150+ Happy Vacation Wishes for Bosses and Colleagues (Huge List)

Gone are the days when all work and no play are what keep people going. Overwork only leads to lost relationships and longterm health problems. According to a study in the UK, taking regular breaks can boost your performance. This is why more employers are encouraging their people not just to take their lunch breaks on time, but also to take their vacation.

Is your favorite coworker or boss scheduled for a short vacation anytime soon? Send them off with happy vacation wishes for an unforgettable vacation ahead. Here’s a list of 150+ vacation wishes that bosses and colleagues will appreciate.

Happy Vacation Wishes for Bosses

• To our dear Boss, we wish that you would have a great vacation with your family. Make the most of that precious time with them.
• Don’t stress boss. We’ve got things covered while you’re out.
• Boss, don’t worry about work. Take the time off and enjoy each minute of your vacation.
• Dear Boss, you have been so busy and hardworking these past months so we believe that you are worthy to have a peaceful vacation. Enjoy!
• Boss: The last time you took vacation time, I was probably still in college. You need a break.
• Our bodies need time to relax. Maximize your vacation, Boss, and have a great time!
• Enjoy your vacation to the fullest, Boss.
• You’ve been sacrificing your happiness for years. Forget about work first and make the most of this vacation.
• Be happy with your family in your upcoming vacation, Boss.
• We sincerely hope that you will make wonderful memories on your vacation, our dear Boss!

Boss, we hope and pray that you will reach your destination safely and have a great time there with your wife.

• Dear Boss, we need you but your kids need you more. Enjoy every minute with them on your overseas vacation.
• Thank you for being such a good adviser, Boss. Maximize your vacation since we know that you need that much-needed rest (from work).
• Have a safe & happy vacation with your close friends, Boss.
• Happy trip, Boss, and make many happy memories!
• Climb the highest mountain, Boss, and swim the deepest ocean. Enjoy!
• Have a fun-filled trip to the mountains, Boss! Don’t forget your jacket!
• This is your much-awaited break! Don’t waste any minute of it, Boss! Have fun and be happy!
• Boss, we know that you will be so pretty in your swimwear! Lie on the beach. Catch the waves! Watch the sunset! Enjoy peace and tranquility in Boracay!
• Our dearest Boss, leave your worries behind and make the most of this vacation.
• Sending you off, Boss, have a safe trip. God bless! 

Leave happy vacation wishes for your colleagues.

Happy Vacation Messages to Colleagues

• How I wish I could be with you on this Japan trip. Enjoy the beautiful autumn scenery in Kyoto!
• Have a nice tan and come back with the glow of contentment!
• Enjoy spring in Korea. Go pick Tangerines & enjoy eating them in Jeju. Be happy!
• We will surely miss your witty remarks for two months but we are here to wish you a safe and happy vacation with your family.
• You know that we will be lonely while you’re gone but don’t worry, we will do our best to stay happy. Enjoy your vacation!
• Make the most of the cold weather in Hongkong! Visit all tourist spots. Make great memories!
• Meaningful moments are those spent with the ones you treasure the most. I’m sure that you will have so many good memories of this trip.
• Have a feast with your family in the USA. Stay safe, though!
• Wishing you all the best in your upcoming vacation.
• Have a safe trip abroad. Don’t worry about us!
• Make the most of your road trip with your furbaby. Have good pictures and videos to upload to social media.
• At last, you will see your son who has been studying in the USA. Have an enjoyable stay there.
• Wishing that you would be able to maximize your vacation with your parents.
• The trip of your dreams is about to happen! Make the most of it!
• From the start of this vacation, relax and enjoy every second.
• You will at last have your long-delayed honeymoon. Be extremely happy with your hubby!
• The summer capital of the Philippines is waiting for you with open arms. Have a nice and relaxing vacation in Baguio.
• May you have a fabulous vacation in Europe! Don’t forget to shop at the night markets!
• We’ll miss you dearly this Christmas season but we pray that you find happiness and find yourself in your trip to Bali.

Happy Vacation Messages for Her

• So envious of you, going to Switzerland, my dream vacation destination! So long, farewell, and happy trip!
• I may not be with you in each moment of this vacation but bear in mind that in spirit, I am present! Enjoy!
• Make the most of the silence. Listen to the winds and the waves. Enjoy life without the kids.
• When in the Netherlands, when you see tulips, think of me.
• Your passion for traveling is so remarkable. May you enjoy every minute of this trip even if I’m not with you.
• Have a safe trip and one with good memories. Be conscious of your surroundings.
• Stay healthy as you travel from state to state in the US.
• Shop till you drop! I will pay for all of your shopping expenses up to $300.

Related Reading: 450+ Positive Monday Captions and Quotes to Boost Your Mood 

• Every night, please call me up before you fall asleep so I would know that you’re safe.
• Soothe your mind on the beach. Leave your sore muscles behind.
• Go to all the fabulous places listed on the Thailand website. Explore and enjoy!
• Life will not be the same without you but I am sure that you will have an enjoyable vacation. Go ahead and fulfill your dream to travel to Europe.
• Visit all the churches in Spain. Pray for your safety and for us here. Have a fabulous trip.
• The beaches in Cebu are all waiting for you. Go gather memories and enjoy the sun!
• Happy holidays! Enjoy being yourself. Be carefree and happy!
• Enjoy your holiday in Paris! Eat at those glorious cafes. Soak in the beauty of the city. 

Happy Vacation Messages for Him

• Gain new experiences! Learn to surf! Drink till you drop!
• Make the most of this trip that you have been planning for a long time.
• Have a wonderful and memorable vacation even if you’re alone. Hike up to the highest peak!
• May you have the strength to fulfill all your dreams in this vacation you will have. Don’t worry about us. Just enjoy!
• As they say, everything is big in Texas, so you are just fit to spend your glorious vacation there! Enjoy it big time! Have big meals!
• Have unforgettable backpacking, sandboarding, and hiking trip with your friends!
• May the best person I know have the best vacation ever!
• After seeing all the wonderful sights in New Zealand, soak in the country’s natural resources. But find time to message me, please, despite your enjoyment!
• Immerse yourself in the culture of the Vietnamese. Your one-month stay there might turn you into a Vietcong! So lucky to win that free vacation!
• At last, you’re about to learn how to surf! Make the most of this Siargao trip! Be a professional surfer when you return home.
• Praying for your safety as you travel to Africa! Don’t let the lions feast on you!
• Have a meaningful retreat in the hills of Tuscany! Come back recharged and blessed!
• May your upcoming Egyptian pilgrimage change you for the better!
• Enjoy every second of the cultural expedition you have joined! Be renewed and come back with the new you!
• May you experience all those exciting adventure activities in India! If I could have the chance to follow you, I will!

Email your boss and wish him an enjoyable time off. Everything will be fine.

Funny Happy Vacation Messages

• To our dearest Boss, please be happy in your month-long vacation so that when you come back to work, you will be in the mood to give all of us a raise!
• Friend, trek the highest mountain but be sure that you’ll not lose your way down! Enjoy each step of your hike!
• My best friend, how can you leave me here for two weeks? I can’t concentrate on my work without you! Seriously speaking, please have a great time abroad but don’t forget to be back before the month ends (before month-end reports are needed).
• Boss, do you know how much we envy you? You’ll be gone for two long months while you scarcely approve our 2-day vacations! Anyway, enjoy!

Related Reading: 200+ Employee Appreciation Quotes for Dynamic Teams of All Sizes 

• Best friend, don’t think of coming back after your vacation if you will not buy those tasty treats I have listed.
• My friend, I am sure that you will have an enjoyable vacation. But please let me be a part of that enjoyment by buying those cute souvenirs before you board your plane in Hawaii!
• To my seatmate who will be leaving me for a month-long vacation in Dubai, I envy you! Be happy & enjoy every minute of your trip!
• Make lasting memories there! Bring home a cute guy!
• Enjoy your mountain hikes but don’t fall on a cliff, please!
• Boss, we know that you’ll be very happy on this vacation you’ll have with your family. Would that mean that you would approve all of our vacation leaves upon your return?
• Take me with you! I don’t want to do your work while you’re gone! Kidding aside, have a satisfying vacation, friend!
• Friend, make the most of this vacation but don’t forget your things in the hotel room or in the plane!
• Since this is your first time abroad, don’t waste any minute of your trip. Go to all tourist spots until you are dead tired! Kidding aside, enjoy your vacation!
• Can you bring me home a suitcase full of those souvenirs? No, just be back safe and sound!
• Enjoy every minute of your trip abroad but don’t forget to keep safe to come home alive & whole.

Enjoy Your Vacation Wishes

• Let this trip bring back the glow in your lovely face. Don’t ever think of anything negative. Just enjoy every moment of your much-needed vacation.
• Seeing you so excited while packing makes me want to join you on your vacation in the Swizz Alps! How I wish I could enjoy the sights there with you!

They say that water is more expensive than wine in Germany so drink a bottle of wine each night! Make the most of every sip!

• I have only one wish and this is for you to have a very good, a very safe, and very memorable vacation in Europe!
• Three months is a long time for us to be apart but all I want is for you to have the most enjoyable vacation of your life in Amsterdam!
• Have a relaxing café-hunting experience in Korea!
• Wishing that you’ll have a spiritual vacation in Rome.
• You can now tick off Barcelona from your bucket list. Make the most of your agile photography skills. Have a fun-filled Barcelona picture-snapping trip!
• Enjoy skiing on your Glacier National Park trip. Just send me photos of those snow-capped mountains and a video of you snowshoeing!
• Relax & rejuvenate in your South Island tour. Be continuously amazed by its majestic mountains and fjords!
• Go & feel the sights, smells, sounds, and tastes of Tokyo! Have a happy trip!
• Take this vacation as a sign that you must love yourself first before anything else! Enjoy every minute of this trip.
• This is the only time you’ll be able to spend with your family. Make good memories with them!

Enjoy Your Time Off Email Examples

• All of us had a very stressful year so I’m very glad that you are going on a 7-day trip to the Maldives! Relax and enjoy your vacation.
• Enjoy your vacation and avoid converting every dollar to peso! Just spend happily!
• Your long-awaited vacation is finally just a few days more! Don’t let work hinder you to enjoy yourself! Forget us, forget work and be happy!
• Make wonderful memories during your vacation in the snow-capped mountains of Switzerland! We all wish you happiness because you truly deserve it!
• Enjoy the Christmas holidays in Berlin while going sightseeing and filling your tummy with their sumptuous food!
• Put aside work from your mind from the time you arrive at the airport and depart for Spain. Have a relaxing and fun-filled holiday!

I am happily accepting responsibility for all of the work you’re handling so that you can make yourself rejuvenated on your USA trip!

• I’m so glad that you’re about to enjoy the most beautiful season of all, autumn, in Korea! Please bring home some maple leaves, if you can!
• Finally, your much-awaited vacation is just around the corner! Don’t worry about work. Just be happy and spend all of your savings in Japan!
• I’m very happy that your vacation leave was approved in just one day. Start packing for that hiking trip and I hope that you will truly enjoy each step you’ll make!
• Make the most of your time off from this stressful work. Take beautiful photographs of all the beautiful places you will go to in Copenhagen.
• While you’re on your vacation in Korea, look for your K-Pop idols! Buy those interesting K-Pop merchandise so you’ll have great souvenirs of your Korean trip.
• Ticking off Amanpulo from your bucket list is the most satisfying action you have done! Enjoy the sand and the sun and the waves!
• Find peace while fishing in the waters of the Bahamas!

Sometimes a handwritten note is appropriate.

Annual Leave Messages

• At last, you can have time with your family. Have quality time with them, please, in your upcoming vacation.
• Our Boss, we will just imagine that we are on that island with you! Enjoy the beach. Gather shells and have a fun-filled rest!
• I can already imagine you in your spring outfit walking in a Cherry Blossom-filled Lane. Wow! Maximize this annual leave and have fun!
• Dear Boss, go sunbathing with your family each day you’re in El Nido. Watch each sunrise and breath fresh air!
• We all had a very problematic and stressful year so make the most of this annual leave! Make unforgettable memories!
• Have a blessed vacation while you’re at Napa Valley! It’s only once a year that we are allowed to have a 2-week long vacation.
• Forget your diet while enjoying your annual leave in Singapore! Make a blast with those spicy Singaporean crabs! Try every sumptuous meal and just go on diet again when you’re back home.
• Wish that you’d find that while lady in the haunted house in Baguio! Happy ghost hunting while you’re enjoying your annual leave!
• Hoping that every minute you’d spend with your family during your annual vacation will be the best so far.
• Dubai will welcome you with open arms. Happy holidays! Make the most of your annual leave.
• Have a blessed journey in the Holy Land. This is the best choice for your annual leave.
• I’m so proud of you since you can travel alone! Enjoy life while you’re young!
• May God shower you with His blessings on your Jerusalem trip.
• Annual leaves are what we look forward to. Have the grandest vacation in Australia!
• I’m so jealous that you will be spending your annual leave with your family. Praying that you will enjoy every minute with them. Make them feel loved!
• So happy that your precious annual leave will be with the love of your life. Let this be your second honeymoon! Enjoy Thailand!

Summer Holiday Wishes

• Relax and enjoy the waves in the Philippines.
• Praying that you and your family will have a fun-filled trip to Hawaii. Make the most of summer there in your strappy sandals and loose summer clothes.
• We always look forward to our summer vacation & here it is now. I want to see you all sunburned when you come back!
• Enjoy the lush coastline of Maui when you travel there next week. Fill up your tummy with all the delicious Hawaiian delicacies.
• Go sunbathing on the beaches of the Philippines. Make yourself feel the Filipino vibe by tasting their street foods and visiting the old churches in the area.
• Enjoy the longer days of summer in Greenland when you can enjoy more in daylight! Ride that perfect boat trip where you will see different sea creatures but don’t forget your thermals!
• Have an exciting summer vacation in Turkey! Hope you’ll enjoy watching those hot air balloons. Have fun visiting their caves, too!
• Summer is best if spent with the entire family. Hope you will all have a good time!
• I know you made the right choice of spending the summer in London with all those pubs you can visit! Happy drinking!

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• Hope that you’ll come back refreshed after your Bali trip.
• Summer at Siem Reap is the best! Enjoy the city by riding a bike or wandering through those narrow alleys! Go shopping endlessly!
• In a budget? They say that prices in Cape Town are low. This means that you can really enjoy your vacation. Have a happy and safe trip!
• I know that you will have a great time in New Zealand this summer since you are a nature lover! Enjoy the scenery and the people!
• Enjoy your summer vacation without me!
• While on your vacation, don’t forget to buy souvenirs for me since I will be doing the work you left.
• Vacations are for the body and mind to rest. Have a restful one!
• Swim and surf in the oceans of Bali! Have fun like there’s no tomorrow!
• Wishing that you’ll find happiness in every corner of Vietnam. Happy shopping, too! Send all that you have shopped in a container van.
• Did you pack your swimwear already? Happy swimming with the dolphins in Orlando!

Annual leave is a time for reflection and rest.

Happy Winter Vacation Wishes

• I really felt so jealous when I knew that you would be spending winter in Japan! Go to the picturesque snow-covered village of Shirakawa located in Gifu Prefecture to have a different taste of winter!
• Winter in Korea is unforgettable! It’s good that you will be experiencing it but don’t forget your thermals, your gloves, and a fleece hoodie! Happy freezing!
• Wishing you a happy winter vacation in the USA. Try to learn how to snowboard or ski. But please take good care of yourself.
• Have you packed your warmest coats and winter boots? Make the most of the snow and enjoy being a kid again!
• Winter vacations are the best for people like us who live near the equator. May you enjoy your trek to the North Pole!
• You might miss our warm climate when you start freezing in Korea! Just be bundled up from head to toe so you can enjoy the cold winter.
• Praying that you’ll enjoy the snowflakes and the foot-deep snow-covered sidewalks.
• Have a happy onsen bath! Eat boiling ramen afterward!
• This is to wish that you would have a safe ski-resort vacation. Please come home with no broken bones!
• Have a romantic winter holiday in Otaru with the Otary Snow Light Path. Make this vacation a memorable one for you and your wife.
• Hoping that you will find the best ski resort and you will be able to learn how to ski!
• Love winters the way you love our summers.
• Have cozy nights bundled up in the warm cottages in your chosen vacation destination.
• Wishing that you would have a budget-friendly winter vacation. Just keep on having hot soup, hot coffee, or hot tea!
• May you experience the best winter ever. A winter that will make you thank God for his creations! 

Vacation Quotes

• “Not all those who wander are lost.” – J. R. R. Tolkien
• “We travel not to escape life, but for life not to escape us.” – Unknown
• “It’s better to see something once than to hear about it a thousand times.” – Unknown
• “I love places that make you realize how tiny you and your problems are.” – Unknown
• “Travel makes one modest. You see what a tiny place you occupy in the world.” – Gustave Flaubert
• “I haven’t been everywhere, but it’s on my list.” – Susan Sontag
• “If not now, then when?” – Unknown
• “Travel is the only thing you but that makes you richer.” – Unknown
• “A vacation is a sunburn at premium prices.” – Unknown
• “A vacation is having nothing to do and all day to do it in.” – Robert Orben
• “The world is a book and those who do not travel read only one page.” – Saint Augustine
• “Traveling – it leaves you speechless, then turns you into a storyteller.” – Unknown
• “A journey of a thousand miles must begin with a single step.” – Lao Tzu
• “A mind stretched by a new experience can never go back to its old dimensions.” – Oliver Wendell Holmes
• “Travel: it gives you a home in a thousand strange places, then leaves you a stranger in your own land.” – Ibn Battuta
• “Man cannot discover new oceans unless he has the courage to lose sight of the shore.” – Aristophanes
• “A ship in harbor is safe, but that’s not what ships are for.” – William Shedd

We all deserve a little break after long months of working on a project, staying late at the office, and getting barely any vacation. So if you have the chance to take a couple of days or weeks off, go for it!