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How to plan yourself a well-deserved vacation in 10 easy steps

Updated: Jun 19

You shouldn't let anything hold you back from taking a vacation this year. You truly deserve it. The hardest part about taking your well-deserved vacation is the research and planning ahead of travel. With this guide, you will be able to plan your vacation in 10 steps.

Check out these 10 easy steps to help you plan your next vacation.

Solo traveling women

1) Pick a time of year

Making time for travel can be the hardest part about actually taking the much needed vacation you've been longing for.

Look at your calendar for the whole year. Is there a month that you have no plans? No big work commitments, no weddings, no events for the kids, no family obligations? That month is the perfect opportunity to fit in a vacation.

Block off a few days or a couple of weeks that will hold you accountable for actually taking the time off. These do NOT need to be the exact dates yet (I'm speaking to all my type A people).

Blocking time on your calendar will help you start mentally preparing for your vacation. It will get you in the mindset that in X month you're taking time off and going somewhere. Even if you don't know all of the details yet.

By blocking time on your calendar, you will find yourself naturally doing the next steps to make your vacation happen.

2) Define your budget & start a travel fund

Knowing your budget for your vacation is the most important step. This will help you make decisions within your affordability on where to stay, what flight to book, what activities to do, what sites to see, etc.

If affording a vacation is the biggest reason you aren't traveling right now, start a travel fund. This can be a jar on your counter, a savings account, an envelope, whatever works best for you. But once you establish your travel fund, that money is not meant to be spent on anything but travel.

By setting aside $10 a day will save you $1,830 in six months and $3,660 in a year. That's your favorite Starbucks coffee or lunch at a fast food restaurant. Think about the fabulous vacation that $3,660 could buy you?

If you'd like to have even more money for your travel fund, check out this hack on how to save $5,050 in only 100 days.

3) Decide who you want to bring

If you're setting off solo you can make all the travel choices on your own.

But, if you'd like to bring someone it is good to loop them in early on. This way you can decide together the major decisions of your trip.

Traveling solo can be intimidating. But if you don't have someone in mind to travel with, you can always join a travel group. See upcoming group trips for Cherish here.

4) Decide where you want to go

This is the biggest decision about your vacation. Where do you want to go? There are a lot of things to consider when picking your destination:

Budget - Does the destination you'd like to go fit within the budget you've defined. Certain places are more expensive than others. Looking into the average daily cost of a place can help you determine if it's the right place for you to visit.

Most budget friendly travel destinations Where do you think would be the most budget friendly place to travel? You might be surprised!

Most expensive travel destinations Would you be surprised that Switzerland is on this list? What about Toronto, Canada?

Goals for travel - Considering what you would like to get out of your vacation is an important part of considering where to go. Would you like to have a relaxing beach vacation? Or do you prefer hiking in the mountains? Is your goal to have an adventure or an escape? Knowing your goals for your vacation will help you narrow down your choices.

Weather - The weather in a place can truly make or break your experience. Even though we cannot control the weather, you can be equipped with information on the best time of year to visit a certain destination considering the weather patterns.

Check out this map to find the best time of year to travel to every country in the world.

Flight prices - The cost of a flight could impact the affordability of a destination. Make sure to do a quick search on the average flight price from your nearest airports to the airports in your preferred destinations.

5) Book flights!

Once you've decided where you want to go, it's time to look at flights. This is the point in the planning process when you can solidify your dates.

In my experience, the most expensive flights are for weekend trips from Thursday to Sunday. Flying on "off" days may help save some $$$.

Stay tuned for a full post on how to find the best flight prices for your travels. Check out a few resources for finding budget flights below:

Always search for flights on an Incognito window without cookies.

I typically look at flights on Google Flights.

6) Start researching your destination and pick must do's

Have fun with this step. I personally like to do a deep dive through the depths of the internet to find out all I can about a particular place. Blogs are my favorite way to get an insider point of view on an upcoming destination.

But there are many ways to research the destination you've chosen to go to. One suggestion that I'd highly recommend is to tap into your resources. Ask your network if anyone has traveled where you're headed and get personal recommendations.

Tourist attractions are a good place to start, certain tourist attractions are popular for a reason and deserve a visit. You wouldn't go to Paris without seeing the Eifel Tower would you?

Picking your must do's doesn't have to be limited to the tourist attractions. Your vacation should be filled with things YOU love to do. Lean into the goals you have for your vacation and spend time on the things that make the trip worthwhile to you.

7) Book your accommodations

Now that you have a list of must do's, look at them on a map. Can you have one home base for your trip or do you need multiple launching pads for all the sites?

Taking your budget, your must do's, and the type of stay you want into consideration, start looking at places to stay during your vacation. I always suggest reading reviews and picking a place that has current photos.

Once you've found the perfect spot, book away!

8) Plan your itinerary

For me, this is the fun part! Your trip does not need an hour by hour itinerary (unless you and your fellow travelers enjoy that). However, it is a good idea to have a general sense of what you'd like to do when. That way you can make the most of your time in your destination. Fill in all the blanks with the little details. Make sure to incorporate all of your must do's and make time to relax.

Sometimes we forget one of the most important part of traveling is for the trip to actually feel like a vacation. I can get carried away in exploring a place that I will have no down time. I come home needing a vacation from my vacation. It helps me to build in downtime or a relaxing afternoon or two into my itinerary.

Lastly, when planning your itinerary, make sure to consider transportation and activities that require reservations. Winging it can be a great way to vacation, but certain items will need a reservation (car rental, certain accommodations, popular restaurants, popular tourist attractions, excursions, etc.). Make sure to get those booked, then wing the rest if that's your style. Me and the other type A people will be working on charting out our full itineraries.

9) Research travel requirements

COVID is still here. Requirements for travel are rapidly changing. Make sure you know all you need to know to make it to your destination.

Even prior to COVID, there are many countries in the world that require certain vaccinations, medications, etc. before traveling. It is always smart to consult with your general practitioner physician prior to any large international travel.

10) Pack your bags & go!

Would you prefer to join a curated adventure with fellow women travelers to some incredible destinations around the world?

Cherish offers impactful and immersive travel experiences for women on a mission to travel with purpose. Each of our small group tours supports women in business in the destinations we visit.

All of our upcoming experiences are listed on our website, view them here.

Subscribe to our monthly newsletter to stay up to date on trip offerings and receive exclusive deals and discounts.

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