How To Plan Your First Vacation Anywhere in the World 2026

Traveling to new places is one of the most amazing gifts we can give ourselves and our children. It can be tricky for people who have never traveled or booked travel before.

This guide will help you plan first vacation step by step, whether you are heading across the country or halfway around the world, and before you dive in, check out my How to Plan an International Family Trip Step-by-Step pillar guide for the bigger picture on international planning.

How Do You Plan First Vacation?

1. Pick your destination and rough travel dates
2. Search flights with flexible date tools
3. Book accommodation that fits your budget
4. Reserve activities and excursions in advance
5. Confirm documents, insurance, and packing lists

How To Plan A Vacation To Anywhere In The World

How To Plan Your First Vacation:

Tips For Booking Cheap Flights

There are several sites to check when booking an airline ticket; however, I consistently use and recommend these three websites below. Since REAL ID enforcement began at US airports in 2025, and TSA’s ConfirmID fee for non-compliant travelers started February 1, 2026, double-check that your ID or passport is REAL ID-compliant before you fly domestically.

Skyscanner

If you are looking to book the cheapest flights you can find on the internet, then make sure to use Skyscanner when searching for flights. Skyscanner allows you to search for travel destinations based on the cheapest place to fly to. I usually put in the airport I am flying from, and then in the box for the airport I want to fly to, I type in everywhere so it can show me the cheapest place to fly to from my home airport. I also use the flexible month travel option to find the cheapest place to travel to for the entire year.

Skyscanner App

Don’t forget to download the Free Skyscanner App also, which is very handy. This is how I was able to get $12.40 airfare from Los Angeles to London, as well as $9.40 airfare from London to Italy.

Google Flights

Google Flights is a great search tool when booking flights, especially for international travel. You can put in up to 5 airports in the departure box and the same in the destination box. So if you want to fly somewhere but are not sure which is the cheapest, you can mix and match airports and search all at once. The Google Flights search calendar is great at showing you the cheapest travel dates to fly on also. Such a great feature.

Momondo

Momondo is another great flight search engine also. Once I find the cheapest dates on Google Flights and Skyscanner, I usually check those dates in Momondo as well to see if I’ll get a better flight rate.

Pro Tip: When using sites like Skyscanner and Momondo, you’ll find that the cheapest flight prices are usually through third parties; don’t let that alarm you. I’ve purchased from third parties like Just Fly and Smart Fares with no issues before. It is usually better to purchase with the airline directly, but I’m all about buying the cheapest ticket, so that’s exactly what I do. I love a good flight deal.

Finding Affordable Accommodation

• Hotels

When booking accommodation at your final destination, TripAdvisor is the way to go because you can read reviews and see photos from other travelers to get a feel of where you will be staying. It’ll also route you to the websites offering the cheapest rate.

• Sometimes, I go to each of the sites below directly and search hotels instead of starting off with TripAdvisor.
  • HotelsCombined
  • Booking.com
  • Hotels.com

Pro Tip: I usually check all the websites above to see which one offers the cheapest rates.

• Vacation Rentals

When searching for vacation rentals, I usually check HomeAway and VRBO for house and villa rentals too. Perfect for when you travel with a large family, and also to save money when hotels are expensive.

• All-Inclusive Resorts

BookVIP is great for booking resorts at over half the cost. Do keep in mind that you’ll need to listen to a 90-minute timeshare presentation. If you don’t mind doing this, then you can definitely save a lot on your next vacation at an all-inclusive resort.

Booking Excursions & Activities

• Viator & Get Your Guide

My favorite websites to search for activities, tours, and especially skip-the-line tickets are Viator and Get Your Guide. This makes trip planning so much easier because you don’t have to search several sites, as both websites have several options to choose from.

• TripAdvisor Attractions

The same also goes with TripAdvisor Attractions – you can search and book activities as well as read reviews and see photos that are posted by real people who have been to these places. It’s a good idea to at least take a look, especially if you’re travelling with kids.

Renting A Car

Instead of checking every single rental car website, I use RentalCars.com, Car Rental 8 and Skyscanner Car Rentals to find car rentals all over the world with just one click. They’ll search all the

If you plan to park at the airport, visit Airport Parking to find the best prices, as well as make a reservation. Sorting out transportation is one of the last boxes to check when you plan first vacation logistics.

Travel Insurance Is a Must

People book trips and forget the most important part: purchasing travel insurance. Because we travel often, I purchase our travel insurance through Allianz for a year at a time, which means that we are covered for all trips within that year. Travel insurance will protect you and your family against theft, injury, illness, flight cancellations, and so much more.

It is a MUST! Locking in coverage early is one of the easiest ways to plan your first vacation without financial stress later. Get a full side-by-side breakdown by checking out my Best Travel Insurance for Families in 2026 comparison before you buy.

I once had my phone, money, and cards stolen while on Vacation in Vietnam; unfortunately, my travel insurance had just expired. So I lost over $2000 worth of stuff that would have easily been replaced if I had travel insurance. If you have a travel rewards credit card, you can often find insurance discounts!

How Far in Advance Should You Plan First Vacation?

1. Domestic trips: book 6-8 weeks out
2. International trips: book 3-4 months out
3. Peak season travel: book 5-6 months out
4. Passports and documents: renew 3+ months ahead
5. Last-minute trips: still doable with flexible dates

PRO TIP

When I am planning a vacation, the first thing I do is search for flights. When I find cheap flights and book them, I then search for accommodation. Sometimes I search for flights and accommodation together because I may find a cheap ticket, but accommodation may be too expensive. So keep that in mind when you plan first vacation.

Also, “Go Where It Is Cheap”. This motto has allowed us to travel more often because we are able to stretch our dollars. We don’t always get to visit in peak season, but sometimes less crowds are best.

Favorite Countries To Travel

We have taken many international flights and been to over 25 countries with the kids so far, and here are the top places they’ve been to.

• Aiden, 6 years old – Cuba because I visited a farm with animals.
• Ethan, 6 years old – Morocco because I rode on a camel.
• Milania, 5 years old – Italy because I rode on a horse.
• Avery, 4 years old – Mexico because I love swimming in the pool.
• The Mom Trotter – New Zealand because of all the wine and yummy food.
• The Dad Trotter – Thailand because it’s very affordable.

How To Save Money When You Travel

Visit my Travel Resources and Amazon page to see all the reliable and trustworthy brands that I use to book my travel with. These are the same tools I used to plan my first vacation, and I still use them today. I only recommend brands that I’ve used and can vouch for, so you’re in good hands!

• How To Save Money On Flights
• Best Websites To Find Cheap Flights & Error Fares
• Tips On How To Make Travel Affordable For Families
• Kids Fly FREE On Frontier Airlines Starting February 2019; YAY

Tips For Traveling With Kids

Traveling with kids and have a few questions you need answers to? These posts below will help your trip run smoothly.

• Best Travel Gear For Kids
• How To Travel With Kids Internationally Alone
• Top Must-Have Items When Traveling With Kids
• Everything You Need To Know About Traveling With A Car Seat

Frequently Asked Questions About Planning First Vacation

Conclusion

Whether this is your first big trip or your fiftieth, the steps above are exactly how I plan first vacation for my own family every time, and they’ll work just as well for yours.