Step by Step Instructions for Planning an Amazing Vacation Itinerary 🏖️

Let me see if I can read your mind…….🕵️‍♀️ You are sick of going places and finding out the stuff you did was lame. You checked into an all inclusive and the food was subpar, so you’re wondering where all the amazing food you keep hearing about was. You are tired of going to the same old place over and over again, but planning to go to a new location is overwhelming and scary?

Did I get it??!! Those are all things I have felt too! So, I have developed a system to help you plan your dream vacation. Let me show you! It’s easier than you think!

Step One: Nail Down the Big Details of your Dream Vacation

Decide Where

Picking the place is often the hardest part. There are SO MANY beautiful places in the world! If you will be driving, is this a road trip with several stops? Or will you be going to one place and then traveling to satellite locations during the day?

If I am flying, one simple mindset shift helped me 10000% – GO WHERE THE FLIGHTS ARE CHEAPEST. 💸 This will mean you can actually afford to fly your family to your destination and have more fun once you get there!

If you are flying, I recommend using the “explore” feature on Google Flights or Kayak to find the most inexpensive places to fly. Then use one of those locations as your springboard. You have to be flexible with dates and be prepared to sift through some super lame flights. The day I wrote this post, I found flights with American Airlines from SLC to Nice, France, for $563 per person, roundtrip! That’s a great price, and could be just the motivation you need to plan a vacation to some exotic place. Just plug in your home airport and hit search!

You should get in the habit of checking every day. This way you will know what is a good deal and what isn’t.

Does someone in your family have a “must see” attraction? Recently, while planning my family’s summer vacation, we were trying to decide between flying to Miami, Seattle, or driving to northern California. My husband really really wanted to see the redwoods. So we are going to NoCA to see – you guessed it – the Redwoods! It made the decision easy.

Decide When

Once you pick where, the “when” will fall into place.

If you picked cheap flights with an “explore” service, you will need to fit into their time frame. You can usually adjust by a few days, but typically, a flight is cheap because the airline is trying to fill seats.

Shoulder seasons are a really nice time to visit touristy places. The weather is still great, but it’s less people-y. You will find reservations easier to book, and flights and rooms for less money. Another bonus is that photos without throngs of people in them are easier to snap!

If you are traveling for something particular, like cherry blossom season in Japan, or tulip season in Holland, make sure to research peak times and book during those days or weeks.

Find a Place to Stay on Your Dream Vacation

Will you be staying in a hotel for your dream vacation? Or an Airbnb or VRBO? Does it need to be pet friendly? What part of town do you want to stay in? What is your per night budget? Do you have credit card points that you could redeem for your stays?

On one trip to Puerto Vallarta, we decided to stay in an Airbnb in the Zona Romantica, close to the beach.

Here is a peek into my thought process: there are lots of super fun neighborhoods in Puerto Vallarta but I am all in for architecture and food. Zona Romantica is the historical district of Puerto. It has darling cobblestone streets, brightly colored buildings and street art, and SO MUCH GOOD FOOD 🌮 (legit, Puerto is a foodie paradise). It’s right on the beach, the malecon (boardwalk), and has great shopping. Zona Romantica it is!

When you are planning your own stay, ask yourself: what attractions are important to me? Are there hotels or vacation rentals within my budget in that area? Is it easy to walk/uber/catch public transportation to where I want to go from my home base?

I love staying in an Airbnb or VRBO. That’s our typical stay if we’re going for 4 or more days. I feel like it allows me to fine tune my location a little better than a hotel. They can be more economical too – be careful to factor in cleaning costs or other pricing add on’s though. Those can add up quickly and make the per night price much more than a similarly appointed hotel (read the listing fine print!).

Find Accommodations That Include What is Important to YOU

Maybe YOU love an amazing resort with a giant pool, a beautiful beach, infinite drinks, and lots of fluffy towels ⛳. Read reviews find one with all of those things in your budget. Then lounge around to your heart’s content! Vacation is for relaxation, after all!

Maybe the room is not so important because you want to spend your money on the ADVENTURE 🪂 and attractions 🎢. You plan to blow all your money snorkeling and parasailing. PERF! That means you will focus on finding somewhere economical to stay. For more help deciding, read my breakdown of the differences between Airbnb and and All-Inclusive here.

✨The most important part of vacation planning is for you to focus on the things you love that are important to you.

Once you have the flight booked, and the perfect room found, BOOK IT! When that is done, you can start planning the fun stuff!

Step 2: Get a Dream Vacation Budget!

This is often the most important step of planning a dreamy vacay. It’s also the hardest for me and I won’t pretend otherwise. If you are a numbers/budget loving person, please leave your wisdom in the comments for our friends. 🤑

Once you have done the research on the cost of your flights ✈️ and accommodations 🏨, pencil in some food cost and attraction costs. Add it all together then divide by the number of months until your trip ($8,000/9 months until take off = $900 per month to save). Going into debt for your dream vacay is sad and no fun. 0/10, do not recommend.

A Word on Credit Cards

Even though I will not teach you to churn cards, I do keep one or two (not 10) in my wallet. I pay them IN FULL every month so that I can rack up points.

My favorite is Chase Sapphire Preferred card. When I shop online I always check the Chase shopping portal. Brands and major retailers often offer 2-5x points per dollar spent for something you were going to buy anyway. The points can be used in a lot of ways, including at World of Hyatt hotels for a great bang for your points.

If you would like to apply for a Sapphire card, use this link to get 75k bonus points. I will also get 10k points when you use my link (thank you)!

Hot Take! 🌶️ You might need to put off the big vacation until you have saved for a while. I will NOT teach you to churn credit cards or go into debt for your vacation. Once a mortgage loan officer, always a mortgage loan officer 🤷‍♀️.

You may need to dial down the spending in some areas of your life while you crank up the saving dials for your big vacation. Quick book rec if you want to learn more about “money dials:” I Will Teach You to be Rich by Ramit Sethi. It’s a great book and if you follow his advice, it can help you get your financial life in order. There are super fun staycations if a “big fancy vacation” is not in the cards for you right now.

Step 3: Search “Things to do in _____.” and “Best Places to Eat in _____.” in Pinterest and Instagram

Pinterest Dream Vacation Plan Process

Start a board in Pinterest for your vacation. You will want to search for things to do and places to eat.

Make this a fun discovery process. At this stage you are just pinning all of the things that look fun or delicious. Don’t worry too much about the budget at this stage. This is the “wish phase” of the vacation planning process.

Every city and town will have loads of fun things to do and see. This is where you discover them and pin them all to your new vacation board.

Look for some low cost things to do along with the costlier things as well. This way we will keep your vacation budget friendly. I like to read through the posts before I pin to make sure they’re valuable and include ideas that seem like things I would actually enjoy doing.

If you are planning a vacation with more than one couple, you can turn this into a board with collaborators. Invite your vacation buddies to pin the things they would like to see and eat as well! First navigate to your board, then hit the little plus person button to invite.

Did you peep my profile selfie I took years ago when my babies were little on my Charleston Vacation Board? 😍

I have a board just like this for all of my planned vacations. It helps me organize all of the things that I want to do. Then while I’m planning that all-time, best ever vacation, I can quickly find and write out my plan.

Instagram Dream Vacation Plan Process

Instagram is another amazing place to research great things to do while planning your dream vacation.

We have all seen the gorgeous reels and posts by our favorite travel influencers. They spend a lot of time putting together informative reels and they include lots of great restaurants and attractions. You should definitely steal some of their ideas.

It’s super easy to use Instagram as a tool by searching for tags like #_____vacation or #_____foodie. Then insert the name of the city you will be visiting into the blank. You can follow tags or accounts and save them to a board named with your vacation.

✨PRO TIP: Do this for the CITY YOU LIVE IN if you need some new, fun ideas for a summer staycation!

Step 4: Create an Attraction and a Food List for Your Dream Vacation Plan

This is where you start the heavy lifting of your dream vacation plan. Get out a piece of paper, or a note in your notes app, or even a spreadsheet if you are really ambitious.

Find one or two attractions each day.

Do a bit of research to figure out how long it will take to get to each attraction from your hotel. Also look at how long people generally spend at each location. This will help you decide how many attractions you need to plan for each day. I typically enjoy doing one thing in the morning/afternoon and then one more thing after dinner.

You will also want to check prices. Depending on your budget, you can blow through the money really fast by paying expensive entrance fees for everyone in your family. I recommend keeping the schedule light so that you have time to be spontaneous. Don’t feel too pressured! It’s also really fun to talk with locals you meet and see what their recommendations are.

A sample morning of your dream vacation plan could look like this:

Monday am: Hiking to “Fun River” Waterfall: Driving time 45 minutes each way. Hike length 2 miles. Picnic time 45 minutes. Total time: 3 hrs. 45 minutes. You will know for the day, if you get up, go eat breakfast, and are out the door by 10 am, you will be back around 2:00.

Time to shower if needed, or take a dip in the pool, and then get dressed for dinner. After dinner maybe you catch a show, or stroll through town looking at lights and window shopping. Maybe you need to swing into a market and buy necessities for the following day.

Whatever you choose to do, make sure you have enough time to not feel rushed, and be flexible. There may be days where you want to mix up the attractions on your list. There may be days where you decide to spend all day at the beach and nix items from the list. Don’t be too hard on yourself! Vacations are meant to be fun, not a pressure cooker!

Find the MUST EATS of Your Vacation

🌮Time to plan my FAVORITE part! Go back through your Pinterest and IG boards and find all of the restaurants that look AMAZING. Pick a couple for each day. Narrowing it down is the hardest part!

They should be fairly close to your attractions or your home base. This way, you don’t spend all day driving from one end of town to the other. Pick the restaurants that line up with where you will be geographically on your list. In a small town this is not such a big deal. In a city, you could add HOURS to your day by picking things that are too far away (think NY or LA).

Pick restaurants that line up with your budget as well. You will want a night or two to get dressed up, and a few to go casual. Make sure to plan for that and adjust other meals accordingly. Do you plan to spend $$$$$ on a steak and lobster dinner? Grab cheap street food for lunch, or drink hotel coffee instead of Dutch Bros for a day or two to save money. Look for ways to be economical so that you can splurge without guilt.

Here’s What We’ve Learned

✅Pick the location by finding cheap flights or a must see attraction. ✅Book your hotel or Airbnb. ✅Make a budget – it can be as loose or dialed in as you want, but you should have some idea of the cost (unless you’re Jay Z?) so that you don’t accidentally overdo it. ✅Start a Pinterest board or IG board and plan one or two activities and restaurants every day that fit in your budget and location. ✅Be flexible and allow for changes in the plan. ✅Get some local recommendations for maximum fun.

☝️One last thing I will mention when you are planning your dream vacation, is that, if you are flying, or cruising, or resorting, you should definitely get trip insurance.

Flights get canceled and delayed, hurricanes blow through, people get sick or hurt, luggage and medications get lost, etc. Having trip insurance for a couple hundred dollars can save you thousands if the worst case happens. Faye Travel Insurance has excellent reviews. World Nomads is used by many world traveling influencers, although I do not have direct experience with them.

You are going to have an amazing vacation, and it won’t even be overwhelming to plan! You can do it!

xoxo, Morgz

Learn more about things to do in Puerto Vallarta here.