How to Decide Where to Travel

Deciding where to travel can feel overwhelming at first. There is an endless array of worthwhile destinations around the globe, whether you want an awe-inspiring experience in nature or an unforgettable cultural journey. How do you figure out where you want to travel when there are so many places awaiting you?

Take a deep breath, close your eyes and exhale — choosing where to travel is easier than it seems. Planning a vacation can be a thrilling and energizing experience, and you’ll look forward to the amazing trip you planned. The key is to break down the planning process into manageable steps and figure out what’s most important to you and what you want to accomplish during your voyage.

In this post, we’ll help you get started. We’ll share top considerations for choosing a satisfying, joy-filled journey that suits your unique preferences and situation.

1. Think About Timing

The first step to deciding where to travel is to determine how much time you plan to spend on your trip. Do you want to get away for a weekend, or are you ready to dedicate a month to world exploration? Perhaps you’d like to plan a trip somewhere in between. Knowing how much time you have will help you narrow your options and come up with a plan.

For example, if you only have a week to travel, you probably do not want to go anywhere too far. The further away you go, the more time you’ll need to get there and adjust to a different time zone. On the other hand, if you have over two weeks to travel, a trip to a distant destination can be life-changing.

Similarly, if you only have a few days to travel, make sure not to cram too many activities into your itinerary. You’ll want to have time to rest between excursions so you can maintain your health and energy levels. You’ll also want to be able to slow down and savor each moment. You’ll enjoy your time much more if you don’t feel rushed.

Also, consider when you want to travel, as that can affect your overall experience. Do you want to explore a new place during the peak of tourist season, or would you rather avoid big crowds and head to your destination off-season? Is it important for you to travel while the weather is warm, or are you comfortable with winter weather? If you want to do a lot of outdoor activities, it may be worth going during a busier time of the year when the weather is ideal. However, if you wish to spend most of your time indoors visiting museums, you might enjoy traveling during a slow season.

2. Consider Your Travel Companions

Who do you plan to take with you on your adventure? Will you be traveling with a spouse, children or friends? Are you excited to travel solo for the first time?

If you’re traveling with your spouse, for example, consider destinations where there are activities you will both enjoy. Maybe you dream of traveling to a fjord surrounded by mist-shrouded cliffs, and your spouse wishes to view exotic wildlife. A trip to Alaska might be the perfect match for you both. Or perhaps the thought of listening to waves crash on the shore while sipping colorful cocktails makes your worries melt away, but your spouse prefers action-packed activities. Costa Rica wouldn’t disappoint either of you. Also, consider your partner’s schedule and physical fitness level to plan a trip that’s restful and fun for you both.

If you plan to go on vacation with a group, you might consider a cruise. That way, the planning and transportation are taken care of once you’re onboard for a stress-free trip. To figure out cruise destinations or anywhere you plan to go, sit down with your travel companions and ask them questions such as:

  • How much time do they have to travel?
  • What do they most want to accomplish from traveling?
  • What type of accommodations do they prefer?

If you plan to travel alone, consider how far you want to step outside of your comfort zone. Do you feel comfortable and safe visiting a foreign country by yourself for a life-enriching cultural experience, or would you prefer to go somewhere less intimidating and closer to home? You might consider booking a tour or staying at a resort if you’re traveling alone for the first time.

3. Choose Your Environment Preference

Think about the type of environment you prefer. This includes factors such as weather and scenery. For example, do you prefer warm, sunny weather? You might consider heading to a destination in a tropical climate such as the Caribbean. Do you feel more comfortable in a cooler climate and like to cozy up in front of a fireplace with a hot cup of cocoa? There are plenty of gorgeous northern destinations to choose from. You might enjoy whale watching in Cape Cod, for example, or be swept away by a roaring waterfall in Iceland.

What type of landscape do you want to wake up to while you’re away? Do you want to watch the sun rise above steep seaside cliffs, or does your heart flutter when you think of waking to the sound of tropical birds surrounded by greenery? Do you want to be in the middle of an exciting, inspiring urban location, or do prefer the peace, quiet and romance of a remote village? It’s all within your reach — you just have to figure out which destination uplifts you the most.

4. Get Recommendations From Well-Traveled Friends

If you have dozens of destinations on your bucket list, we understand it can be trickier to plan a vacation than if you were someone who has clearcut likes and dislikes. It might help to speak with a friend who has traveled extensively. Here are some questions to ask an experienced traveler for inspiration and recommendations:

  • When and why did you decide to travel?
  • What sites are must-sees in the places you’ve traveled to?
  • Are there any places you recommend for beginner travelers?
  • What was the most memorable experience of your last trip?
  • What advice do you have for someone who wants to travel?
  • How do you choose your destinations?
  • Where do you want to travel in the future and why?
  • What’s your favorite place you’ve been to so far?
  • Where would you go again if you could?
  • Would you move to any of the places you visited?
  • What inspires you when you travel?
  • What experiences do you like to have while you travel?
  • What’s the strangest food you’ve ever eaten?
  • How important is knowing the local language?
  • What item would you never leave home?
  • How long do you need to travel?
  • Do you recommend going off the beaten path?
  • What was your favorite city?
  • What surprised you the most while traveling?
  • What was the scariest experience you had abroad?

If you aren’t acquainted with any world travelers, you can easily find travel blogs and advice online provided by people who love to share their experiences and tips. You might try asking bloggers and Instagrammers for a recommendation.

It’s true that an experienced traveler can give you valuable advice about choosing a destination, how to prepare and what to expect. However, there’s one important tip to keep in mind regardless of what they say — go to the place that excites you.

We asked leading travel influencers the questions above, below you’ll find what they had to say about traveling!

Why did you decide to travel?

So many things inspire me when I travel — which is why I can’t seem to stop! I get very inspired by the natural beauty of the world, whether its a meadow filled with wildflowers in Italy or a deep turquoise bay in Thailand. But I also get inspired when I meet people who are pursuing their passions. Like the woman who quit her job as a lawyer in Canada to become a nomadic food writer, or the guy who moved from his small town in China to make gelato in Italy, or the New Zealander who started his own winery in Slovenia. These people had the guts to jump outside their comfort zone and take a big risk in life — all because they were passionate about living to the fullest.

– Jane from My Five Acres

I’ve always liked traveling since I was a kid. I’ve just ventured out farther and farther exploring the world. Life is short and the world is wide! I believe that when you explore the world around you, you discover the world within you.

– Ady Meshke from Verbal Gold Blog

What advice do you have for someone that wants to travel?

You should travel the way you want to and not how other people tell you how you should travel. You definitely should keep a journal to document your trip. I love my journals which remind of the things I’ve been through.

– Mary Charie from A Mary Road

Go with the flow and prepare for the unexpected. Enjoy it!

– Krystal from Sunny Sweet Days

The more you travel, the more you realize that you haven’t seen a lot. On top, I see traveling as a way of learning. While traveling you always learn about food, culture, history etc. It’s the best classroom!

– Paulina from Paulina on the Road

Don’t put it off for when everything is perfect. There’s never a perfect time to travel. You just have to do it. Plan it and stick with the plan. As soon as we get back from a trip, we start planning another so we never lose momentum.

– Laura Lynch from Savored Journeys

What experiences do you like to have while you travel?

I love exploring different cultural and historical experiences whenever I travel. Personal immersion to the country’s key historical places/landmarks and getting to know their culture is like looking at the soul and knowing the identity of the country.

– Ryazan Tristram from Everything Zany

I like to experience as much as possible when I travel. I want to see the tourist hot spots as well as the hidden gems. I enjoy learning about the destination’s cuisine and history. Some of my favorite things to do in new destinations are boat tours (if applicable), museums (art and history), historical sites (castles, ancient monuments), food tours or cooking classes, and local markets.

– Anisa Alhilali from Two Traveling Texans

When I travel, I try my hardest to get away from the normal crowded touristy sites and experience where I am from the eyes of the locals. Traveling has become so much more to me than simply getting the perfect photo in front of the #1 must-see. When I’m aimlessly wandering the unfamiliar streets of a new city, picking the brain of a stranger who now feels like a friend, sinking my teeth into a local delicacy for the first time, I feel the most at home. I feel the most like me.

– Lauren Bonheim from Lauren on Location

Where do you want to travel in the future, and what’s your favorite place you’ve been to?

I’ve enjoyed visiting some of the Caribbean islands and have been struck by how different they are.The Cayman Islands is a paradise for divers and watersports lovers, while Grenada is green and lush with fruit trees and cocoa plantations. In St Kitts, I enjoyed the gracious old plantation houses, in Aruba the sophisticated food scene and in St Lucia the majestic volcanic scenery. I’m looking forward to visiting further Caribbean islands to discover what each has to offer.

– Heather Cowper from Heather On Her Travels

Do you recommend going off the beaten path?

Yes, of course, we recommend going off the beaten path! Actually, we hate the crowds. We usually travel off the season, to lesser-known destinations. The people are usually more friendly there, you have a chance to observe the everyday life of locals, and visit the places no tourist have been before.

– Karolina Patryk from Lazy Travel Blog

Oh, yes!! I like to get off the beaten path, simply because it usually gives you a much better insight into the country and culture you are traveling in. Getting off the beaten path can also mean to just take public transport, not something many travelers do. It also means being spontaneous and talking to locals and people you meet along the way, hear their stories and share your own with them.

– Carolin Pilligrath from Breathing Travel

I absolutely recommend going off the beaten path when you travel. Some of my most memorable experiences have been ones that most people wouldn’t think of doing- hiking down a live volcano in Guatemala, feeding sharks in Tahiti, a Temazcal ceremony with a Shaman in Mexico and sleeping in an ice hotel in Canada. You really truly get to know yourself and develop a greater sense of appreciation for everything when you get out of your comfort zone.

– Kimberly from Jetsetera

What was your favorite city?

Santa Barbara, a small beautiful beach town in California two hours north of LA is hands down my favorite city on earth. There are great restaurants here, great shopping, wonderful hotels and so much to do outdoors. You can read my Santa Barbara Bucketlist for tips on what not to miss in this amazing little city.

I also love, love, love Positano on the Amalfi Coast. This is a great little walking city with a beautiful beach, great hiking trails and amazing restaurants. (I’m half Italian so I know good Italian food!).

– Vanessa Rivers from We Are Travel Girls

What item would you never leave home without when you leave for a trip?

I will never leave without my camera. I do not have the greatest memory so going back and seeing my photos are a great way to remember all the places I have visited. It is a way to relive each of my adventures. It is also the tool that allows me to share my experience with other people. I have loved to take photos since I was little and traveling has made that possible.

– Jazmin Harb from Travel to Blank

Are there any places you recommend for beginner travelers?

England and Ireland are great overseas destinations for beginning English speaking travelers because the language is the same and they’re compact countries. London is packed with world class museums, many of which are free as well. We spent 6 years living in Ireland and The Netherlands and have helped many with their travels to those countries and beyond. The rugged coasts and rolling hills on the Emerald Island are dramatically beautiful. Countries like The Netherlands, Denmark, Sweden and Norway are also great destinations for beginning English speaking travelers because English is quite prevalent and cultural differences are less prominent. Stockholm ranks as Europe’s cleanest city. Cruises are another great option for beginning travelers because you can move from destination to destination without having to worry about transportation details. It’s a moving hotel!

– Alex Kallimanis from Wanderlust Marriage Travel

What was the scariest experience you had abroad?

Aside from getting lost a few times, I’m grateful I haven’t yet had a scary experience. Even when I got lost, locals helped me find the way back and I ended up stumbling into places I wouldn’t have explored otherwise, so, it turned out well!

– Nicolette from CultureTrav

What’s the strangest Food you’ve ever eaten when traveling?

I’ve been vegan since 2013 which is limiting me when it comes to food. But to be honest, some of the exotic fruit I can taste on the road can seem ”strange” to some people. Even my entire plant-based diet can seem so to many! Let’s say for example, guanabana fruit which is one of my favorite fruit ever. So sweet!

– Alex Kovacova from Crazy Sexy Fun Traveler

5. Focus on the Experience You Want to have

Planning a vacation based on an interest in a certain country may be a good starting point, but it can also be overwhelming. Most countries offer hundreds of different sights to see, foods to taste and areas to explore. So, instead of saying you’d like to visit Italy or Mexico, for example, think about specific experiences you’d like to have. The more specific you can get, the better. You’ll have an easier time choosing and planning a destination. To help you get started, consider which of the following experiences appeal to you most:

  • Wildlife viewing: Do you feel immense joy when you catch a glimpse of an elusive mammal, bird or reptile in its natural habitat? You might want to build a trip around wildlife viewing, and you’ll be glad you did. Consider traveling to national parks or wildlife refuges. For example, you might visit the Kodiak National Wildlife Refuge in Alaska, which is home to thousands of brown bears. Or you might head to Loh Liang in Indonesia to look for Komodo dragons, whales, dolphins, turtles and other wildlife.
  • Outdoor adventures: If you want to have memorable experiences hiking, climbing, swimming or doing other outdoor activities, make it a priority to go somewhere that will nurture your love of adventure. Maybe you’d like to go kayaking in the Sea of Cortez or glide on a zip line through a tropical forest. Think about the type of outdoor activities you enjoy the most and the top experiences you want to have.
  • Eating: Do you have a favorite food you want to learn more about? Or is there a type of cuisine you’ve always wanted to try but never had the opportunity? If you enjoy treating your taste buds to new and exciting flavors, you might plan a trip around culinary thrills. For example, you might go to Sorrento to learn about limoncello production or taste fresh, delicious locally-grown products like Caprese salad and bruschetta. If you appreciate food and the process that goes into making certain dishes, you can’t go wrong choosing a destination that feeds your culinary curiosity.
  • Festivals: Do you want to partake in a music festival or vibrant cultural festival? Research what’s going on around the time you wish to travel. You might find a festival you won’t want to miss. That can help you choose a destination, and it may be the perfect way to plan a trip if you only have a few days to travel.
  • History: History buffs can use a vacation to satisfy their love of history. There are so many fascinating historical spots around the world to see from the Acropolis in Athens to the castles of Edinburgh. Think about the periods of history that fascinate you the most. It’s a sure way to have a satisfactory trip you’ll never forget.

Overall, thinking of what kind of experiences you want to have can help you choose a destination you will genuinely enjoy. If this requires you to go off the beaten path, don’t overthink it — let your bliss take you wherever you need to go.

6. Get Inspired

Still feeling stuck or torn between destinations? You might need a dose of inspiration to help you find a place that feels irresistible. As long as you have an internet connection, inspiring photos and stories are just a few clicks away. You may only need to see a photo of Venice at dusk or a picture of turquoise water lapping over a powdery white shore to discover the place that calls you.

To get inspired, look at different social media accounts. Facebook, Instagram and Pinterest are bountiful in gorgeous photos of places people have traveled to and shared. You might see somewhere you would’ve never thought of or discovered otherwise. Or, maybe you’ll realize you can’t go another year without finally soaking your feet in crystal blue water. Also, check out various travel blogs for ideas and recommendations.

You might also look to your favorite shows, books or movies for inspiration. Maybe you’ve seen a film that takes place in a visually striking setting you’d loved to experience firsthand. Or perhaps you’ve always wanted to explore the real-life setting of your favorite novel.

Lastly, you might pick up a travel book or magazine and let yourself get lost in captivating photos. You might find yourself aching to travel far to an exotic location, or you might feel dizzy with excitement at the sight of a domestic destination. When it comes to choosing a travel destination, sometimes it’s best to follow your instinct and let your heart be the decision-maker.

Contact Windstar Cruises

Where do you want to travel? At Windstar Cruises, we can take you where your heart wants to go. We’ve designed our cruises to create fulfilling, memorable journeys to destinations around the globe. Sail aboard one of our intimate yachts, and we’ll take you to pristine shores the big ships can’t reach.

If you long to roam medieval streets in the Mediterranean or behold the tranquil beauty of secluded islands, we’re glad you’re here. We can’t wait to accommodate you and make your voyage comfortable and relaxing as we take you to your dream destination. Contact us today about booking an unforgettable cruise for your next vacation!

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Thank you for all the pointers and comments from your readers and bloggers. We are looking at a cruise in November but are in our 70’s and wonder how strenuous this would be for people like us and our target readers. We are looking for opportunities to people to expand their horizons through my new blog – It is just getting started and i would like to mention appropriate events rather than find out too late that it is not ‘age friendly’.

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