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How to Decide Where to Travel

You want to see the globe, experience new culture, taste different cuisine and view world-class art. But where do you want to go?

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?

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. Soon you’ll be hitting the road, soaring the skies and sailing the seas in no time. Gather your guide books and get ready to plan.

1. Think About Timing

The first step to deciding where to travel is to determine how much time you have for 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. In general, the number of places you can see changes with how long you’ll be traveling, from:

  • Months: If you’re able to block off a couple of months for travel, you can visit multiple destinations. Unless you’re in a large city with lots of events, you may run out of things to do in one location with all that time. Vary up your destinations throughout your travels with a cruise. Getting from one destination to the next will already be planned for you, so you won’t have to worry about calculating multiple transportation expenses.
  • Weeks: A few weeks can have the same impact of months since, depending on where you go, you may exhaust your list of things to do. A shorter cruise, in this case, might be your best option since you’ll get to see plenty of locations, even in a shorter amount of time. It’s the perfect option, especially if you’re interested in seeing several nearby areas.
  • A week: One week is an ideal amount of time to explore one location, especially a larger one. You can get meals at multiple places, see all the sights and not feel rushed. If you still want to see more parts of the world with limited time, it is possible within a week. With the right itinerary, you could visit multiple destinations. Again taking a shorter cruise might be perfect. You’ll see the highlights of each location, which you can always come back to on your next big trip for some in-depth exploring.
  • A few days: Make sure not to cram too many activities into your itinerary if you have less than a week for your travels. 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.

The time you can spend traveling will also help you figure out how far away your destinations can be. 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.

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 essential 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. Establish Your Budget

Your budget, along with timing, is the most significant consideration you should make as you plan your next big trip. No matter where you go in the world, you’ll end up spending something. Your expenses will include categories for:

  • Transportation
  • Accommodation
  • Meals
  • Entertainment
  • Souvenirs
  • Miscellaneous

Depending on how far you go, where you go and how long you’re there, your expenses will fluctuate. In general, you can expect to pay the most for transportation and accommodation. To sort out your budget to have enough for those and other costs, you should:

  1. Review your finances: Consider any savings you have specifically for travel along with your income and current bills or expenses. Estimating how much money you can spend beforehand will make choosing a travel destination easier. You’ll use this budget to guide the other steps.
  2. Organize your expenses: Do some research about the area you’re going to since the average cost will change depending on where you go. Remember that cities tend to be more expensive, especially when they’re top destinations, while obscure travel destinations may be cheaper. Designate an amount for each of the categories we listed above to help organize your expenses.
  3. Stay within your budget: Add up the categories above and see if they fall within your budget. Try to give yourself a buffer for emergencies and miscalculations. If the total is over or at your budget, see what you can cut out. Can you choose cheaper options for a meal or two? Streamline your souvenir list? With enough planning ahead of time, you may end up with extra funds that you can use to treat yourself on the last day of vacation.
  4. Convert to your travel destinations’ currencies: Remember to convert your local currency to that of where you may travel. Have a clear idea about the monetary difference to give you context for your expenses, especially once you’ve reached your destination.

Once you have a budget, be sure to think about how you’ll access it. Will you get some foreign currency before traveling to have on you once you arrive? Will you use a debit or credit card, and are there any fees with international travel? Be sure to factor in those extra costs because they can add up if you aren’t careful. Planning a budget will narrow down or expand your options, so it’s an essential first step to deciding where to travel.

3. 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. Since you’re traveling as a couple, you may also want a romantic destination. Any trip can be romantic as long as the two of you are together. But sharing wine in Italy, basking in the Northern Lights around Iceland or relaxing on a private beach in the Caribbean takes your romantic getaway to the next level. Even if you’re traveling alone or with a group of friends, these are still wonderful experiences to have.

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 on board 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 if you’re traveling alone for the first time.

The best option for solo travelers may be going with a tour company or a cruise. You’ll get the perks of exploring areas or relaxing alone with the security of others looking out for you. Participate in their itineraries and events to meet fellow travelers or enjoy some alone time on your well-earned vacation.

4. Choose Your Environment Preference

Think about the type of environment you prefer, including 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 explore. 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 you 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.

5. 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. 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 crucial tip to keep in mind regardless of what they say — go to the place that excites you.

We asked leading travel influencers questions from the list above, and 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 fromMy 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 who 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 fromA 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 fromEverything 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 fromLazy 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

6. Focus on the Experience You Want to Have

Planning a vacation based on an interest in a particular 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 Alaska or Mexico, for example, think about specific experiences you’d like to have.

The more specific you can get about what you want to see and do, the better. You’ll have an easier time choosing and planning a destination. To help you get started, consider what type of traveler you are. You might be a:

  • Relaxer: You’re looking to unwind on vacation. You want to sit poolside or beachside, enjoying luxurious views. For your travels, you should head somewhere natural and exotic with the perfect weather to lounge outside, preferably something on the coast of clear blue seas. The Caribbean islands or the Mediterranean coast may be right for you. To enhance your relaxation during your travels, opt for a cruise to take you from port to port.
  • Taster: The iconic food and drink of a location draw you into pubs, bakeries, restaurants and more. You want a taste of the world, of the fare that makes a destination so special to locals and visitors alike. You should visit destinations known for delicious dining and handcrafted beverages, like Mediterranean classics or unique Asian stops.
  • Adventurer: When you go on vacation, you’re always on the move. You want to see as much of the land as possible, whether through biking, hiking or other activities. You’re lining up snorkeling and diving sessions or learning how to surf the waves. No matter what activities you enjoy, many destinations will suit your needs. Go snorkeling in Australia or hike through some natural wonders in Northern Europe.
  • Photographer: You want scenery and exotic locations. You’re looking for everything from the obscure villages to traditional landmarks. For your travels, head to stunning natural locations, world heritage sites and cities sprawling with ancient architecture. Any spot in the world will be perfect for a photo op, so the choice is yours.
  • Learner: You’re a history buff, an art lover or a nature fanatic. You want to see what’s out there and learn how people of the past and present live. Travel to the sites of ancient Greeks and Romans, niche artisan cities or destinations that host wildlife reserves to learn all you can.

You may even be a mix of the travelers above, and that’s perfectly fine. Many destinations offer a range of experiences, suiting any traveler’s vacation goals. If you like adventure and relaxation, rest up on a cruise until you get to port, where your exploration can begin. If you’re a photographer and taster, try your hand at some food photography to remember your delicious meals.

What matters most is that you make your vacation work for you and your desires. 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.

7. Plan to Learn About a Different Culture

Among the most rewarding aspects of travel is experiencing a different culture from yours. From food and language to art, history and religion, many facets come together to create a culture. In some way or another, you probably want to learn about another culture, and the best way to learn is with experience.

The difference between traveling to and traveling into a destination is immersing yourself with the culture. To experience another way of life, be sure to:

  • Travel to a country or continent you’ve never been to
  • Research local festivals, galleries and more
  • Go where the locals go to eat, relax and play
  • Embark on guided tours of destinations

You can learn about unique cultures if you travel to obscure destinations, witnessing their art and history that are so different from ours. Various continents contain an array of cultures, giving you more to explore. Streamline your choices based on the cultures you’re most interested in, from areas throughout:

  • The Mediterranean: If Italian, Greek or Spanish food excites you, consider a cruise through the Mediterranean. On the coast, you can sample fresh seafood and local wines while basking in a warm climate. Tour ancient palaces, amphitheaters and ruins to learn about the cultures of the past.
  • Northern Europe: Go a bit north from the Mediterranean Sea for entirely different cultures. As you traverse the lochs and fjords of Northern Europe, you’ll learn about how towns and villages built lives around them. Taste their unique cuisine and explore their storybook cities with classic architecture.
  • Central America: Take a cruise through areas like Costa Rica and across the Panama Canal for a Central American experience. Learn how locals live among tropical jungles and islands and how they used nature to create art and other ways of life.
  • Asia: Witness ancient traditions as they combine with modern life throughout countries in Asia. Whether you visit Japan, Indonesia, Hong Kong or take a cruise to different locations, you’ll experience something new.
  • The Caribbean: Walk through exotic markets accompanied by local Caribbean music. With so many islands in the area to explore, get on a Caribbean cruise to island-hop. You’ll have access to unique, delicious tastes along with a glimpse at local life.

No matter where you travel, try to head out on a guided excursion or other enrichment programs. On these experiences, you’ll get the chance to meet the locals and participate in their traditions, cuisine or way of life.

8. 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, check out:

  • Social media: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.
  • Your favorite shows, books or movies: Maybe you’ve seen a film that takes place in a visually striking setting you’d love to experience firsthand. Or perhaps you’ve always wanted to explore the real-life setting of your favorite novel. Research these settings or filming locations and get ready to see the destinations you’ve only previously read about or seen on a screen.
  • A travel book or magazine: 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. Check out updated or current travel materials since these will have the most accurate information and photos.

While the inspiration of others’ travels may be enough to kick-start your ideas, you should focus on what you want in the end. When it comes to choosing a travel destination, sometimes it’s best to follow your instinct and let your heart be the decision-maker.

Travel With 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. Request a call or contact us today at 1-855-978-9073 about booking an unforgettable cruise for your next vacation!

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4 years ago

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’.

Would love your thoughts, please comment.x
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