Planning your dream vacation in 5 easy steps

Planning your dream vacation is easy and this article will explain where to start and how to make it happen in 5 easy steps.

1. Inspiration and brainstorming

One of my favourite parts of travel is researching and exploring all of the possible options and places to go. I am constantly scanning travel information for new ideas and there are numerous free resources available.

• Travel blogs – Google “travel blog” and you will find a wide variety of blogs, often targeted to certain a niche of travelers (e.g. traveling with children). This is a great place to view pictures, read stories and learn from the blogger’s personal travel experience in different destinations.
• Online Articles and E-newsletters – One of my favourite online newsletters is the Conde Naste Traveller Postcard of the Day. I have a free subscription for their postcard of the day which includes a daily travel photo, a short blurb about a new location, and a link to learn more. I’ve discovered a lot of really interesting locations that I never knew about or I hadn’t thought of traveling to.
• Another great online newsletter is the G Adventures online newsletter which will inspire you with ideas about group travel around the globe. You will be the first to learn about G Adventures promotions and get useful travel tips delivered to your inbox.
• Public libraries usually have a travel section with guidebooks, travel stories, and magazines that you can flip through to get ideas and see pictures of different locations. Some of my favourite travel magazines include Afar, Conde Naste Traveller or Travel and Leisure.
• Social media – Instagram and Pinterest  are filled with beautiful travel pictures to inspire you.
• Groups -Numerous travel groups exist to share information about travel including Facebook or Meetup groups. I’ve attended presentations both in person and online where people have shared their experiences travelling to locations I am curious about. This is a great option to ask specific questions that you would like to know.
• Travel Agents and Group Tour Companies – Promotional materials, such as booklets or pamphlets with guided tours, cruises, and travel itineraries, are widely distributed through travel agents or group tour companies. Similar to travel magazines, there are many different types of experiences available and even if you don’t book through that specific company you can still get ideas about where to go.
• Talk to friends, family, co-workers, and others about favourite places they have travelled to and would recommend. Most people love to share their experiences with others.

2. Determine what type of experience you want

Its important to understand your key criteria for your trip. Ask yourself the following:

• How much time do I have to travel? What is the maximum amount of time that I can be away? How much time do I want to spend getting there or in transport out of the total time to travel?
• Is there a maximum budget that I have to spend?
• Am I traveling solo? If not, who am I traveling with (friends, family, couple, etc.)?
• Do I have a certain time of year in mind that I am able to travel (e.g., over the summer)?
• What travel pace do I want? Slow and relaxed or fast-paced with many things to see or do.
• What kind of experiences or activities am I interested in? Do I have someplace in mind?
  • Active or sporting activity (for example, diving or golf trip)
  • Hiking and outdoors
  • Adventure and exploration
  • Art, dance, culture, and entertainment
  • Sightseeing – monuments, historical sites, cities, etc.
  • Wellness and relaxation
  • Wineries and food
  • Boating or cruising
  • Beachy, warm tropical holiday
  • Volunteering
  • Live like a local
  • Shopping

3. Travel style – Planning Your Dream Vacation

Decide whether you want to have your travel and itinerary organized and planned by someone other than yourself or if you prefer to do it yourself. I enjoy planning trips and almost always prefer to organize travel myself but there are times when I want someone else to be responsible. Consider how much flexibility you need and the pros and cons of each option.

Fully guided tour (private or group tour)

Pros

• You don’t need to worry about most of the details as many things will be organized for you and problems will be resolved by someone else. Depending on the tour this could include planning your flights, accommodations, transportation, activities, schedule, food, and insurance.
• You may feel more comfortable because you will have a knowledgeable person to answer questions, to resolve issues that arise, and help you navigate in an unfamiliar place. If you are in a country where you don’t speak the language the guide may also speak the local language and be able to interpret.
• There are a wide variety of tours available at different price points, with varying itineraries, and levels of comfort or activity, so you can choose the option that works best for you.
• You will have an idea of what many of your fixed costs are in advance which can make it easier to budget.
• Groups may be able to secure volume discounts for accommodations or other costs that you would not be able to get as an independent traveller.
• A set itinerary ensures you know what to expect and what you will see and do. If this aligns with what you wanted to do anyway then a guided tour may be a good match.
• There is safety in numbers, and you may feel more comfortable travelling with others in destinations where safety is a concern or where it would be difficult to navigate on your own.
• Guided tours have been carefully planned to cover as many locations as possible in the time available. They will know how to do this as efficiently as possible and will have local knowledge of the best places to go.
• Tour groups can be a great option for solo travellers who want to make connections with other people, dine with others, and share the experience. Some guided tours are “woman only” or “solo traveller only” tours so you can choose to travel with others in similar circumstances and develop friendships.
• Private guided tours are an option that allows for full flexibility and customization. This type of tour comes at a significant premium so you will need to consider the impact on your budget as it can be too expensive for many travellers.

If you are looking for a reputable fully guided tour operator G Adventures is one of my favourites. They have been around for over 30 years and their tours are organized by travel style. This allows you to pick the style of tour that will work best for you such as an active tour, living like a local, or a classic tour. They have a wide range of tours at locations across the world to choose from and you can count on them because they offer 100% guaranteed departures.

One differentiator for G Adventures is that they offer small group tours with local guides and they always include an opportunity to interact with locals and give back to the community you are visiting.

Cons

• The itinerary and schedule are set so there is little room for flexibility and spontaneity in what you do. Most guided tours will have some “free time” built in but it may still be challenging to organize activities or things to do if you want to do something different than the schedule or what the rest of the group is doing.
• Most guided tours are a package deal and there will likely be restrictions in making changes to items that are included in the price. For example, if a certain accommodation is booked for the group you likely can’t swap it out for a different location that you would prefer to stay at.
• Guided tours are a business so there is always a profit built into the price. You will need to analyze the inclusions and exclusions and estimate any additional costs to determine the “total cost” of the trip.  They may be able to get better pricing with volume discounts but generally, I have found that it costs less to book the same activities on my own as I am not making a profit.
• Usually, there are additional costs for optional excursions or entrance fees, some meals are not covered, flights might be extra and, it is also customary to tip for the services of your tour guide and driver. If you are travelling as a solo traveller and want your own room you will likely need to pay an additional fee called a single supplement which will increase the cost of the trip.
• Group sizes and the cost of the tour will vary depending on how many people you are travelling with. You may not want to be part of a 30-50 person tour and may want a more intimate or personalized experience.
• In my experience, guided group tours are very busy without a lot of downtime to just sit and relax. If you are seeking this type of experience this might not meet your needs.

Self-organized travel

Pros

• With a bit of research in advance, you can easily travel to many locations in the world on your own both safely and comfortably.
• You can often book travel more economically by booking on your own because there is no additional charge to earn a profit. You can control your budget by deciding what you will spend less on and what you might splurge on. There may be an opportunity to take advantage of mileage, points, or loyalty programs, or promotions to reduce expenses.
• You will have the freedom to choose. You can choose your schedule, itinerary, where you go and what you do at the pace you want. You will also have the flexibility to adjust and make changes if you wish.
• If you are travelling with a group of people or have specific restrictions (e.g. physical mobility) you may prefer to self-organize your travel. This will allow you to take breaks when you want, to accommodate certain travellers in your group, or to have the flexibility for different individuals in your group to do different things at the same time. You could also choose an option such as renting a whole home for a large group rather than paying for individual hotel rooms.

Cons

• Some people find it overwhelming to organize all of their own travel arrangements or they don’t want to spend the time researching different options.
• You could overpay for your travel expenses by self-booking if you don’t research the going rates.
• You are on your own. If something goes wrong, you miss connecting transportation, you don’t speak the language, or there is any type of problem it is on you to figure out the solution.
• It may be less “efficient” to get around if you are not familiar with the location and are figuring it out as you go.
• There are some locations where conditions are unsafe or dangerous and it is not wise to travel on your own unescorted. For example, even if I could, I would not rent my own vehicle and drive across the African savannah on my own to spot wildlife.
• If you are traveling solo some people may miss the camaraderie of traveling with others or may also feel less “safe” travelling alone. However, there are many guided day tours that solo travellers can sign up for to have a guide for portions of the trip and often solo travellers meet other people along the way. There are also mitigations for safety similar to what you would do at home. For example, it is a good idea to let someone know where you are going to be, to check in, book accommodations in a safe area, not walk alone at night or drink too much alcohol, and carry trackers such as air tags.

Partially planned – travel agent, tour company, or all-inclusive

Somewhere between a fully guided tour and self-organized travel is the option of booking through a travel agent or tour company. 

Travel agents can do the research for you, they have knowledge of a wide range of destinations, they can help resolve issues, and they may be able to secure discounts that an individual traveller won’t receive. They can help you to plan a customized itinerary that meets your needs and has some flexibility. Typically, they receive a commission or fee and many people feel it is well worth it for the service received.

Another great option is working with a local tour company in your destination. They often have local expertise and connections, ideas for popular itineraries, preferred pricing on tours and accommodations, and the ability to fully customize your vacation. In the past, I booked a Greek island hopping tour through a local tour company. They worked within my budget, recommended fabulous accommodations, with flexibility for changes, and booked all of our ferries, and transfers. A local guide greeted us on each island, acted as a resource and emergency contact, provided an orientation, and transferred us to and from our hotel. After that, we had the freedom to do whatever we wanted on our own schedule.

Some destinations or cruises allow you to book a trip that is all-inclusive or almost all-inclusive. If you want most of the details to be taken care of with some flexibility to do what you want once you get there this can be another attractive option.

4. Create a rough outline of your itinerary and budget

Once you’ve decided who is travelling, what experiences you want, where to go, when, and how you want to travel you can start to create a rough budget estimate to begin planning your dream vacation.

If your trip is available through a guided tour, start with a Google search of the destination you want to go to and find a tour with an itinerary that appeals to you most, matches the approximate length of your stay that is departing at the time of year you want to go. A number of companies advertise these types of tours including Tour Radar, Intrepid, G Adventures, Gate 1 Travel, and Exoticca. A detailed itinerary, list of inclusions and exclusions, and base cost of the trip is usually available online. Make note of any exclusions that you will still have to budget for such as a single supplement, additional tours you would probably sign up for, flights, etc.

Tour Radar is a particularly great place to start because their search engine amalgamates tours offered by a wide range of the top tour operators worldwide. Instead of having to look through the website of each individual company they will compare similar tours to the same location. This way you can see at a glance the price with different operators and the differences between each tour operator and itinerary.

This is a great general benchmark of the cost of this itinerary even if you decide not to book the guided tour and want to have a travel agent or tour company book the trip, or if you plan to self-organize your travel. If you decide to book through a travel agent or tour company you can suggest the same itinerary to them and ask for a quote. Alternatively, you could ask the travel agent or tour company to recommend an itinerary based on your needs. Compare quoted costs with a fully guided group tour.

For self-organized travel, I normally create an estimated day-by-day itinerary to prepare a rough budget of what I would spend, even if I am not 100% certain about the dates of travel. My completed template includes estimated travel dates, travel days to and from the destination, and how many days are anticipated for each location. Its important to travel at a reasonable pace, leaving plenty of time for transportation between locations. List the general activities or experiences you would like to do at each location.

If you are self-organizing your trip your expenses will generally fall into the following categories:

• Transportation – flights, trains, busses, ferries, transfer services, or vehicles to your destination(s)
• Accommodation – hotels, bed and breakfast, or rented apartments or homes
• Transfers and getting around– to and from airports/stations, getting around a city by Uber, taxi, rentals, or public transport
• Food and drink
• Activities and tours – entrance fees, guided tours, rentals
• Tips, taxes, and insurance – resort fees, city tax, tips, trip cancellation or medical insurance
• General spending money – gifts, souvenirs, spa treatments

Budgets will vary from person to person but generally, your highest costs will be transportation, accommodation, and food and drink. Check out my Customized Personal Travel Planner and Itinerary Template article which provides steps to create your travel budget when you are planning it yourself.

5. Put down a deposit to book accommodations and your main transportation to the destination

I wrote an article on how you can save money when booking hotels and recommended booking accommodation as early as possible for the best selection and pricing. I have found that prices may vary a bit as you get closer but the best accommodation, in a mid-range budget, typically fills up well in advance of your departure. My advice is to book accommodation well in advance with a full cancellation option.

I usually try to book around 9 months in advance so I always have a guaranteed place to stay but if I find another great option later or the price drops, I cancel the original booking. I used to look for the best possible price to book even if it is non-refundable but now I look for accommodation with the most flexible booking and cancellation options. After the hassles of trying to rebook accommodations during Covid, I will always choose the most flexible option over the cheapest option.

Booking.com

I frequently book through Booking.com and I love the flexibility of their “pay when you stay” and free cancellation options. They have a great free Genius loyalty program that you are automatically enrolled in, with different levels, and discounts up to 20% off, or sometimes they offer free room category upgrades or free breakfast with your stay. I frequently book multiple accommodations with them, without paying anything, and then cancel the ones I don’t need if the prices go down later or if I find something I like better. Hotels.com also has a similar “pay when you stay” option and with their One Key loyalty program you earn OneKeyCash that can be used to book eligible travel on Expedia, Hotels.com, and Vrbo.

Flights and trains are trickier to find the best time to book. There is no single best time to book and it will vary by the location you are travelling to and the time of year. For example, when booking trains in Europe I have sometimes found that if you wait until too late to book the mid-range or cheaper options are already booked and you need to pay a premium for a ticket.

One tool that I regularly use, particularly for trains or ferries in Europe is Omio. Omio has a search engine that will compare transportation options for you so you don’t have to check each individual website. At a glance Omio compares transportation schedules and prices of all available trains, ferries, busses, and flights for your route and you can select the one that will work best for you.

For flights, follow my 19 Best Flight Booking Hacks to Save Money on Airfare to get a cheap flight. As a start I would suggest setting up an alert through FlightHub and checking for any current deals. Then go to Hopper to “watch” a trip that you are interested in.

FlightHub has a great “Deals of the Day” list on their homepage from your preferred airport which is a great inspiration to book a trip. Once you’ve set an alert for a specific trip you will get emails whenever cheap flights are available to your destination.

Hopper has an interesting price prediction feature where it will analyze past flight prices and will tell you if you should wait to buy because prices seem higher than normal or when you should buy because the price is a good deal.

Ideally, I try to get the best cancellation option I can for flights, unless you have already purchased trip cancellation insurance. Flights with the option to get cash back are often very expensive so I rarely pay for this. Most often I’ll pay for a flight where I can get a partial cash refund or a flight credit if I cancel. That way if something urgent or unexpected comes up I can take the credit and plan the trip another time.

You did it!

It’s exciting to take the plunge and book that dream vacation, especially if you have been looking forward to it for a while. As you count down the days to your departure you can start to look into the fun details of your trip. I usually like to pick up a travel guidebook to learn more about my destination, and check out blogs, YouTube videos, and online reviews to get ideas about each location. I also create a detailed day-by-day itinerary using this template to plan my transportation, tours, and fine-tune my budget estimate.

Read More Travel Tips to Save Money