Accommodations,  Travel,  Travel Planning,  Travel Tips

How to Travel to a Place You Have Never Been

The sky is the limit when you have the time and resources to travel. There are many places in the world that even the most avid jet setter has yet to see. You might be very familiar with one part of the world and not the other, or looking for a new adventure to satisfy your wanderlust. Then once you settle on an all-new destination, you want to pack your bags and go. However, there are still some factors to take into account before you leave home. Here are our key tips on how to travel to a place you have never been.

Also see Jenny in Wanderland article How to Choose a Travel Destination

Choose the Right Time – How to Travel to a Place You Have Never Been

Assuming you have already picked your travel destination, your next step is to figure out the best time to visit (for yourself and for your travel companions, if any). On a personal level, your ideal time should take into account your own flexibility. It should coincide with holidays, vacations, or weekends, in order to plan for a time that puts the least amount of stress on your schedule.

Then, as long as it fits into your timeframe (and visa laws if traveling internationally), your trip can last as long or short as you want. Be sure to plan accommodations and luggage accordingly!

Travel Planning - How to travel to a place you have never been
Image by MaeM

Pinpointing Your Travel Dates

Now that you have one or more time periods in mind for your trip, you can narrow it down to the best dates. Before you make any plans to travel somewhere you have never been, research how popular it is for visitors. More specifically, consider when it attracts the most or least tourists and why. A number of factors can affect this, including weather, seasonal holidays, travel prices, and special activities (Ex. festivals, cultural events, and so on). Then you can decide when you want to book your trip.

Maybe you want to avoid the surge in tourists (and pricing) by visiting at a less popular time, even if it means more extreme weather, or missing out on an event. Likewise, maybe you don’t mind planning your trip during peak season because you prefer the action. The decision is ultimately up to you, your budget, and your schedule.

*Pro-Tip: If you do choose to visit your destination at its most popular times, be sure to book travel tickets and lodging ahead for the best prices and the first pick of accommodations.

Factors to Choose Your Sights and Activities – How to Travel to a Place You Have Never Been

When you decide to visit a place you have never been, you most likely did not throw a dart at a map. Something about the destination spoke to you and attracted you to visit. Maybe it was the impressive sights, the plethora of activities, or the rich culture present. Regardless, you can make the most of your trip by planning what you want to do ahead of time.

Plan Ahead

While doing your research, be sure to choose popular sights, museums, shows, and activities ahead. If something is on your bucket list, you do not want to miss it and be disappointed. Especially during busy travel times, things can sell out. You can book specialized tours, seats, and activities for many destinations in advance.

*Pro-Tip: If you plan to take part in a special activity such as diving, golf, or surfing, check to see if on-site rentals are available or if you need to be bring your own equipment. Then, budget for rentals accordingly or leave space in your luggage. *Also, remember it is contra-indicated to dive within 24 hours flying. See this PADI article for other activities that should be avoided after a dive.

If there is a trendy restaurant that you absolutely want to dine in, reserve it in advance. Tables can get booked up for well known chefs and in big cities. Also, if you have a specific date or time that you would like to do something and you it is not flexible, that is another great reason to reserve ahead. This said, do not feel obligated to book every step of your trip in advance. Leave room in your itinerary for flexibility and changes to your plans. Sometimes the best parts of our trips take us by surprise.

Who is traveling?

Activities and travel pace also depends on who you are traveling with. Here are some questions to consider for your checklist:

  • Are you traveling alone or with a friend? A romantic partner? Will everyone traveling be interested and able to partake in your plans?
  • Do you have children with you? If so, you will want to consider family-friendly activities and sights.
  • Are you traveling with older people? You may need to potentially eliminate events with serious amounts of physical strain.
  • Do you (or anyone in your party) need special accommodations? If so, be sure to ask the venues you plan to visit ahead of time if they can provide. Prioritize visiting the ones that are able to accommodate.


Image by Photo Mix

Although it can be fun to cover everything when traveling in a new place, budget often needs to be considered. Your budget should account for travel to and from your location, as well as at the destination. Budget should include lodging, insurance, food and drinks, souvenir-shopping, emergencies, and any tours, sightseeing, and activities. Always include some extra money in case you end up having to stay at your destination longer than planned due to a delayed flight or emergency.

Depending on the size of your budget and how long your trip lasts, you can then narrow your list of sights and activities down to those that best fit.


Whether you are traveling solo or with others, it is always necessary to travel safely. Consider your activities, the people running them, their reputation, and your level of experience when choosing what to do while traveling. Be sure you have appropriate traveler’s insurance if abroad, especially if you plan on adventure activities, but accidents can unfortunately happen anywhere, as can illness. See Jenny In Wanderland tips on getting insured before you go.

When thinking about how to travel to a place you have never been, ask yourself:

  • Will you be visiting an area safe for tourists?
  • What do you need to watch out for? (Is petty theft a common problem, etc.)
  • Should you dress or pack a certain way to detract attention or to be respectful?
  • What are the safest times to visit? The most dangerous? (Natural disasters, Rough seas, Turbulent elections, etc.)
  • Which parts of the area should you avoid and why?

If taking part in physical activities, account for these questions in your research and on sight:

  • Are the organizers taking appropriate safety measures?
  • Do you have appropriate traveler’s insurance if abroad?
  • Is your body physically prepared for the activity in question?
  • How strenuous is the activity? Does it require special qualifications?
  • Can you stay properly hydrated and protected?
  • Do you have the correct equipment?

Also see Jenny in Wanderland articles Handing Emergencies and Safety Contacts


*Pro-Tip: Make sure you properly research the type of cuisine available at local eateries at your destination, especially if traveling abroad. This way, you can identify any dietary allergies or restrictions ahead of time so that you are able to avoid them (or tell the staff) upon arrival. Likewise, you can compile a list of places that serve items you can eat so that you have a safe group of establishments to visit. If possible, see if you can call or message the restaurants in advance to inform them of your restrictions as well. *If severely allergic, consider travel with an Epipen, especially when in remote locations.

Proximity and Transportation – How to Travel to a Place You Have Never Been

Image by David Mark

The next element that factors into how you choose your list of sights and activities is their proximity to lodging and transportation. If you are on limited time and staying in one city, you may want to avoid a sight that is a day’s travel away. Ideally, you want to visit places that are in the vicinity in order to maximize your time. They may not necessarily be within walking distance, but within one to two hours by car (or bus and train).

It is a great idea to map out your must-do sightseeing. Then you can arrange your day to see several sites in the same area versus wasting time running back and forth across a city. Efficiently planned travel saves time and cost. Then you will have more time to enjoy.

For further away sites, book a package that includes a guide and transportation. Many cover several destinations in one outing and provide interesting local knowledge. Best of all, you can sleep or watch the scenery while someone else is driving.

Although, there are always exceptions! See Jenny In Wanderland article, Staying in One Place Versus Moving Around for more planning ideas.

Pack the Right Things – How to Travel to a Place You Have Never Been

Image by Hans Braxmeier

When thinking about how to travel to a place you have never been, it is also crucial to pack appropriately. You must pack enough clothes and personal items to last for the duration of your trip, but not to overpack as it can weigh you down and limit your ability to travel freely. It is especially important to bring any specialized medication you need. In addition to casual travel clothes, you should also include one outfit that you could use, in case there is a dress code at a restaurant or an unexpected event.

It is also necessary to pack for the specific weather at your destination, so be sure to research properly. A seemingly sunny place might be warm in the daytime but chilly at night. Similarly, a colder destination might also see random days of heat. You could encounter frequent wind and rain, so take that into consideration while choosing your apparel. Some destinations will require sunblock, extra layers, or a coat and gloves. Footwear is definitely a consideration, especially if you are hiking or the if beach has stones. So, always check the weather, consider your activities, and pack accordingly.

For more on packing, see Jenny in Wanderland articles How to Choose the Best Travel Luggage and Top 10 Ways to Simplify Packing

Consider these Jenny’s Favorites versatile bags for easy carry-on, versatile backpacking, or durable checked luggage.

Book Your Travel – How to Travel to a Place You Have Never Been

How to travel to a place you have never been
Image by mohamed Hassan

Whether you are traveling domestically or internationally, you want to get the most out of your travel. For some, this means maximum comfort, and for others, the best price. Always check cancellation policies and know if your choice is non-refundable. Depending on what you prioritize, compare a few booking options prior to committing. You might find special discounts on the same flight, room, or car, at different sites. One of Jenny’s favorite travel websites offers great deals for travelers booking new travel!

Car Rental

Also consider your mode of transportation for once you arrive at your destination. Perhaps you plan to rent a car. At many popular locations, rental cars are booked up months in advance, or very expensive at last minute. If you know you are going to need a car, it is usually beneficial to book a rental car ahead.

Public Transport

Train travel is a popular way to get around many countries. Purchase a rail pass prior to your trip. Often rail passes offer deep discounts on multiple day train travel, but mostly can only be purchased in your home country.

Bus travel is also a great way to tour various areas if you prefer not to drive. Many countries offer comfort class coaches with tons of routes. In many areas there are “local” busses versus the slightly more expensive, “luxury” lines. Know your comfort level, compare routes, and even reserve your ticket ahead.

Even if you do not pre-arrange transportation, get familiar with the transportation available at your destination so you can be sure that you will have a reliable way to get around upon arrival.

Also see Jenny in Wanderland article How to Safely Use Taxis and Ride Shares

Best Travel Lodging – How to Travel to a Place You Have Never Been

Hotel Room - How to travel to a place you have never been
Image by Peggy und Marco Lachmann-Anke

Last but not least, finding the right lodging is one of the most important parts of planning travel to somewhere you have never been. In addition to considering the price of your lodging, you also want to consider how safe the area around it is and how close it is to the airport and sights you plan to see. Will you be able to walk everywhere? Will you need a car? Is there parking? Is there a train or bus nearby? These are all considerations when choosing where to stay.

Make sure your lodging has the amenities (breakfast, free Wi-Fi, swimming pool, shuttle services, etc.) and comfort levels you seek, while remaining in budget.

When looking for the best place to stay, consider these questions:

  • Does it fit with your budget?
  • How will you choose your room?
  • Have you read reviews from other travelers on the place you plan to stay?
  • How far is it from the airport? From local sights and events?
  • Are there amenities?
  • How much time will you spend in your room as opposed to outside? Is a view important?
  • Do you need more than one bed or bathroom?
  • How easy is it to communicate with the staff?
  • Is the hotel, apartment, or surrounding area safe for visitors?

For some travelers, lodging is not as important as the trip itself, but for others, lodging is the most important part. If you fall into the latter category and want a certain level of luxury, make sure to budget accordingly.

*Pro-Tip: It is always safest to book your lodging in advance, especially during periods of peak tourism at your destination (sometimes, it is necessary to book several months in advance). Try this booking comparison tool to get discounted prices for your stay.

Also see Jenny in Wanderland articles How to Choose the Best Accommodation and How to Find the Best Price Accommodation

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