hours doing something else.
Do you dream about going to exotic places such as the Amazon Rainforest, Great Wall, or an African safari but have concerns about illnesses rarely seen in your country? Although it is true that visiting certain destinations will require more care, don’t let your fear stop you from pursuing your wanderlust. There are several ways to protect yourself against unfortunate parasites, and travel vaccines are one of them.
IAMAT – International Association for Medical Assistance to Travelers is an excellent resource. They offer important and up-to-date information not only about immunizations, but also health risks, climate, food, and water safety conditions about each country.
14. Notify someone close to you about your trip details
Due to the world’s political tensions, traveling abroad has been more challenging than ever. Although it won’t stop us from seeing all the beautiful places out there, extra care can definitely bring us some peace of mind.
Every time we travel internationally, we have a family member who knows about our flights, itinerary, and hotels where we are staying. If anything goes wrong, they will easily find out about us. We also email them our passport identification pages and save copies on Dropbox. If the passports are lost or stolen, it will facilitate the replacement.
Moreover, I recommend registering with the nearest U.S. embassy or consulate through the State Department’s travel registration website, especially if you are visiting a country that presents security concerns.
15. Download good travel apps that will make your adventure easier
When it comes to planning and taking a vacation, we have been relying on our smartphones more than ever. Whether organizing an itinerary, or already enjoying a destination, having the right apps on our phones can be the difference between a good trip and a fabulous one.
These are our most-loved apps. Some may be familiar to you, while others may still be undiscovered.
Organizes the itinerary into a detailed summary, complete with confirmation codes, maps, and other info all in one place. We use the standard TripIt version, which allows me to share my travel plans with family and friends. It doesn’t require Wi-Fi, allowing access anywhere. Easy to navigate.
While I do the initial research and booking using my laptop, this app allows me to easily access my reservation information on the go.
Have I already said that I am a planner? Yet, HotelTonight is a dream for last-minute booking. Allows booking the same evening or up to seven days before the stay, and offers fantastic last-minute rates. Take advantage of the daily drop feature, where you swipe to find a personalized deal with a special price only valid for 15 minutes after it’s unlocked.
Waze is an excellent navigation app whose data comes from millions of Waze users. We get real-time information on the roads around us, including congestion, accidents, construction zones, and even notifications about speed traps. The app has a speedometer that makes sure the driver is staying within the speed limit.
Perfect for our family as we need to create multi-person packing lists. Packing Pro sets reminders to pack certain items and encourages uploading photos, so we know exactly which items we have in mind. Once your list is generated, it will sync to your iCloud for easy access. We have friends and family members who still prefer a paper checklist. Pick whatever works best for you.
When navigating, we switch between Waze and Google Maps. However, Google Maps is the first one we open when searching for a nearby place to eat or just wandering around when having some time to spare because it is more comprehensive.
Although not all countries have Uber (hello Spain!), I love the convenience of this service. I choose the location to be picked up, and the payment is made without touching my credit card. Plus, the cost is usually less than a taxi.
It is the first process utilizing authorized apps to streamline U.S. citizens and Canadian visitors’ arrivals into the United States. Using this app allows us to complete a paper form or use an APC kiosk. As a result, we experience shorter wait times, less congestion, and more efficient processing. Just don’t forget to actually bring your physical passport, as the app doesn’t replace that!
Although English is first for the number of people who can speak a language, and the third most spoken native language in the world, Google Translate is the one app I can’t live without. It plays an important role in our travels. From translating signs instantly and helping us to talk with Uber drivers to figuring out what to order from a menu and reading museum placards, its use is countless.
Instead of relying on printouts, we save digital copies on Dropbox, a cloud file storage platform that gives us access to all papers we may need during our travels, even when we don’t have an Internet connection. I’m talking about our boarding passes, contact info for travel buddies, hotel details, maps, itineraries, etc.
16. Assemble your travel First Aid Kit
Having a first aid kit is a vital part of our packing, especially when traveling overseas. Although I keep it small and light (look for travel-friendly sizes), our medical kit contains all essentials to deal with an unexpected injury or illness. I don’t claim to have the perfect kit, but it never failed me.
Besides any prescription we may use, I also pack:
- 1% hydrocortisone cream
- antibacterial ointment (for minor cuts and scrapes)
- Assorted band-aids
- Pain and fever reducers (ibuprofen)
- Allergy medication (Benadryl)
- Alcohol wipes
- Small scissors
- A digital thermometer
- Disposable gloves
- Electrolyte powder
- Bandage wrap
- Adhesive tape
- Eye drops
- Sunscreen (no matter where we go)
- Mild sedative (Tylenol PM)
Alternatively, American Red Cross sells small first aid kits, and Johns Hopkins provides a comprehensive list of what should be included in a traveler’s health kit.
Some locations have their own challenges, so depending on where we are going, we will have different needs. For example, when visiting the Amazon Rainforest, we must add insect repellent and anti-malaria medications. Refer to section 13 (above) for more information.
17. Be flexible and have fun
Seeing beautiful places and learning about other cultures are the reasons why we travel. Over the years, we have learned that proper planning helped us to manage our time well, but it didn’t prevent unexpected events. Setbacks happened, and there were times when we had no choice but to accept what could not be changed and adjust. We have learned that the ability to adapt is as important as the ability to plan. For us, every trip is a unique experience with which we do not miss the opportunity to learn, explore, and have fun.