11 ESSENTIAL STEPS: Planning For Vacation

Don’t just wing it. Planning for vacation is important to minimize extra costs and headaches. Keep reading for my 11 steps on how I plan my own vacations and trips around the world.

I am a natural planner. I’ve always looked ahead to optimize my experiences by putting time into the details that will make my vacation amazing.

Below I have 11 steps I follow for every trip. Through my years of experience, and many, many mistakes, I found these areas are the most important and vital to have a smooth sailing trip.

1. Set Your Vacation Budget

Before any more planning for vacation happens, set your travel budget and determine how much you can spend for the whole trip. This maximum budget includes everything from airfare, to tips at restaurants to souvenirs you bring home. 

All other planning elements fall within your maximum budget. If you’re planning an anniversary trip with a large budget, then go all out with first-class plane tickets, a beautiful hotel suite, and fine dining restaurants.

Even if you have thousands of dollars to spend, you still need to know how much is too much.

If you are a budget traveler, more attention and time are required for your planning, making sure no dollar is wasted. 

Either way, set a number and stick with it.

If you plan on saving up for a trip and don’t know how much it will cost, do a quick search on flights and hotels, which gives you an idea about the bulk of your expenses.

As for daily costs, expect to pay 50-100 per person per day at a minimum with more extravagant trips at least double the cost. 

2. Narrow Down Your Vacation Dates And Length

How many days off work can you manage? Is this a quick weekend getaway or a two-week stint through Europe?

When planning for vacation, the longer your trip the more money is needed. Keep this in mind when planning and setting your travel dates

I also find that with shorter trips, little costs slash into your maximum budget for the sake of convenience.

You want to spend more time exploring a city and less time in transit, waiting in line, or wandering around aimlessly. 

More days allow you to travel farther, and easier. If a flight is longer than 6 hours, I don’t recommend traveling if you have less than five days.

Travel time and jet lag mean muscling through uncomfortable circumstances and not fully enjoying your travels.  

3. Pick The Perfect Vacation Destination

Now the fun part of planning for vacation begins! Let’s go through how to pick the perfect destination that fits your budget and time available. 

How Far Are You Traveling?

The farther you travel the more time and money are needed. Although this is a general rule, it fits most cases for those reading this post. 

Take into consideration that trips that require longer flights take up whole days for just travel. Traveling from the United States to Spain takes two whole days just in transit time alone, turning a seven-day trip to just five days available for exploring the country.

You can still make far away vacations in Europe and Asia affordable, you just need to pick countries that are cheap and fit into your max budget.

Consider The Season and Time Of Year

Time of year is one the largest factors when I pick a destination. Weather is important because it dictates the accessibility to activities. Visiting Vietnam in July means facing the monsoon season where the streets flood regularly. 

Season also affects tourism and dealing with large crowds and inflated prices. Visiting Rome is less remarkable in June, where you fight the sweltering heat and swarms of tourists, waiting in long lines for every attraction. 

If you have the option, travel during off-peak times for the best weather and fewer people. Off-peak means traveling between the high and low tourism seasons. 

How Do You Want To Spend Your Time?

The single most important factor in picking a travel destination is what you’ll do while visiting. 

Have you always dreamed about visiting the Louvre in Paris, setting your eyes on the Mona Lisa? How about hopping to different Buddhist temples and learning the history and cultural heritage of Bangkok? 

Your travel destination should intrigue your senses, helping you understand more about a place and hopefully learning more about yourself. 

Even if all you want to do is sit on a beach and sip margaritas with your friends, all travel has the opportunity to change us for the better. 

4. Purchase Cheap Airfare

After determining your budget, dates of travel, and destination, it’s time to start setting a few details in stone. 

When planning for vacation, purchase your plane tickets before booking anything else.

Your trip revolves around when you arrive and leave your destination, and once your tickets are booked, you can start planning everything else. 

Although there are set rules I follow when booking tickets, it’s important to save as much money here, because, a few details can determine if you spend or save a couple hundred dollars.

Check My Other Articles About Booking The Cheapest Airfare
Are Flights Cheap Last Minute?
When Do Prices Drop For Flights?
What’s The Cheapest Day To Fly?

5. Planning The Perfect Vacation Accommodations

Now that your arrival and departure are set, let’s focus on picking the right accommodation. 

Consider The Location First

Consider your location and pick the right room close to the activities that interest you.

A central location close to public transit is my usual choice so I can hop on a train or bus to travel all over the city in minutes. 

Although hotels outside the city book for lower prices, your time spent transiting from the outskirts to the city center will eat your travel budget and precious time. 

Booking Hotels For Vacation

As the easiest but priciest option, hotels remain the usual choice for travelers, especially on shorter trips.

Hotels provide the easiest convenience with rooms cleaned daily and everything you need at the front desk. 

Hotels are the best option if your goal is to relax and let others take care of everything else.

If a pipe bursts, someone will be up to your room pronto to fix it. Need a toothbrush? A brand new toothbrush is ready when you are. Curious about where to eat? A hotel concierge will make the necessary reservations.

The only real challenge is finding cheap hotels that fit your budget. Don’t wait too long before pulling the trigger, because timing is everything when finding affordable hotels.

Although different ratings and styles of hotels determine the overall experience, hotels gain a reputation as the best option, but sometimes that’s not always the case.

There are more options available if you have different needs. 

Booking Rentals For Vacation

For an affordable option with a few comforts of home, vacation rentals have moved beyond just beach houses and into every type of home imaginable. 

Rentals best suit travelers looking for accommodations with kitchens, living rooms, multiple bedrooms, washers, and dryers. 

I usually find a rental cheaper than most hotels, using a basic apartment that contains all I need. 

If you are traveling with a large family or a group, rentals are the way to go with everyone under one roof. 

Airbnb is my personal go-to option for its ease of use and great customer service. After a few minutes browsing their site, you can see the extensive availability and variety in any city.

For my long trips when I need to be in a city for weeks or months at a time, Airbnb remains my first choice.

Booking Hostels For Vacation

With thrifty travelers in mind, hostels are known for their low cost rooms aimed toward the young backpacker.

When on a tight budget, travelers can book a bed in a dorm-style room for a fraction of the price of a hotel. 

Hostels provide more than just dorm-style rooms. I’ve booked private rooms in hostels all over the world because the accommodation was exactly what I needed at the right cost.

Even if you have the funds for a hotel, try booking a hostel to meet new people and get plugged into local activities. If you want to socialize and stay active on your trip, a hostel might be the best option. 

Book The Room You Need

Think about the most important aspects of your accommodation and what you really need.

Do you just need a place to sleep as you adventure out during the day? 

Are you looking for high class, 24 hour room service to end the night with a perfect meal?

How about a kid free pool area so you and your spouse can lounge without interruption? 

All these are important aspects that your accommodation can fulfill. Think about what’s most important and don’t compromise on the necessities. 

6. Planning For Vacation Meals and Restaurants

Now let’s look into food. Everyone loves to eat when they travel, and if you are on my website, food takes a top priority. 

The main reason to start considering food now is to make sure to book reservations for the right restaurants or plan which meals take precedence over others.

Reservations For Busier Restaurants

If eating at restaurants that rank in the World’s 50 Best or the Michelin Guide sparks your interest, then you have no choice but to plan ahead. Every restaurant is different with its own method of booking and managing reservations. 

Sometimes, websites like Open Table work great, but most notable restaurants will release their reservations months in advance, booking up completely in minutes. 

These restaurants use systems like Resy or Tock which require a credit card to book a reservation and sometimes pre-charging for the whole meal like a ticket system. 

If you want to try these famous restaurants, the farther you look ahead the better. 

Plan For The Best Food

If I want the best croissant in Paris, I’m going to plan my options ahead of time and make this pastry a top priority. I already know where to go and what to expect. 

Sometimes, people wait hours for amazing food. In Austin, Texas, I waited four hours in line for the best bbq brisket on planet earth. 

I planned ahead and knew the line started growing around 7 am, and that Franklin BBQ sells out EVERY DAY. I made this food stop a top priority, knowing very well it would be an all-morning event.

Make a list of which foods you want to try and which restaurants offer the best versions. Sometimes there is a line or the shop could sell out or they have unusual hours that conflict with your travel plans.

Plan ahead to know where and how to find the best food in your city.

Plan Meals That Suits Everyone

Consider who else is traveling with you. If you have a family with young children, plan ahead to find kid friendly restaurants that still serve amazing local dishes.

I know you want to chow down on local delicacies but it’s important to have the rest of the family try it too. 

If you have dietary restrictions, planning out vegan, vegetarian, gluten-free, and dairy-free options will save you from “hoping for the best” when you venture out. You are prepared with restaurants at the ready. 

Plan Meals Around Activities

If your plans keep you adventuring in the city for long periods of the day, plan a few meals close to these activities.

Overpriced and mundane tourist restaurants pack the streets around attractions, so look ahead to find better, cheaper food close by. 

If you plan on seeing the Coliseum in Rome, plan which restaurant you want to visit before or after. Having a few options at the ready will help you avoid compromising and eating a dried out panini at the corner Starbucks. 

7. Plan A Few Vacation Activities 

Forget the hour by hour itinerary, but still plan a few activities that really interest you. Doing your research informs you of what to expect with the attraction, ticket prices, and wait times.

If you are visiting a bucket list attraction, don’t risk “winging it” and possibly miss your only chance to fulfill a lifelong dream.

When I visited Granada, I went to the Alhambra, one of Europe’s most famous attractions. I looked ahead at times and ticket prices and booked a month in advance.

These tickets are notorious for selling out, and I wanted to avoid spending 200% above normal tickets at third party sites. 

Also, when I traveled to New York City for Christmas, I saw a line wrapping around a whole city block to later find out it was the line for the Empire State Building with waits estimated for over three hours. No thank you.

Plan ahead to avoid these unfortunate surprises and guarantee your admittance. 

8. Plan Vacation Safety And Emergency Logistics

In the unfortunate event of an emergency while traveling, what is your plan? If you run into trouble do you know where your embassy is in the city? What if there is a natural disaster like a flood or an earthquake?

Although I don’t dwell on gloomy possibilities, I still make emergency scenarios an important part of my planning. I save a few items on my google maps knowing I have their locations and addresses handy.

• Find the closest hospital to your accommodation.
• Save the information of your home country’s embassy or consulate.
• Understand the possibilities of natural disasters in your area of travel.
• Have images of your passport printed and pictures saved on your phone.
• Know the local emergency phone numbers for immediate help.
• Take a first aid certification course.
• Know the bad neighborhoods you should avoid.

These are just the basics and good to know for the off chance emergency. While traveling in Taiwan and Mexico, I experienced earthquakes and found myself shocked not knowing what to do. Luckily, the shakes were minor, but I think about what would I have done if it was worse.

Staying prepared is important and don’t overlook the possibilities of emergencies and think, “This will never happen to me.” 

9. Sort Out The Little Details Way Before You Leave

Traveling leaves local responsibilities unattended, and effectively planning for vacation means not worrying about what’s happening at home. Avoid waiting until the last minute to get these details sorted out. 

• How will you get to and from the airport? Do you need to reserve a ride? 
• If you have pets, do you need to book a kennel, daycare or find a friend to feed them while gone?
• Are you taking your kids? What items do they need to have a comfortable trip?
• Who do you call in case of an emergency?
• Who will check your mail or pick up any packages being delivered?
• Do you need travel insurance?
• Do you have the right Vaccines? Some countries require vaccines for entry or they are highly recommended. Common vaccines are: yellow fever, typhoid, and hepatitis A.
• Do you have your prescriptions for the duration of your trip?

Lots of details to think about and consider, but write out your own list of important items to plan and organize. Waiting too long means compromising on the best solutions leaving you anxious during your trip. 

10. Plan Your Arrival

More goes into planning a proper arrival than most people realize. I’ll run through a few items and scenarios to consider. 

Early Arrival

I’m no stranger to red-eye flights and have flown unusual hours both domestic and international, leaving me in a new city in the wee hours of the morning. 

Accommodations won’t allow for super early check-ins, so I suggest booking the room for an extra day for the day before your arrival, so your room is ready when you arrive in the morning. 

Be sure to let the hotel or rental host know of your early morning plans to ensure a smooth check-in. 

If you are running on a bare bones budget, hotels allow guests to drop off their bags early until their rooms are ready in the afternoon. This means you must occupy yourself until then.

I’ve done this after an overnight flight from Denver to New York City and ventured around a completely empty Times Square at 6:00 am on a Sunday. No sleep, but that’s ok. I just needed to save money so I could indulge in the amazing food. 

Late Arrival

If your plans bring you into a new city late at night, I always opt for taking a taxi or Uber over public transit when going from the airport to my accommodation. Traveling through an unfamiliar city late at night puts you at risk for all sorts of mishaps. 

Although I am an advocate of using public transit, don’t try to venture through a new city at night.

Also, if you are arriving late at night and you’ve been traveling all day, what will you eat? I know it sounds strange, but think about it. What will be open around your accommodation super late at night?

While traveling to Lisbon, our flight landed around 1:00 am after a grueling 12 hours of travel. After getting through border security and getting our bags, the time showed 2:10 am, and I very well knew the restaurants in our area of the city were closed. 

I stopped at the airport bodega and picked up a few sandwiches which we ate promptly after entering our Airbnb. 

International Arrival

Planning for vacation includes having your ducks in a row for international arrival.

Make sure to have your passports, entry documents, and visas ready to go before landing. A little research goes a long way.

In some countries, visas are filled out and paid for online. Others are done in person before entering the county. In some countries, you don’t need a visa at all. 

For entry into Vietnam, I filled out papers online, paid my visa fees, and printed the documents as instructed by their website. I also need two passport sized photos ready to go. 

After arriving in Vietnam, the whole process took about an hour for an immigration official to check my documents, print forms for me to sign, and place a huge visa informational sticker on my passport. 

Yes, lots of details and moving parts there, but missing anything could mean fines, a longer immigration process, and even denied entry. 

Information is your friend here, so double check entry requirements and make sure everything is filled out correctly. 

11. Packing For Vacation

As the date draws closer it’s time to start planning for vacation necessities. What’s the weather forecast for your time there? What activities require specific items? 

Sometimes, items are better brought with you than bought on location. 

While in Nassau, Bahamas, I forgot sunscreen and went to the hotel resort store to find the right bottle. 

$14 for a 6oz bottle of sunscreen. Yes. $14. This exact bottle costs $3 at my local drugstore. 

Planning a winter vacation skiing? Bring warm clothes with you! Socks, long underwear, jackets, gloves, goggles, and ski pants. 

Buying these items on location will cost you dearly, sometimes marked up double than buying them locally and packing them with you. 

Conclusion: Enjoy Your Vacation!

Hopefully, these planning tips make your trip run a little smoother with fewer headaches and uncertainty. Although you can’t plan for everything, this list covers the basics that I use when planning a weekend trip or a six month hiatus around the globe. 

With all the planning, remember not to over plan, and enjoy your trip.

Although I am a type A personality, I forgo the tightly structured itinerary and focus only on the essentials I want for my trip. Have fun and enjoy yourself because that’s why we all travel.