How To Plan Your Dream Vacation For Your Bucket List! (2024)

Coconut with straw in it.

Traveling can be an amazing way to relax and explore, but the process of planning a dream vacation can be daunting. From researching the best destinations to finding the right flights and accommodations, it’s hard for novice travelers to know how to get started.

But, you don’t need a travel planner or have a ton of money in order to have the trip of your dreams. With a little bit of research and preparation, it is possible to plan your perfect vacation even on a budget.

As someone who has traveled extensively (every two months since creating my bucket list!), I have learned a lot about how to plan a great trip. In fact, I’ve become so used to navigating the planning process that when my family members go away on trips they often call me up asking for help with their itineraries!

So if you’re looking for tips on how to plan your dream vacation – from researching destinations and picking dates, setting budgets, making plans with sitters and more – keep reading! I’ll share all my best advice on creating an amazing getaway experience without having to hire an expensive travel agent.

Note: This page contains some affiliate links. This means that I may receive a commission at no cost to you, if you click on the link and decide to purchase.

Here Are 18 Steps To Planning Your Vacation!

Green cenote with water at bottom and greenery at the top.

1. Research Destinations

The first thing is deciding where you want to go. I recommend making a travel bucket list that you can refer to when picking your destinations. It doesn’t have to be in order where you want to go 1st. Just pick the one that calls your heart the most and fits with what type of activities you want to do.

Here’s a list of 119 travel ideas you can steal from. Plus here is a list of 30 names for your bucket list once you’re done making it. When doing research on your dream trip, look at things like the weather, seasons to go, and things to do there.

For instance, if you want to relax on a beach and you’re thinking of doing so in Jamaica then you can look to see what month works best for you and other activities they have to offer. If things aren’t looking right based on weather, activities, or timing then it’s okay to pick another destination.

Action Steps:

  • Pick your destination
  • Pick your travel month
  • Look up the weather during that month
  • Write a list of activities you want to do there

Here Are 119 Destination Ideas To Add To Your Bucket List!

2. Pick Dates

The next step is once you have your destination picked and the month you are going, it’s time to nail down the exact dates you will be there. Look at your personal calendar and work schedule to see how much time you can spend here, how much PTO you will need, and the dates you will arrive and depart. 

When planning your dream vacation, consider maximizing weekends and holidays to extend your stay without feeling rushed. Optimize your PTO by strategically using the minimum required. Also, factor in flight costs. Typically, it’s more affordable to fly during the week rather than on weekends.

Action Steps:

  • Pick dates for your trip and mark your calendar tentatively

3. Research the Cost

Speaking of cost next is to search what is the average cost other people are spending there per day and see if it aligns with how much you are willing to spend. From personal experience when doing a quick Google search on “how much to visit (your destination here)” and then comparing how much I actually spent once I got home. I found that I should add 500 to whatever they say most people spent.

*Note I typically fall under the “mid-range” category. You can check out some of my past travel budgets here to get a feel of how I travel and what I spend money on. Mexico budget, Las Vegas budget, and Italy budget

Things to check prices on are: flights, lodging (hotels, Airbnb, campsites, hostels, RVs) food, transportation; i.e. local transportation, car rentals, or ride shares and activities you know you want to do. Write it all down and add it up.

During this process, you should also be saving the links to the flights, lodging bookings, and activities you plan to use. When you check for flights to see how much they cost, and happen to find one at a decent price and with good departure times then you should save that flight. Same thing with hotels you are researching.

Action Steps:

  • Check the price for flights
  • Check the price for different lodging
  • Check the price of food (eating out and groceries)
  • Check the price for transportation modes
  • Check the price for activities (excursions)

Read my Italy 1 week Budget Here!

4. Set Your Budget

Now it’s time to finalize your budget. This is just adding up the total numbers that you did in the last step and comparing it to how much money to know realistically you can spend. If you know you can put more towards the trip then that’s great news.

It can go towards better accommodations, nicer restaurants, or more excursions. I personally choose the excursions as that’s the type of traveler I am. Some people are foodies and they choose to put more money into food. While others love the luxury lifestyle so they put it to upgrade seats on flights or upgrade hotels. It all depends on you and what your travel style is.

If however your budget is tight or you know you won’t have the amount that you have calculated, don’t worry you can still go on the trip. There are ways to save money and cut costs. You can remove some of the activities you wrote down and change them with free things to do. One thing I love doing to save money is DIY city and food tours. You can stay in a cheaper place or rework your timeline and dates to find cheaper flights.

Action Steps:

  • Calculate the totals from each category
  • Rework your categories as needed
  • Don’t forget to figure out spending and miscellaneous money

Read How To Make and Stick Your Travel Budget Here!

kaylee Janell in Positano Italy

5. Plan The Itinerary

The next part is now that you know what you can afford it’s time to put it all together and make a plan. Start creating your itinerary so you have a plan for what you will be doing on your trip. I start with the dates and times I will arrive and depart, then fill in the between after.

I use a monthly calendar view 1st so I can see things from a glance then switch to a weekly calendar for more details. When planning your dream vacation, utilize Google Maps to identify nearby attractions.

Grouping locations that are close together saves time and money on transportation, preventing unnecessary trips across the city. Maximize your efficiency by planning your day strategically. When planning your dream vacation, make sure to allocate enough time for the main attractions you want to visit.

Consider sights like Versailles in Paris, which require several hours or even a whole day to fully explore. By allowing ample time for these experiences, you can avoid feeling like you’ve missed out or wasted your resources on just a glimpse. Plan ahead to make the most of your trip!

Leave plenty of room for mistakes to happen. You are at a place you have never been before. Leave space in between activities to account for mistakes like catching the wrong bus or a train being late. Or you booked the activity for the wrong date so now you have to talk to an employee to see if you can still catch the showing for today instead of next week when you’ll be back at home. 

Action Steps:

  • Create an overview of the itinerary i.e. month or week view
  • Create a day-by-day itinerary (with times jotted down)

I created a fun and really cool itinerary template. It’s made to be in brochure form that way you can easily walk around with it or store it in a bag. You can download it for FREE by signing up below!

6. Book Your Flights

Now is the time to book that flight that you saved when you created your travel budget. I use Cheapoair the most but also check on sites like Google Flights, or Sky Scanner when buying flight tickets. I do a quick research again to make sure I am still getting the best deal out there before making my final purchase.

Make sure to save your confirmation emails and other useful information you need after booking. I like to include this info on the back of my itinerary brochure I create so It’s in my hand while traveling.

Action Steps:

  • A quick check on flight deals
  • Book Flights
  • Save confirmation email

Check Out My Resources Page For All My Recommended Travel Tools!

7. Research Local Transportation

Next, you need to research local transportation. Now that your flight is set you need to figure out how you are getting from the airport to your hotel and from your hotel to everything else. When planning your dream vacation search what the locals are using and what makes sense for you to use in the time you have.

You want to know what is closest to where you are staying and where you will be spending most of your time. I like to use Google Maps again and mark all the locations I will be visiting to see what part of town they are in and how far they are from the airport or train station. 

If the majority of things are near each other then I now know I want to be staying near this region or as close as I can based on my budget. I also look at how much the local transportation is and if there are any day or week passes I can get to save money.

You can check out Omio to figure out how to get to where you need to go. For places that don’t have a great public transportation system then I’ll book a rental car.

Action Steps:

  • Research local transportation
  • Book airport ride/ purchase Metro passes/ Book car rental

8. Figure Your Eating Style (Groceries/ Restaurants)

For this how-to plan your dream vacation step once you see how you will be getting around and a look at the destinations via maps you can search what the eating options are. Are there plenty of restaurants or will you need to stop at a store and stock up there? This will depend on what’s available and your budget.

Some hotels don’t have refrigerators or microwaves so you will have to depend on outsourcing your food. If you’re staying in a place with a kitchen you can be more flexible with your eating. Eating out allows you to explore different foods and flavors from around the world, as well as experience the culture of the area.

On the other hand, cooking can provide a sense of comfort and familiarity while on a dream vacation. Although it may not have the same atmosphere as eating out in local restaurants, home-cooked meals can bring a feeling of warmth and nostalgia that is unique to each traveler.

Action Steps:

  • Figure out your eating style whether groceries, restaurants, or both
  • Check online for hotels with a kitchenette
  • Make a meal plan
Swans floating in a river with birds flying above. In Zurich Switzerland

9. Book Your Accommodations

Next is to book your accommodations. Now that you know how you’re going to get around and where the food is, you can book your accommodations in the area that makes the most sense to you.  My favorite tool to use is as they have a city center feature plus I can filter based on my budget.

I also use VRBO for more unique stays, like when I stayed in a vintage RV in the middle of nowhere in Texas but on a vineyard. Bookmark the location of where you will be staying on the maps that you will be using for your trip for easy access.

Also, make sure to note the price on your budget to keep track of your spending. has a feature where they will tell you the amount you still need to pay when you arrive even if you already paid. Some locations require you to pay city taxes in person, I make sure to note this on my budget as well.

The last feature that I love for is that with some bookings you can pay the whole price when you get to your destination. This allows me time to save for the hotel I want, with the dates I need even though I’m not financially ready to pay just yet.

Action Steps:

  • A quick check on accommodation deals
  • Book lodging
  • Bookmark where you’re staying on Google Maps

10. Purchase Travel Insurance

Next is your travel insurance. Now is the time to purchase travel insurance if you have not. Most travel credit cards cover insurance if you booked using the card. So you can skip this step if you have one. If you want more coverage you can use World Nomads.

World Nomads Travel Insurance is a comprehensive and reliable travel insurance option for global travelers. It provides coverage for medical expenses, trip cancellations, baggage loss, and other emergency scenarios.

Travel insurance provides financial protection in the event of an unexpected emergency when traveling, so it is important to not skip travel insurance in order to safeguard yourself against potential financial losses.

Action Steps:

  • Research travel insurance coverage
  • Book travel insurance with World Nomads

11. Plan What Clothing You Will Wear

This step on how to plan your dream vacation will be based on the weather and activities you will be doing, or if you’re really into fashion like me, it can be based on the location’s colors and culture too. I use Pinterest for inspiration on outfits and to see what others are wearing. You can put together a mood board and see what pieces of clothing you already have.

Note the items you don’t have and will need to buy. You want at least one outfit per day of your vacation plus extra items like swimsuits, ski clothes, or rain jackets. If you’re trying to pack light you can mix and match items from your outfits to save room.

For example, if you’re going on a camping trip, you can wear the same pair of jeans or shorts multiple times with different tops and accessories. This will help save space in your bag and give you a fresh look each day! Don’t forget to bring a few basics like bandanas for when you need an accessory but don’t have anything else!

Action Steps:

  • Check Pinterest for outfit ideas
  • Create a mood board
  • Make a list of items needed to buy

Here Are 109 Activity Ideas You Can Do On Vacation!

12. Create A Packing List

Next on how to plan your dream vacation, once you have an idea of what you’re going to wear you can put together your packing list. I like to section mine into 4 categories. The 1st is what’s going in my personal bag. This bag stays on me during my travel to and from my destination and will go under the seat on my flight. These are things I want easy access to if I know there’s a good chance I’ll need them.

2nd is clothing, using the Pinterest board I made and knowing what clothes I will need to complete those looks. I write everything down in this section. Don’t forget under-clothes and items that make you feel comfortable like shapewear.

The 3rd section is toiletries which is everything you need to feel clean and put together. Plus the items that take you the extra mile as-in makeup, perfume, and hair styling products.

The last section I call miscellaneous, which is everything else I might need like a battery fan if I’m going to a hot destination or close pins to hang dry my swimsuit in the shower. You can check out my carry-on packing list here. It’s the perfect basic list that I put together to use for all of my bucket list trips.

Action Steps:

  • Write down your packing list

Here is your Minimalist Packing List for all Vacations!

A hot chocolate on a cafe table on the side of the road in Paris France

13. Shop For Last Minute Things

After you made your packing list it’s time to shop or borrow the items that you don’t have and will need for your trip. There are often items that you don’t want to go out and buy for just one trip, like a sleeping bag or camping stove. See if family members or friends have these items that you can borrow. If you want to travel more so you can finally tackle your bucket list, buy travel-sized refillable containers.

That way you won’t have to buy things like tiny shampoo and sunscreen for every trip. This way they take up less space in your suitcase too. I want to also mention here that you should plan how to document your travels.

If you’re going on many adventures to check off your bucket list it’s a great idea to document all your trips and combine them in some way. If you plan on scrapbooking you’ll want to purchase the items necessary to do so. Another cool way is to take your travel photos with a disposable camera and place them in a photo album.

Action Steps:

  • Shop for last-minute items
  • Borrow last-minute items
  • Figure out how you want to document your travels
  • Buy items to help you document your travels

Here Is A List of 25 Ways You Can Document Your Travels!

14. Make Plans With The Sitter

When planning your dream vacation you’ll need to make plans with your sitter. Whether you need someone to watch your kids, pets or house now is the time to let someone know what you are needing of them. Let them know the dates you need them to stop by your house or when you will be dropping your dog off to them. 

You should prepare a list of instructions you need them to follow and where items are located like “the cat litter scooper is under the sink” or how to access the pet food that needs to be kept with a child lock on it. Or maybe what plants need to be watered and which ones they can skip.

Action Steps:

  • Reach out to the sitter
  • Write instructions for them
  • Make your setup easier for them (placing everything they’ll need in one spot)

15. Notify the Bank of Traveling

Exploring new destinations is exciting, but understanding how to plan your dream vacation can make your travel journey smoother. That is why you should check if your bank has the option to notify them of travel plans. This is best to do so they don’t lock you out of your account. This happens because they think scamming or fraud is trying to happen in a foreign location.

You don’t want to be locked out of your money while you’re away from home and need it most. Some banks have the option to do this via their app so check what yours needs from you before leaving. You’ll have access to your own funds when you’re out and about.

Another thing is to keep track of exchange rates as the value of currency can change rapidly while abroad. Have a rough idea of how much different goods cost so that you can budget accordingly and be aware of potential costs.

Action Steps:

  • Contact the bank and let them know you will traveling
  • Check the exchange rate that your bank charges for the location you will be visiting
Cows in green grass with a lake and mountains behind them in switzerland

16. Order Foreign Currency

Here is one of my best tips on how to plan your dream vacation. If you are leaving the United States and going on an international trip, Get all the cash you will need from your local bank. The exchange rate fees will be cheaper and you won’t have to waste time looking for ATMs and having to pay a fee each time you take out money.

Also, be aware that depending on your bank they may charge an exchange rate for every swipe you make on your card. This adds up very quickly! My local bank needs about a week to order the money and then wait for it to come in.

I usually go in person and place an order a few weeks before my trip so I have time for it to come in before I leave. I use this cash for tips, shopping, and eating out. That is because I pay for all my bookings and excursions in advance with my card before leaving my home.

This system makes my travels more smooth and enjoyable. However, if you are the type of traveler that is spontaneous this method might not work for you.

Action Steps:

  • Add up how much you want to spend on non-booking items (food, clothes, tips, cabs)
  • Calculate how much it is in the foreign currency. You can use this site here
  • Go to your local bank and ask for that amount in cash (they will take your USD from your bank account or cash if you have it and also charge an exchange rate)
  • Go back to the bank before your trip to pick up your money (they will call you once it is ready to pick up)

17. Check If Cell Service Is Available

Imagine sitting down to plan your dream vacation and not checking if your phone service will work in your dream location. That’s a big no-no. Check with your cell phone provider to see what you can and can’t do in another country without being charged extra fees.

Some companies let you talk and text but not use data or vice versa. You will need to know this so you can plan if you need to purchase a SIM card or see if your provider has a limited-time travel package they offer that covers your destination.

Airalo is a revolutionary mobile virtual network operator that offers flexible and affordable international cellular plans built for travelers and digital nomads. With Airalo, you can access prepaid data plans in over 100+ countries, so you never have to worry about not having data when you travel abroad. After checking with my phone provider I check with Airalo to see which is cheaper.

Action Steps:

  • Check your phone plan
  • Check out Airalo

18. Arrange a Ride To the Airport

The last thing to do on the how-to plan your dream vacation list is to find a ride to the airport- if you are flying to your destination. Of course, it’s cheaper to catch a free ride from your mom or pitch in for gas.

Another option that we mostly use is ride shares from companies like Uber or Lyft. If your city has a great public transportation system that takes you to the airport then that can be a great option. Lastly and most costly depending on your airport is parking your car in their garage at the airport, but this can add up depending on the length of your trip.

And that’s it! After you have completed all the steps you are ready to go on your well-deserved vacation!

Action Steps:

  • Ask a friend or family member for a ride to the airport
  • Schedule a ride share to the airport
  • Book a spot in the airport garage

If you want to elevate your travels I created a travel planner that will help you create unforgettable trips. This isn’t just an everyday planner but more like your own personal travel planner. It comes with my carry-on packing list, dream vacation planning checklist and so much more!

Elevate Your Trips and Craft Unforgettable Journeys!

Final Thoughts-

I hope you learned how to plan your dream vacation. Whether you’re heading to a tropical paradise, an exciting city, or anywhere in between, planning your dream vacation can be a little overwhelming. With the right tips and tricks, though, you can make it happen easily.

Happy exploring!

Kaylee Janell's signature

Read More About Fulfilling Your Bucket List Dream!

PS. If you found this post helpful, please share it to Pinterest! You can use the image below for easy pinning!

Pinterest pin for step by step guide vacation planning!

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