How to Plan Your Next Trip

girl sitting on balcony in Maui HI

Yes, planning a trip can sometimes be overwhelming; however, we all know it’s not impossible!

Efficiently planning a trip is all about being realistic about your budget, destination, timing, and desires. As long as you have those items defined, then you will plan the perfect trip.

Follow my guide on how to plan your trip and I guarantee it will help you execute the perfect itinerary!

girl standing in the bamboo forest on the Pipiwai Trail

Type of Trip

This may be an easy step, depending on the type of traveler that you are. But before I plan a trip, I like to decide “is this going to be a relaxing trip or more of an adventure?” This simple question will influence all the next steps, so make sure you know what kind of trip you plan to take before proceeding.

Recently, my trips have been more focused on adventure and exploring, so they have required more planning than usual.

Budget

The next thing that I like to do before planning a trip is decide how much I want to spend. For example, what is my overall budget? And what is that top number that I am not willing to exceed?

The reason I do this is I like to travel multiple times throughout the year. By creating travel budgets, it ensures I am not overextending myself. This also leaves me plenty of wiggle room for planning more trips within the near future.

Ok so for your trip’s budget, I recommend setting a range. Figure out your sweet spot number first. This should be the total cost you will spend. Next, determine your hardline amount. This number will represent your red flag area, meaning once you’ve hit this, then you know you need to start re-evaluating your itinerary.

Now if you’re unsure of how much you want to budget because you don’t know the average cost of things at your destination, then that’s ok! Even just throwing out a ballpark number or maximum costs number will help keep you in check as you are building your itinerary. You can easily adjust these numbers later if needed.

When considering your budget, PLEASE PLEASE be realistic. As much as we all love miracles, we cannot expect to fly halfway across the world and only pay $500. So, if you are planning an international trip, make sure your budget accounts for additional expenses like higher plane ticket prices, travel insurance and visas.

Costs to consider in your budget:

  • Flight
  • Hotel/Airbnb
  • Local Transportation (Car rental or Uber)
  • Food
  • Activities

Destination

If you already know where you would like to go, then skip this section. BUT! If you’re not sure, then let’s get started.

You know you would like to go somewhere, but that “somewhere” is unknown. Well, whenever I find myself in this situation, I like to use Skyscanner or even Google Flights. I suggest heading over to their sites and using the “explore” and “travel anywhere” features.

These sites will give suggestions on most affordable places to travel during specific windows. Once you find a location or at least narrow down your area of choice, you can adjust the time frame and trip length as needed.

Another site that I use to find places to travel to is Pinterest! Simply searching for something like “best places to hike in the US” or “Unique stays in the world” will give you suggestions of cool destinations to visit.

Timing

If you find a destination that draws your attention, next step to determine is timing!

This is an important step in planning your trip, as it can influence the activities you do on your trip. This is why you often hear travel bloggers mention “peak season” vs “off-season.” Peak season is known as the busiest time for tourists whereas “offseason” will be the complete opposite.

So, unless you love dealing with enormous crowds and endless searching for dinner reservations at popular local spots, then I highly recommend avoiding peak seasons. On the contrary though, the ONLY time I will disagree with that statement is if there is an activity that you would like to do and it is only offered during a specific timeframe. In that case, then go for it! An example of this would be seeing the Northern Lights in Finland.

Another trick for picking the best time to travel is to visit right before or right after the peak season. This allows you to still enjoy the popular spots without as much hustle and bustle that comes along with large tourist crowds. However, if you do this, be sure to research historical weather reports during your travel time as well. For example, if your goal is to travel somewhere tropical, then sometimes visiting after peak season could mean traveling during hurricane season. Taking the time to research past weather reports can help you avoid your sunny tropical vacation being completely washed out. Weather Unground is an excellent site to use for this.

Once you determine the timing that works best for you and your travel plans, then head back to Google flights and Skyscanner. Now, if the original suggested time frame aligns with your travel plans, then GREAT! But if not, use the calendar view to adjust the time frame. The calendar view on Google Flights is great because it shows you which days have the most affordable flights. Adjust the dates until you find the flight that better fits your budget.

girl on Boat in Ka'anapali Maui HI

Desires

Ok, so you know where and when you are going! It’s time to figure out what places you want to see, foods you want to try, and things you want to do. For this step, try to avoid booking anything. The primary goal here is to just explore the potential activities in the area. I will explain more in the next step why you should wait before booking activities.

To discover activities, restaurants and local favorites, I like to use the following sites.

  • Tripadvisor

Tripadvisor is great for finding popular places to see at your destination. Simply log onto their site, select “things to do” and then type in your destination. Tripadvisor will bring up tons of suggested categories, such as day trips, cultural tours, and outdoor activities. Skim through the categories to see if there are any local activities that draw your attention. If you find something that stands out, be sure to visit the company’s actual website to learn more about their services.

Also, what makes Tripadvisor an excellent tool is their review section. TripAdvisor has a unique filtering system for their reviews that can be extremely helpful for narrowing down feedback based on the type of visit (solo, couples, family) and even by travel month.

  • Viator

Similar to TripAdvisor, Viator is a great tool for booking tours and excursions. Recently I used Viator to book a Sunset Catamaran tour in Maui. A unique feature to Viator is that they often offer free cancellations as long as completed 24-48 hours before your booking. They even allow you to reserve some tours in advance and will not charge you until 24 hours before your tour.

Instagram tags view screen
  • Instagram

Ok, I know you must be thinking Instagram… really?? Well, hear me out.

Hashtags are literally the driving force behind social media these days. I guarantee you will find countless photos if you search your destination in the hashtag search engine! Scroll through the popular and the most recent pages and click on the images that catch your attention.

Most times, I find people tag the place they are visiting. I find this to be helpful in finding local favorites, whether that be hidden beach spots, hiking trails or even just restaurants.

I used this method recently in Sedona to find a local coffee spot on the outskirts of the town. There were never any crazy tourist lines, and the baristas were so nice. They even ended up giving us advice on hidden hiking trails, which made our trip even better!

  • YouTube

If you are doing an international trip, I highly recommend researching local cuisine dishes. I like to watch youtubers like Mark Wiens and Strictly Dumplings to find the best food spots and discover must try local cuisines.

If you are adventurous and are open to trying many foods, then I highly recommend watching Mark Wiens videos. His videos are hilarious, so be sure to scroll through his content if you are planning an international trip.

Google drop pins feature

As you are finding activities and local spots, I recommend using Google Maps and the drop pin feature. This will help you get a bird’s-eye view of all the places you would like to see. This is helpful for laying out your itinerary, so your time can be spent more exploring as opposed to in a car traveling to the next activity across town.

Vdara living room in Vegas
Vdara bedroom

Hotel and Transportation

Now that you know all the places you would like to see, it’s time to find a place to sleep! The reason I do this last is so that I can find a central location in relation to the activities that I am planning.

For example, during a recent trip to Maui majority of the activities that I wanted to try were on both the west and east side of Maui. To make my commute easier, I stayed in central Maui.

Here are some other things to consider when booking your stay:

  • Would you prefer to eat locally or would you prefer to eat onsite at your stay?
  • Are you staying in a major city? If so, what does your transportation situation look like?
  • Do you want amenities? If this is a relaxing trip, then is a pool and spa a necessity?
  • Are you planning to explore most of the trip? If so, does an Airbnb make more sense?

So yea, these are the steps that I go through when planning my vacations. I know it may seem like a lot, but if you tackle each category separately, you will be just fine! If you have suggestions on planning trips, comment on them below!

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