How To Plan A Weekend Birthday Trip (& Enter to win a decades box from Old Time Candy, ends 4/13)

Drugstore Divas received a product from Old Time Candy for this post. All thoughts and opinions belong to Drugstore Divas.

Planning a weekend birthday trip? Get all the details and tips on how to plan one from

My father-in-law’s 70th birthday was recently, and we’re heading to Washington, DC next month to celebrate. We’re really excited. Pete and I have been planning a weekend birthday trip for his dad, and I figured our planning could really help if you’re planning any upcoming weekend birthday trips.

How To Plan A Weekend Birthday Trip

Pick a location.
First and foremost, you have to figure out where you’re going. For a weekend, you’re probably not going to fly anywhere. Instead, you probably need to head somewhere within driving distance. Look at a map and find somewhere you can get to in a handful of hours.

For us,  Pete realized DC is halfway between us and his dad.  We could both drive there in a morning and still have the afternoon and evening to hang out.

Find activities.
Once you figure out where you’re going, figure out what you want to do there. Look on Pinterest, travel sites, the city’s Visitor Bureau, etc. Write down a ton of ideas, then start to narrow them down based on where everything is located. You don’t want to overbook yourself, so be sure to choose a couple great activities for each day. But leave time in case there’s traffic, an activity is crowded, etc.

Book a hotel.
Once you’ve settled on a location and found things you can do there, book a hotel. You can ask friends for recommendations or look on discount hotel sites. In addition to prices, those often have reviews from people who have stayed there previously. Be sure to check out amenities as well. A hotel could be a great price, but if you’re paying a ton for parking, it’s not a great deal anymore.

Personally, I prefer hotels that offer a complementary breakfast. If you can have breakfast in the hotel for free, you won’t have to spend as much money outside of the hotel.

Figure out what you need for the weekend, including any dressy clothes if you’re planning on heading to a nice dinner to celebrate, plus shoes. And pajamas. I’m writing that because I have a tendency to forget to pack pajamas when we go away, and then I end  up wearing whatever Pete packed.

Bring a gift.
If it’s your birthday, you don’t have to bring yourself a gift. I mean, you could, but that would be a little ridiculous. If you’re going away for someone else’s birthday, bring a gift with you.

Planning a weekend birthday trip? Get all the details and tips on how to plan one from

I’m going to let you in on a secret, but you have to keep the secret if you know Pete’s dad. We are bringing him a decade box from Old Time Candy. Let’s chat about it for a minute. Old Time Candy is a site where you can purchase, you guessed it, candy from the past. You can pick and choose, or you can purchase by decades: 1950’s to 1990’s. (You can search candy back to pre-1920’s, but this box starts at the 1950’s). The site suggests you pick the decade when the recipient was 10, so we picked the 1950’s box.

Now, obviously, I was not around in the 1950’s, so I wasn’t sure what to expect in the box. When it arrived, some of the candy was familiar to me, like wax bottles and a candy necklace. But there were some that I had never seen before, like a licorice pipe. That one had me laughing. Could you imagine how up in arms parents of today would be if stores sold licorice pipes?

There was a great mix of full-size candies (like Raisinettes and Bonomo’s Turkish Taffy) and small, individually-wrapped candies (like Honeycombed Peanuts and Walnettos). It was so fun for me to look through everything, and it wasn’t even my nostalgia. I was just imagining how I would be with the 1990’s box, snapping back to my childhood as I picked up Warheads and Cry Baby’s. And that made me think of how Pete’s dad would be going through this box. It’s less about the candy and more about the memories.

Planning a weekend birthday trip? Get all the details and tips on how to plan one from

So of course, that made me think about how much my dad would love this. Yup, I just found his Father’s Day gift (and maybe his Christmas gift too). But back to this box for Pete’s dad. The decades box can be personalized with a “birthday with a zero” box top. Since we are going on this trip for a birthday with a zero, this was perfect.

Do you know someone this would be perfect for? You’re in luck. We are giving away one 4-pound decade box from Old Time Candy. This giveaway starts now and ends at 11:59pm EST on April 13. The winner must be a US resident who is 18 or older. The winner will be contacted via email and will have 24 hours to respond before another winner is selected.

a Rafflecopter giveaway

Drugstore Divas is not responsible for prize fulfillment.

  1. Tom Gibson

    March 30, 2017 at 1:40 pm

    I live near many beaches so my first choice would be a birthday picnic on the beach.

  2. Marty

    March 30, 2017 at 2:03 pm

    I always make the mistake of trying to pack too many activities into a weekend. My hint would be not to get over-ambitious and leave plenty of time to relax and visit.

  3. Alison

    March 30, 2017 at 3:03 pm

    I like to go online and find restaurants in the area that offer birthday specials and freebies. It’s always fun to try a new restaurant, especially when they offer a free birthday dessert!

  4. marie yoon

    March 30, 2017 at 3:40 pm

    probably stay safe and hydrated and pack a emergency kit in your car when on the road

  5. Scott

    March 30, 2017 at 4:29 pm

    I like to pack the finest box of wine money can buy. I layer that with a fine assortment of Slim Jims and Tylenol PM. Make sure the hotel has comfortable beds and a pool area to bathe in. And always pack your birthday suit.

    1. Dee

      April 13, 2017 at 10:24 pm

      I would recommend taking notes on post cards of places you visit so when u get to postibg pics for family, you have memories to share

  6. Lisa Simon

    March 30, 2017 at 5:28 pm

    I like to pick a new or unusual restaurant to try for a birthday night out that has been highly recommended by reviews on Trip Advisor or Yelp.

  7. Shannon Baas

    March 30, 2017 at 6:02 pm

    Have fun close to home.

  8. jenny stratton

    March 30, 2017 at 6:53 pm

    I don’t have beaches near me and that would be my first choice. My husband and I went to a bed and breakfast this year and that was fun.

  9. Valerie Mabrey

    March 30, 2017 at 9:07 pm

    I love to do a childhood memory lane weekend. Going and doing things that we did when were young. Like roller skating and park walking.

  10. Jenny Scheldberg

    March 30, 2017 at 9:07 pm

    Planning the perfect weekend getaway is tough. Often we hold it to high standards and are disappointed when it’s not perfect. We have to just enjoy the moment.

  11. Edye

    March 30, 2017 at 10:03 pm

    My best advice would be to take lots of pictures!

  12. Nancy Bowers

    March 30, 2017 at 10:55 pm

    Pack light and enjoy each moment as it happens.

  13. pu ye

    March 31, 2017 at 4:33 am

    like to pick a new or unusual restaurant to try for a birthday night out that has been highly recommended by reviews on Trip Advisor or Yelp.

  14. Ashley C

    March 31, 2017 at 7:26 am

    My tip is to think about what the birthday person enjoys most and try to do that activity while on your trip!

  15. vickie couturier

    March 31, 2017 at 8:20 am

    taking him to his favorite ball park or race track

  16. Darlene Owen

    March 31, 2017 at 8:24 am

    My idea for a weekend birthday trip is to have fun and enjoy.


    March 31, 2017 at 8:39 am

    My birthday weekend would be golf and more golf

  18. April

    March 31, 2017 at 8:40 am

    Taking the birthday person to their fave restaurant and fave thing to do!


    March 31, 2017 at 9:06 am

    A great birthday weekend for a kid includes a trip to the zoo and a museum.

  20. Lisa M

    March 31, 2017 at 9:16 am

    Creating a fun birthday weekend would include laughter and memories. Pictures are important. A fun ride to the zoo and some go cart action.

  21. Candice

    March 31, 2017 at 9:20 am

    I would love to go to Vegas next year and catch an NHL game.

  22. Jocelyn Brown

    March 31, 2017 at 9:42 am

    My tip is to make sure you check in with the birthday boy/girl and see what they want to do. You don’t want to spend $100 on a family boat trip, just to find out they’re afraid of boats! :)

  23. Kristyn M.

    March 31, 2017 at 9:53 am

    My biggest tip would be to make sure to take some time to relax!

  24. Vicki Wurgler

    March 31, 2017 at 11:12 am

    I prefer some location close-don’t like spending all my time in the car. I like to stay at B&Bs and you usually get a great breakfast

  25. monique s

    March 31, 2017 at 11:25 am

    I recommend going to a park and either exploring nature or playing some Frisbee, catch, or other type of game

  26. Gabrielly

    March 31, 2017 at 12:10 pm

    My best tip would be to take lots of pictures.

  27. Michele Cupp

    March 31, 2017 at 12:17 pm

    We like to go on a family hike out of town and enjoy a good meal at a new or favorite restaurant after.

  28. elizabeth miller

    March 31, 2017 at 12:38 pm

    Verify reservations needed for that special birthday dinner place and for the rest, have a list of ideas of things to do ready but leave it open to just some plain birthday relaxation and fun on the go.

  29. Samantha M.

    March 31, 2017 at 1:46 pm

    I would like a trip to The Billy Graham Training Center to have fellowship with women of like faith.

  30. Julie Bickham

    March 31, 2017 at 2:47 pm

    My tip is plan what you want to do for your birthday. It’s your day so do things that you want to do!

  31. jeremy mclaughlin

    March 31, 2017 at 3:02 pm

    Try to plan an event close to home.

  32. Julia Barnes

    March 31, 2017 at 6:38 pm

    For a weekend birthday trip, I love a mixture of relaxing and fun. Chattanooga was the best weekend trip!

  33. Stephanie

    March 31, 2017 at 7:15 pm

    i would love to go to the beach

  34. Christina T

    March 31, 2017 at 8:05 pm

    That it is someone’s birthday and whatever they want to do or choose to eat, always have an open mind to others choices.

  35. Barbara Fox

    March 31, 2017 at 8:40 pm

    My hint is to take lots of chewy candy for the car ride. You won’t feel the need to pull over and eat and can get to your destination quicker.

  36. Virginia

    March 31, 2017 at 9:32 pm

    I would not over pack. Pick a place within 2 hour drive and make a rule of no electronics for half the weekend.

  37. Christa Bengtsson

    March 31, 2017 at 9:40 pm

    I don’t have any tips as we don’t do weekend birthday trips. Maybe after the kids are grown then hubby and I can afford to do that.

  38. heather s

    March 31, 2017 at 9:48 pm

    Make it fun, bring games, snacks and just enjoy yourself. Don’t have a strict time schedule

  39. Dawn Monzu

    March 31, 2017 at 11:16 pm

    I would say keep it simple, and make sure you are organized. Then again…if you are like me, I like to be spontaneous! So if you like that kind of trip, then don’t plan every little thing!

  40. Deborah

    March 31, 2017 at 11:40 pm

    A trip to a nice cabin and celebrate its grand babies with cake popcorn and movies and lots of fun

  41. Tracy Davis

    April 1, 2017 at 3:49 am

    My tip is to take a lot of pictures.

  42. Angela Saver

    April 1, 2017 at 4:07 am

    My best tip is to take lots of pictures and make a picture book when you return home so you get to document and enjoy your memories of the trip!!

  43. Darlene Cruz

    April 2, 2017 at 1:36 am

    Pack snacks of every kind and drinks, save you money and time. Bring cameras to take pictures and electronic gadgets to watch movies for the little ones in case they get fussy.

  44. Richard Hicks

    April 2, 2017 at 2:45 am

    My tip is make sure when packing that you bring everything you need.

  45. Ellie F.

    April 2, 2017 at 5:31 am

    Stay at a hotel with a full kitchen and/or room service! Stay in and enjoy your company! Bring board games to pass the time!

  46. Julie

    April 2, 2017 at 6:50 pm

    My biggest tip is to make sure the food is good!

  47. Chrystal D

    April 2, 2017 at 7:01 pm

    Look on Groupon & see if you find any deals on there that may be appealing.

  48. Kimberly B Miller

    April 2, 2017 at 7:11 pm

    Groupon and good food.

  49. Danielle Magee

    April 2, 2017 at 8:19 pm

    We like to find deals first and go from there for Birthday fun.

  50. Michelle Levine

    April 2, 2017 at 9:36 pm

    My tip is to make the best of the weekend and make sure to take a lot of photos so that you remember it.

  51. Timmy

    April 3, 2017 at 1:32 am

    A mountain picnic.

  52. diane

    April 3, 2017 at 5:46 am

    My tip would be to have the birthday party at an amusement park, where are the kids would really enjoy themselves.

  53. Elizabeth S

    April 3, 2017 at 9:03 am

    I never go anywhere so I’m not too sure. Just take it easy and don’t sweat the small stuff, I guess.

  54. Jill Rivera

    April 3, 2017 at 9:47 am

    My tip is to choose an all inclusive trip, so you do not have to worry about blowing a budget.

  55. Jane Wright

    April 3, 2017 at 1:17 pm

    Visit with someone you haven’t seen in a long time and relive the good old days.

  56. Damien

    April 3, 2017 at 2:28 pm

    Go online and book a reservation at a restaurant.

  57. Jenn Beckett jennpup

    April 3, 2017 at 2:46 pm

    We get a hotel with an indoor swimming pool, and always pack chips, candy and drinks for the room – making it super fun for all of us!

  58. Sarah Hall

    April 3, 2017 at 3:03 pm

    My girlfriends and I like to go on weekend trips to a casino that is in a nearby state. We always have a lot of fun.

  59. Natalia Gonzalez

    April 3, 2017 at 3:53 pm

    I would grab some friends and first go to do our nails, then go to the beach and enjoy the day.

  60. Linda G.

    April 3, 2017 at 4:12 pm

    We like to go on little trips to our beach towns and walk around and eat.

  61. sarah

    April 3, 2017 at 4:24 pm

    remember to ask the birthday kid what they want to do!

  62. Kim K

    April 3, 2017 at 5:29 pm

    i would plan to go somewhere within a 3 hour drive. The closer to home the better for just a weekend get-away.

  63. beth shepherd

    April 3, 2017 at 8:15 pm

    We like to take weekend getaways with just my amazing hubby and myself. Its awesome

  64. kelly g

    April 3, 2017 at 10:01 pm

    Have a few close family and friends around and it will be perfect.

  65. Cheryl Chervitz

    April 4, 2017 at 8:21 am

    We like to go to a restaurant with family for out birthdays.

  66. Jillian Too

    April 4, 2017 at 7:23 pm

    I recommend that you bring a camera to take lots of photos.

  67. Karen Propes

    April 4, 2017 at 8:21 pm

    Pick a place your guest will want to go and explore, like if your girlfriends then somewhere you can ride a train or fast transit. Hotels are always the best bet. Easy to be with everyone and have a great relaxing time and explore the area.

  68. Jean Fischer

    April 5, 2017 at 6:18 pm

    I like to check airbnb for a cool place to stay

  69. Kevin Gildersleeve

    April 5, 2017 at 6:34 pm

    It’s pretty simple, but remember to plan things the person the weekend is for likes, not just things you like. Bonus points if its something they like that your not a big fan of.

  70. Monica Allen

    April 5, 2017 at 8:35 pm

    My tip is to turn up and have fun and don’t sleep until it is over!

  71. Rosanne

    April 5, 2017 at 8:47 pm

    We would go to one of the local parks. We have a lot of them in the city I live in. We’d have a picnic and play on the equipment and have some organized games

  72. Tracy Shafer

    April 5, 2017 at 9:23 pm

    To have all my friends, and just eat, drink and have lots of fun!


    April 5, 2017 at 10:50 pm

    Make sure you surround yourself with your love ones. It doesn’t matter where you go as long as your with people who love you.

  74. darla

    April 6, 2017 at 2:51 am

    I suggest the mountains (whichever are nearest to you). It’s sometimes nice to go in the summer because I think it’s a little less crowded as people head to the beach instead.

    Then again, the beach could be more fun as usually there’s more things to do in a beach town.

  75. Jay Jackson

    April 6, 2017 at 11:50 am

    A golf trip near the beach is great for a birthday getaway

  76. Denise Sachs

    April 6, 2017 at 1:17 pm

    I would plan lots of eating out at my favorite places and head to the mountains.

  77. Melanie Tucker

    April 6, 2017 at 4:09 pm

    I would recommend a nice hike followed by a local farm-to-table restaurant!

  78. Diane Hamel

    April 6, 2017 at 6:47 pm

    I like to pack special treats for my weekend trips to Montreal. A box of candy would fit into my lifestyle!!!

  79. Aubrey

    April 8, 2017 at 12:51 am

    My tip for a weekend birthday trip is going camping.

  80. Azeem

    April 8, 2017 at 8:52 pm

    I like to Google nice places to visit if I am going to a relative in a different state or plan activities ahead.

  81. Erica B.

    April 8, 2017 at 9:40 pm

    Have backup plans!

  82. Erin Madigan

    April 8, 2017 at 11:16 pm

    My best tip would be to pick somewhere that is all-inclusive! Relax and enjoy!

  83. Danielle Day

    April 9, 2017 at 4:21 am

    Make lots of lists

  84. Brittney House

    April 9, 2017 at 12:13 pm

    I would say to make sure you have plenty of drinks and snacks.

  85. amy rice

    April 9, 2017 at 7:58 pm

    Watermarks make for great birthday destinations in the summertime.

  86. Susan Smith

    April 9, 2017 at 8:39 pm

    My idea for a weekend birthday trip for my husband is to take him to a baseball or football game where his favorite team is playing.

  87. Jennifer Reed

    April 10, 2017 at 12:31 am

    I think for a birthday weekend trip my suggestions would be to keep it simple with a nice restaurant for celebrating and an activity that the birthday person enjoys.

  88. Heather B

    April 10, 2017 at 9:45 am

    I have never done a birthday trip so I don’t really have any tips but I have found some great ones reading these comments!

  89. susan smoaks

    April 10, 2017 at 9:50 am

    i think a birthday trip with hubby to a beach location and a nice hotel would be fun and easy to pull off. it sounds amazing.

  90. Nicole Ackerman

    April 10, 2017 at 12:07 pm

    It depends what your favorite things to do are such as a nice hike or a fancy dinner!

  91. Angela Williams

    April 10, 2017 at 2:09 pm

    The best tip would to not be on the phone but to “unplug” and to enjoy every moment. Every year we get a year older…it is such a gift in itself.

  92. Kyl Neusch

    April 10, 2017 at 3:12 pm

    My birthday weekend would be golf

  93. Renee Grosskreuz

    April 10, 2017 at 6:11 pm

    I would go on a nature hike for a birthday.

  94. Lisa V.

    April 11, 2017 at 6:29 am

    I like to find a restaurant that everyone can enjoy, especially for the birthday person.

  95. Linda Lansford

    April 11, 2017 at 11:24 am

    I would include the beach and casinos

  96. Jennifer H.

    April 11, 2017 at 3:23 pm

    I would say grab a cake on the way and don’t forget a pack of candles!

  97. John H.

    April 11, 2017 at 4:29 pm

    I would suggest getting a group of friends and go out to dinner.

  98. Samantha

    April 11, 2017 at 8:40 pm

    My tip is to leave your worries behind and just enjoy yourself!

  99. Shea Adams

    April 12, 2017 at 7:00 am

    I would make sure you take plenty of snacks and drinks and bring great friends!

  100. BusyWorkingMama

    April 12, 2017 at 8:36 am

    I love a birthday scavenger hunt! You can set one up at home and make it fun!

  101. Candra Evans

    April 12, 2017 at 9:59 am

    You should pack light, be versatile with your itinerary, and be open to try something new.

  102. Jae Park

    April 12, 2017 at 10:18 am

    The last time we did a weekend trip was to Las Vegas since it’s only 3 hours away. It was a great time for all…buffets, a little gambling and we saw a show.

  103. Dee Hadley

    April 12, 2017 at 10:34 am

    It helps to have some kind of plan but spontaneity is also a great time.

  104. jules m.

    April 12, 2017 at 12:42 pm

    plan it around what they like to do. if they like looking for seashells, go to the beach, if they are into antiques, plan the trip around some cool stores,etc

  105. Barbara Butler

    April 12, 2017 at 3:59 pm

    one day road trips love em you never know what ya find

  106. Ed

    April 12, 2017 at 8:09 pm

    A beach and a hammock are always welcome!


    April 12, 2017 at 9:31 pm

    would love to go to the beach and just relax!!

  108. BILL HOFF

    April 12, 2017 at 10:22 pm

    A quiet dinner and a good movie on Netflix is a perfect birthday for an old grouch…lol

  109. Sarah C

    April 13, 2017 at 1:45 am

    My tip for planning a birthday weekend would be to bring a camera to take lots of pictures!

  110. Kathy Pease

    April 13, 2017 at 6:39 am

    My ideal would be a birthday trip to the beach

  111. Philip Lawrence

    April 13, 2017 at 11:39 am

    My tip for a birthday weekend trip is do not do anything you will regret in the future!

  112. Brad Merrell

    April 13, 2017 at 2:10 pm

    Don’t overplan it. If you’re going to a park or a beach, just relax and enjoy it. Go with the flow,

  113. Kaycee F

    April 13, 2017 at 3:34 pm

    My Birthday plan would be to pack up a nice picnic basket, and enjoy and outdoor musical jazz event!

  114. DanV

    April 13, 2017 at 4:05 pm

    We like to have a family park day.

  115. Jennifer ODay

    April 13, 2017 at 4:52 pm

    Don’t expect perfection, expect the unexpected and embrace it!

  116. Amy Deeter

    April 13, 2017 at 5:37 pm

    Tips i have for a weekend birthday trip is a birthday dinner, cake and ice cream at home, followed by their favorite movies

  117. Tarissa

    April 13, 2017 at 8:48 pm

    I think a birthday trip to somewhere like Branson, MO, would be AMAZING.

  118. Mary

    April 13, 2017 at 9:19 pm

    First plan on something that is new and exciting. Enjoy some type of special celebration that you might not do regularly!

  119. Laura Emerson

    April 13, 2017 at 9:21 pm

    My tip for a weekend birthday trip is to try something new. It can be a new food or a place you have always wanted to go to but never have.

  120. Melissa Rodriguez

    April 13, 2017 at 9:35 pm

    I pack for all weather. Rainy, windy or sunny. I also back a first aid kit just for safety when traveling with my kids.

  121. maria s

    April 13, 2017 at 9:45 pm

    Oh wow, that’s so personal to the person whose Bday it is! No matter what they choose, they should be surrounded by friends and family! Even a simple restaurant becomes fun if you’re surrounded by the right people!

  122. Crystal Young

    April 13, 2017 at 9:49 pm

    I like to pick a new or unusual restaurant to try for a birthday night out that has been highly recommended by reviews on Trip Advisor or Yelp.

  123. Crystal Young

    April 13, 2017 at 9:49 pm

    I like to pick a new or unusual restaurant to try for a birthday night out that has been highly recommended.

  124. Trisha McKee

    April 13, 2017 at 10:15 pm

    Last weekend was MY birthday weekend! I held a dinner party- me and thirteen wonderful women from all parts of my life. We had such a wonderful time telling stories and sharing memories! It was great seeing my friends get to know each other.

  125. cindy norman

    April 13, 2017 at 10:52 pm

    Don’t forget the present. I don’t know how many times I have forgotten the present or the card

  126. Carolyn Daley

    April 13, 2017 at 11:15 pm

    Keep it inexpensive and fun. We have some amazing local and educational places like the Loggerhead Marinelife Center. It is a sea turtle rehabilitation center on the beach. We love to visit the turtle patients and recently learned that they do birthday party for kids.

  127. Jenny Q.

    April 13, 2017 at 11:38 pm

    I like hiking trips for a short weekend trip.

  128. Kim jos

    April 13, 2017 at 11:39 pm

    The tip i have is always pack mints. The pure mints are heavenly .clears the sinus and your thoughts. Bring your own favorite throw. Theres something homey about sleeping in ur own throw

  129. Jerry Marquardt

    April 13, 2017 at 11:45 pm

    I would love to take a trip down to the beach and just relax and get a nice tan for a birthday trip for-the-weekend.

  130. Kathryn C

    April 13, 2017 at 11:49 pm

    include a spa day even if it is a mini spa like just a pedicure or facial or massage

Comments are closed.