7 Steps to Planning an Affordable, Flexible, Bucket List Vacation

I am a very normal person, living a very normal life. I work full-time as a 2nd-grade teacher, I am completing grad school, and I love my daily life. Even though I am 75 percent a homebody, I LOVE the occasional adventure. I do not live in a van or have unlimited time off (or money). BUT by using my vacation days to the fullest, I have been able to see so much of our amazing earth. I still have many, many places to see and things to do, but in the meantime here are the 7 steps I use when planning (affordable and flexible) bucket list vacations.

steps to planning a bucket list vacation

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Table of Contents

Step 1: Where do you want to go?

I always have a (growing) list of places I hope to visit someday. I am not particular about the order or time, which allows me to be flexible and find the best deal.

Soooo, your first step is to spend some time on Pinterest deciding on places you may want to visit. I drive my husband crazy with how many trips I am constantly planning. Sometimes I think I like the planning part as much as the trip itself….probably because it can be done on my couch. 🙂

Action Step: Write down your bucket list of places you want to visit someday!

Step 2: Research the destinations

Next to your list of places, do a little research about the best time to visit. Write the range next to the place. For example, if you are worried about crowds, find non-peak times. If you are counting on swimming, research the weather.

Action Step: Next to your list of bucket list locations, write the best time to visit, peak times, and weather.

Step 3: What do you want to see?

This is my favorite step! I start making a list of all the possible hikes, activities, attractions that I may want to see/things I want to do. My top must-do’s in each location. I use Pinterest, Instagram (using hashtags), Roadtrippers, blog posts, and Trip Advisor to look at reviews.

Hint: Roadtrippers is an AWESOME planning app that allows you to search all the things to do, places to eat, and stay along your route. Sign up for ROADTRIPPERS to find even more amazing stops right along the route! Use this code (BTR5QTP) to save 5 dollars off your yearly subscription (ONLY 20 DOLLARS!!).

Action Step: Next to your bucket list locations, write down possible things to do.

Step 4: Your Available Dates

Now to the actual planning…Due to being a teacher, my available dates always fall in peak time. In order to save the most money, I try to have a flexible start and end date (within 3 days). Write down the date range you are able (or want) to travel.

Action Step: Reality Check! When can you actually travel? When do you have time off? Write these dates down and narrow down your list to the places that work during that time.

Step 5: Search for Flights

Using your list of places, research, and your flexible dates, start searching for flights. My favorite to use is Google Flights. It is a wonderful tool that shows you the cheapest dates to fly with their calendar. Book the best deal you find that works with your dates.

Tip! Use Incognito mode to search for flights so the cookies do not track your usage!

Action Step: Which flights are the most affordable and work best with your available dates? Narrow down your list to your final choice.

Step 6: Create a “Rough” Intinerary

Now that you have decided on dates and a destination, you can make a “rough draft” itinerary. I like to do this before making any reservations in order to find the best plan and fit the most activities.

First, I pick my top activities and start to research distance, open times and reservation details. I will also start to research the best area to stay, what kind of car to rent, and travel time between activities. Then, I will then start my “rough itinerary”. Use the free printable to help!

I call it a “rough” itinerary because it is important to be open to change.

Sometimes things do not work out as you hoped (weather, travel, time) so I am always open to switching days around and going with a backup plan.

I typically will plan activities (or relaxing) for the morning, afternoon, and night. I try to stray away from planning hour to hour. That doesn’t sound like a vacation to me. I like to provide backup activities in case something goes wrong. Best to be over-prepared.

Action Step: Divide your available days into “Morning, Afternoon, and Night” and write down activities to do during those times.

Step 7: Reservations

My last step is to book my Airbnb or hotel, car, and one or two of my top activities. I look at which activities are the most popular and which activities I would be the most upset about if I did not complete them. I like to wait on the others to allow a flexible plan.

For example, in Hawaii, we didn’t book our snorkeling trip until two days before to allow up to have the best weather. I knew there were many companies offering the tour so I would be able to find an opening and I could easily switch around my hiking days.

Tip: Use the budget printable to see how much of your budget you have leftover after the necessities.

Tip #2: Use Hotels Combined to search for hotels as it will search all of the search engines to find the best deal!

Bonus Tips!

1. Book a late flight for departure – This gives you a free day to explore without having to pay for a hotel.

2. Stop at the grocery store on your first day. Pick up sandwich supplies, granola bars, protein drinks, breakfast options (if staying at an Airbnb) to save significant money on breakfast and lunch. This way you only have to go out for dinner.

3. Limit your drinking . When I travel, I like to explore the new place… I can drink anywhere and we all know that alcohol adds up.

4. Search different tour groups to find the best deal. I always use TripAdvisor for this. There are oftentimes different coupons to use depending on the tour group.

Do you have any other tips for planning an affordable and flexible vacation? Share them below!

Click here for your FREE planning printable!