How to plan a vacation you'll love, travel planning process

How To Plan a Vacation You’ll LOVE in 10 Steps

When planning a trip, where do you start? With your budget, or the destination? NO! Neither will get you what you want the most. (Yup, even the destination! Hear me out.) This 10-step guide on how to plan a vacation you’ll love starts with the MOST important thing: the experience you want.How to plan a vacation you'll love in 10 steps, travel planning process pin

Follow the step by step travel planning process below to plan a trip you will LOVE. These 10 steps help you define the experience you want, build your travel itinerary, and then get ready to go.

Grab your notebook and pen, and let’s get started!

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How To Plan a Trip You’ll LOVE in 10 Steps: Step-by-Step Guide

Step 1: Start with the EXPERIENCE you want

Where do I start with planning a vacation? With the EXPERIENCE you want to have. Start by asking yourself, “When I get back, what will make me say this was a fantastic trip?”

SO many bloggers completely miss this all-important first step for planning a trip. Some start with the budget, but this can hamstring you before you get started. Some start with the destination, which makes sense at first, but can be disastrous if you go with the wrong people.

The first step for planning a trip is to define the REASON you want to travel. Then you have a much better chance of actually getting it!

Do you need to wind down? Wind up? Stretch your mind, or your physical boundaries? Spend quality time with family or friends?

Whatever you want the most, write this at the TOP of your trip planning documents.

For more on this step, check out Trip Planning Step 1: Define the EXPERIENCE You Want.

Meterora, Greece (Credit: Jason Blackeye from Unsplash)

Step 2: Identify your PRIORITIES and constraints (time, money, activities)

The second step in how to plan a vacation you’ll love is to consider your priorities and constraints. This second step for planning a trip will give you your boundaries, so they don’t distract and frustrate you from getting that experience you defined in step 1.

How much TIME do you have? Are your dates and length of trip flexible or pre-defined?

How much BUDGET can you set aside for your trip? Again, is this pretty flexible, or is it strict?

Are there certain ACTIVITIES you must do, or really want to do? Do they only happen during certain seasons, or in specific locations?

Once you know your priorities and constraints, EMBRACE them in the travel planning process. Even if your time is limited or your budget is tight, you can still plan a fabulous trip that gets you the experience you’re after. Use these priorities and constraints to guide your most important decisions.

Step 3: Clarify what you KNOW (where, when, who)

Next, clarify what you KNOW about your trip and let it guide what you don’t know.

Do you already know WHERE you’re going? If yes, when would be the best time to go, and for how long? Who would you most want to experience that place with?

Do you already know WHEN you’re going? If yes, what type of destination is best to experience in that season, or within the amount of time you have? Who could go with you then?

Do you know WHO you’re going with? If yes, what type of destination would be most fun for both of you, together? When can they go?

Use what you already know as inspiration in the travel planning process. Be careful not to “put a square peg in a round hole,” by mixing up where, when and who. For example, when your kids are going with you, pick a destination they’ll enjoy, too, and give yourself extra time to get there.

Step 4: Understand your travel STYLE (preferences, rhythm, limitations)

Mammoth Lakes, USA (Credit: Robson Hatsukami Morgan from Unsplash)

The next step in how to plan a vacation is to understand your travel style. This includes how you like to travel, and how you don’t like to travel.

If you’ve traveled a lot, you probably have a pretty good sense of your travel style. Ask yourself questions, like:

  • How busy do you like to be? 
  • What’s your typical sleeping and eating schedule? 
  • What luxuries do you want available?
  • How much walking or driving do you like on vacation?

Every trip is unique, depending on the experience you most want, your constraints and what you know. But even then, you have default preferences. So, take note of them.

And compare your travel style with those going with you. How similar or different are your travel styles? When traveling with other adults, it’s a very good idea to chat about your styles before your trip and how you can accommodate each other. 

For example, my family likes making simple breakfasts and picnic lunches on trips, but I hate going into mega stores on vacation. So, we plan our itinerary to include a visit to a farmer’s market or local grocer.

As another example, my mother-in-law likes relaxing mornings with her coffee. So when traveling with her, we know to relax too or to plan morning activities she doesn’t want to do.

Explore travel styles in more detail at Trip Planning Step 1: Define the Travel EXPERIENCE You Want.

Step 5: RESEARCH your destination

Steps 5 to 9 in how to plan a vacation are all about building your trip itinerary. Start by putting on your detective hat!

My favorite way to research a destination (or destination options) is to get a Lonely Planet travel guide and colorful erasable highlighters and pens, and head to my favorite coffee shop. Lonely Planet travel guides are written by local experts, and include hidden gems and super-useful tips for visitors.

Go through your travel guide, marking up places you definitely want to see and maybe want to see. Once you have a sense of your must-do and maybe-do activities, check out reviews online to confirm what’s most important to you. My favorite places to research travel reviews are Google and Tripadvisor.

Want more ideas on researching your destination and building your itinerary? Check out How To Build Your Travel Itinerary.

Step 6: MAP out your interests

As you research your destination, hopefully a natural itinerary begins to emerge. That’s what you want! It’s much easier to start building your travel itinerary once you have a sense of where things are that you want to see and do, and how much time they’ll take.

If your travel book has a map, highlight places you want to go. If it doesn’t, create a Google Map to plot out these spots. Create a layer for must-do and maybe-do activities, color-coding each one. (Later, you can drag-and-drop activities into a layer for each day of your travel itinerary.)

Choose one or two main activities per day, with a few backup options depending on how you feel that day. Then, pull these into a calendar view, and you have a rough travel itinerary for your trip. Done!

Tip: For a more relaxed travel experience, plan a free day at home before and after. This gives you mental space to transition from (and back into) everyday life. Whenever I’ve done this in my travel planning process, my trips have felt SO much more relaxed.

Step 7: Pick ACCOMMODATIONS for your trip

Oia Greece accommodations, how to plan a vacation
Oia, Greece (Credit: Hello Lightbulb from Unsplash)

I’m always amazed when travel bloggers down-play the importance of fabulous accommodations in how to plan a vacation you’ll love. Even if you’re on a budget, pick a place you want to go back to at night.

Make a quick list of what your travel accommodations MUST have or be. Safe and without bed bugs. In a good location (whatever that means for your trip). Within your budget. Comfortable for everyone in your travel party.

Then, make a list of what you really want, too. A rooftop pool and bar, perhaps? Onsite restaurant, spa or golf course? A beautiful beach, view or kids club?

Start your travel accommodations search with a picture of what you WANT, to help you find a great fit.

My process for finding fabulous travel accommodations is this:

  • Start by searching Google to get a sense of locations, prices and reviews. 
  • Then, check guest photos and more reviews on Tripadvisor. Look for any concerning patterns, like bed bugs or bad customer service, and trust your spidey sense.
  • Find the best price on Google. is my favorite place to book, as it’s usually the cheapest price and easy and friendly to use.

This is actually my favorite step in how to plan a vacation. My husband wants to relax in the evening, so I’ve learned to find travel accommodations I enjoy, too. A romantic lighthouse inn. Charming historic mansion. Or a classy boutique hotel with a great pub downstairs.

For more on finding great travel accommodations, visit How to Find BETTER Travel Accommodations.

Step 8: BOOK the critical pieces

By now in how to plan a vacation you’ll love, you defined the travel experience you want and acknowledged the factors that’ll help you get it. You found activities and travel accommodations that fit that experience you want. The next step for planning a trip is to book it!

Four travel essentials to book as soon as possible:

  • Transportation: Including flights, car rentals, and train tickets. My favorite place to research and book is Expedia.
  • Accommodations: Even if you like winging it, book the first and last nights, plus any nights you know where you want to be. My favorite place to reserve accommodations is Booking.
  • Must-do activities: Make sure you get the days and times that work best with your travel itinerary. For tours, check out GetYourGuide.
  • Insurance: Recommended if you’re traveling internationally. A helpful post on buying travel insurance is by fellow travel blogger NomadicMatt

Save confirmation numbers in your travel itinerary.

How far in advance should you book your flight to get the best deals? This graphic from CheapAir tells you! Based on flights originating from the U.S. Read more on Business Insider here.

Step 9: Deep breath … then fill in the gaps

The hard work in how to plan a vacation you’ll love is done! Woohoo!!

Now is a good time to take a deep breath and walk away for a bit until trip planning is fun again. Then, revisit your must-do and maybe-do activities and fill in any gaps. Chat with those going with you to make sure everything’s still good to go.

This is also a great time in the travel planning process to look into highly-rated restaurants, pubs and short excursions. These are icing on the cake, to take your travel experience to that next level. Slot any you definitely want to check out whenever it fits best in your itinerary, and book them.

Step 10: Count down to a vacation you’ll LOVE!!

Vance Creek, USA (Credit: Karsten Winegeart from Unsplash)

Ideally, give yourself three months to leisurely get yourself ready for your vacation. This gives you plenty of time to enjoy the anticipation … and to remember all those little details.

Like travel documents. Child care and pet care. Travel gear and essentials. Emergency contacts. Foreign currency, electronic gadgets, and playlists. And packing those bags!

For much more detail, check out Your ULTIMATE Vacation Countdown Checklist.

Get your FREE trip planning template

Ready to start the travel planning process? Use this FREE trip planning template to plan a vacation you’ll love. It’s a 6-page fillable PDF that’s easy to use, and has lots of space for notes. Includes pages for brainstorming, building your itinerary, and a 3-month countdown checklist.

Enter your email below to get this template PLUS our travel bucket list template, too.

Trip planning template samples

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