How to Have the Best Vacation of Your Life

Co-authored by Archana Ramamoorthy, MS and Eric McClure

Last Updated: March 27, 2021 References

Regular vacations are great, but there’s no doubt that some of them are certainly better than others. The best way to make sure that you’re going on the vacation of a lifetime is to take control of the planning process. This way, you have total control over where you go, when you go, and what you’ll do when you get to your destination. Keep in mind, there’s no single way to plan an awesome vacation—what sounds fun to one person may sound miserable to you and vice versa. Keep that in mind when looking at reviews or reading about popular sightseeing spots.

Method 1

Method 1 of 3:

Planning Your Trip

1
Organize the vacation yourself to build anticipation and take control. Many people don’t enjoy planning, but you’re more likely to look forward to your trip if you’re picking and choosing things that appeal to you. Organizing the trip also gives you ownership over the vacation that makes it feel like it’s your trip—not someone else’s trip that you just happen to be going on.^{[1]
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- It’s best to start planning at least 6-8 months in advance. This will give you enough time to research rates, sights, and book tickets.
- If you’re travelling with other people, feel free to plan together so that everyone is happy. Just make sure that you’re involved in picking the location, dates, and activities to stay invested.
- Skip the travel agents and the professional organizers this time. They may pick some fun stuff for you to do, but they’re also less likely to identify things that appeal to you personally.
2
Choose fun people to travel with if you’re travelling with others. If you really want to share an experience with your partner and children, take them with you! A trip is also great time to rekindle an old friendship. You also can’t go wrong with your good friends. Choose travel companions that you know you’ll have a blast with.^{[2]
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- If you plan on doing some partying, bring that crazy friend from college. If you want some philosophical conversation on the trip, take that friend working on their doctorate degree.
- There’s nothing wrong with travelling alone. A solo trip can be a great way to get back in touch with yourself and recharge your batteries.
- Try to avoid inviting people that aren’t comfortable with trying new things. People that love sticking to a routine may keep you from switching it up and discovering something new.
- Try to stick with 1-4 friends or family members. When your travel party gets bigger than that, transportation, lodging, and agreeing on a place to eat can get pretty complicated.
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3
Pick a new destination based on the sights and activities that appeal to you. Think about what you enjoy doing in your spare time and use that to determine where to go. If possible, choose a new location that you’ve always wanted to visit. There’s no right or wrong answer here, so pick a city or country that looks appealing to you. For example, if you aren’t a big beach person, Aruba probably isn’t the best spot for a dream vacation.^{[3]
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- If you really love visiting cities and going out on the town, pick a major city. If you’re a fan of the beach, pick a tropical island or coastal town. There are hundreds of options when it comes to finding great destinations for bicycling fanatics, foodies, and art lovers alike.
- If you’re big on nightlife, pick a destination famous for its clubs and breweries, like Amsterdam or Budapest. If you’re a big hiker, Ireland, Sweden, and Switzerland are quite famous. You can’t go wrong with a major city known for its food if you love to eat—like New York, Chicago, Paris, or Tokyo.
- Unless there’s a destination you’re completely obsessed with, it’s probably better to visit a place you’ve never been if you’re looking for the best vacation ever. You’re more likely to have memorable experiences if you aren’t comparing your trip with other trips you’ve been on.^{[4]
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- You don’t have to go out of the country to have an incredible vacation. Think about visiting a new city or region in your home country!
4
Travel to 2-3 locations near one another if you love seeing new things. If you’re planning a longer trip, consider stopping in 2-3 destinations that are relatively close to one another—especially if you’re traveling far from home and may not get back to the corner of the world anytime soon. Pick a few destinations that offer unique sights and amenities to really get the best experience possible.
- There’s nothing wrong with staying in one place for the duration of your vacation. If you’ve been dreaming of visiting South Africa your entire life, why bother stopping at Morocco, Madagascar, or Botswana?
- Island hopping is a great way to experience different parts of the world. For example, the volcanic Big Island in Hawaii is a lot different from the big cities on Oahu!
- Consider travelling to multiple cities in different countries. This is a great option if you’re going to Europe, since the trains and EU regulations make it easy to go from Prague to Berlin to Paris, for example.
- Avoid choosing destinations that are incredibly similar if you can. For example, you’re probably going to see a lot of mountains in Colorado. Maybe taking that short flight to Portland won’t seem quite as interesting after 2-3 days of hiking and craft beer in Denver.
5
Schedule your trip a little outside of the busy season if possible. You may get frustrated if you visit during peak season and every tourist site is packed with other travelers. However, you may miss out on things if places close during the off-season or the weather isn’t great. Optimally, pick dates for your trip that are 1-2 months outside of the super busy season.^{[5]
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- For example, Italy gets the most tourists from June to August. If you’re planning on checking Rome out, April, May, and September are ideal times to visit.
- The main exception to this is if you’re planning a beach vacation where the weather really matters. For example, it may drop to 45–55 °F (7–13 °C) in Los Angeles when it’s December.
- You don’t need to worry about this if you’re visiting a place a little off of the beaten path. Even during the peak tourist season, places like Mongolia, Peru, and Berlin don’t get huge influxes of tourists.
6
Plan to spend 6-8 days on your vacation to take the ideal trip. Trips shorter than 6 days are likely going to feel too short and you may feel like you missed out on a lot of stuff. If you’re staying 9 days or more, you’re very likely to get bored of the location or feel like going home early. The sweet spot for vacations is between 6-8 days, so select your dates accordingly.^{[6]
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- If you’re travelling with your family, pick one thing you really want to do or see and plan to do it alone. Let your family or friends know ahead of time what you plan on doing. This will give you a special little experience for you to hold on to, and it’s a great way to sneak in something that isn’t kid-friendly if you’re travelling with your family.
- For maximum enjoyment, pick your dates to give yourself a 1-day buffer at home when you return. For example, if you work Monday through Friday, plan to return on Saturday night or Sunday morning.
7
Pick a fun place to stay and spend a little extra on lodging. Booking a cheap hotel is typically the best way to save some money when you travel, but booking a nice place to stay is the best way to upgrade your vacation. If you can afford it, look for higher-end hotels or resorts where you’re really going to feel like you’re living in luxury.^{[7]
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- Look at high-end bed and breakfasts as well. There’s some really nice stuff out there if you can stretch your budget a little.
Tip: Don’t sacrifice your activities or destination for nice lodging. This is really only a good choice if you can afford to spend a little extra on a nice hotel.
8
Choose a handful of activities and sites that really appeal to you. Choose 4-5 key sites and activities that sound really fun to you and book tickets in advance if you need them. Spread your activities out so that you don’t pack too much into any single day. If you plan 3-4 activities into every day, you’re going to stress yourself out and wear yourself down. If you don’t plan anything though, you’re likely to miss out on something fun.^{[8]
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- If you love great food, find some famous restaurants with unique regional cuisine. If you’re into the great outdoors, look up the best hiking routes in the area.
- The activities you choose depend on where you’re going and what you’re interested in. You can take tours, rent bikes, go hang out at the beach, or visit a famous site. There are no right or wrong answers here, so choose activities that sound fun to you.
9
Don’t overload your trip with too many sights or too much travelling. The easiest way to keep your vacation from being the best is to push yourself too hard to pack everything into your trip. You aren’t going to have fun if you try and do as much as you possibly can while you’re visiting a new location. It’s impossible to do everything and you’re only going to stress yourself out on your trip if you try to do too much.^{[9]
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- The pressure you put on yourself to have the best vacation ever can, ironically, keep you from having the best vacation ever.

Method 2

Method 2 of 3:

Enjoying Your Vacation

1
Take a few hours after you arrive to relax and rest. Once you get to your destination, you’re likely going to be a little wiped. When you get to the hotel, take 4-8 hours to sleep, shower, relax, or have a drink at a nearby bar. If you land and start running around immediately, you’re going to wear yourself down. It’s better to relax for a little and start fresh after you’ve replenished yourself a little.^{[10]
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- You can probably skip this if you’re only travelling 1-2 hours to get to your destination.
2
Confirm your transportation for each day to keep things running smoothly. When you’re having your morning coffee or taking the first walk of the day, make a quick call to any drivers you have scheduled to take you around. Double-check that train map or look up the cost of a taxi to confirm the price. If you get on the wrong bus or blow all of your spending cash on taxis, you may end up annoyed or missing out on something you were really looking forward to.^{[11]
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- If you are traveling in a major city known for its easy public transit, like Paris or Chicago, go ahead and take it. It’s probably not a great idea to mess around with confusing transit systems, though. For example, it can be pretty hard to navigate buses in India and Tokyo’s trains can get pretty complicated.^{[12]
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3
Spend at least one day doing something interesting on your own. If you’re travelling with others, pick one activity or day to do something unique by yourself. Pick something only you are interested in, or simply spend a few hours walking around the city or tourist spots on your own. This will give you something memorable to hang on to and ensure that you get to do something you personally enjoy.^{[13]
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- For example, if you’re travelling with your children and partner, set aside 3-4 hours to go check out a famous tavern, or visit a site that the rest of your family won’t find interesting.
4
Socialize with locals whenever you get the opportunity. This may not be possible if you don’t speak the language, but if you can communicate with locals, chat them up whenever you can. This will really make you feel like you’re experiencing something new and they may tip you off to a site, restaurant, or activity that only the locals know about.^{[14]
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- Taxi drivers, tour guides, servers, and the folks hanging out at a café or bar are usually more than happy to share their insights or give recommendations to travelers.
EXPERT TIP

Archana Ramamoorthy, MS
Experienced Solo Traveler
Archana Ramamoorthy is the Chief Technology Officer, North America at Workday. In 2019, she went on a three-month sabbatical from her work and solo traveled throughout Southeast Asia. She is a product ninja, security advocate, and on a quest to enable more inclusion in the tech industry. Archana received her BS from SRM University and MS from Duke University and has been working in product management for over 8 years.

Archana Ramamoorthy, MS
Experienced Solo Traveler

Community Experience: When I was in Cambodia, someone told me about some islands with really great beaches. Even though I hadn't planned on going to a beach in Cambodia, I boarded a bus, then a ferry, and I went to the islands. They were the most beautiful beaches I'd ever seen and I ended up staying there for 5 or 6 days. If I'd stuck to an itinerary the whole time I was in Cambodia, I probably never would have made it to that place.
5
Live in the moment and embrace new things to have the most fun. Regardless of where you are or what you’re doing, focus on being present. Breathe in the air, enjoy looking around, and don’t worry about anything going on at home or work. Be open to trying new foods, drinks, and meeting new people. The more distracted you are, the less likely it is that you’ll remember this vacation as the best of your life.^{[15]
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- Unless you have a tour or something, don’t worry about the clock. Paying way too much attention to the time will keep your brain focused on the schedule, not the experience.
6
Deviate from your plans if something more interesting pops up. Don’t stick to the guidebooks and itinerary if you stumble on something that catches your eye. If there’s a cool restaurant, a hidden beach, or a zip-lining spot the locals keep talking about, ditch your plans. Not only will this mindset give your vacation a sense of freedom and adventure, but it’ll also give you the chance to experience something new and unexpected.^{[16]
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Keep the pressure off and allow yourself to relax or skip things. Allow yourself to change or cancel your plans if it starts to feel like you’re running all over the place. It’s much better to stay relaxed and peaceful and you aren’t going to have fond memories of the vacation if you wear yourself thin.^{[17]
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- If you finish up a tour and you’re totally wiped out, go ahead and skip the museum visit you have scheduled an hour from now. If you find yourself getting sleepy on the beach, take that nap.
8
Minimize the amount of time you spend on your computer or phone. If you brought your laptop, avoid using it for anything other than some casual web surfing every once in a while. Keep your phone in your pocket unless you’re taking a photo to avoid getting swept up in something going on at work or home. This will limit distractions and ensure that you fully experience everything your destination has to offer.^{[18]
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EXPERT TIP

Archana Ramamoorthy, MS
Experienced Solo Traveler
Archana Ramamoorthy is the Chief Technology Officer, North America at Workday. In 2019, she went on a three-month sabbatical from her work and solo traveled throughout Southeast Asia. She is a product ninja, security advocate, and on a quest to enable more inclusion in the tech industry. Archana received her BS from SRM University and MS from Duke University and has been working in product management for over 8 years.

Archana Ramamoorthy, MS
Experienced Solo Traveler

Expert Tip: Be very careful with your phone when you do take it out. Don't leave it sitting out anywhere, like a table at a restaurant, because then it's very easy for someone to just grab your phone and run away.

Method 3

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Coming Home on a High Note

1
Choose something really fun to do on the day before you leave. If you end with something really awesome, you’re going to go home feeling energized and you’re more likely to remember the vacation fondly. Save the activity you’re most looking forward to for the day before you plan on flying out or driving home.^{[19]
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- This will also give you something to look forward to while you’re enjoying the other parts of your trip.
- If you’re a huge foodie and you go to that famous restaurant on the first day of your vacation, you may spend the next 5-6 days wishing you could go back and enjoy that meal all over again.
2
Spend the 12 hours before your flight relaxing and resting. Avoid doing anything exhausting or overly-stimulating in the 12 hours leading up to your flight. Instead, take your time to pack, enjoy a meal at the hotel, or hang out on a balcony. If you end up rushing or running around before you leave, you’re going to come home stressed.^{[20]
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Tip: Give yourself plenty of time to get to the airport and go through customs. Rushing to the airport is one of the worst feelings in the world!
3
Treat the trip home like it is part of your vacation. If you’re flying, go ahead and order that extra drink, upgrade your seats if you can, and snatch that window seat if the flight isn’t full. If you’re driving, take frequent breaks, stop at a tourist spot on the way home, and treat yourself to something better than fast food when you stop for a meal.^{[21]
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- This will really make your vacation feel like it isn’t over and ensure that you come home happy and refreshed.
4
Set aside one extra day of relaxation after you land. Travelling can take a toll on you, even if you’re having fun while you’re doing it. Sleep in a little, make yourself some delicious food, and spend the next day doing something relaxing. This will give you time to recharge and get you ready to reenter the normal swing of things.^{[22]
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- Feel free to catch up on some work emails if you have hundreds of them waiting for you. Just don’t overdo it by spending more than 2-3 hours working on a day you set aside for yourself.
5
Create a photo album to remember your trip fondly. Your trip will be more memorable if you compile an actual photo album for the trip. This will give you a way to share your experience and really commit everything you did to memory.^{[23]
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- Putting a photo album together also gives you a chance to revisit everything you did. This is a phenomenal way to take a sort of mini-vacation for a few hours as you sort through all of the great photos!

Community Q&A

Question

Where's the best place to go in New Mexico for a vacation?

Community Answer

It depends, if you like skiing, go to Los Alamos, Red River, or Angel Fire. Just be sure to go at a time where there is enough snow but medium/small crowds. If you are more interested in hiking/physical activities, visit places such as White Sands National Monument, Bandelier National Monument, Carlsbad Caverns, or Brazos Cliffs. Make sure to go at a time that is not too cold, but not flaming hot. If you are more interested in history, check out the National Museum of Nuclear Science & History, Georgia O'Keeffe Museum, or Loretto Chapel (religious).
Question

How can I have the best time with my parents?

Community Answer

It depends on the things you like to do in common. Plan to start the trip with something everyone will enjoy, then have a few days where everyone does their own thing. The final portion of the vacation will then be something everyone will enjoy. This way nobody misses out on what they really like and you can enjoy quality family time.
Question

What can be done in Pennsylvania?

Community Answer

Pennsylvania provides visits to many historic sites, e.g., Liberty Hall, Gettysburg, the first White House.