How to Plan a Trip

Empty sandy beach with tire tracks, ocean waves, and a cloudy sky.
A smiling couple stands on an escalator with the Eiffel Tower replica and Las Vegas skyline in the background.
A woman standing next to a pink car decorated with a large pink bow and a sign reading 'Congratulations.' The car has a plush bear on the front seat and is surrounded by red rope barriers at night outside a building with large windows.
People walking towards the entrance of an amusement park with a large archway and colorful buildings, palm trees, and a blue sky in the background.
A woman and a man taking a selfie outdoors near a body of water during sunset, with trees in the background. The woman is smiling and wearing sunglasses, and the man is sticking his tongue out.

So you have a destination, but now what? Planning a trip can be stressful and overwhelming…flights, hotels and activities, oh my! I want to share some secrets I’ve discovered over the last few years of traveling that can help. After all, trips are supposed to be fun and exciting! Not anxiety-inducing nightmares.

When Should I Visit?

The time of year you choose to visit a destination can elevate or devastate your experience. When choosing dates for your trip, keep a few things in mind;

1.       Weather: things like hurricanes or blizzards can derail any trip in a hurry so either choose a time when these things are less likely to occur or have a contingency plan in place if they do occur over your scheduled trip.

2.       Planned Activities: if you’re going to Colorado to ski then June probably isn’t the best time to visit. If you’re going to walk endless miles at Universal Studios Orlando then cooler months in the fall or winter might be the best time to visit. Having a clear idea of the activities you’ll be doing on your trip can help you choose an appropriate time of year to visit a particular destination.

3.       Peak Traveling Times: Holidays and spring break week cause increased pricing for everything, not to mention the amount of people that could be visiting certain destinations. Usually a quick internet search can tell you when to avoid visiting certain places and when they tend to be less busy.

Still struggling after considering those points? I find that “best time to visit (destination)” in a search engine can often give some clarity. Remember that the goal is to have fun on your trip so choose a time of year that will assist with that, not hinder.

 

Booking Flights

Now that you have your destination and dates picked out it’s time to start looking at flights. I think we all know how to book flights so I won’t get into that here, but I do have a few morsels for you to consider when looking at flights;

1.       Baggage: are you checking a bag or bringing a carryon? Make sure to read what each airline includes in their fares and what costs extra. This may help you rule out certain airlines and decrease the number of options you have to pick from.

2.       Timing: do you want to be at the airport taking off before dawn or would you rather sleep in and make your way to the airport in the afternoon? I will usually set my ideal times, but remain flexible with what the airlines are offering.

3.       Monitor Apps: there are many apps and websites that will monitor airline pricing and alert you when it’s the best time to buy. I personally use both Hopper and the Capital One Travel apps to monitor air fares so I don’t have to. One less thing on your to-do list.

4.       Buffer Time: if you have already purchased tickets for events or made dinner reservations for your trip, make sure to leave enough time in between those activities and your flights. Delays are an unfortunate norm when flying these days so be prepared.

One side note on booking flights, be cautious when using third party websites. Third party websites compare prices for you on different websites to give you the best deal and while that can sometimes be the case, it can also cause nightmares while traveling. If you choose to book through a third party make sure to keep any and all paperwork you receive from them regarding your reservations and keep the customer service number readily available.

 

Booking Hotels

No matter what you’re doing throughout the days of your trip, the hotel is where you go every night to rest, relax and recharge for the next day. The room should be clean and comfortable while also having great customer service. A few things to think about while searching for hotels;

1.       Look at a Map: if you already have activities planned for your trip then looking at a map to see a central area for those locations is a great way to start looking for hotels. That way you know you are close to whatever activity you have for any given day. If you don’t already have planned activities, choosing a hotel in an area with a lot of shopping and food is a great place to start.

2.       Amenities: start out with a list of amenities you want or need your hotel room to have and make sure that any hotel you book meets those minimum criteria. Examples would be a mini fridge, pool, room service, gym, free Wi-Fi etc.

3.       Parking: keep in mind that some hotels in big cities are valet-only parking while others may have a self-park option that isn’t exactly close to the hotel. Always check the parking situation (if you’ll have a car to park) and whether or not it costs extra money before booking a hotel.

4.       Recent Reviews: checking recent reviews of the hotel is a must. The 4 star review you see online could be over many years – the hotel may not be worthy of 4 stars in its current state.

5.       Rewards Programs: joining a hotel chain’s rewards program is always worth looking into. Sometimes those memberships give you perks you wouldn’t get otherwise. Those rewards points can also be used down the road for upgrades or saving some money on future stays.

Again, be cautious when using third party websites to book hotel rooms. If you choose to book through a third party make sure to keep any and all paperwork you receive from them regarding your reservations and keep the customer service number readily available.

 

Should I Nerd Out and Create an Itinerary?

Yes, yes, yes! I cannot stress this enough. The people you travel with may tease you at first (my husband certainly did), but once they see the value it brings to the trip they will see the magnificence of your ways. Imagine you have just finished perusing a museum and you are absolutely famished. Now begins the long process of everyone agreeing on where to eat, but only after you find out what’s even nearby. If only someone in the group had a list of restaurants in their pocket with the locations, hours of operation and type of cuisine. Then the group might know there’s an Italian restaurant just around the corner that’s open and ready to serve you. So much time saved. This could be you!

Creating a list ahead of time allows you to pick out the restaurants you really want to try while you’re at your destination and whether or not they are actually worth trying. Since my husband is a vegetarian, it also allows me to check menus prior to us ever leaving our home. Same argument applies for activities. When you’re ready for something to do or have time to kill before your next event then you can pull out a list and see what there is to nearby.

I highly recommend that any activities requiring tickets or restaurants requiring reservations are sorted before you ever leave for your trip. That creates what I call a rough itinerary and the lists are used to fill in the blank spaces as needed. Trust me, once you try this you will never go on a trip without one again.

 

In Conclusion…

Remember that this whole process should be fun and exciting! The whole planning process discussed here can be done from the comfort of your couch while on your phone. Let’s be honest, you’re probably on your phone anyway so use it to your advantage!

Happy Travels

A person smiling, wearing a hoodie, standing near a wall with a quote. The quote says, 'The people you love become ghosts inside of you and like this, you keep them alive.'
A woman with short dark hair, wearing a black sweater, looking to her right in a warmly lit restaurant or café with wooden interior and a large window in the background.
Two people taking a selfie in front of a green leafy wall with a neon sign that says 'Once in a Blue Moo' and some small orange flowers
People walking through a series of heart-shaped floral arches decorated with pink and yellow flowers.
A woman in a long orange dress and a man in a formal outfit taking a selfie in a decorated indoor setting. They are standing in front of a mirror with string lights and orange garlands.