How to Plan a Vacation Like a Pro

Travel planning today can be quite complicated with all of the travel restrictions and requirements constantly training. No longer can you simply buy a travel package (flight and hotel) from an online travel agency and call it a day. Now, you have to investigate every destination and what you will need to enter. Not only when you first book your trip, but continually through your vacation as these requirements can change day by day.

It’s enough to drive anyone crazy!

Though this is the case currently, travel planning does not need to be a stressful affair. If you all of the little details you should be looking for and where to look, you will have everything you need to plan an incredible vacation.

This goes beyond just planning for travel restrictions and requirements.

By knowing what to plan for, you can craft vacations beyond what you ever thought possible – including all the little details that turn an average vacation into something truly incredible.

So how do you know what to look for and where? That’s where we come in. It is our mission to teach you and provide everything you need to plan better vacations. Whether that is through our blog posts and YouTube videos or through our digital resources, we’ve got you covered.

In our 15+ years in the travel industry, we’ve found there are specific steps to take when planning any vacation. By following this method, you can ensure your vacation will go as smoothly as possible (yes, there are unforeseen circumstances, but we guide you through planning for these as much as possible).

These are the 6 essential steps for planning a vacation:

1. Pre-Planning

Every great vacation starts with pre-planning. This is where you decide on your destination, what style of vacation you want to experience, settle on your budget, and begin brainstorming what you want to see and do. Without this piece, you may plan and buy everything only to realize later there was something else far better if you had only given it a little more thought.

As professional travel advisors, we find this has the most impact on the vacation itself. If we don’t take the time to understand what we really want, it makes it exponentially harder to plan a great vacation. It is here we recommend everyone start and think through carefully.

Visualize What You Want Your Vacation To Be

Close your eyes and visualize, pull out a journal and write…heck, draw it out if you have to. Whatever your preferred visualization technique, use it to explore and dream about what you’d like this vacation to be.

Are you wanting to relax by a beach sipping Mai Tais? Or be active, exploring mountain trails or soaring over picturesque landscapes? Exploring history or the seven wonders of the world? Diving into the culture of a new country? Experiencing luxurious resorts and amenities? What do you want your vacation to be? Choose the feel and style of vacation you are wanting to create.

Decide On Your Budget

Next, decide on what you want to spend overall and for each aspect of your trip. How much are you willing to pay for flights? Lodging? Activities and food? Shopping and extras? Transportation?

Knowing your budget will help keep you on track as you begin researching options. It’s so easy to look at one hotel or area, then see something slightly better, then something better than that…next thing you know you’re wanting something far beyond what you want to spend. Knowing your budget will help keep you within the limits you have set. It also helps narrow down options when you are flooded with far too many choices (which is always the case).

Our digital travel planners and paperback planners both have budgeting worksheets to help you cover all potential expenses.

2. Research (But DO NOT Book Anything…YET)

This is the step where you begin to research all of the possibilities that will fulfill the vacation vision you created. It is at this point that you will begin making a list of potential destinations and areas, activities, restaurants you want to try, and experiences you want to have. This is also when you’ll begin looking at travel restrictions to make sure you can (and are willing to) do what they are expecting.

Destination Ideas

If you are still narrowing down your destination options, our favorite tool is the Google Flights Explore tool.

Check Travel Restrictions & Requirements

No matter where you are going, it’s always necessary to check on travel restrictions. Especially with new variants and spikes coming and going, even domestic locations can have new restrictions you are not aware of.

To do this, simply conduct a Google search for “your destination + travel restrictions (or travel requirements).” Look for the most recent dates, but also reputable websites, such as the State Department, Tourism Boards, Border Control, Ministry of Health, Diplomatic sites, and Embassies. Here are a few sites we’ve found valuable:

Check Your Passport Expiration

If you are planning to travel internationally, it is vital you make sure your passport expires more than 6 months from your travel dates. If it does, you will not be able to travel with it.

Also, if you do not have a passport yet, you will need to make sure your travel dates allow plenty of time to get one (or renew if yours is expiring soon). The current wait times for passports are upwards of 18 weeks and climbing (and the expedited option is 12 weeks and climbing). So do not procrastinate on taking care of this and make sure your dates are far enough out to accommodate the waiting time.

Use YouTube and Google

YouTube is our favorite place to conduct research on potential destinations, lodging options, activities options, food options, and to learn more about the culture, safety, and transportation options of areas. Nowadays, there’s a video on just about any destination and several on specific recommendations.
If you’ve narrowed it down to a couple of potential destinations, spend some time surfing YouTube to get more ideas about where to stay, what to do, and what to eat (be sure to also note culture and safety issues as well).​

Research Potential Activities & Experiences

Next to pinpointing where to go and where to stay, deciding on what to do is the next most important planning item. How you fill your vacation days can be the difference between an awesome trip or one that is boring or too exhausting. ​There are worlds of things to see and do in every destination – the trick is finding what will work best for you. To that end, we usually start to note everything that looks potentially interesting. Don’t weed anything out at this point, just note everything you might like. ​

The places we have found to consistently have incredible activity options are:

AirBnB Experiences

These are not AirBnB housing, these are completely separate options. They are activities/tours/experiences offered by locals in the destinations you are visiting. For instance, in Japan you can have a local take you on a food and sake tour, in Italy you can learn to make pasta with a local grandmother, and in Hawaii, you can learn how to fire dance. We recommend taking at least one experience near the beginning of your vacation as the local always has tons of tips and ideas that you can incorporate through the remainder of your vacation.​


Viator is our favorite place to book tours and activities around the world. With over 2500 destinations and 395,000 attractions/tours/activities, there is always something for everyone. We also love their flexibility (to reserve now and buy later) and their generous cancellation policy (can cancel up to 24 hours prior to your activity). Viator is a staple for any vacation.

3. Make An Itinerary Rough Draft​

Now that you have a massive list of options, start playing with them. On a calendar, begin planning your days and playing with various options. Here are some things to think about:

  • Try to keep activities to 1-2 daily so that you have plenty of time to relax and to keep options open if you find something amazing you want to add in while there.
  • Consider time change when planning. For instance, is your time zone far ahead of where you are going? Then you will likely be up super early the first 1-2 mornings, so these would be ideal for any sunrise activities you’d like to explore.
  • Consider locations and how long it’s going to take you to get between activities. Make sure you build in time to get back and forth, change (if needed), and relax before heading to the next activity.
  • Consider transportation options for getting to your activities. Is the lodging you’ve chosen centrally located or at least easily gotten to from everywhere you want to go? Or should you switch lodging locations?
  • Are the activities you want to do open and available on the days/times you want to go?

Once you have a rough draft, make alterations as needed to lodging, arrival/departure times, and anything else to help smooth out your vacation and make it as stress-free as possible.​

4. Call Your Concierge/Host or a Local

This is a secret ingredient to planning vacations. In talking to someone in your destination, such as your concierge (or any quality hotel concierge) or the host of your vacation rental, you can get valuable feedback on a variety of things. Including:

  • What do you need to know regarding safety?
  • Are credit cards used often or will you need cash?
  • What other activities do they recommend?
  • What is REALLY the best transportation option for where you want to go?
  • Do they recommend any restaurants?

Locals are a gold mine of information to make your vacation amazing. You can also use other methods to reach a local, such as through a foreign language sharing app like iTalki or your Airbnb Experiences guides.

5. NOW Make Your Reservations and Bookings

The reason we recommend waiting to purchase until now is to ensure you have everything exactly the way you want it before you start committing. During your rough draft or even calling the concierge step, you may find that you want to trash your whole plan and start over. Or, change around times, days, or even locations. It’s best to wait to book until you are certain of what you want.​

Book/Reserve/Buy Tickets/Make Appointments For As Much As Possible. With the pandemic, travel is more chaotic than ever. There are limited capacities, reduced hours, ever-changing entry requirements, and much more to deal with. Because of this, it’s VITAL that you be as organized and on the ball as possible. The more you can plan for, the better your trip will go.

To help you with planning, we’ve created our digital travel planner and paperback planners with guides, resource links, planning pages, and worksheets to make sure you don’t miss a thing.

6. Plan the Logistics

This is the final, and perhaps most important step, to any good vacation plan. It is the little details that can make all the difference in your vacation experience. Here are some things to consider:

  • Currency (including if you need cash or if a credit card is fine)
  • Safety
  • Convenience (what can you plan ahead for to make your travel more convenient?)
  • Comfort (what can you add that will make your trip more comfortable?)
  • Can you ship your luggage ahead so you don’t have to deal with them at the airport?​
  • Can you gain access to Airport Lounges? (Priority Pass is a membership program we recommend that offers entrances to lounges worldwide)
  • Are there any add-ons or amenities you can request from your hotel to make your stay more comfortable?
  • Think through each day – is there anything else that can make things better?
  • Transportation options
  • Apps that might help (we’ve created this video all about our favorite apps)
  • Health issues such as – is the water drinkable?
  • Travel restrictions for both going AND returning to your home country

​The following video shares our #1 tip for planning the logistics:​

For more help in planning your vacation, please see our recommendations page. For more video tutorials, visit our YouTube channel. Or feel free to Contact Us anytime.

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