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Madeira 2 • June 24-July 10, 2023

Sunsets and Swimming!

July 10, 2023

Saying goodbye to this group was not easy. We write this with heavy hearts as this energetic and tight knit group walks to their gate to travel home. These past 17 days have been nothing but smiles and laughter. It was a true joy getting to share the amazing islands of Madeira and Porto Santo with this group. Every single person in this group brought something unique and important to the group. It would not have been the same without one of them. John and I can’t thank you enough for sharing your wonderful kids with us. It was a blast and we all made memories that will last a lifetime.

Our time in Porto Santo was filled with sunshine, swimming in the ocean, and lots of ice cream! The sun came out as we arrived at the island, and we spent the afternoon soaking in the beautiful sand beaches and crystal clear waters. It was named one of the best beaches in Europe and for good reason! This island is truly beautiful and we were all in awe. All of the girls jumped off the pier multiple times and swam back to shore all together.

After enjoying some time on the beach, we headed out for sea kayaking and stand-up paddle boarding. We laughed all along way along the way. We had kayak races and enjoyed each other’s company in the sun. Kaitlyn was the best SUP boarder and Will zoomed past us all in the sea kayak. It was a great day! We ended the day with Moonup on the beach as the sun went down.We didn’t think it was possible, but the next day was even better. Our amazing outfitter, Gonçalo, took us to a hidden gem on the island, a series of natural swimming pools on the coast. We spent the day coasteering, which consists of walking, climbing, jumping, and swimming along the waters edge. As we pushed on further down the coast, the natural pools became more beautiful. It was the clearest water any of us had ever seen. We were all truly in awe of the beauty of our surroundings.

We spent the morning swimming and jumping into pool after pool. After eating lunch on the beach, we headed back to town for ice cream, music on the beach, and pier jumping! Cooper and Julie Anne were our bravest souls during the pier jumping. They each took the highest jump multiple times in a row. Will, Jack, Joe, Crawford, and John played tips on the beach while AC, Shaffer, Kaitlyn, and Annie worked on their stunting skills. After dinner we had another delicious ice cream stop at our favorite local place in town. It was a two ice cream kind of day! We had ended the day with a special Moonup on the beach as the sun was setting. We have been ending each Moonup with our peaks, valleys, and horizons for each day. Today we all agreed that it was a “no valley” kind of day. It was unanimously the best day ever!

Right before heading in for the night, Cooper had the idea for a spontaneous sunset swim in the ocean. Annie, Julie Anne, Shaffer, Vivi, and I all ran after Cooper into the water. The impromptu, post-Moonup sunset swim in the ocean was the perfect end to a perfect day. We woke up the next morning to more blue skies and sunshine. Grant led the pack snorkeling, and we all enjoyed a morning in the water looking at fish, starfish, and sea cucumbers! We finished off our time in Porto Santo with more pier jumping, stunting on the beach, and one final stop at our favorite ice cream stand! We were sad to leave the stunning island, but we were all excited to get back to Porto da Cruz for another day of surfing.

Our second surfing day in Porto da Cruz was unlike anything we have ever done before. This group braved the big waves, and everyone got in the water. Everyone was able to get up on the boards even with 5-7 foot waves! It was a challenging but rewarding day on the water. Jack was the MVP of the day and caught giant wave after giant wave. We had delicious, homemade chicken Caesar wraps for lunch and then went back out on the beach to soak up the last hours of sunlight in Madeira. After a delicious banquet surf and turf dinner, we went back out on the beach for a final Moonup. There were happy and sad tears shed, as we are all so grateful for our time together but sad to see it come to an end. This group turned from friends to family over the past seventeen days. Each day was a blast filled with laughter and pure joy. John and I had the best time exploring, adventuring, and hanging out with this crew. Thank you again for sharing your wonderful children with us. This group is unforgettable, and we miss them already!

All the best,

Hailey and John

Surfing and Soccer!

July 7, 2023

Time really does fly when you’re having fun! These past few days have been filled with adventure and so much laughter. This group has the best energy and they are truly hilarious. Since we last spoke, we have been canyoning, rock climbing, and surfing! On the first day of canyoning, Kaitlyn and Joe led the way as LODs. Everyone was all smiles during this new and fun activity. Cooper loved being in the water so much that he kept jumping in and getting out until it was time to keep moving down the river. We enjoyed a relaxing afternoon and ended the day with steak frites and Apple Brisa soda, a Madeira special, of course! We had Moonup outside as the sun was setting, and it was the perfect end to a great day.

The next day we jumped right into Level 2 of canyoning with higher repels and jumps and even more slides! There are no fears in this group! Everyone did a great job braving all the obstacles and helping each other along the way. Cooper and Ana Collins were LODs and did a great job leading us through the more difficult route. We enjoyed a chocolate snack at our halfway point and finished with the most exhilarating obstacle of them all: a two part water slide and jump. Everyone slid down the natural slide first before quickly walking back up to the top for the high jump. Our crew loved it so much there were three or four jumps each at this spot. There is truly nothing better than seeing such smiley and happy faces come up from the water after each jump! After our canyoning, we transferred to the quaint beach town of Porto da Cruz. We stepped into our hostel with our awesome cook, Ricky. Will, Joe, Jack and John played a friendly soccer game across the street with a few Czech vacationers and some locals. We had burger night at the hostel, and it was a HUGE hit. Will even said it was the best burger he has ever had!

We woke up on the 4th of July and this group didn’t lack any national pride or excitement! Joe and Julie Anne won best outfits with their patriotic clothes! We wore red, white, and blue beads and outfits all day and listened to our favorite classic American music to celebrate the holiday away from home. Everyone enjoyed rock climbing but Annie, Shaffer, Will, and Cooper were our spider monkeys who conquered all the hardest routes! After rock climbing, we enjoyed a refreshing dip in the ocean. After a week of trekking and canyoning, this crew was so excited to finally get into the ocean. We ended the 4th of July with a competitive soccer game against a group of locals. We all cheered on “Team USA” as the boys went up against the locals. Although we didn’t win the game, it was still a blast and a great way to celebrate America!

Yesterday we completed our first day of surfing! We had a quick breakfast before getting in wet suits and paddling out to our surf spot. The waves for a little choppy which made for a rewarding challenge! Vivi and Shaffer rode biggest waves and we all got so excited to see Ana Collins surfing her very first wave! It was such a blast getting to start the day together in the water and many of the kids agreed that this was their favorite part of the trip so far. We returned to our hostel and had a delicious big brunch and celebrated one of our beloved outfitters’ birthday! We had a chill afternoon with lots of singing, guitar playing, friendship bracelet making and Uno games!

We ended the afternoon with a cooking lesson from our hostel chef, traditional Arepas with a delicious meat filling.

After our meal, we finished our day with very special and memorable Moonup led by Kaitlyn and Crawford. Crawford and Grant had us all in tears, we were laughing so hard. It was a great way to end a spectacular day! We can’t believe we only have a few more days with this amazing group. We are excited for the next days of adventure and are going to soak up all our time together. John and I wanted to thank you all for sharing your wonderful kids with us this summer. Their energy is unmatched and their excitement for each day is so much fun to watch. Our stomachs hurt from laughing so hard. It’s been a treat getting to be their leaders!

Here are a few words from our crew:


Shaffer: hey fam! Thank you so much for sending me on this amazing trip. I’m having the best time. See you soon!

Jack: hey guys! Thank you for sending me on this trip. I’ve met so many friends and I’m loving Portugal.

Annie: thank you so much mom and dad. I’m having the best time ever. Love y’all so much!

Joe: hey guys. Thank you for the opportunity to send me on this trip. Love you guys. Bye!

Will: hey mom and pops. Thank y’all so much for sending me on this trip. Love y’all!

Kaitlyn: hi mom and dad. Thank you for sending me on this trip! I’m having so much fun! Say hi to Black Jack and Callie for me.

Vivi: hi mom and dad! I’m the best time ever here. Tell liver I say hi. Thank you for so much for sending me here. Can’t wait to see you when I get home.

Grant: hey mom and dad. Love you thank you for sending me on this trip. See you soon.

Crawford: dear Kelly and Parker, this trip has been amazing. Thank you so much for sending me on it. I’ve had the best time and can’t wait to tell y’all about it.

Ana Collins: hey fam! Thank y’all for sending me on this trip. I’m having so much fun! Love y’all see y’all soon!

Julie Anne: hi mom and dad! Thank you for so much for sending me to Madeira. I’m having the best time and can’t wait to see y’all and tell you about it.

Cooper: hi mom and dad. I miss you both so much. I love you and thank you for sending me on this amazing trip. I can’t wait to tell you about it.

Hello from Madeira!!

July 2, 2023

Hi friends and family! Despite a delayed arrival to Madeira, this group never skipped a beat. Our trip officially began when John and I greeted twelve happy, excited travelers in the Madeira airport. After finally being united, we enjoyed a big pizza dinner to fill up after a long few days of travel. From the first dinner and Moonup, this group brought high energy and excitement. This spectacular attitude hasn’t diminished, and we’ve had a blast during our trekking section!


We celebrated Shaffer’s birthday on our first day of trekking! We hiked to a private waterfall in the morning, and everyone was brave enough to face the cold water for a swim. Will stayed in the waterfall the longest and we all enjoyed lunch while drying off in the sun. We ended the day with a delicious pasta dinner cooked by the pasta master, Grant. After birthday cake and lots of cheer stunting, the group settled into camp after a great first day of trekking!


Our second day on trail was a difficult but rewarding day. Joe shared his delicious egg recipe that helped us all fuel for the day ahead. Julie Anne led the pack all day and Vivi and Kaitlyn kept the spirits high by admiring each beautiful view. The girls kept the group entertained on the trail with lots of singing, especially during a tunnel crossing where their voices echoed. Our efforts were rewarded with ice cream overlooking the beautiful mountains and clouds. We cooked a Mexican feast, listened to music, and got to bed early to rest up for our hike to the highest peak in Madeira the next day!


After an early wake up and quick breakfast, our group was off on our journey to Pico Ruivo, the highest point on the island! Will, Joe, and Jack sported matching outfits that kept us laughing while Annie’s positive encouragement helped us push up to the top. At the top of the peak, we enjoyed lunch with spectacular 360-degree views. Ana Collins was actually the tallest person in Madeira as she was the flyer in a cheerful stunt once we made it to the top! After a challenging but amazing day, we enjoyed showers and had the traditional Madeiran wedding meal of duck risotto for dinner! Everyone cleaned their plates and we all reflected on how amazing of a day it was!


Yesterday was our last long day of trekking. We woke up and fell asleep above the clouds! At our lunch spot, Crawford discovered the special Madeira soda, Apple Brisa, and he has been on the hunt for more ever since. Shaffer and Vivi taught Jack and Cooper how to make friendship bracelets and we enjoyed a relaxing evening at our campsite. We ended the day with one of our favorite meals yet, a pasta salad with grilled chicken and homemade balsamic dressing. Today, we finished up the trekking portion of our trip with a trek down to Funchal, the capital of Madeira. We took a toboggan ride down and reflected on how in the past 48 hours we have gone from the highest peak in Madeira all the way to the sea!


This group has incredible energy and their excitement for each day is unmatched! We can’t believe how fast the first portion of our trip has flown by, but we can’t wait to jump right into canyoning, rock climbing, and surfing! This is a fun and special group of kids, and we can’t wait to watch them grow closer. We have been ending Moonup each night with our peak, valley, and horizon of each day, and most of us struggle to find a valley each day. Life is good here in Madeira! We are having a blast and will catch up in a few days! In the meantime, here are a few words from our crew!



Julie Anne: hi mom and dad. I miss y’all and I hope that you’re having fun by yourselves. I’m having a lot of fun, everything is really beautiful! Love you! Say hi to Samson for me, I know he misses me the most.


Shaffer: hey fam! Love and miss y’all! Hope Greece, Colorado, and Nashville are all amazing. Tell Nelly I say hi. My group is awesome. See you soon!


Ana Collins: hey fam! Love y’all! Miss y’all! Having a great time and tell they Harrells I say hello


Vivi: hi fam. I love you so much and I miss you. Hi to all my friends especially liver. Love yall and can’t wait to see you when I get back.


Kaitlyn: hey fam! I miss y’all. I’m having a great time in Madeira and am making lots of great friends. This place is really cool and pretty!


Annie: hey friends and fam! Love and miss y’all and happy late birthday Eleanor. Give Miller a hug for me!


Will: hey y’all I got y’all surprise presents. Love y’all bye


Jack: hey family. Thank you for sending me on this wonderful trip. It’s the best. Love you


Crawford: dear Kelly and Parker, I miss y’all and I’m loving it here with my new mom and dad. Love y’all


Joe: hi family. I love you I miss you guys. See you soon.


Cooper: hi mom and dad. I love you and hope you’re enjoying your time alone. Can’t wait to see you.


Grant: hey mom and dad. Love you miss you having a great time


  • Annie
  • Ana
  • Cooper
  • Grant
  • Jack
  • Joe
  • Julie
  • Kaitlyn
  • Vivi
  • Will
  • Shaffer
  • Crawford