How to Plan Your Dream Vacation: Unveiling Our Easy Step-by-Step Guide
- Alanna Gabbett
- Nov 29, 2024
- 12 min read
Updated: Apr 3
Planning a vacation can be thrilling, but it can also feel a bit overwhelming. Whether your ideal getaway includes relaxing on a sun-drenched beach, hiking through lush forests, or wandering through vibrant city streets, thoughtful planning can transform your dreams into reality. This guide will ensure that planning your dream vacation is not just efficient but also enjoyable.
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Define Your Dream Vacation
Before delving into the details, take a moment to picture your perfect vacation.

Reflect on these questions:
What destinations have always sparked your curiosity?
What type of vacation are you looking for?
What places or activities are on your bucket list?
What types of activities bring you joy?
Who will you be traveling with?
What time of year will you travel?
Perhaps when you hear the word vacation, you envision lounging on a beach, basking in the sun. Or maybe you yearn for adventure, like ziplining, kayaking, or hiking through the wilderness. Are you a city lover who enjoys exploring new cuisines and the latest cafes and restaurants? Or a history buff eager to see ancient ruins and cutting-edge museums?
There's no single way to vacation, and when planning, you need to customize it for yourself and your family to maximize enjoyment. Identify your interests and determine the kind of trip you want. Then plan accordingly.
Do you have a list of must-see destinations or experiences to complete in your lifetime? Perhaps it's time to check off an item or two. If you haven't created a bucket list yet, now is the perfect time to begin. Grab a piece of paper or open a Google document and start visualizing your list. This is an excellent way to inspire you to select the perfect destination for your journey.
Additionally, it's important to consider the time of year you will travel. Having flexibility on this is great for making sure you have the widest range of destination options available to you. Consider the best times of year to visit dream locations as well as typical weather patterns during various times of the year. Consider traveling in off-peak season to avoid crowds and increased prices.
And of course, don't forget to consult traveling companions so you find a trip that suits everyone so your entire group can have an enjoyable time.
Research your options
Ensure you research different destinations thoroughly. Identify places that offer everything you desire. Selecting the right vacation spot is just the start, so be sure to research and consider your options carefully. Evaluate several choices, and if you're traveling with someone else, be sure to get their input too.
Seek recommendations from friends and family about places they've visited to gain inspiration for your search. Explore travel blogs or watch YouTube videos of various destinations.
One of our initial steps in choosing our next destination is to select a few options and head to YouTube. We view travel videos from different vloggers and channels to truly understand what these places are like and what activities are available there. This helps us gauge whether the location matches our travel preferences and budget.
For instance, if you are a history lover, you may consider a dream trip walking through ancient ruins. In this case, you may be looking at Rome, Athens, or Egypt.
If you are an avid skier, your dream vacation might include a trip to the Swiss Alps.
Or if you're an animal lover, you may dream of a safari in Tanzania or a snorkeling trip among the fish at the Great Barrier Reef.
Take the time you need to research all your options to select the right destination for you and your family.
For inspiration for your next trip, click here!
Set a Budget
Establishing a budget is crucial for making decisions about your trip. A clear budget helps you prioritize where to allocate your funds. Here’s a breakdown to consider:
Accommodation: Options range from luxurious resorts to cozy Airbnb rentals.
Transportation: Budget for flights, car rentals, or public transport.
Food and Drink: Decide on dining preferences, whether it's street tacos in Mexico or five-star cuisine in Paris. Consider grocery shopping to save money.
Activities and Entertainment: Factor in costs for entrance fees to museums, guided tours, and other experiences.
For example, if your total budget is $3,500 for a week in Italy, you could allocate $1,200 for flights, $1,000 for hotels, $800 for meals, and $500 for activities.
Make sure you thoroughly research each category above in order to set a realistic budget for your travels. You also want to consider allocating a buffer of about 10% that can cover unexpected expenses or last-minute splurges and treats.
Saving for a trip
If you don't currently have the funds for a trip, it will be important to set a realistic budget for the trip and plan to save accordingly. Start by researching your destination and the likely cost of flights, accommodation, food, and activities. Add about 10% to this number and consider this the total budget for your trip. Then you can begin saving.
The easiest way to save for a trip is to set aside an allocated amount each week or with each paycheck. Take the total amount you need to save and divide that by how many paychecks, weeks, or months you have left to save.
For example, if you need to save $3,500 for a trip and have 20 weeks to do so, you will have to set aside $175 each week, or about $700 per month.
It's important to make sure that this number is within reason of what you will be able to save.
Choose Your Destination
With your budget in hand, select a destination that mirrors your dream vacation and fits within your financial plan.
Evaluate options based on:
Climate: Check historical weather data to choose the best time to visit. If your vacation involves outdoor activities, avoid visiting a destination in the rainy season.
Cultural Experiences: Assess what unique attractions and experiences the location offers. Look for important festivals and events that may be offered at certain times of the year, such as Christmas markets, Oktoberfest in Germany, or other local cultural events such as Holi in India and Carnival in Brazil.
Accessibility: Investigate how easy it is to get to your chosen destination. If you want to visit somewhere remote or far away from any international airports, this will come with extra planning. Additionally, if you are a wheelchair user or need to bring a stroller for a child, considering accessibility within particular cities is important.

Research Accommodations
Now that you've identified a destination, focus on finding your ideal place to stay. Here’s how to navigate your options:
Location: Look for places near popular attractions to save travel time.
Reviews: Explore guest feedback on platforms such as Airbnb, Booking.com or TripAdvisor.
Amenities: Check for essential features like free breakfast, Wi-Fi, and pools.
Consider the following questions:
Will you have a car or use public transport?
How much space will you need? How many rooms/beds?
Will you need a kitchen for cooking?
What other amenities will you need; a washer, T.V., Wi-Fi...?
What part of the city would you prefer?
Consider what the must-have amenities and features are in your accommodation, including proximity to local attractions. If you will have a car, make sure your chosen accommodation has private parking, especially in larger cities where it can be difficult to find public parking.
Always check multiple sites, such as Airbnb, Expedia, and booking.com. Filter search results to your chosen specifications and compare options based on comfort and affordability.
Additionally, when looking for accommodation, check your hotel reward programs for free nights or points that can be used for upgrades and other amenities.
For hotel bookings and free nights, we use the IHG Premier Credit Card and its related rewards program. IHG is one of the world's largest hotel corporations, with its most famous brand being Holiday Inn. When searching for hotels, many times we notice the cheapest options are IHG hotels. The brand offers budget stays as well as luxury and with over 6,000 hotels in around 100 countries, you're bound to find at least one at your destination.
With their free rewards program, IHG One Rewards, you can earn points on eligible stays that can eventually turn into free upgrades, extra amenities, and even free nights.
With their IHG Premier credit card, you gain access to a generous sign-up bonus that equates to up to 4 free nights! Annually, you also get an anniversary free night stay, automatic platinum elite status, $50 United Airlines Travel Bank Cash, $100 statement credit, 10,000 bonus miles, along with tons of other benefits.
Additionally, you get 26X points when booking a stay at one of their hotels or resorts, meaning more points for free stays in the future. And when you use those points to redeem 3 consecutive nights, your fourth night is free!
Plan Your Itinerary
A well-structured itinerary can enhance your travel experience. Planning this out allows you to savor every moment without feeling rushed.
Consider including:
Day-by-Day Breakdown: Structure your days with planned activities, meals, and downtime. Including a detailed itinerary for each day can give you the confidence that you will see and do everything you want to during your trip and make sure you don't forget places you want to see.
Flexibility: Leave space for spontaneous experiences. Allow for free time to explore and include alternative options in case of bad weather or unforeseen business closures.
Local Events: Look for festivals or local happenings that you might want to attend. Additionally, make sure there are no events occurring during your trip that would result in business or attraction closures.
For example, when planning an itinerary for a specific city, we try to group activities that make the most sense. It may be as simple as grouping activities in one part of the city on day 1 and activities on the other side of the city on day 2.
When creating a detailed itinerary, make sure to include travel time between attractions that mentions either walking time or public transport options. Also, include the opening and closing times of attractions so there are no surprises. You don't want to arrive at 9:00 am at the first attraction of the day if it doesn't open until 10:00 am.
Additionally, research cafes, bakeries, and restaurants ahead of time and give yourself a few options near that day's attractions. Take time to research specific foods you want to try as well as the reviews, ratings, and menu prices at specific establishments.
When traveling with children, especially young ones, always factor in nap times, breaks, and a bit of extra time getting from place to place.
Book Transportation
Transportation plays a pivotal role in your travel plans. While international flights are necessary, consider how you will get around your chosen destination:
Flights: Book in advance to find the best deals. Use comparison sites to gauge prices. Additionally, carefully consider flight arrival times as they can influence your transportation options into the city.
Set flight watches and price alerts so you know when a flight is a great deal and be sure to book ahead of time to secure the best rates.
Local Transportation: Research public transportation systems like subways, buses, trains, and trams. We use the Moovit app when navigating around a new city. It makes it easy to get directions from point A to point B with real-time updates on local public transport options. The app even alerts you when your stop is approaching, which can be helpful when traveling with kids who may act as a distraction.
Use ride-sharing platforms such as Uber or Bolt to save money and time. You can easily book a ride on the platform and get up-to-date arrival times. A bonus is that you can see the price ahead of time so no need to worry about haggling the price of a taxi.
Car Rentals: If you're heading to less urban areas, consider renting a car for added flexibility. This is especially convenient if you would like to visit multiple cities, towns, or even nearby countries. Always check multiple sites to ensure you get the best rate. We usually use Discover Cars, but will also check other sites like carjet.com or economybookings.com to book all our rental cars as we've noticed their rates are always better than other third-party sites.
Additionally, check requirements in your destination ahead of time to know the specific rules of renting a car and to see if you need to get an international driver's permit.

Prepare Travel Documents
Ensure you gather all essential travel documents well before your trip:
Passports: Make sure it is valid for at least six months beyond your travel dates. This is a requirement of most countries, and no exceptions are offered. Allow time to renew your passport if it is expiring soon.
Visas: Research visa requirements for your destination well in advance. Depending on your nationality, you may need to apply for a tourist visa in certain destinations. Others offer free visa on arrival or visa-free stays up to a set number of days. Be sure to check official government websites to check on and apply for visas.
Travel Insurance: This is a safety net for unexpected issues like cancellations or health emergencies. Keep in mind that some countries will require proof of travel insurance as a condition of a visa or stay. We always book our travel insurance on the Squaremouth platform. We love that it allows us to filter through options to find the exact amount and type of coverage we are looking for. It's also a great advantage that prices are super affordable, which helps when traveling with a large family.
Itinerary Copies: Keep both digital and hard copies of your itinerary and emergency contacts, as well as contact information for your local embassy.
Vaccine Records: Make sure to check if your destination country requires vaccinations such as malaria or yellow fever. In this case, bring copies of vaccine records and other documents.
Being prepared can alleviate stress as your travel date approaches. With this said, make sure to make copies of all documents and store them separately in case of damage, theft, or loss.
Pack Wisely
Packing may seem tedious, but with a thoughtful approach, it can be straightforward. Here are some helpful tips:
Make a Packing List: Consider what you will need based on your vacation activities and the climate. To avoid forgetting essential items, make a detailed list and make sure to go over it before you depart for the airport.
Layering: Select clothing that can be easily layered for changing conditions. Always bring a light rain jacket and fleece in case of rain or cold evenings.
Leave Room for Souvenirs: Set aside space in your luggage for items you might purchase during your travels. Try not to stuff your luggage to the brim (something we still struggle with!), so you have room for any extras you purchase on your trip.
Stay Informed and Safe
Once you arrive, it's vital to prioritize safety. Here are some tips to ensure a smooth experience:
Local Customs: Familiarize yourself with the customs and etiquette of your destination to foster positive interactions. Educate yourself on any pertinent laws and regulations so that you don't find yourself in a tricky situation.
For example, it may be pertinent to understand tipping customs, proper dress attire, and dining etiquette when abroad.
Stay Connected: Consider international data plans to remain reachable. We highly recommend purchasing an eSIM for your cell phones, rather than using your cell plan from back home. This is because it can save you a considerable amount of money. Our favorite eSIM plans are Holafly (for unlimited data) and Airalo (for pay per GB data). We recommend using WhatsApp to communicate with friends and family back home.
Emergency Services: Know local emergency numbers and the locations of nearby hospitals or embassies. You should always have with you the local emergency number as well as the contact information and address for your local embassy in your destination.
Enjoy Your Vacation
Finally, the essence of your trip is enjoyment. Here are ways to make the most of your experience:
Embrace Spontaneity: Allow yourself to explore unplanned opportunities. Having a rigid and moment-by-moment itinerary can sometimes take the fun out of exploring a new country. While proper planning is essential, allow freedom for unplanned experiences or simply time to sit and rest, taking in your surroundings.
Capture Memories: Use photos and journals to document your adventures. We love taking along a professional camera to capture our favorite moments, whether it's in the form of a photo or video. Make sure to also bring along extra batteries so you never miss a moment.
Disconnect: Take a break from technology to experience your surroundings fully. Put the phone down and enjoy the moment. Create core memories with your family that will last a lifetime.
Plan Your Dream Vacation
Your Journey Begins
Planning your dream vacation can be an exciting adventure in itself. By following this step-by-step guide, you can streamline the process and focus on what truly matters: enjoying your journey. Embrace every aspect of your travels, from the planning stages to unpacking your bags upon returning home. Happy travels!
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