Milestone Birthdays and Anniversaries – How to Plan a Trip to Remember

Growing up I remember reading “The Face on the Milk Carton” by Caroline B. Cooney, one of my favorite books for a time.  In the book, there is a fleeting line about Christmas being about presents, but birthdays was about trips.   As I grew older and in charge of my own birthday and budget I took that to heart.  It started with my 30th, a combined babymoon / birthday trip.  Then it was my husband’s 40th, my friends group trip for his 40th, and so on. 

When my son was around 8 years old, we made the decision that when he turned 10, we would start a tradition.  For our children’s 10th birthday they could pick where they wanted to go to celebrate.  They could choose, anywhere in the world.  My son went through a slew of choices (Philippines!  Paris!  Disney World!) until he landed on his final choice, Hawaii.  My daughter, who turned 8 this year, is already planning for her 10th birthday.  Right now she is oscillating between Oregon and Puerto Rico.  I’m hoping she lands on the later. 

What goes into planning a good milestone birthday trip?  And how do you make sure it fits all your needs?  Here are some tips I’ve learned along the way on how to make the milestone celebration trip that fits your needs. 

Who do you want with you?

Part of a trip that makes it memorable is who is on the trip with you.  Who do you envision besides you?  Just the nuclear family?  Multi-generational trip?  Best Girlfriends? Solo?  My advice on this is to go with your heart.  This is about you; it’s ok to be selfish.  Pick who you want to be on this trip, who will make you happy and celebrate with you.  Determining your trip posse will help drive other decisions. 

Who will join you on the trip?

What is your budget and who will pay?

Whenever you are planning for a big trip, budget is an important consideration.  You may want to go Monte Carlo but have the budget for Minnesota.  Understand how much you are personally able to spend on this trip to help set realistic expectations. A few things to consider:

  • When inviting others, how much are you expecting them to contribute? 
  • How will you split the costs of accommodations?  Transportation?  Meals?

You will need to have an honest conversation with your friends about expected costs and where people will contribute so there are clear guidelines.  Discuss and come to agreements on where you guys want to splurge, and where you want to save.  Make sure you and your travel companions are in alignment so there are no hard feelings.

You may be in a position to cover most of the costs, and if so, that’s great!  It’s still important to talk with your companions on what you are planning to cover, so they understand that if there are any extras they want to cover, how to budget their own money. 

Will it be luxury hotels and fancy meals? Or cooking in an apartment and eating on the side of the road?

Where do you want to go?

Now that you know who’s going and how much you are planning to spend, it’s time to get to the fun stuff, picking a place!  Remember, this is an important celebration, so you want to pick a location that fits your needs.  What do you want to be doing to celebrate your birthday or anniversary?  For my 40th birthday I told my husband I wanted to be on a beach, with a drink in my hand, in a country I have never been in before.  Using that criteria, we planed a trip around Bali.  My best friends, who’s a December baby, wanted to be in Europe with her best girl friends, where it wasn’t too cold.  Looked for the cheapest flights and landed on Malta.  Figure out what is important for you to feel like this is the ideal celebration.  And then you will be able to help land on a location. 

There are so many places in the world to explore

What type of trip do you want?

Is this a vacation where you sit and relax the whole trip?  Or do you want every day jam packed with activities?  Are you planting in one location or going from place to place?  My 40th birthday was during a time when I was also caring for my sick father.  I wanted a combination of relaxing and exploring.  A travel agent helped up plan the perfect itinerary and took care of all the transportation so we didn’t have to.  My 30th I was pregnant and wanted to do nothing but sit at the beach. We booked a hotel with chairs by the water so I could “beach” myself there every day.    Make sure you and your travel companions are on the same page, or you set aside some time for people to do their own activities.

On the go exploring or planting and enjoying?

What special activity / meal will mark the occasion? 

This is a vacation to celebrate you and reaching this milestone!  Make sure to pick one special activity or meal to make the trip memorable.  It could be as dramatic as skydiving for the first time or as mild as a a meal at a special restaurant.  For my 30th I went on a snorkeling trip.  For a friends 40th, he brought in a private chef so we could have a house party in the place we were staying.  But make sure to pick one really special activity to prioritize as the celebration of your birthday. 

Make sure there is something truly special that makes it a celebration

What to plan

You’ve got your location, you got your crew, you know what type of trip you want, and you have your one special activity.  Now you just need to work out the logistics.  A few things you need to remember to plan:

  • Flights – Especially if people are coming from different locations, make sure to coordinate when everyone gets in, and plan transportation to and from your accommodations.
  • Transportation – Rental car, airport transfers, public transit, etc.  Make sure you know how you are getting to and from all the activities you planned.
  • Accommodations – Plan where you plan to stay.  Think about your group.  Depending on the type of trip you want and the budget you have.  For our girls trip to Malta, we stayed in a big apartment so we could cook some meals at home (and drink a lot of wine and fall in bed).  For Bali, we stayed in 3 star hotels with pools so we could relax and entertain the kids. 
  • Activities – You don’t need to schedule every day, but you need to make sure to book the must dos before you leave.  You don’t want to get to Paris and discover that the Eiffel tower timed entries are sold out for every day you are in the city. 

Remember, while nice, a milestone celebration trip doesn’t need to have a passport stamp or be weeks long.  One of the best milestone birthday trips I went on was a friend’s 40th.  We went to Bodega Bay, 45 minutes away from home, with a big group, rented a big house, and hiked, drank, and had meals together for two days. Especially with the current pandemic, this is just as valid and just as fun. It was low key and intimate, and exactly how the birthday boy wanted to celebrate his day.  The trip is for you to remember and celebrate your years and wisdom that has come with it.  Maybe it’s your 20th and you are just entering the world of adulthood, maybe it’s your 80th and you are celebrating a long life with all your family around you.  Regardless of what it is, you deserve this and should enjoy every minute.

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