How to Plan a Dream Vacation

Sometimes I think I like the planning part of a vacation as much as actually taking the trip. But I’m also one of those weird people who has a spreadsheet for EVERYTHING. As in my husband and I track our power bill in a spreadsheet that has a graph and all the stats. Planning is definitely one of my biggest strengths and one huge reason that I started this blog! I hope these steps will help all of you to stress less about your vacation and have more fun. I’ve broken this process down into three big steps and in each one there are multiple questions you can answer to help figure out all the details you’ll need to plan a dream vacation.

Step 1 – Dream

A man canoeing down a pale blue river with lush jungle surrounding him. Plan a dream vacation and this could be you.

1. What is your budget?

Your budget will drive every decision you make after this point, so it is one of the most important! Arguably the most boring, but if you can set a budget and stick to it then you will deal with a lot less stress and frustration. This will determine how long you’ll be able to stay on vacation, whether you can fly, what type of accommodation you can stay in, and I could go on and on. So please just set a budget first!

2. What type of vacation do you want? What does the plan for your dream vacation look like?

Which activities do you want to do while you’re on vacation? Are you looking to relax? Looking for adventure? Want to go to the beach? Mountains? City? Everyone’s ideal vacation will look different, so think about what you and your family or friends love to do. Or just you if you’re going solo.

3. Where will you go!?

This is where the budget really comes into play. Will you fly somewhere or drive? Go outside your home country or no? Can you afford luxury accommodations or do you need to look for a deal? Also think about the type of getaway you’re looking for. Camping in the mountains or gallivanting through the big city? Look through blogs and do a quick search using the vacation type for keywords to get some inspiration. If you need to stay local then do a search within your state for the best vacation spots. You may be surprised at what you find. Make a choice and then the real fun begins!

Step 2 – Plan a Dream Vacation

A dark haired girl sitting on the beach on a foggy day overlooking rocky outcroppings. She is holding a guide book to plan a dream vacation.

I do love the dreaming phase, but this is the stuff I geek out over. Logistics are my thing.

1. Flights

If you are flying, be sure to try and book your flights well in advance! For domestic I recommend about three months out and for international, six months. First place I would look is Google Flights. I used to use Expedia, but now Google Flights is the only thing I use. I would price check each time and they were always cheaper. If your dates are flexible, then use their date grid to find cheaper departure/arrival combinations. You can also look at trends on their price graph of the prices over time. Plus they let you know if there is a cheaper airport in the area that you can fly to or from! That is super important for us since we are in between Charlotte, Raleigh, and Greensboro. They do not show flights for Southwest airlines though, so you may want to check them out separately. Scott’s Cheap Flights has a great article about using Google Flights.

When you book be sure to check that they allow you to bring a carry-on free of charge. Airlines like Frontier will advertise low fares, but charge you for each carry-on and checked bag. Most of the time we travel carry-on only because it’s easier and you don’t have to pay for that checked bag. Also, if you fly a good amount I would highly recommend applying for TSA Precheck. It’s $85 and lasts 5 years. Totally worth it when the lines are long. The last tip about flights is to be sure and sign up for the airline miles programs! I always book with the cheapest airline, so I probably don’t maximize my reward potential but they’ve gotta add up sometime right?

2. Accommodation

Buildings set up high on a cliff side with a beach down below.

There are so many options for places to stay! Again, think about what type of vacation you’re looking for. Here are some accommodation options and resources for each:

  • Hotel: Trip Advisor, Expedia
  • Hostel: Hostel World
  • Bed & Breakfast: Airbnb, BedandBreakfast.com
  • Lodge: Airbnb, You can also do a google search for lodges with the name of the city you want to be close to and that will give you good results.
  • Vacation Rental Home: Airbnb, VRBO
  • Camping and Glamping: This is another good one to search “camping in ” and look through the links.

As you can tell, I am a huge fan of Airbnb. I love staying in places that are off the beaten path and most of their options are adorable! When booking accommodations think about what you want to be close to and whether it’s worth driving a little further to save a few bucks. Also if you have to pay for public transportation that can eat into your budget and precious vacation time. Another thing to think about is do you want a kitchen? That gives you the options of cooking a few meals yourself. Make sure to research peak season, shoulder season and off season where you are going so you know when rooms should be cheaper.

3. Activities

Next start thinking about what type of activities you want to do! If you are looking for a more nature-centered vacation you could look at hiking, biking, fishing, renting a boat or jet-skis, stand-up paddle boarding, kayaking, or skiing/snowboarding depending on season. Those are just a few of the options! Look around the location you chose and see if there are any national or state parks which are my go to for outdoor activities. If you are looking at a city vacation instead then it all depends on your preferences! Each city has its own specialties but here is a list of ideas: walking tour, museums, art gallery, food tours (my personal favorite), city parks, shopping, local markets, tour churches, or see a play or concert at a local venue. It all depends on your interests. When I plan my vacations I typically use Pinterest and Trip Advisor to figure out the activities that I want to try.

4. Food

A cheeseburger with a sesame seed bun and french fries on a wooden board.

Now comes my favorite part! I LOVE looking at all of the options for places to eat and deciding which ones I’ll try. I use Pinterest a ton for this part of the trip. My goal is to find the best places for a reasonable price, unless it’s somewhere like Halls Chophouse in Charleston, SC. Then I don’t care about the price; it’s just that good. Food is one of the items that I’m willing to spend a little more on, but if it’s not a huge deal for you then maybe cook a little in your room (if you have a kitchen) and explore some food options on your own. You never know what you might stumble across. In many foodie cities, every restaurant is good anyways. My recommendation though if you love food like me, check out a few blog posts about food in the location you are going and see if any of the restaurants are mentioned multiple times or if anything peaks your interest. It’s always good to have a general idea of the options.

Step 3 – Go!

A look out the window of a plane at the wing.

You’ve done all the background research, so now it’s time to go and have fun!! Forget about all the stress of everyday life for a week or weekend or however long it is and have an adventure that you’ll remember for a lifetime. Make sure to collect a couple souvenirs to spark your memory each time you see them. I love collecting little memorabilia from each place I’ve visited. Remember to take lots of pictures too!

As with anything, if you can break down the planning process into smaller steps it will seam much more manageable. I hope these steps will give you a little bit of direction with your trip and take your stress level down a notch when you try to plan a dream vacation. Vacations are supposed to allow us to take time out of our everyday life and enjoy the things we love. So just remember that and have fun with it!

Have I missed any steps in how to plan a dream vacation? Let me know in the comments below!

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