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Monday, March 2, 2026

Hello Monday and Hello Diana's Senior Trip in Aruba!

 



Hi Friends and Happy Monday!  I am here with Sarah and I am recapping our trip to Aruba- Diana's Senior Trip.  

 

It was certainly one for the books and a core memory for both of us.  So grateful we could make it happen and so thankful for the wonderful memories and quality time spent with friends.

 

Here is what it looked like...

 

Saturday

 

Our alarms were set for 2am and we left the house by 2:30am.  Rob and Eva drove us into Logan.  We were very lucky.  Our flight was only delayed about 30 minutes and it did take a big longer to take off as our plane has to be de-iced.  That is a really cool process that I had never seen before.

 

(travel outfit- thank you Amazon)

 

Coffee AND Selfie Stop ;)


It took about 4 and 1/2 hours to get to Aruba- very smooth flight- we read and watched movies and got more and more excited the closer we got!

 

When we landed in Aruba it was a smooth trip through the airport and immigration.  We waited for our bags and then grabbed a tax to our hotel- the Holiday Inn.  We did the all-inclusive package as it was more affordable since we had booked this last minute.

 








 We checked in but our room wasn't ready so we hit the beach and met up with our first friends who got there.

 

Some other friends were delayed so we didn't get to see them until later that night.  Before that, though, we grabbed dinner at the resort's Mexican Restaurant Agave.  

 



Our tacos tasted great- fish for Diana and steak for me but we both got sick hours later (like 5 hours later- so we never did go back there) 

 

The girls didn't waste anytime.  Once we had dinner and saw our friends in the lobby, the girls hustled to get ready and then they headed out to the nearby beach club called Moomba's.  They met up with their guy friends from town and had their first night of fun.  All decked out (not everyone was there yet for the week)





 

 I didn't sleep well this night due to not feeling well AND being nervous about Diana but she really impressed me and listened to my rules and stayed with the kids- it ended up all working out and being great :)

 

 

Sunday

 

We got up bright and early to reserve chairs on the beach for our group.  Diana humored me by capturing some pics of me in my favorite yoga poses ;)

 



We then met up with our friends at the breakfast restaurant and headed out for our first full day in the sun and we were joined by some of our favorite Boy Mamas

 






 



 
 

That night, after showering and getting dolled up, we headed down to Moomba's for a Mama's Dinner- it was great to all catch up

 


 and the girls got all dolled up in black so they could match at the club :)

 



 After dinner, I crashed but snapped a few pics of the hotel at night



 

 Monday

 

Our little girl group got picked up at 7:30 am for our excursion- swimming with the turtles.  I knew I wouldn't get in the water with turtles but I was up for a boat ride.  Anyway- there was no boat ride.  The van brought us to a place further down the coast and the participants put on their gear and got right into the water so I was "staff photographer" from the shore- ha!

 


There were many laughs- I guess it was a huge workout and Diana made them all laugh saying Ella must be on the swim team as she was always a mile ahead of them- too funny!

 















 

 After that, it was breakfast and the beach...vaca mode

 







 Then we were able to get all of the kids together for a big pic on the beach!  That was one of our goals

 


 

 After that, we headed down to the Marriott Stellaris where most of the boys families were staying.  We hung out in their awesome pool with the Mamas and had a great afternoon.  We saw several other Windham families there too!

 



That night we hit the Seabreeze restaurant at our hotel.  Unbeknownst to us, our steaks weren't part of our all inclusive so there's that- sigh...anyway...the food was great


 

 


 

 I crashed hard after dinner...the kids were out at the club every night...I swear the girls dressed up more and more each night- they were so cute!

 

Tuesday

 

Breakfast and Beach to start the day again 

 




 Then we did a late lunch with some boy mamas at the Pelican Bar which is a cool spot on a nearby dock





 After that, we all went back to our rooms to shower and get ready for our fun evening.

 

We had an excursion planned for the entire group- The Jolly Pirates Sunset Cruise complete with a rope swing- the kids had an absolute blast!

 


 






 Bethe and me- Kindred Spirits



 





The Class of 2026 getting a good luck wish from The Jolly Pirates!

 


 After that, the girls and some of the moms wanted to go back and shower and get ready for the evening.

 Danielle and I were already ready so we decided to find a cute little bar for a pre-dinner cocktail- this little hole in the wall was the perfect place






 Then we walked across the street to meet the rest of our big crew for a fun Mexican dinner at Kalins- the kids deemed this their best night of the trip- it was an absolute blast- we laughed so hard and loved watching the kids living their best lives!  The music was kickin' too :)

 











 


After dinner, the Mamas decided to spy on the kids at Moomba's but it didn't last long- they were not having it- ha!


 

Time to crash- darn it ;)


Wednesday

 

Diana and I decided to start our day at Eduardo's and we enjoyed our acai bowls right on the beach- it is an Aruba tradition and a must try place!

 




 

 Half of our crew was leaving so we spent some time on the beach with them and enjoyed one last lunch together

 

Then Melissa had Danielle and I over to her hotel (the Marriott Surf Club) for some swimming and our new favorite cocktail- vodka, soda and a splash of pineapple-delish! 

 







 That night, our three families headed to dinner downtown at Bricca- it was awesome.  It was a great way to walk off our calories too!

 

Then for our last night, we met up with our favorite boy Mamas at the Marriott Stellaris for a  Goodbye Cocktail.  We had so many laughs and shared our favorite things from this trip. 

 

 

The Kids- living their best lives- it was so fun to watch and I felt gratitude all week- gratitude for being able to pull this off- gratitude for the wonderful friends Diana has finally made-gratitude for other Mamas and kids who have been through similar struggles in high school and gratitude for all of the joy and heartbreak all at once


 
The kids were up extra late this night so it took us some wrangling...they really wanted to stay in the hot tub until dawn but we were successful gathering them all and getting them back to their rooms at a decent  hour....I did survive on very little sleep but relaxing on the beach every day made me feel rested for sure!
 
 
Thursday
 
 
Diana and I headed down to breakfast and then over to the shops to pick up something for Eve.  Spotted this cute mirror and beautiful message so had to snap a shot and it ended up being the only picture I took on our last day- our travel day
 
 

Our last day.  We ended up hanging out with Melissa and her girls at their palapa at their hotel.  We even enjoyed lunch there before we had to leave for the airport. 

 It was a smooth trip home and Rob and Eva were waiting for us at Logan.  Grateful that we made it home safely and dodged a blizzard while we were gone- it has been a brutal winter here!

 

Friday

 

I was back to work on Friday and it was a great day to dig out, get organized and I even made a placement! 

 

That night, Rob had a gig and the girls and I enjoyed our Friday Night Pizza Night at Pasquale's.

 


 Eva and I crashed early and Diana headed out to the movies with her friends.

 

Saturday

 

We were up bright and early and Rob and I hit the rail trail- despite the cold, it felt so good to be back!

 



We got caught up on laundry and organizing for the week.  We watched more of Love Story on Hulu- it is the JFK Jr and Carolyn Bessette story and it is awesome!

 

 

That night, Eva had Chech sleep over, Diana headed out to the hockey game with friends and Rob and I enjoyed dinner with Lynn and John at Andiamo in Andover- highly recommend! 

 

 

 Sunday

 

Rob and Eva headed out to softball, I took Chech home and then headed to the gym for my lifting class.  After that, it was meal planning and groceries and doing some cooking for the week. 

 

I also started a major closet purge.

 

Last night, we headed to mass then crashed.  What a week!  Just simply grateful!

 

 

 

 

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24 comments:

Maria Rineer said...

Your trip looks awesome! I was worried for you that you wouldn't it make it out of Boston. But obviously you did- great pics of your fantastic time with Diana and all the students/mamas. That's a big group that was able to go! Good job whoever planned it!! What great memories for all. Though her senior year is winding down (EEKS!), it looks like it's been such a great one for Diana and for you guys, too.

Joyce said...

What a fabulous week! I love Aruba and it looks like you had a wonderful time. So much fun to have a mother-daughter getaway. And what good timing because that snow storm was no joke. Hope you have a nice week easing back in to work and life.

Jen White said...

What an amazing trip filled with memories! Now I need to add Aruba to my bucket list of places to go.

Jenn Lloyd said...

What an incredible trip! I love all the memories you made, and seeing all the pictures makes me want to go there. I know you'll both remember this trip for the rest of your lives. You were a busy woman, coming home to keep going like you did! I think that might be the best way to re-enter, though...to just keep going like that and not think about how tired you must have been. I hope you have a great day, my friend! Happy Monday!

Amy Scott said...

How fun! Aruba is so pretty! I love all of your pictures and they have me dreaming...
Love the all black the girls did!

Kim Carberry said...

Oh wow! What a wonderful trip and fab photos! It looks like everyone had the best time! How cool to swim with the turtles and good on the kids going out every night. I think I would have been taking myself off to bed most nights too.

Natasha said...

Such a fun and memorable trip! So happy you got to celebrate with Diana and her class!

Holly said...

It was definitely the trip of a lifetime- so happy for her that we could make it happen :)

Holly said...

We really dodged a bullet Joyce!

Holly said...

Yes- you would love it! Weather is always perfect :)

Holly said...

Yes I liked the re-entry- eased into it- got organized and ready to rock today :)

Holly said...

They looked like a million bucks every night- I kept thinking that I never looked like that at their age- ha~!

Holly said...

Yes! I can only rally for so long- ha!

Holly said...

Thank you friend :)

Joanne said...

That sounds like such an incredible trip!

Holly said...

it really was :)

Everyday Maddie said...

What gorgeous pictures and fun memories! Looks like you guys had a great time (minus getting sick the first night- boo!) Glad you had safe travels both ways. I would love to visit Aruba some day!

Stacy said...

Oh my goodness now FUN! It was awesome that so many of her friends were able to go along! Man your photos make me miss the warm weather and sunshine lol! It's still so COLD! :) You have a beautiful daughter and I LOVE your yoga post photos! What fun memories :) Hope you guys enjoy the last few months of her senior year!!!

Laura @ Our Grand Lives said...

What a week indeed! So fun to read all about your adventures! Looks like Diana and her friends and their mamas had a fabulous week that's bound to fill you up with great memories! Thanks for sharing!

Marilyn said...

Oh Holly, this looks like an amazing trip! I'm sorry y'all felt bad early on & I am so impressed with the late nights and mornings. The views are so pretty. What a gift to have this time with her and for her friends. And glad you got a break from the snow for a few days!

Holly said...

Add Aruba to your bucket list Maddie- you would love it!

Holly said...

Thank you Stacy :) It is freezing back home now too- ugh -we need spring already!

Holly said...

Memories to last a lifetime- yes! :)

Holly said...

It really was Marilyn- thank you :) I will cherish these memories forever!

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