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4 Simple Steps to Making the Perfect Itinerary!

Hey, I’m Sam, and I am so glad you stopped by! Let’s plan a trip, shall we?!

Have you ever been on a family vacation? You know, the ones with the WHOLE family? Where it takes 4 hours for people to decide where to eat, and then everyone is grumpy because they’re all hungry, and then you just end up going to the Pizza Hut down the street because you’re tired of trying to decide? Don’t you loveee trips like that?! … yeah me too! 😉  My hope is that this little blog post will help eliminate some of that wasted time and indecisiveness! 

My goal is to provide you with the most concise, yet helpful information when it comes to travel, DIY, fashion, etc! I think life is so so beautiful and it is truly such a gift to get to experience it all (even the chaotic family trips). I would love to connect on Instagram @samantha_ellison to get to share my adventures in little more detail. But, anyway, let’s get started on how to plan the BEST trip EVER!

Flights

The first step in planning your dream trip is finding the best flights available. Scott’s Cheap Flights is how I find so many affordable tickets to places I could only hope to go one day (for example, they helped me save $400 on my flight to Aruba. Literally so amazing). When you sign up for a free account, you select places you want to go, and they will email you a link to Google Flights to purchase tickets when flights to your dream destinations drastically drop! They do all the work for you. Again, AMAZING. 

If a certain destination is not sent to me on Scott’s Cheap Flights, I do a manual search in Google Flights. If your trip dates are flexible, just type in the airport you want to fly out of and then click the blue words right above the map on the right of the page that say “Explore Destinations.” So, for example, flights into London right now are currently cheaper than into Paris, so I could fly into London, spend a couple days there, then book a $30 flight from London to Paris (because flights, once you are in Europe, are super cheap). You can also use Skyscanner to do this, but it is a little less user-friendly. 

Also, make sure you check different departure airports. I live about two hours from both the Atlanta and Charlotte airports, so I always compare flight prices from the two different airports to find the best deal. Once you have compared alllll the options and your flights are purchased, you can begin choosing all the things you want to do!

THE ITINERARY

I have a lot of energy all the time – and I don’t drink coffee.. crazy, I know! – so when making an itinerary, I always include LOTS of options of things to do. Now, I do this knowing I may not, in fact, get to do all the fun things planned if we end up staying longer somewhere, or choosing to do something different – but I always have a wholeeee list of options, because who wants to waste time on their phone researching fun things to do rather than actually getting to do them?! You have to be so flexible on trips, too, so having a general list of cool things in the area is helpful to have in case one of the other options happens to not work out. 

When I plan, I pull ideas from Pinterest and just scrolling around on Google Maps on my computer (pictures of the location pop up when you put your mouse over it, so it’s really easy to get an idea of what you are actually going to be seeing when you go to a place). After I have compiled a list, I then check Instagram, Tik Tok, Google images, and websites of selected locations to decide if something looks amazing and like I should add it to the itinerary or not. Once I have narrowed down my list of sightseeing spots, restaurants, shopping centers, etc., I begin adding in the specifics on my itinerary. 

Again, using Google maps on my laptop, I get an idea for the area we will be staying in. For example, on my trip to Aruba we didn’t have to drive very much and could pack a lot into each day, seeing as how the island is only 30 minutes to drive across! When I am listing things on the itinerary each day, I check the map and try to put activities that are in the same vicinity on the same day. This saves on 1) time, because you don’t have to spend the day driving all over the place, and 2) gas money in whatever car you may be using or money spent on Uber, taxis, etc. Grouping activities based on location is the most efficient way to make the most of your vacation, allowing you more time to do everything you dreamed of! 

Once I have decided on the places I want to see, restaurants to eat at, etc., I make reservations for those places that need it. If you are going to places in the busy season, making reservations for restaurants is really important because you don’t want to waste time waiting in line or end up eating at McDonald’s or Taco Bell every night just because you didn’t take the two extra minutes to make a reservation on their website. (Not that there’s anything wrong with fast food, but I love to eat at new places that I don’t have access to at home.) In Hawaii, we ended up cooking most nights because the food was so expensive there. So just get a feel for what you are wanting out of your meal experiences and plan accordingly!

PLACES TO STAY

Next, I start looking for the best places to stay! I do this after making the itinerary, so I can choose stays that are central to all the activities I want to do/places I would like to see. Airbnbs or VRBO properties are usually the cheapest option, but sometimes hotels are better, especially if they are in a convenient location. On every trip I go on, I try to stay in a fancy hotel just oneee night for fun, then save money by using the rental property options for the remainder of the trip. I really just appreciate interior design and unique accommodations, so I usually opt for Tribute Portfolio hotels if there are any in the area I am staying in. If not, I look around for cutie boutique hotels owned by locals. The appeal for me also of staying in a hotel is that they often have a pool… and give you cozy robes and slippers and they typically have other fun amenities, too!

When searching for hotel rooms, I compare prices on my Orbitz and Booking.com apps. If you find a good price, you have to be decisive and book quickly, because sites like these only have a certain number of discounted rooms and they get taken if you don’t book quickly enough. I also call hotels a lot to ask if they have any discounts that are not listed on their website or the apps. If you are a AAA member, hotels often give you discounts, so I always call and ask the front desk about that before making a reservation. 

Airbnb and VRBO is a less complicated process. I just scroll through both apps and look at about the first 50 listed (may be excessive, IDK, but I am determined to find the best one). I make a specific board on each app for the trip and save them as I go, then narrow them down later. Once narrowed down, I make a final decision after comparing options on both apps! Always calculate the final price with tax, cleaning fees, etc. because some properties become significantly more expensive when you add that in.

THE TRANSPORTATION

In places like Europe, you can take the Eurail to travel around, but also you can book flights within Europe for super cheap, as I mentioned earlier. So step one when I look for transportation is to do some research to decide which option is going to be most efficient. For example, in Las Vegas, I rented a car for one day to drive out to the Hoover Dam, and then just walked everywhere the rest of the trip because Vegas is one strip that is very walkable in the right shoes. But in Aruba, it was SO important to have a car the entire trip to see all the beautiful places without having to wait for a tour guide or a taxi.


Once I have decided on what kind of transportation is necessary, I start comparing prices. This mostly applies to car rentals. I use the Orbitz, Booking.com, and Turo apps to compare prices. Once I find a car and price I like, I book immediately because prices can change very quickly and with no warning. There isn’t really a pattern I have found for the best day to book a car rental, just make sure you do it right away once you have found one you like.

IN CONCLUSION

Planning is one of the most important parts of a trip. I believe a trip can be fantastic whether you have an itinerary or not, but things are so much easier if you already know what there is to do around you. I love efficiency (I really think I would’ve been an engineer if I actually enjoyed doing math), so planning ahead and putting all the pieces of a trip together like a puzzle is the ideal day of work for me. 


I know a lot of times, you are planning a family vacation, bachelorette trip, etc. that may involve other people, so I’ve made a sharable planning checklist and itinerary template linked here if you want to make a copy of it and start planning your own trip alone, or with your friends and family!! Feel free to reach out to me on Instagram (@samantha_ellison) if you have any questions or want more advice on how to plan the perfect trip! Cannot wait to dream with you!!