Trip Planning 101: How to Plan a Vacation
Let’s face it, planning a trip can be an overwhelming experience. It’s easy to spend countless hours reading reviews, comparing prices, and researching attractions to craft the perfect itinerary. Fortunately, there are more trip planning tools and resources than ever before to assist you every step of the way.
In this guide, we’ll share some of our favorite trip planning tips to help you bring your dream getaway to life.
The Benefits of Planning Ahead
According to Squaremouth data, travelers in 2024 plan their trips roughly four and a half months in advance. While planning this far in advance may not be for everyone, I think we can all agree that it has its perks.
For starters, making travel plans ahead of time gives you first dibs when it comes to airfare, accommodations, rental cars, excursions, and other itinerary items that require a reservation. As each day passes, your options may start to dwindle.
It’s also common to see prices increase when booking flights, hotels, and other trip reservations at the last minute. Much like other goods and services, most travel suppliers use dynamic pricing structures that operate on supply and demand. Whether it’s airplane seats or hotel guest rooms, rates usually skyrocket when inventory is low, making it a smart financial decision to plan ahead.
Where to Find Trip Inspiration
Travelers have used Squaremouth to insure trips to more than 250 destinations globally. In other words, the world is a big place, and sometimes we may need some help deciding where to go. If you’re searching for travel inspiration, we recommend the following resources.
Travel Websites
There are hundreds of websites and travel apps dedicated to showcasing the beauty found around the world. Whether you’re in the mood for an iconic destination or want to discover more unique travel experiences, travel sites can point you in the right direction.
A few of the most popular travel websites that we’d recommend for inspiration include the following:
- Lonely Planet: A popular vacation resource best known for their in-depth travel guides for popular destinations.
- Travel + Leisure: A major travel publication great for hotel recommendations, trip ideas, and vacation packages.
- Conde Nast Traveler: A luxury-focused travel site that showcases unique experiences around the world.
- Squaremouth Travel Advice: Our personal travel blog, which highlights popular destinations and industry trends.
Social Media
In addition to websites, which are often run by travel experts, you can get tons of vacation planning inspiration from most social media platforms. Visual platforms found on your phone’s app store, such as Instagram, Tik Tok, and Pinterest, provide endless travel content published by users around the world.
To get the most out of these platforms, we recommend following accounts that share similar interests and travel habits as your own. You can also use hashtags to help search for travel related posts. Make note of destinations you come across that stick out to you.
Finding Budget-Friendly Airfare
Once you’ve decided where in the world you want to visit, it’s time to figure out how you’re going to get there. Unless you’re taking a road trip, the first payment you make on your trip will likely be airfare.
Flight tickets are constantly fluctuating. Airlines use algorithms that factor in everything from demand to fuel costs to generate their prices. Travelers can employ a wide-range of tactics, such as traveling off-season, to get cheaper tickets. However, if your travel dates are set in stone, there are a few websites dedicated to finding the best flight deals.
The following sites help travelers compare flights from different airlines and allow users to set up automated email alerts when prices drop.
Choosing Between Hotels & Vacation Rentals
Another important consideration when planning a trip is where you’re going to stay once you arrive at your destination. With a steady increase in hotel options and the relatively recent emergence of platforms like Airbnb and VRBO, there are essentially millions of accommodation options to choose from.
In this section, we’ll discuss which type of property might make the most sense for you.
When to Book a Hotel
Hotels, including resorts and hostels have been the trusted accommodation choice for travelers for hundreds of years, and that’s still the case today. Many travelers love the familiarity that a hotel provides, and it’s not uncommon for them to grow loyalty to specific brands over time.
Many hotels provide additional services and perks aside from a place to lay your head. For example, things like a concierge desk, turn-down service, valet parking, and room service can help you feel relaxed while away from home. Other perks like a pool, fitness center, and spa can also help elevate any getaway experience.
Hotels are a great option for those that want to avoid risks and unwanted surprises that may come with a vacation rental. Most hotels are located in convenient locations, making it easy to navigate once you arrive.
When to Book a Vacation Rental
According to a recent Squaremouth survey that polled more than 7,000 travelers, roughly 20% of respondents revealed they were staying in a vacation rental at some point during their trip. Vacation rentals are known for offering unique, bespoke experiences that can make you feel like part of the community you’re visiting.
This type of accommodation has rapidly grown in popularity, and vacation rentals can be found all over the world. If you’re planning a family vacation, renting a home can allow you to stay together under one roof. Vacation rentals can also be cost-effective in certain situations, especially if you’re traveling with a large group.
We recommend this option to travelers that are looking for something different than your standard hotel room. Be sure to read reviews and use reliable platforms to find the perfect vacation rental for your vacation.
Excursions & Things to Do
Every destination offers a unique adventure, with distinct food, culture, attractions, and experiences. It’s likely you won’t be able to do and see it all during your trip, so planning ahead can help you make the most of your time.
To find out about local things to do, we recommend utilizing sites like TripAdvisor and other online travel forums. These sites feature discussions from other trip planners that have been to specific destinations, who shared what they most enjoyed or wished they avoided. It may also be good to get recommendations from friends and family that have visited the region you’re traveling to.
Another great way to discover excursions is through sites like Viator or Airbnb Experiences. Both offer travelers the ability to compare and reserve excursions from different tour operators online using a credit card prior to arrival. These excursions can range from boat tours to cooking classes, so there’s bound to be something for everyone.
Protecting Your Trip
A trip worth taking is one worth protecting. Like other types of insurance policies, travel insurance is something you’d rather have and not need than need and not have. Most policies provide reimbursement if unforeseen events, such as a medical emergency, trip cancellations, or significant delay, result in financial loss.
Travel insurance can be found a wide-range of price points, making it easy to find travel protection that’s within your budget. Since they’re so many providers and policies on the market today, it’s always recommended to compare plans from multiple providers on a travel insurance comparison site like Squaremouth to ensure you’re getting the best policy at the best price.
Be sure to check out our Help Center if you’re new to travel insurance or have questions about the coverage it can provide.
Other Helpful Trip Planning Tips
When it comes to trip planning, there really is no end to how detailed you can get. Some travelers love having every minute of their trip accounted for, while others prefer to play it loose. Regardless of which tactic you pursue, be sure to consider the following additional tips before you depart for your vacation.
- Research Entry Requirements: While rare, some destinations may require travel documents in addition to your passport, such as a visa or proof of medical coverage. Spend time researching what’s required to avoid problems at the airport.
- Check for Travel Advisories: The U.S. Department of State’s Travel Advisories are designed to alert travelers to any relevant dangers or threats. Advisories can include everything from civil unrest and terrorism to natural disasters.
- Pack Accordingly: Part of planning the perfect trip involves being prepared for the unexpected. When packing, take into account the various activities you may participate in while away from home. You can use our packing checklist to help get started.
Bottom Line
Trip planning can seem like a daunting task, especially if you’re planning a high cost bucket list vacation or are traveling with a large group. We recommend breaking the process down into steps and tackling them one at a time. For most travel planners, the process may look a little like this:
- Find a destination
- Purchase airfare
- Choose the right accommodations
- Book a few attractions or excursions
- Invest in trip protection
- Research entry requirements and advisories
- Start packing
You may find that a different approach works better for you, which is completely fine. What’s most important is that you plan a trip that fits your budget and your lifestyle. Happy planning!