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An ultimate guide to trip planning

An ultimate guide to trip planning

Many people have told me that they want to travel, but are overwhelmed by the idea of having to plan their travels. Budget, travel route, booking accomodations and transport can involve varying degrees of research, and of course, stress.

I’m here to help. Read on for my in-depth guide to trip-planning.

Often times, style of trip planning will depend on the traveler and their personal comfort levels with knowing and unknowing. On long-haul trips, I have often felt comfortable with minimal travel planning, finding accommodations as I arrive at a destination. On shorter trips, I prefer to plan in advance so that while on the trip I don’t have to put the energy towards planning. On the rare occasion that I want absolutely nothing to do with planning, well, that’s what all inclusive resorts and cruises are for!

Whatever your comfort level and preferences, read on to to get a glimpse into my trip planning process, including my favourite websites and resources.


Your first task in trip planning? Decide where you are going! I tend not to be picky about destination. My partner and I typically have a couple places in mind, and then the choice is ultimately made based on price. I use various resources to keep an eye on flight prices. You will also want to consider your style of travel. Organized tour? Cruise? Resort? Backpacking?

Mistake fares have snagged me great ticket prices to Costa Rica, Guatemala, Europe, Vietnam, and Jordan! Our return flights from Toronto to Amman, Jordan we snagged for a sweet $390.00 CAD.

If budget is no question, think about what kind of trip you’d like to have. Consider what activities you would like to do, what kind of weather would be ideal, whether you prefer beaches, nature, cities,  and what kind of cultural immersion (if any) you would like. Knowing these preferences will guide you in picking a destination for your trip.

General Trip Planning

How much you need to plan depends entirely on you: your travel style, preferences, and comfort with the unknown. Research is the key to good planning. Everything from figuring out an itinerary to discovering restaurants can be done by browsing various sites and resources. Some of my favourite trip planning resources for inspiration include:

  • TripAdvisor

  • Girls Love Travel (Facebook Group)

  • Reddit (check out r/travel)

  • Various blogs (I am sporadic with blogs, and typically find them via Google)

  • Instagram. Search hashtags related to your destination!

Your general reading will inspire your itinerary and activities, but will also give you an idea of how much you need to plan in advance to travel comfortably. I find the amount of planning I do for a trip depends on the length of trip I am taking, and where I am traveling. For example, on long haul trips (3+ weeks) I do not plan beyond the first week, because I enjoy the freedom of developing my trip as I go. On shorter trips, I plan everything (hotels, transport) in advance to avoid having to spend precious time doing that while actually on the trip. The destination will impact planning as well. For example, I traveled Japan in the low season, meaning that it was never difficult to find affordable accommodation on short notice. If I am headed to a destination during high season, I am more likely to plan accommodations in advance, because availability will be more limited.

Packing is a huge part of planning, as well! I always aim to pack light. You can read my full guide on packing for trips, here.

Planning Hostels & Hotels

I use various tools to book accommodations. Here are my top websites for booking:

I have always been a fan of hostels. In my solo travel days, I loved the hostel environment because they were affordable and offered a fantastic social environment. I made many friends in hostels, often in the common room or cooking my dinner in the kitchen. This is another perk of hostels: they often offer kitchens! Nowadays I still enjoy hostels, but tend to book private rooms when traveling with my partner. These offer us more privacy, but we can still socialize with the other backpackers. And! Private rooms in hostels tend to be cheaper than hotel rooms. I typically book through Hostelworld, or I browse the hostels on their site and contact the hostel directly to book (this saves you booking fees!).

I find myself using Airbnb more and more. In most cases, I find Airbnb to be a more affordable option, especially in cities that are notoriously expensive. Moreover, they often offer perks such as earlier check in times and kitchens. As with hotels, be sure to select places that have many reviews, and be sure to read those reviews thoroughly. Keep an eye out for mentions of bed bugs!

Booking and Agoda (and Expedia) are all third party booking sites. While they are convenient for seeing what is available and hotel reviews, I do try to book directly with the hotel. I typically will browse third party sites to find a suitable hotel, and then track down the hotel’s email to book with them independently. This often results in a better rate, because third party sites charge service fees.

I have named Hotels and Agoda because I have had consistently positive experiences with these sites. I tend to use Agoda in Asia and the Middle East, and everywhere else. On two occasions, Agoda provided me a refund for hotel rooms in India that on arrival, were not as advertised. offers a rewards system that is fantastic for long term travel. For every 10 nights, they offer 1 night free. This rewards system is useful if you are traveling long-term, or often. Do beware that after one year, your collected nights towards the free one expire.

Planning Transport

Confession time: I never book transport until I have arrived in my destination. I find that when traveling anywhere beyond Europe and North America, travel information that you receive from locals is far more reliable. Booking in advance through agencies will often cost significantly more, as well. I will sometimes browse forums to learn about the modes of travel, travel times, and estimated costs, but always prefer to book in person. The only exception? Renting cars. When I intend to travel by car, I make sure to book the rental well in advance.

Planning Activities

One of the most profound realizations I have had as a regular traveler is that planning activities well in advance is not necessary, and, is always more expensive. If you are a budget traveler, I recommend waiting until you’ve reached your destination before booking your activities. I do always research enough to know what activities I am interested in, and some names of reputable tour companies, but I never book in advance. Instead, I explore my options once I have arrived at the destination. Never once has this compromised a trip for me, in fact, I have likely saved hundreds of dollars this way. Example: To book my hiking guide for Volcan Acatenango in Guatemala would have cost over 100 USD in advance. By booking through my hostel while in Antigua, Guatemala, I paid only 40 USD.

The added benefit of planning and booking activities once you’ve arrived in your destination are the local resources. The internet is great, locals are better. If you have questions about activities and planning, chat with your hotel or hostel staff as well as local tour agencies.

Trip planning can absolutely feel overwhelming, but can also be fun. I love the planning period because it is an opportunity to learn about your destination, and hype yourself up for the trip. If trip planning stresses you out, then be sure to give yourself enough time in advance to plan, and organize. There are fantastic tools to keep your organized while preparing for a trip:

  • Google Maps and Maps.Me allow you to pin locations in advance! As you research for the trip, you can pin your hotels, restaurants, and sites you’d like to visit.

  • Google Docs to keep note of your hotels and other bookings. By keeping this information together in a web-based drive, you will always have access to it, through any device.

  • Back up travel documents via email or Google Docs. This is a wise move in the event that you lose your passport or other important travel documents.

Wondering about how to pack for your trip? Read my Ultimate Guide to Packing for Trips.

An ultimate guide to packing for trips

An ultimate guide to packing for trips

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