Check into Venue

Welcome Pizza Dinner

Wine Tasting

The Night Before

Wedding Day

Check out

Our Wedding

As a little gift to each other, we each wrote our own version of our story without reading the other’s first. It was so special to see our journey through each other’s eyes, and we hope you enjoy reading both perspectives as much as we enjoyed writing them.

Her Version: 

For me, it all started the summer of my junior year of high school. A friend invited me over to a hot tub party and we ended up at Jack’s house. That night I met a kid who was super cute, kinda weird, extremely smart and funny and definitely had a girl friend. All I could hear was my mom’s voice in my head, “Don’t worry, people break up. You can always be friends”. So that’s exactly what I did, I became Jack's very best friend. Luckily, it didn’t take long for them to break up and I became his shoulder to cry on. From that point on we were inseparable. We even scheduled our wisdom teeth surgeries at the same time so we could spend recovery together, drooling on the couch and surviving off of mashed potatoes. At the time, I was working at Yogurtini. Jack would spend almost every night hanging out with me while I worked. I didn’t have a car yet, so he would drive me home. Of course I paid him in unlimited yogurt. It didn’t matter if we were spending the weekend in Vail, doing homework, or driving around with no where to go, we always had so much fun together. The highlight of it all was our trip to Puerto Vallarta with Jack’s parents. I remember feeling so grown up getting to spend an entire week together! Before long it was time for college and we had a decision to make. He was going to CSU, I was going to UNC. The colleges were only an hour apart and we thought.. well we went to different high schools and it was fine. What could possible go wrong? Let’s stay together! Unfortunately, long distance turned out to be harder than we anticipated. After a few breakups and makeups, we eventually decided to call it quits junior year. We went our separate ways and spent the next few years figuring out life on our own. Until one day, I was just minding my own business when I randomly saw him again. I was tubing in Golden with friends and stopped at the Golden Mill for lunch. Just as we were leaving, another group walked in looking for a table. As they got closer I realized it was Jack and his friends. I couldn’t believe it. Part of me hoped he didn’t see me so I could quickly grab my stuff and make a run for it. Luckily, Jack was much braver than I was and came over to say hello. Seeing him again after all those years was surreal. It truly felt like fate and just like that we picked up right where we left off. 💕It didn’t take long for us to realize this time was different. He won my heart all over again, not just by the way he loved me, but also by the way he fell in love with Harlow. Since then, we have built a beautiful life together. We have gone on countless adventures, bought our first house and adopted the sweetest little kitty, Atlas. Then, came the easiest "yes" of my life. My sweet, nervous man spoke from his heart, and I've never felt so loved or so seen. After we got engaged, I knew I wanted to soak up the "fiancé bubble" for as long as possible, so we decided on a long engagement and a destination wedding. I feel so incredibly lucky to have a partner who makes every adventure sweeter and every dream feel possible simply because we're chasing it together. I couldn't be more excited for all the chapters still to come and blessed I get to do life with my best friend by my side.

His Version:

Chapter 1: The Beginning Olivia and I met long ago in a town far, far away, called Highlands Ranch, Colorado. It was 2012, and mutual friends brought us together for a hot tub party at my parents’ house. It was love at first sight! Just kidding, I had a girlfriend at the time, so Olivia and I became just friends. However, little did I know that Olivia was patiently waiting, biding her time for a chance with this handsome stud. When she finally got her chance, after I was single again and we went to an 18+ club for some dancing in Denver, and I decided to make the first move. After that, it was love! One milestone and big life event after another, we stuck together and dated into college. Even though we went to different schools, we visited each other all the time, we made it work. Unfortunately, the “college experience” took its toll, and we split after three and a half years together. Chapter 2: We Were On A Break! But really, we took a long break. Five years went by, we saw other people, graduated college, started full time jobs, and made new friends. During this time, we found ourselves, matured, became real adults, and experienced our own ups and downs. I think both of us realize how important this chapter really was. Chapter 3: The Reunion Less long ago, in another far, far away town, called Golden, Colorado, I was enjoying one of my favorite summertime activities, tubing on Clear Creek. Little did I know, so was Olivia. While we didn’t see each other on the river, fate had a way of bringing us together. After tubing my friends and I went to a local bar, and while we were searching for a table, one of Olivia friends waved us over saying that they were leaving and we could have it. I quickly recognized Olivia and decided at that moment to let bygones be bygones, and said hello to Olivia and her friends, suggesting we catch up and get a drink sometime. Olivia agreed. Chapter 4: Old Sparks Olivia quickly realized that she had blocked my phone number… so she couldn’t hear from me or get a hold of me… uh oh! Luckily, she reached out on Instagram asking if I was interested in getting that drink, to which I happily obliged. A date at Parry’s Pizza led to another date hiking at Saint Mary’s Glacier, where I got to meet Harlow, a rambunctious puppy who I would soon fall in love with and come to call my own. A few more dates and soon we were at Red Rocks for Olivia’s birthday, when I decided enough was enough and it was time to let fate have it’s way, asking her to be mine once again. Chapter 5: Us Time flies! We’ve been together now nearly as long as we were apart. I can’t imagine my life without Olivia. We’ve had so many adventures and milestones together, I’ve lost count. Harlow accepted me as her dad, and we became “You, Me, and the Dog”. We moved in together. We bought our first house together! Olivia supported me through the challenges and long night of grad school, cheering me on every step of the way. We adopted our sweet, sweet kitty, Atlas. And somewhere along the way, I decided Olivia was the one. I bought a ring, took Olivia to BANFF for “my birthday”, and proposed on top of the tallest mountain in Canada (probably). I was pretty nervous, so all I remember saying is “I love doing life with you.” I think I remembered to ask her to marry me. Chapter 6: What’s Next? I can’t tell the future, but I do know that the future is bright. We have an amazing wedding planned for TUSCANY with our family and our very best friends. I can’t wait to achieve more milestones, go on more adventures, build a family, and keep “doing life” with my best friend; and our dog, and the cat. Life with Olivia is amazing, and I can’t imagine where I would be without her.

Our Story

Our engagement photos were taken at the top of Guanella pass in Georgetown, Colorado. 

Photos

Emmy Davis 

Cody Walker 

Brooke Melvin 

Josh Weemes

Sophia Romero 

Tyler Thorn

Alyssa Walker 

Tony Crudele 

Caroline Newman 

Jon Newman 

Wedding Party

Q + A

We are so excited to invite you stay with us in our Villa: Quercia Al Poggio.Address: Strada Di Quercia Al Poggio, 4, 50028 Barberino Tavarnelle FI, Italy. Traveling to Italy: -Please note that Europe now uses a digital entry/exit system. This may lead to longer wait times at passport control and customs. We recommend allowing extra time for connections or considering arriving a day early (or extending your layover) to make your journey as smooth and enjoyable as possible. -If you choose a layover in another Schengen Area country, you will complete passport control at that country. Your connecting flight to Italy will then be treated similar to a domestic flight, meaning you will not need to go through passport control again when arriving in Italy.-Some convenient layover options from Denver include :-Germany (Frankfurt or Munich)- France (Paris)- Netherlands (Amsterdam)- Switzerland (Zurich) Airport options in Italy:1. Florence Airport (FLR)-Recommended)-About 50 minutes to venue by car.-Shuttle transportation to and from the airport will be available from FLR. 2. Pisa Airport (PSA)- About 1 hour and 15 minutes away from venue. 3. Bologna Airport (BLQ)-About 1.5- 2 hours from venue 4. Rome Fiumicino Airport (FCO)-About 3- 3.5 hours from venue We recommend comparing flight options and choosing the airport that works best with your itiniary! Bringing family along for the adventure?For guests traveling with parents, children, or additional family members, we've included nearby accommodation recommendations close to the villa. We recommend reserving early, as availability is limited throughout the Tuscany region.

Hotel Borgo di Cortefreda

Park Hotel Chianti

Travel

All the Villa has to offer:

Enjoy two swimming pools and a variety of recreational amenities including tennis, soccer, basketball, and beach volleyball courts, as well as bocce ball, ping-pong, and foosball. The surrounding countryside offers hiking through woods and vineyards. Taxis will be available to take you in to town, however be aware that they may take a while/ be expensive since we are deep in the countryside. Sharing rental cars with other guests are a good option to explore outside the villa!

Restaurants nearby:

Great spot for breakfast, just 15 minutes away.

IL CELLARIO

Bar Sport 21

Ristorante Triocco

La Locanda di Pietracupa

Trattoria La Vecchia Capannina

Antica Trattoria La Toppa

Places to go: 

We are about 35 minutes away from San Gimignano. A walled medieval hill town in Tuscany, Italy! Top things to do:-Climb Torre Grossa:&nbsp;At 54 meters, this is the tallest tower in the city. A ticket to the top includes entry into the Civic Museum inside the Palazzo Comunale.-Explore the Piazzas:&nbsp;Wander through the triangular&nbsp;Piazza della Cisterna&nbsp;and the adjoining&nbsp;Piazza del Duomo.&nbsp;-Visit the Duomo (Collegiata):&nbsp;Step inside this 12th-century cathedral to view remarkable, vividly preserved Renaissance frescoes.&nbsp;-Taste Famous Gelato:Stop by the world-renowned, award-winning ice cream shop Gelateria Dondoli&nbsp;in Piazza della Cisterna.

Visit San Gimignano 

About 45 minutes away you will find Siena, a medieval gem nestled in the heart of Tuscany, beckons travelers with its rich history and artistic heritage. Renowned for its stunning Gothic architecture, vibrant cultural scene, and deep-rooted traditions, Siena offers a unique blend of old-world charm and modern excitement. Must see:1. Siena Cathedral2. Torre del Mangia3. Piccolomini Library4. Basilica of San Domenico

Visit Siena 

30 minutes from our venue you will discover one of Tuscany's more unique wineries. Spend the day touring the estate, tasting incredible wines, taking a hands-on cooking class, or enjoying a meal at one of their beautiful restaurants. (This winery is on the way if you are traveling to or from Florence.)

Antinori nel Chianti Classico

If your travels take you south of our venue, don't miss Cascate Del Mulino, location about 2.5 hours away. This stunning hot springs makes for a relaxing day and and opportunity for some stunning photos!

Cascate del Mulino

Things to Do

Registry

jackandoliviapendergast.com

Jack & Olivia

Jack & Olivia

Photos

Our engagement photos were taken at the top of Guanella pass in Georgetown, Colorado.