My husband and I always liked to celebrate milestone birthdays with trips. When my oldest was little, we decided that for their 10th birthday we would do a trip instead of a party. They would get to pick where they wanted to go, anywhere in the world. They chose Hawaii, and so started a fantastic tradition of celebrating the milestone birthdays with amazing adventures around the world. From Argentina to Bali, Hawaii to Paris, we have managed to make amazing trips. But how do we do this? Deciding who is coming, setting a budget, and putting some parameters in place has helped make this process work for my family. In this article, I’ll break down how we pick a destination and make sure that this trip is all about having fun and making the birthday person feel celebrated throughout.
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Step 1: Put the Guest of Honor First (With a Reality Check)
For us, the birthday person gets to decide the trip. We start with their vision. When we start planning we start by asking a few key questions:
- What kind of trip do you want: Relaxing? Adventurous? Sightseeing? Art? History? Let them define what they want out of this trip.
- Where might you want to go: Beach? Mountains? City? That lets the person help narrow down the location.
- Who do you want to join us: Is this just for the immediate family? Are you inviting grandparents? Will you allow them to invite a friend? This helps set the budget.
The trip should be focused on the one celebrating their birthday. They should choose the vibe, theme, and/or location. However, make sure to set some expectations if there are constraints that they have to factor in. For example, my daughter wants to bring her best friend on her “Quince” trip. I agreed if she agreed to do a smaller trip that fit within the budget. It makes it a win/win for everyone.
Step 2: Establish the Travel “Footprint” Early
Once the birthday person has put in their input, it’s time to figure out the important logistics of the actual trip. It’s important to understand these things:
- Who is going? – A small family of 3 has different needs than a big multi-generational trip where grandparents, cousins, and maybe even others are going.
- How long? – Is this a weekend getaway or a 10-day trip through 3 different cities? Those have very different budgets and planning needs.
- How are you getting there? – Driving (road trip) or flying? If you are flying internationally, does everyone have their passports up to date?
Having all these details down early will help you with understanding what needs to be planned and how to set the budget.
Step 3: Match the Trip Type to the Birthday Milestone
A kids 10th birthday trip is very different then a grandparent wanting to celebrate 60 with all their family around. The birthday person’s desires should always supersede, but here are some ideas for the person who is stuck, or just wants someone else to do the planning for them (I’ve been there).
The Kid/Teen Milestones (Double Digits, A Quince Trip or Sweet 16, Graduation Trip):
Your kids and teens are focused on action and fun. They don’t want to explore a winery. They want to go ziplining in Costa Rica or enjoy a beach in Hawaii. This is a great time for a first trip to Disneyland or Universal. You could also consider a National Park Road Trip, where you hike through some of the most people places on the West Coast. My oldest loves all things water and picked Hawaii for both their 10th and their Quince trip. We not only did the beach and pool and relaxed, we also snorkeled with Manta Rays in Kona and tubed down irrigation canals in Kauai. My daughter, the dancer, wanted Paris the founding location of ballet for her trip. We went to see A Midsummer Nights Dream performed by the Paris Ballet in the Opera Bastille.
The Adult Milestones (30s, 40s, 50s):
When you are celebrating a round birthday, you want to focus on celebrating where you are in life. No longer your broke 20s, you can choose the vibe, luxuries and experiences that you want to celebrate in this time. Again, here the vibe the birthday person wants but some excellent ideas include food and wine regions, city trips with shopping, theater and history, or even a private vacation rental in a scenic spot to just spend time with the people you love. For my 40th birthday I told my husband I wanted to be in a foreign county, on a beach, with a drink in my hand. He planned an epic Bali adventure. For my husband’s 50th we did a three week trip through Eastern Europe with lots of food tours in each location. With my best friend, we did a girls trip in Malta for her 40th, full of wine, food tasting, history, and lots of fun in the shared Airbnb.
The Grand Milestones (60+, Multi-Generational Focus):
Sometimes when you hit big milestones where you want to celebrate with your extended family, you are looking for something that can bring together mutlitple generations. You in your older years want ease, accessibility, and comfort. You want to consider things like cruises, resorts, or a big villa or Airbnb where you can hang together but take easy day trips from. When we were on our cruise, we saw a ton of multi-generational families, in matching shirts, enjoying the cruise together. During the day, kids can go in the pool or kids club, mom and dad can relax at the adults area, and the grandparents can enjoy the casino or lectures onboard. Everyone gets together at night for dinner and to celebrate together.
Step 4: Budget Transparency & Accommodation Styles
The Budget Talk
Once you have the vibe, the parameters and the destination, it’s time to start talking budget. With my kids I set the budget and they plan the activities that they want to do within that budget. As I mentioned earlier, my daughter wanted to bring a friend on the trip. She agreed to a smaller trip to accommodate her friend in the budget. Are you traveling with other family members? Then talk about the budget before you go on the trip to manage expectations. How will you split costs? How much are you all willing to spend? Having this talk before leaving makes it easier when on the road and helps avoid surprises.
Picking the Right Home Base
How many people are going drives picking the right home base. If you are a large group that expects to separate and return together, getting a vacation rental with a large common space is key. It is great for breakfasts and dinner together, or late night chats, or for cozy downtime. It’s also nicer when you are family with younger kids to have the ability to put kids down for bed at night and still be up and an adult a little later.
If you are on a girls trip, or it’s a smaller group, a hotel or resort works great. Especially if you are looking for a little bit of luxury. Sometimes you just need a comfortable bed with nice sheets and a great view.
Step 5: Build in “Me Time” and “We Time”
When you are planning these trips, when it’s younger you are usually together all the time. But as you get into the teenage years and beyond you want to make to sure to schedule time together and time apart. Here are a few things to consider:
- Avoid over-scheduling: If you pack in every minute, you leave no room for rest or to explore surprises. Trust me, you don’t want your teenager loudly stomping off, saying they are done learning about the holocaust in the middle of Berlin with everyone watching.
- The 1-3-1 Rule: Plan one main group activity a day, leave three hours unstructured, and keep 1 meal together.
- Creating a Special “Celebration Moment”: Dedicate one specific evening/activity purely to the birthday person (a special dinner, a private boat tour, or a custom toast at sunset). It should be a time to make sure you honor the reason you are there.
At the end of the day, the best milestone birthday trip isn’t about perfection, its about being memorable. In Paris my husband’s wallet was stolen, but we remember more the awe we felt seeing the Eiffel Tower for the first time. My oldest was sick on my actual 40th birthday, but the kids remember the hotel room with our own pool so they woke up and went swimming in it first thing in the morning. Those are the memories that will live on forever. At the end of the day, it’s the birthday celebrant who needs to feel special. Keep their wishes in mind and it will all work out.
* Starred Photos taken by Atma Photography
Edited by: SKS
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