How to Plan a Trip to Anywhere – Step by Step Guide + Our Mexico Vacation

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Planning a trip can be super fun and exciting, but it can also be stressful if you are new to doing it!

When me and my now husband went to plan our first trip together, it was the first for both of us so we had to learn the hard way of what to do and what to watch out for.

From booking the flight, deciding on a hotel and going through the travel decisions, it was one of those situations I wished we had someone walking us through it.

Hopefully, this guide with be that for you and I can lend a hand in some way to make your trip planning super fun and not stressful so that you can look forward to it and not start your vacation off with heaps of worry!

So… what do you do first?

How to Plan a Trip to Anywhere

Whether you’re with your partner, family or friends traveling within the states, overseas or to an island get-away, you’ve come to the right spot to look like a pro (do it the simple way) when it comes to booking your trip!

Something else you need to plan besides the trip itself is having your home life taken care of while you are away. This includes children, pets and your home.

Be sure to plan for:

  • babysitters
  • house sitters
  • pet sitters
  • someone to get mail or postpone your mail
  • watering plants
  • mowing the lawn
  • snowblowing and/or shoveling

Let’s get you booked!

Step 1. Where will you go on your trip?

First, you will need to determine where you are going.

If you are unsure where you’d like to take a vacation, it’s best to consult who you will be going with to see what type of atmosphere you would like.

Things to consider when going on vacation include:

  • special amenities
  • all-inclusive resort (meals, drinks, etc are all paid for as part of the package)
  • adults only
  • touring options
  • preferred weather

Step 2: Where to book a trip – online or with an agent

We have done both. When I have gone online to book a trip, I usually go through or For either one, you often have the option to use a financing choice, and I would highly recommend seeing if they have this option because it helps if you cannot spend all that money at one time or upfront.

Some fun trips I have booked include:

  • Las Vegas, NV (Golden Nugget downtown and the Luxor on the strip)
  • Cancun, Mexico (GR Solaris Resort and Fiesta Americana Condesa)
  • New Orleans, LA
  • San Francisco, CA

Every year, our friends have gone on some type of trip around February. We plan a get-together around November to all book together so we can get it done and have a little party to hang out while everyone does it.

One time, there was a big deal going on earlier than expected in October so all our friends got together to book the Cancun Mexico all-inclusive package for $2700 for 2 people. We didn’t have the money ready at the time so we had to pass. Little did we know there was a financing option to book and get the deal at that price. When we went to book the trip later when we had the money, thinking there would still be a deal, we ended up paying $3500 and we were able to do the financing…. but if we would have known about the financing before we would have been able to save $800.

The financing was through a company called It was a portion upfront, I believe about 1/3 the total so around $1200 and the remainder was financed. The financing was for 12 months at around $150/month.

The financing fee was not very much either (as in there was not a huge interest charge). I think the financing only added on another $200 which isn’t much at all if you think about it. So to us, the financing option was completely worth it.

The other option can be through a travel agent.

For a trip to Jamaica, our friends chose to go through an agency and then they sent out the links to all their friends to book directly with them. Most agencies have this option to ensure your traveling group gets the proper discounts and group amenities.


Step 3: Booking a Trip & What To Look For

Planning a trip can have a lot of moving parts, but once you do it, it will come naturally to check off a lot of these things without even thinking about.

But, if you’re like me in any way, I always like to run down a quick checklist of items to make sure I’ve got myself covered and prepared as much as possible.

You can’t plan for everything, but you can plan the best you can.

Here is a list of items to keep in mind when booking your vacation:

  • your flight out location
  • travel to airport
  • flight out date and time
  • luggage option & fee
  • number of stops (non-stop or multi-stops) – remember this will take up more traveling time
  • where the flight ends
  • traveling from the airport to the resort destination
  • is the resort included in your package
  • if you are choosing all-inclusive or not
  • whether you want specific luxuries, like ocean-side, ocean-front, ground floor, etc
  • room amenities (larger room vs king bed vs work area)
  • other special needs you may want
  • insurance for package (in case of cancellation, postponement, etc)
  • luggage protection

I know it appears to be a lot of things to keep track of when you plan a trip, but I will tell you it is so much better to go through the list and pre-plan and prepare for as much as possible.  If there are any hiccups or issues along the way, you can at least have a grasp on a lot of the items that are taken care of. It allows you to flex if needed.

Planning a trip has many parts but if you can prepare and pre-plan, you will be very happy you did.

Step 4: Itinerary for Your Day-to-Day

Are you a site-seeker or a “sit on the beach” type of traveler?

It’s important to know before getting to your destination what exactly you will be doing while you are there. Do you plan on traveling? Will you be doing “touristy” things? Do you have certain sites that are on your must-do list?

While me and my husband are definitely the types of travelers that just want to enjoy the destination slowly, sit on the beach, drink, and eat, we are often with others who may be go-go-go type of people. It’s good to know if there are days or times that you will have by yourselves or be doing group activities, taking trips to other locations or needing to travel outside of your location.

A great example is when we were in Cancun, Mexico, our group wanted to go to Isla Mujeres island. For this, we needed to be sure to get to the dock and purchase tickets well in advance to the boat that took us over there. We also needed to rent a go-cart for travel on the island (which we rented 2 for our group).

These were things that we needed to pre-plan not only with coordinating times to actually do this, but also with the group.

Here are some cheesy photos from the island.

It was a great time and we enjoyed taking a break from the resort for a day.

There are a TON of fun things you can do while on the island so if you get a chance, plan these 16 Cool Things To See While On Isla Mujeres

Step 5: Packing & Travel Tips

When it comes to packing and other traveling items, there are a few things that are a must-have in our book just from experience and knowing what we know now to make traveling SO MUCH EASIER AND FUN.

Shop around my favorite travel items on my Amazon storefront for Best Travel Items >>

You can take a look at a bunch of pins we have on Pinterest for Tavel and Vacations >>

Packing Tips:

  • pack plenty of underwear (and socks), at least 1 for each day with 2 to spare
  • don’t forget to put your soaps, shampoos and lotions in travel-size containers if they are going to be carryons
  • bring backups of clothes and sanitary items in your carry-on just in case something happens to your checked luggage
  • always keep your tickets, phone, passport, money, and IDs ON YOU… AT ALL TIMES WHEN TRAVELING…Use an easy document travel organizer. When at your resort, lock them up in the safe provided in every room
  • plan for layering – tank tops, t-shirts, short sleeve shirts, and versatile zipper pants that can minimize your clothes and you can mix and match
  • contact your dr to get your prescriptions available near where you are traveling to just in case you misplace yours
  • pack with room to spare – you might need room for gifts or other bought items
  • label your luggage vividly and clearly – we’ve used bright luggage tags and colored luggage to easily identify ours
  • bring a heavier overshirt (long-sleeved or sweater) for an unexpected chill
  • be sure to pack multiple swimsuits and/or shorts – often you’ll have one hanging up to dry while you wear another
  • as a bonus, bring extra singles for tipping – we found this an extraordinary benefit and added to the way we were treated by being able to leave a few dollars for housekeeping, tip the bartenders, waitstaff and anyone. We brought about $100 – $150 in singles on each vacation.


I hope this has helped you plan your trip like a pro. I know after I booked my first trip I was able to feel a bit more organized for next time.

Good luck and have a great time on your vacation!

~~ And as always friends, take care, be kind to yourself and others, and always keep learning to be better and do better.

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*We sometimes use affiliate links on our site for items that I use, recommend, and love. The links are free for you to use and it helps support my site by providing a commission for the recommendation. I greatly appreciate you clicking on any recommended links I provide.*

Items from this article:

Go directly to my full list on Amazon called: Best Travel Items >

Or Check out my Amazon storefront with ALL MY FAVORITE THINGS! > 

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Other Related Articles:

17 Cool Things To See On Isla Mujeres – Cancun, Mexico

How to Plan a Trip to Las Vegas, Navada


Looking for things to do on a vacation to one of the spots I’ve been to? Here are links to a bunch of places you should check out while you’re there…..

  • Must see in Las Vegas, NV
  • Our must-do and see in Cancun, Mexico
  • Top 5 sites not to miss while in New Orleans, LA
  • Memorable sites to visit in San Francisco, CA

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