Some people like to brag about never taking a day off or going on an extended vacation. But what’s the point of working 40 hours a week for a paycheck if you aren’t able to enjoy the fruits of your labor? Still, many dedicated employees can’t help but think about all the tasks and projects they might miss out on while they’re away. So much so that they spend much of their vacation checking emails and forgetting to take a step back and actually enjoy themselves for a bit.

If your cubicle mate or manager is going on a vacation, you can send them messages to let them know you’ll miss them or remind them not to feel guilty about taking a break. In this blog post, I share more than 105 enjoy your vacation message samples you can send to colleagues at all levels.

Vacation Message Samples for Colleagues

  • You’re finally taking the vacation you deserve. Have a blast and come back refreshed and recharged.
  • I envy you! I hope you eat lots of good food, meet great people, and have the time of your life. You deserve this vacation. Enjoy and make sure to take lots of photos.
  • Please don’t check your work email more than twice per day of your vacation. You should be taking in the sites of Rome instead of looking at an inbox.
  • I hope you take this time to slow down and not think about work at all. You deserve time off because you’re the most hard-working person I know. Stay away from work and have the best time there.
  • Keep me posted on the places you’re going to! I am so jealous of your 2-week vacation but I know you’ve been planning this for ages and you haven’t taken a break in the last 5 years. Have fun and make lots of good memories with the kids.
  • I know you’ve had that destination on your travel bucket list for years and I am so happy you’re finally going. Don’t forget to take photos and send me. I want to feel like I am there with you even if I will be stuck working here.
  • Make friends, make memories and keep yourself stuffed with all the good food. Make sure you get some tan, too! I can’t wait to hear all the stories you’ll have once you’re back.
  • I will miss you! I won’t have my office best friend for 2 weeks but I am happy knowing you will be miles away from work enjoying yourself in a magical place! Don’t be shy to talk to strangers and meet new people too!
  • I can’t wait to hear all the stories you’ll bring back from your 2-week vacation. I am so jealous you’re finally going on this trip but I am also so happy and excited for you!

Make sure to send me photos for updates! I can’t wait to see what experiences you’ll have on this trip! Enjoy and don’t worry about work!

  • Finally, you’ll have a time off for yourself! You deserve this! Have fun on your vacation and don’t forget to take lots of photos!
  • You’ve earned this vacation. Take the time to look into your children’s eyes and take a deep breath. You’ve worked so hard for this.
  • It’s been years since I told you to take a time off and go on a much-needed vacation. I think I’m going to cry happy tears now that you’re finally going. Don’t you dare think about work. Enjoy yourself and see you when you get back!
  • For someone who’s a workaholic like you, it’s a miracle you’ve finally taken a week off for vacation. You deserve this. Keep your work phone off until you’re back. You deserve quiet time without stress.
  • I know you’re heading out on a staycation of sorts, but don’t forget to enjoy yourself. Hit up a happy hour. Forget about our problems if only for a little while.
  • Wishing you a great time in the Maldives! I know it is your dream vacation and I also know how long you’ve been saving for this. Have lots of fun.

Thinking about what to write to a colleague heading out on vacation?

Vacation Messages for Bosses and Managers

  • You’ve been an inspiration to everyone because of your hard work and dedication. But now it’s time that you give yourself a break and enjoy a much-needed vacation! We’ll make sure things won’t go downhill too far while you’re gone.
  • I heard that you haven’t taken a day off in the last 6 years. We appreciate your dedication to the company but we also want you to enjoy yourself and have a sweet vacation you badly needed.
  • Hi Mr. Sy, I hope you take this time to be off your phone so you can truly enjoy Europe. You’ve been putting off this vacation for years but now is the time to finally go and have the time of your life. Have fun with your family.

Carlson, I am so excited about the stories you will share with us from this vacation. You’ve been wanting to go and explore Asia for years and now you’re finally doing it. I hope you take this time to enjoy, relax, and truly have a good time.

  • Don’t worry about us back here because we will make sure everything runs smoothly even while you’re gone. Happy vacation!
  • You’ve trained us well over the past 3 years as my direct manager. We are able to continue operating this well oiled machine while you’re out. Don’t stress!
  • You’ve been working so hard for everyone and taking care of each one of us. Now, it’s time to take care of yourself and have a break from work and stress. I hope that you enjoy your vacation with your family and that you come back refreshed and energized. Enjoy!
  • You never take a day off but you allow us to leave early whenever possible. For a boss as appreciative as you, I could only wish you take care of yourself too. I hope this vacation gives you all the positivity you need in life. Have a good one!

Related Reading: 158+ Honesty & Integrity Comments for Performance Reviews 

  • I know leaving the restaurant for a week will be difficult. It feels like you live here. But I assure you the break will deliver all sorts of mental health benefits.
  • No one in this company deserves a vacation more than you. As my manager, I see you work hard every day, giving your all to every presentation and project. I really wish you would take a vacation more often because you deserve it.

A hardworking boss like you deserves the best vacation. Please take this time to enjoy yourself and take a break from office work and stress. Happy vacation!

  • A boss like you has always been very hardworking and considerate of others. With all your passion and care for the people you work with, you deserve only the best in this world, especially a 3-week vacation in Paris with your wife. Enjoy the vacation! We can’t wait for all the stories!
  • The best boss in the world deserves the best vacation in Asia! I hope you have a blast and don’t worry about a single thing back in the office. You’ve trained us well to do good even while you’re away. Enjoy and happy vacation!
  • It’s now your time to take a few weeks off work and have a blast in Europe! I really hope you take this time to relax and enjoy life! You’ve always been so hardworking and everyone knows that but you. Enjoy yourself and come back with all the stories you can share!
  • Make sure to turn off your work phone and don’t think about work for 2 weeks. You deserve this break so enjoy it!

Enjoy Your Time Off Messages

  • You’ve been working so hard and saving up for your dream vacation and now it’s finally time to go and have a break from work! Enjoy your time off. You deserve this!
  • I know how much you’ve been looking forward to this 2-week vacation and I am so excited you finally get to enjoy it! Don’t think about work! Have a blast!
  • I can’t wait to hear all your stories about Paris. Have a wonderful vacation! Enjoy and relax!
  • You are the most hardworking person I know and you, of all people, deserve this vacation. Please don’t feel guilty taking a time off. You worked hard for this.
  • You never take a time off because you always believed you should be working hard every day, and believe me, you are. But we all need a break, especially you. Have fun! Take lots of photos!
  • You are working every single day of the past year, making sure you’re saving enough money for your dream destination. With the bonus you got last Christmas, I know you have more than enough for your vacation. Enjoy it because you deserve it!
  • Have fun on your 2-week vacation! You deserve this time off. Please don’t ever check your work emails!
  • You are my best friend and I only want the best for you right now, I know that you need this vacation so please go and enjoy!! Can’t wait to hear all the stories.
  • You are the most workaholic person I know. You don’t take time off’s and you always work overtime. Please take this break and have a great vacation!
  • You’ve been waiting for this day and now it has finally come! Take a breather, enjoy, have fun and relax! You deserve this time off. Call me when you get there!
  • You don’t usually believe in taking a vacation but deep inside I know you want to take a break too. Don’t feel guilty because you deserve this time off! Enjoy and have fun!
  • To the most hardworking person I know, please enjoy Italy. This is your dream destination and I know how long you’ve been saving up for this. Have fun!
  • You deserve time off and you know that! Stop working too much. Love yourself too.

Maybe write an email instead of a note?

Enjoy Your Leave Messages

  • I’m so happy you’re finally on leave. Since you joined the company 5 years ago, you’ve been working so hard and not taking your leaves. Don’t do that again! Enjoy your leave!
  • You don’t always have to drown yourself in work, remember that. Happy day off! Enjoy and have fun!
  • I’m hoping you’ll be spending your leave with your family and enjoying the great outdoors!
  • I can’t wait to hear stories about how you spent your leave with your brothers and sisters. Have fun!!
  • Vacation leaves are meant to be taken. Remember that! Don’t ever feel guilty for taking a leave.
  • When you’re on leave, don’t ever check your work email if you don’t want your day ruined. Have a blast!
  • I will miss you at work this week but I’m glad you’re taking the time off to take care of yourself. See you when you’re back!
  • I can’t believe you’re finally taking your vacation leaves! I’m so proud of you!! Enjoy! Don’t miss me too much.
  • I’m surprised to see my seatmate, not in the office but I am happy you’re taking your leave! Can’t wait for your stories on how you spent your 5-day leave!
  • You won’t believe how happy I am that you’re not going to work this week. You deserve that break! Don’t feel guilty. Have fun and can’t wait for your stories!
  • I thought I heard wrong when they told me you’re taking the week off. But I am so proud of you! Finally! Have fun!
  • Hey, pretty mama! I heard you’re taking the week off! Where are you planning to go? Well, wherever that is, please enjoy yourself! Can’t wait to see the photos!
  • What a surprise not having you here beside me this morning at the office! But I am so happy you’re finally taking a day off work and relaxing! Please do that more often. Take care and enjoy!

Enjoy Your Trip Messages

  • I am so envious of your Euro trip! Take lots of pictures! And please buy me anything you think will suit me. Have fun!!!
  • I know you’ve been planning this trip for months! I am so excited for you! Don’t be afraid to meet people and enjoy yourself.
  • This trip is one on your bucket list and I know how long you’ve been wanting to push through with this. Now it is finally happening! Enjoy but always remember to take care okay? Call me when you get there!

It’s not every day that you go to Australia for your birthday so I am so excited for you!!! Have a blast! I know you’ll have the best time of your life.

  • The Caribbean has been your dream destination for years and I am so glad you’re finally going on this trip! Don’t forget to take photos you can print later! And don’t be scared to talk to strangers. Be safe and enjoy!
  • This is the highlight of your year and I know it! Have fun with your parents! I hope you all enjoy this holiday vacation outside the country!
  • You’ve been talking non-stop about this vacation and it’s finally coming true! Don’t worry about work and just focus on enjoying yourself. Can’t wait to hear your stories. Send me photos if you can!
  • This is the trip you’ve been waiting for for months! I am so glad you are finally going! I am so envious!! But have fun and enjoy!
  • You’re so lucky you’re going to Greece! I’ve also been wanting to go for months but can’t afford it yet. Have the best time there!
  • This birthday trip is going to be the highlight of your year! I can’t wait to see the photos! Keep safe but enjoy as well!
  • When you get there, promise me you won’t be checking your work email. This is your time to relax. Have fun!
  • You owe yourself this time off. Enjoy and make sure to keep yourself safe! Don’t hesitate to call me if you need anything.
  • I will miss you while you’re on vacation but I’m so happy you’re finally taking a week off work. Have a blast in Paris!

Enjoy some warm weather and Vitamin D for a change.

Enjoy Your Vacation Quotes

  • “After a while, just staying alive becomes a full-time job. No wonder we need a vacation.” – Michael Zadoorian
  • “I hope your vacation gives you the pleasure you need so that you don’t have to think of any problems back at home. Enjoy your vacation.” – Anonymous
  • “It’s a period of travel and relaxation. A time to spend and treat yourself. I hope you have the best vacation ever.” – Anonymous

“When people went on vacation, they shed their home skins, thought they could be a new person.” – Anonymous

  • “Vacations mean a change of pace, a gentleness with ourselves, a time of rest and renewal, a time to stretch ourselves and encounter new people, new lands, new ways, and new options.” – Anne Wilson Schaef

Related Reading: 105+ Employee Review Phrases on Accountability / Ownership 

  • “In the end, we only regret the vacation we did not take.” – Anonymous
  • “A vacation is having nothing to do and all day to do it in.” – Anonymous
  • “A vacation is what you take when you can no longer take what you’ve been taking.” – Earl Wilson
  • “Wishing you a ton of joy, fun, and happiness for your vacation.” – Anonymous

“A vacation should be just long enough for the boss to miss you, and not long enough for him to discover how well he can get along without you.” – Jacob Morton Braude

  • “Neglecting vacation is neglecting success because every success needs an accumulated positive energy.” – Mehmet Murat Ildan
  • “Each person deserves a day away in which no problems are confronted, no solutions searched for. Each of us needs to withdraw from cares which will not withdraw from us.” – Maya Angelou
  • “Read a lot when you’re on vacation but nothing that has to do with your business.” – H. Jackson Brown Jr.

Everything you need for an office escape.

Annual Leave Messages Samples

  • Before you go on your vacation, please know that you don’t need to worry about work at all. We can handle this!
  • Have a blast and don’t check your work email. I promise we can survive without you. Enjoy and have fun!
  • It’s been years since you used your annual leaves so I’m happy that you’re finally taking a break! Don’t think about work because work will still be here when you get back.
  • Promise us you won’t be working when you get there. Don’t ruin your vacation! Take a break because you deserve this you hardworking woman!
  • Don’t ever feel guilty about taking the week off. I promise you, work will be the same when you get back.
  • I can’t wait to hear your stories about your grand vacation. You should do this more often! Enjoy and have a good time!

Wow, I can’t believe you’re finally taking your leave! You haven’t done that since I joined the company 3 years ago so I’m happy you’re doing this for yourself now. Have fun!

  • You should stop checking your work email when you get there, please. Take this time to focus on yourself and your beautiful surroundings. Have a blast!
  • There’s nothing that I like more than knowing you’re taking a break from work because one, you’re a person, and two, you deserve it. Enjoy!
  • I love that you’re finally doing this! I’ve been telling you to take your leaves because you need to and that there’s nothing wrong with taking a break!

Related Reading: 105+ Performance Review Examples for Customer Focus (Good + Bad)

  • Don’t let work stop you from enjoying your vacation. You have an excuse not to think about us for a week. Have a blast!
  • I am so envious you’re going on a cruise! But please make sure you don’t think about work or else you will ruin everything.
  • Promise me you’re going to start using your leave more often now. You deserve it, darling! Taking a break from work doesn’t make you an irresponsible human being.
  • Wow, I am so glad you’re finally taking a leave from work! I’ve been looking forward to this day! I hope you have the best time of your life! Don’t dare think about work while you’re on vacation!
  • Hey! I heard you’re on leave for the whole week next week. I’m so envious but so happy for you! You haven’t taken a day off since you started working here. Now is a perfect time! Have fun!

Eat all the good food, don’t feel guilty for having fun, and never check your work email while you’re there. Promise me!

  • You should take your annual leave often, you know! So happy you’re doing this! Send me photos and make sure you eat all the good food!
  • So you’re finally taking your annual leave! Good for you! I’ve been telling you to do that since your first work anniversary. Can’t wait to hear your stories! Send me photos if you can!
  • I thought I heard it wrong when they told me you won’t be here next week! I’m so happy for you! London has been my dream destination for years but I am happy my favorite colleague is going there!
  • Tell me all the good things about your trip so I know what to do the next time I’m going! Have fun!
  • I can’t believe you’re finally taking your annual leave! After 4 years of being the company, you’re only doing this now, wow! But please have fun and stop thinking about work.
  • The number one rule of taking annual leave is not feeling guilty about it. So please, don’t feel guilty. Take more annual leave in the next couple of months!
  • It’s about time you take a leave of work! I am proud of you for taking this step! While you’re away, don’t worry about work, okay? Do your best to enjoy yourself and not feel guilty!
  • It’s our right as human beings to be able to take a day, a week, or a month off work. So don’t let anyone let you feel guilty about it! Have fun!!!

Tips for Sending a Professional Vacation Message at Work

No matter how close you are with a coworker remember to keep things professional since you are in a work environment. Here are few tips to remember when drafting these sorts of well wishes:

Keep it short – Whether it’s for your boss or a manager, a short, straight to the point kind of message is enough when sending a vacation message at work.

Be respectful – Even if you are sending it your work bestie or your office crush, always make sure to be respectful especially when you’re sending your message through your work email.

Know your boundaries – It is nice to send a vacation message to your colleague but if you’re not exactly the best of friends, you shouldn’t just say anything you want to say. Know your boundaries and just send out a simple message.

Last but not least, don’t forget to use every one of those vacation days you’ve earned. According to reports, 768 million vacation days go to waste every single year. Just imagine all the things people could have been doing instead.

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