Last Updated on February 19, 2024 by AMANDA CASTILLO
How to plan the perfect Trip is soooo key when thinking of going some where. Lets start with…Location, Location, Location! I like to have a bit of both, vacation and traveling when I am taking a trip and I usually pick locations that aren’t too landlocked. When it comes to picking a location, I always start with looking at what weather and water temperatures to expect around the time I am planning on going. Sometimes this can be a deciding factor for me because I am not one for the freezing cold. Places like Iceland, Antarctica, Alaska just don’t appeal to this LA girl!
What Kind of Trip?
For me I think about the kind of trip I want to have. Will it be a traveling trip or a vacation? Because again I think of the two as totally different! With that being said how I like to plan a trip is for a little bit of both. Being a fish like I am, the majority of the destinations I choose to go to tend to be around water of some sort. Croatia for instance has sooo much history but there are also the infamous Croatian Beaches that are said to be some of the most insanely beautiful beaches in the world. I had to make time for both.
Even though you’re away though, you don’t have to be doing something every second. Give yourself room to breathe and time to take in the things you weren’t planning to do or see. Go with the flow and try to carve out some time to relax too. Most of the time your itinerary will go right out the window but you will find a rhythm perfect for you. My favorite breather from a day full of activities is to sit and people watch with wine and appetizers before moving on to my next adventure.
How Many Days?
One of the things I have started to make a habit of before I book anything is to do a search of “how many days you need to visit xyz”. When you have an idea of what the majority of people and articles are saying about how long to spend there you can start to plan your itinerary accordingly. 
If you only need a few days somewhere why not plan another stop nearby? I’ve done this several times and have never regretted it!
For example, Croatia is somewhere you can add a bonus stop. When you’re visiting Dubrovnik or Split, if you’re driving to either of those places you need to cross through Bosnia. While in Greece I took the ferry from Santorini to Crete which was an incredible experience. Why not stop for lunch or the day etc. and add it to the list of places you’ve been.
Check Travel Restrictions or Requirements
Once you have decided on where to go it’s important to look at travel restrictions and visa requirements. I also like to research any national holidays, big parades or any major events going on while I am planning to visit. For instance Spain celebrates Semana Santa or Holy Week which is so cool but unless you’re there for that specifically it could mean higher airline and hotel prices. If you plan to visit in the off season when it is typically less expensive it’s also important to research when the “season starts” and if things will be open for tourists when you will be there. Some sites, restaurants and excursions stop business altogether during the off season.
Accomodations
I like to start with searching for “the best area to stay when in xyz” and use that as a starting off point. I usually search for places to stay walking distance to where most of my time will be spent. I’ll also look into whether having a car would make sense including doing a GPS search prior with the hotel as the starting point and the location of something I want to see just to get an idea of proximity. Being a free bird and the Wondering Lotus that I am, I like to go at my own pace. With having a car you can see more and get a bit of the local feel. I also start to research the area I will be staying in for recommendations or any info I can find, however the best recommendations come from locals! Don’t be shy to ask. No itinerary can prepare you for everything you never knew you were missing out on and will experience when you take a local’s advice.
Read reviews!!!! Take the time to sort through different pages and read what people have to say about the place you’re thinking of not just visiting but staying at. I tend to read the bad reviews first. You also want to compare prices to locations and obviously what you’re paying for. Some travelers think “I am just kicking my shoes off and showering. I don’t need much”. For me that’s just not how I roll. I like a balcony and a view when possible and a pool to dip in if I’m somewhere warm! I definitely consider myself a bougie traveler …on a beer budget. Sometimes. There are occasions where you just have to say…if not now when and be ready for the sting of your bank statement when it comes. Whether traveling or on vacation, you’re there to enjoy yourself and you deserve to soak in the trip you want.
Booking Your Flight
When booking your flights something also to consider, although I’ve never done it myself, is to plan an adventure during your layover. It may be less expensive to have a longer layover and not a bad idea since you’re already there and paying for the flights. For me this seems rushed and a little hectic. I prefer a short layover and to get to my destination not overly exhausted. Flying is stressful enough let alone having to worry about going through security again and any possible delays etc. If you do decide you’re up for the adventure, I would highly suggest you look into airport rules and regulations for foreign travelers when leaving the airport. Check out the list of places I’ve been or places I’ve posted about and see if any float your boat.
Step 1: RESEARCH
Step 1 in planning is RESEARCH: This can be super daunting and totally time consuming but not to worry, I have a few tips and tricks to share. You can also check out my resource center for more information on the places I’ve planned and mastered the do’s and don’ts for. Now, let’s think about what you want to do when you have actually arrived.
My jump off point starts with a nice fresh Google Doc. At first it is just throw-up on a page of all my random research of things to do, places to see and I start stacking my ideas. A vision board of sorts. I find it extremely useful and exciting to start with researching the history of where I am visiting.
The first search engine I use is Google itself. It’s a good place to start because it really allows you to filter your search. Trip Advisor can also be helpful when you start to plan although it’s not my favorite site. Sorry TripAdvisor. It comes off a little messy and not in line with my style of traveling. Whatever the tool I am using for research, I am interested in the most recent articles, and I like to use keywords like “top ten, the best, hidden or unique things to do in XYZ”. I also search keywords like traveling with your best friend, with a significant other, solo, with family depending on who I will be on an adventure with. There is a page for everything these days. Pinterest tends to be a favorite because it’s user friendly and who doesn’t like pictures.
Another great resource is the actual tourism board for the location itself which is generally run by officials or residents. These boards describe the city, attractions, food, and basic tips for visitors. Being a foodie like I am, this brings me to learning about what type of food to expect, where to eat and what to order. I want the full experience even if that means being a bit adventurous with my palate.
Even more important in planning is to research what the weather is like, especially if visiting somewhere near or on the water. What will the water temp be?! This is also a big part of packing (see tips on what and what not to pack).
Researching tours is a little planning hack. Shhhh don’t tell. Not necessarily to go on them but to see what the hype is about, what attractions they are stopping at, how they are getting there and how much time to allot for. This also leads me to searching about transportation. However, if I am planning a trip with activities, I book with Get Your Guide. When I was in Greece for instance my best friend and I visited Santorini which had a very easy to use public transportation system.
We had a car pick us up from the airport but used the local bus to get around Santorini, the ferry to cross over to Crete and then we rented a car for the remainder of our time in Crete! We dropped off the car at the airport and flew home from Crete. Again, it’s all about the type of “trip” you want to have. My best friend and I wanted to see as many Cretan Beaches and visit as many churches as possible. We were able to do that and more, making it the trip of a lifetime. Check out my post on Greece to see pictures and all the need to know when visiting.
Last but not least…Travel Blogs! These can be gold. Finding a blogger with similar interest as yours to pull ideas from is so helpful! Many helpful guides, off the beaten path, sights and activities, I have found from fellow bloggers. You also get good tips on what is worth seeing or avoiding saving time and or money on. Travel Blogs also allow you to comment, ask questions and hear from others on their experience using the recommendations. Shout out to my fellow bloggers for all your help planning my own trips!
Step 2: Organizing Your Trip
Now that there is a smorgasbord of ideas it’s time to organize your trip. Process of elimination here we go. From your Google Doc start to copy and paste a list of must see, do and try things at the top of your doc. This is your own preference of things you really don’t want to miss out on. It’s also important to have the length of your trip figured out so you can plan accordingly. Star and make bold the absolutely necessary, exclamation points for I don’t want to miss and question marks meaning I could live without. I am big on color coding, I also change the color for each location if visiting multiple places and coordinate the color with places, activities, etc. to try so it is easier to reference. It sounds crazy but check out my templates and I promise it’ll make sense.
Step 3: Itinerary
The most time consuming and my least favorite part of planning is the itinerary itself. This part means further crossing things off the list, wishing you could change your flight plans or extend your trip altogether (for a Gemini like me I am the most indecisive person so this can be truly painful).
With my style of trips, I prefer not to have something to do every second of every day. I want the trip to be enjoyable and do things at my leisure. Your itinerary should be what you want it to be and even if you have an itinerary, it’s ok to go off schedule. Meet locals, ask around for tips and take in every moment. You made it to your destination!
The first thing I look at are the must do things on my list and check if there is a tour available and worth it or if there is anything else from my list that I can check off on a tour. A lot of tours visit multiple locations i.e., on boat excursions or day trips so this can be a nice way to see more. Keep in mind how long to allot for a tour, at minimum this will cost you a ½ day. Depending on what your plans are, this may be the only thing you do on a given day but that’s ok you don’t need something booked every second.
When I am on a trip regardless of if it’s a vacation or if I am traveling, after a tour I always make time for a siesta, a wardrobe change and then get ready to enjoy the night! I usually don’t plan an early start the next day since this will likely be a late night. With a second wind it’s just enough time to make it a memorable evening. Roam around and take it all in.
There will undoubtedly be things you can’t get to so start with the top 3 things you want to do and see how to fit them into your trip. This leaves you with lots of free time and a list of other things you have at the ready to check out if you want to. Try and note when researching what else you can see while visiting a top 3 site or area etc. These are just ideas and backups. You’re on vacation, focus on having fun. Refer to your list when needed but you decide your trip not a list. Be prepared for things to not go exactly as planned either.
Traveling with a companion can also mean compromise. You want everyone to be in on the “itinerary” ahead of time to avoid that awkward moment when you are actually there.
There will be a lot of cut, copy and paste happening during this time. Don’t get overwhelmed! You’re on your way to having the most amazing trip!
Finally: Plan Your Arrival
Personally, I like to think my trip starts when I check the luggage and have my first celebratory drink. After flying, going through customs, and getting the luggage, I just want to see a driver holding a name sign waiting for me. The driver will have all the details of my flights in case of any delays and also all of the hotel information, so I don’t need to do anything! After all, we are on vacation.
