Planning the Perfect Mother-Daughter Trip: Everything You Need To Know

mother daughter trip

There are few relationships that come close to a mother-daughter relationship. We resent our mothers, we love our mothers, somehow we even turn into our mothers. And who knew there was something as fun (or frightening) as a mother-daughter trip to turn that around?

I was always curious as to why my mother didn’t stay a city girl and instead chose the married with 4 kids life. I always wanted to be a fashionable, successful city girl. And here I am, the city girl wondering (just wondering) if I’ll ever be happily married with kids.

I didn’t realize that what my mother and I needed at this point in our relationship, as two adults, was some girl time in the city.

Why I Started Traveling with My Mom:

A few years ago, my dad passed away. And one of the things that my parents loved to do was travel and visit their friends and family. Since I was the single one in the city, I thought I should be my mom’s new travel partner. This is interesting and a change in pace, since I only visit my mom once a year at Christmas. After one trip, I realized the value of getting to know your mom in your 30s. I saw my mom differently and appreciate her in a new way.

I was turning 30 and my mom and I discussed taking a trip. There were a few American cities that were on my list, but we ultimately chose to go to Boston. Somehow, I got the memo (the wrong memo) that Boston in the fall is the place to be. I realized that when we went to get breakfast and a local told me, ” Somebody lied to you about Boston in the fall. It’s just another cold city.”

My mother grew up in New York City, and Boston happened to be the city that my mom loved. I didn’t realize that until I met her at an Oyster bar downtown and saw the look in her eyes. She was so happy. She looked exactly how I did when I came to Chicago and fell in love with the city. I took my parents around Chicago and tried to show them the Chicago food scene, but they were happy with chains or Greek diners and especially Chinatown. But in Boston, my mom loves tea and seafood and we got to live out our best city life eating cannolis, standing in line for over an hour on the North End for the best Italian food, and going to tea shops for a proper cup of tea before hiking up another hill.

Mother-Daughter Trip to Boston:

I had booked a nice AirBnB for us (AirBnB has even put together mother-daughter trip wishlists), and I was nervous about it because my mother has never been to an AirBnB and she likes privacy and the comfort of a hotel or staying with friends and family. To my surprise, by the end of the trip, my mom fell in love with the apartment and said it would be a perfect place for me to live in if I was single in my 40s. It was the first time I realized that my mom didn’t have this pressure on me to get married. She knew I was a city girl and it felt nice that she thought I would be as successful to live in a high-rise.

On the mother-daughter trip, we went and explored a lot of historical sites and museums, as one naturally would do in Boston. We both took turns being silly and posing next to statues. We went to the Boston Tea Party Museum and came alive helping to re-enact those fateful nights in history.

Mother-Daughter Trips as Kids:

My mom and I have had special trips growing up. One of them was when we planned a Girl Scout trip to Savanah, GA where the two Girl Scout Group leaders took their daughters for a getaway to see Juliette Gordon Low’s (the founder of Girl Scouts) home and earn a few badges. It was then, I realized my mom’s heart and love for art and history. We took that trip when I was a teenager and my sister was also there. Since then, we’ve also had mother-daughter trips in larger groups on a mission’s trip. We went to North Carolina and did community work and then had fun sliding down Sliding Rock and I saw that my mom liked the outdoors and had an adventurous and carefree side. But, we had never had a one-on-one girl’s trip as adults.

It was a trip where I got to see my mom doing the things that she loves and really coming into her element.

Creating Memories Away from Home:

Overall, it’s sometimes hard for me to connect with my mom. She’s a different person than I am with a different lifestyle. During the mother-daughter trip, in between walking through gardens and in libraries, we stopped. I was sitting in Boston Common, and I remember just opening up to my mom. When we move away from our moms, sometimes it’s hard to really have these moments to connect. I shared how I was really doing and feeling. We haven’t lived together or really hung out in a long time. We never would have had that moment if we didn’t go on that trip.

I can’t tell you how stressful it can be to plan a trip. I didn’t know if we would have a good time or if I would like Boston. And I’m so glad that it didn’t prevent me from going. Our parents do so much for us to help us have the best life. I’m lucky I had a great mom who prayed for me, encouraged me to do what I loved, and is proud of me.

What we needed at this point in our relationship was some girl time in the city. I’m really glad I took a weekend away. This mother-daughter trip helped me to get to know my mom for the person she is and not just as my mom. I hope to make it a yearly thing. We were supposed to go to Italy last year, but Italy was shut down due to COVID, so I took an imaginary vacation there. There’s a lot of places to go to and cities to see. I’m excited and honored to be my mom’s travel partner. It’s helped us grow closer and get to know her in ways I couldn’t imagine.

Tips to plan a Mother-Daughter Trip:

Pick a place that you both want to go to and include things that you enjoy. I can’t stress this enough. When my parents came to Chicago, I didn’t know what to show them. Including my mom in the planning of the trip and brainstorming together, helped us organize activities and plan a trip where we both could enjoy. My mom was so excited to go on this trip and tell her friends. It just made the whole experience better.

Leave buffers to debrief and have time on your own. A whole weekend with your mom can be stressful, especially if you aren’t best friends. Add in some moments where you both can explore on your own. I got an AirBnB with a floor of amenities. At the end of the day, I would unwind with a cappuccino overlooking the city up there, and my mom might take a quick nap. Adding in breaks helps to break up the trip but also gives you your own space to rest and relax.

Cheers to better relationships with our mothers! Where are you going for your mother-daughter trip?



Amanda Whitfield
Amanda Whitfield

Amanda Whitfield is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.

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