easy trip plan

Creating an Easy Trip Plan in 6 Steps

Picking a destination and planning a trip can be daunting for the trip planner, but always satisfying when done right.

We recommend the simplified steps below as a basic framework for your trip plan. Start here, peruse the site for guides, and cheers to Easy to Breezy travels!

Disclaimer: Some of the links in this post, like hotel links, are affiliate links, meaning at no additional cost to you, we make a little bit of money if you click through and end up booking. That said, we would never recommend something we don’t stand behind 100%.

6 simple steps to a no-stress, don’t-look-back trip plan

Step 1: Determine who you are going with

Knowing who you’re going with sets not only the tone of the trip, but it starts you thinking about when that group/your family is free, the ability to do a long flight, the type of activity at the destination, etc. It’s the first building block of your trip plan.

Step 2: Think through your travel goals

This one has multiple parts.

  1. First, think through what type of setting you want. Adventure? Beach? Hiking? National Park? Road trip? Including a concert? It’s okay to want multiple types at this point.
  2. Second, isolate how long you want the vacation to be in terms of days.

By looking at these two together you can start to feel out if you have enough time to do multiple destinations or settings in one trip or if you need to choose one. In general, 2-3 days is best for one city or stop. For 4-7 days, you can get as creative as you want by visiting a few destinations that are accessible to one another.

Step 3: Get a short list of trip destinations

This is my favorite step. Gather inspiration and dream of where you can go.

Ask friends, use our Destinations guides to gather information and explore options, and then use flight schedules to find convenient destinations that meet your travel goals. Nothing is worse than getting excited about a trip and then realizing the flight duration or connections do not make sense from your starting point.

This is also when you should check if you have any miles/points/etc. to utilize and if that limits your travel choices. It’s important to dream, but it’s also important to be strategic with your resources, right?!

  • If you’re using your credit card rewards, you may need to book through their portal with their inventory of rooms.
  • Airline programs will sometimes change point/mile redemptions based on how much demand is on that flight or destination. The points you need to burn to redeem the flight may limit your choices.
  • Similarly, you may have a particular hotel, card, or airline brand you want to book with directly to gather loyalty incentives or meet a needed status or reward threshold.

Step 4: Check these destinations for ideal itineraries

Does the destination truly have what you need for who you’re going with and what type of vacation you want (building on Steps 1 and 2)? Double-check the airfare or driving plans again for feasibility.

Do a deep dive into your destination during this step. It will be your longest one, but one we work to make simple with our easy travel guides and posts. Sometimes at this step, I’ll go ahead and book refundable travel items (often hotels and tours, and sometimes airfare) that could book up. There is nothing like going all the way through planning and then realizing your favorite option is no longer available. Oh yes, speaking from real experiences.

Step 5: Decision made!

Once you find a perfect destination for your trip, it’s time to secure the flight and accommodations if you haven’t already. You can book directly with the hotel or airline, your credit card portal, or use an aggregator that offers price comparisons. If you have loyalty with a specific brand and are gathering or spending Bonvoy points, for example, that is always a great option.

For those looking for the lowest fares alone, utilize an aggregator so you can do price comparisons along the way.

Flights: Expedia or SkyScanner or Google Flights (my favorite for flight exploration).

Hotels: Booking.com, Expedia , VRBO, AirBnB

Step 6: Book and plan your itinerary details

Time to go back to your vacation planning and work through the details. Create a list of the restaurants you hope to visit, book things to do (tours, adventures, etc.), and note out any hiking areas, parks, or museums you want to explore. 

Things to do: Viator or TripAdvisor – Each site offers a large volume of reviews filtered to people who did the actual tour or activity. You’ll definitely learn a lot, and most bookings have an easy cancellation policy.

That’s it! No more trip planning steps. Begin your packing prep. Let the joy set in and happy, breezy travels!

Breezy Tip: Please remember to check your passport expiration date if traveling internationally. Note that some countries need 6 months of validity before your expiration date, and others need a full 12 months. As always, for the most up-to-date information on getting or renewing your passport, check the Department of State site.

One more Breezy Tip: Download offline maps before you go. You’ll use less phone data and if there is any lack of coverage where you are, you’ll avoid panics about losing your bearings 🙂 Exploring and mapping out routes will be much less stressful.


Travel Planning FAQs for going from Easy planning to Breezy travel.

This can be a tricky step if you choose when you want to travel and then pick a destination that turns out to be “off-peak” for the activities you want. A simple Google search will answer what the peak travel time is for where you want to go. I recommend considering the benefits of off-peak travel before you scrap the plan — it’s cheaper and less crowded, most often, but be aware of things that close seasonally. If it is a non-starter to go off-peak, then pick the plan back up when it is better timing (and plan another trip in the meantime for the time you’re free!).

To be sure, everyone plans a bit differently. These will help if you’re like me — You want a memorable and picturesque trip that isn’t too cumbersome to plan, but that provides a unique experience. Some of your things to do on the trip are planned, but there is still room to unplug and really enjoy where you are. You might call it “breezy”.

I recommend that someone is the point person. And when it does come down to sharing trip details and spending money on the trip, there are great tools now for sharing itineraries, dedicated group chats, ways to split spend (Splitwise), etc. Good news is that there are a lot of resources.

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