Directional sign with far off destinations such as Amsterdam and London

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Can’t Decide Where to Go, Is Travel Planning Too Hard…Join The Club!

I committed to myself that 2023 would be the year of travel, and so far, I have only one trip planned. I started the year with a goal of 4 adventures. But I keep second-guessing my choices, trying to find the perfect time to go, the ideal place to visit, the perfect everything.

It’s a combination of life changes, retiring from my full-time job in January, restarting travel post-pandemic, and too many choices. So I decided to investigate a better way to plan a trip. It starts by asking yourself some questions.

The Why Of Travel

The first step is determining why I want to travel, whether for relaxation, escapism, adventure, or in search of cultural experiences. It doesn’t have to be just one reason; it can be several. But it would help if you had a focus, a goal.

In my case, I want two things, I want an adventure, and I want to escape my ordinary life. I don’t have time constraints for the first time in my life. I don’t have to worry about leaving my business. But I have to balance my travels with my spouse’s work schedule, which has always been more flexible than mine.

What do you want? Do you want a beach vacation? Would you rather tour a city and have a cultural experience? Do you want to escape crowds? Do a book, and a beach sound good? Would you prefer to be alone on a mountaintop? All of these are valid and important questions.

So your first step is to determine why you travel. Mine is an adventure and an escapeism.

What Are Your Constraints?

Next, ask yourself if you have constraints, time, budget, or fears. You might want a month-long adventure, but you have two weeks of vacation you can use at this time. A trip to an expensive destination is much more challenging to plan on a limited budget. Or you might hate the thought of flying, so a transatlantic flight might not be a good idea.

The first step is setting a budget. Will you be traveling using fequent flier points or hotel points. Does the currency exchange rate have an impact on your destination and budget?

Determine how long you can go. Also consider what time of year you want or need to travel. These can both have big impacts on your budget and your options.

Another constraint might be you only want to visit someplace new. That’s my goal this year to avoid repeating previous trips. I sometimes revert to the old tried-and-true destinations to think or plan less. But last fall, I went somewhere not on my bucket list and loved it.

Here are my constraints are as follows: 7-10 days in length, multiple trips spread out over the year (so something in May/June, then another trip in August/September, and then another trip in December). Budget is also a factor. Since I plan on taking several trips, I want to control the cost as best I can.

Adventure awaits mug with mountains and lake in the background
Photo by Matthew Sleeper from Unsplash
Who’s Traveling?

It’s essential to determine who is joining you on this trip. Are you traveling alone? If so, is there a destination you feel safer traveling to alone? Are you taking a family? If so, how do you balance the needs of everyone and the cost? Will friends be joining you, if so what are their constrains?

In my case, all of my trips are a two-person affair. And luckily, we both have similar travel styles and requirements.

What Activities Do You Want On Your Trip?

Are you looking for an outdoor adventure? If so, a trip to a busy city isn’t the best choice. Do you want a beach and a book? Do you love museums or tours?

My interests are varied. But for 2023, I want one or two of my trips to be outdoor-focused, another to be a beach and book trip, and another to be a cultural experience.

Where Can You Get Inspiration?

It’s hard not to return to the same place repeatedly. I often want to try a new restaurant, but when it comes time for dinner, I usually end up at the same old place because it’s easier. The same can be true with travel. And nothing is wrong with going to the places you love most. But if you want a new adventure, where can you get inspiration?

Here are 5 places you can turn for a little help:
  1. Travel Blogs. Ok, this is an obvious one, your visiting one right now. But there are thousands of bloggers with different takes on travel; some can guide you to new destinations. Here are a few of my favorites: The Planet D, Nomadic Matt, Atlas and Boots, Never Ending Footsteps, and Wandering Wheatleys. Believe it or not, bloggers love to read each other and find inspiration for each other all the time.
  2. Travel Magazines and websites. I have always found Conde Nast Traveler, CNN Travel, and Travel & Leisure great places to get inspiration. I also find Tripadvisor to be a huge help, even when looking for inspiration.
  3. Friends and family. Other people’s experiences can be great inspirations for your travel. If you have similar interests and tastes, they can lead you to new places.
  4. Pintrest and Instagram. You can search for inspiration through photos. Search for keywords on social media, and you might run across a picture that inspires you. The initial reaction to an image can lead you to a never-before-thought-of destination.
  5. Do you have a hobby? Do you love to golf, then search for golf vacation ideas. Into gardening, look to garden blogs or websites for inspiration. Many of these resources even have organized trips for people with similar interests.
Start Your Planning

Just starting your planning can narrow down your choices. I will begin with either a destination or a time of year and then work back. Searching first for airfare. Once I find a few dates to travel or places to visit, I search for my accommodations.

Make The Commitment

The hardest part sometimes is pulling the trigger. But this fear of commitment can stop you from starting your journey at all. Nothing will ever be perfect, especially if that is the bar you set for a journey. But not going at all will almost always be worse than going and not loving the destination completely.

So I did my research. I found my inspiration, and I decided on two trips. A tourism website for Utah inspired my first. I will tour the Mighty 5 National Parks in Utah in the early fall. This trip combines my love of national parks with hiking, biking, and sunshine. My second inspiration came out of left field; I stumbled across an article on European Christmas Markets, which I have always thought would be fun. I found great airfare in December to several European destinations. I then reached out to an old high school friend who I recalled posting pictures of her trips to European markets a few years ago. She inspired me to check Vienna and Prague for the markets.

I hope your planning process yields results. And I will update you on the planning process for both of my trips. Bon Voyage!

Below are links and resources to help you plan The perfect trip

Travel Resources

  • HOTELS
    Booking.com and Expedia.com are great resources for accommodations around the world. Book almost any hotel directly from these links.
  • TOURS
    The best places to book tours and activities are Viator or Get Your Guide . From great food tours to guided hiking adventures to local walking tours, you will find great experiences to add to your travels here.
  • FOOD EXPERIENCES
    EatWith is a great resource for authentic culinary experiences with passionate locals worldwide. Connecting travelers with hosts in over 130 countries, providing unique, intimate, and immersive experiences in private homes and exclusive venues.
  • TRAINS
    Trainline is Europe’s leading train and coach app. They work with over 210 rail and coach companies to help their customers travel to thousands of destinations across 45 countries. 

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