5 Planning resources for planning a family trip yourself
There is nothing more stressful than 20+ tabs open, a convoluted spreadsheet with random, unlabeled links, and unbooked plane tickets when trying to plan a trip. Trust me, I’ve been there. Here’s my favorite resources to stay sane.
FIGURE OUT WHEN YOU CAN GO: A SOLID FAMILY CALENDAR
If you have kiddos in school / child care, their schedules are going to be the most restrictive part of your vacation scheduling. We love a monthly family planner like these ones from Plum Paper: https://www.plumpaper.com/shop/category/planners. You can also manage this on Google Calendars and subscribe to your kids’ school calendars. We like to look for:
official school breaks
short weeks / long weekends
Depending on your school district and country, missing school for vacation is looked at really differently. Be sure you know the policy where you live!
find a deal: GOOGLE FLIGHTS / skyscanner
People love to ask us how we pick our destinations. We look at school schedules, budgets and ideal weather. We come up with a trip vision and plan ahead for the year. Our final step may sound nuts but stay with me here! We ultimate let the flight deals decide. Flights are the biggest driver of variable cost on trips for our family of 5. Accommodations are up there too but they are within the same range for most places we go so that amount stays pretty static.
We love to use Google Flights and Skyscanner, which are a flight search and comparison tool, not booking sites. They both help you find and track flights across hundreds of airlines and online travel agencies, then send you to the airline or seller to book. You can search for flights from your home airport(s) to “Anywhere” and include either specific or general dates. We like to filter for 1 stop or less and set an upper limit for price per person. We also always exclude Basic Economy, which is the cheapest airfare category offered by many airlines—but it comes with strict limitations. It’s designed for travelers who want the lowest possible price and are willing to give up flexibility and comfort and we aren’t willing to do those things.
I used Google Flights to help us pick our fall trip. While we originally planned on Turkey, we ended up booking a flight to Vienna with a stop in Copenhagen because the flight deal was too good!
confirm the destination: TRIP VISIONING TOOLS
Before you book that trip, get the family’s blessing by involving them in the process. Avoid whining and trip disappointment by setting and sticking to your trip vision. Use our Guide to manage this process.
Chat with the kids about what would be the most fun for them with our Discovery Convo Cards. You may be surprised what you learn! My elementary school kiddo told us he really wanted to walk around in a historic town on our next trip. Who knew?!
Getting the kids and extended family involved early on is the best way to narrow down your focus and ensure everyone’s wants and needs are being met Everyone needs a beach? OK, that trip to Paris won’t work BUT maybe we head to the coast!
BOOK THE flights: CHASE and flight apps
We like to book the flight deal directly from the airline website or through our Chase card portal to maximize our points. We really love our Chase Sapphire card and really prefer to deal with the customer service at Chase than try to find someone at the airline. Here’s our referral link. We have the Chase Sapphire Preferred. It has a reasonable fee and a sign on bonus. I’m not a points gal but it’s great and we find the customer service to be excellent. You can also use Expedia or Booking.com (mentioned more below)!
Next, we always download the airline app, sign up for email / text updates about our trip. We also sign up for frequent flier / loyalty accounts. They are free and you get lots of perks, like earlier boarding for Delta!
find your lodging: Expedia / Booking.com
OK, you’ve got the flights locked down. Next up is lodging and ground transportation. Our favs are Expedia, Booking.com, and VRBO.
Expedia and Booking.com are great one-stop shops to search for deals on flights, accommodations, activities and more. Expedia allows you to book any of the below items all together or individually and Booking.com let’s you bundle flight and hotel.
✈️ Flights
🏨 Hotels & vacation rentals
🚗 Rental cars
🚢 Cruises
🎟️ Activities & attractions
📦 Travel packages (flight + hotel, etc.)
We like to use these sites to get a sense of accommodation in the area and then we can either book there or on VRBO, where we find a lot of great spots. With our family size, we are usually in rentals instead of hotels.
BONUS: BUILD THAT ITINERARY WITH FUN ACTIVITIES
You’ve got your flights and lodging. Now it’s time to build your itinerary. Here’s our guide to help you go through it step by step. Then you can book fun tours on Viator or Get your Guide.
Both sites connect you to local operators running activities. You can read the itinerary, details and reviews. Examples include:
Guided tours (walking tours, food tours, city highlights)
Day trips & excursions
Tickets to attractions and museums
Cooking classes, workshops, and cultural experiences
Adventure activities (snorkeling, biking, hiking)
We booked a day trip to Sayulita from Puerto Vallarta on Viator and it was so good!