From Yes to I Do: My Real-Life Guide to Starting Wedding Planning

Welcome our special guest blogger, bailey. she shares her experience of how she started the wedding planning process for her destination wedding in italy.

Bailey sharing her guide to wedding planning featuring her engagement to her fiance. Showing off her engagement ring.

Bailey shares her experience on starting the wedding planning process. Here she is with her now husband during her family vacation to Switzerland.

The Guide to Starting Wedding Planning:

Trey and I had been dating for nearly five years when we went on a family vacation to Switzerland. I have family there that I hadn’t met and my grandparents wanted to take us all over there to reunite with her cousins and spend time together in such a stunning landscape. On the most incredible day exploring small villages in the region, with a backdrop of a running river, lush green mountainside, and the most adorable brown cows, Trey got down on one knee! It was such a special, unique, and private way to get engaged that felt so “us”. 

At 30 years old, my Notes app and Pinterest board weren’t short of dreamy inspo, but after soaking in the engagement for the next few days, my thoughts started becoming “where do I even begin?”

I think many of us daydream about our wedding as children and some of us have attended/been in other weddings, but when our own engagement happens, we’re awestruck and feel frozen in time!

The questions from friends and family start coming in. We’re trying to live in the moment and enjoy this short chapter before marriage all while anticipating the future. We have decisions to make, but where do we start?

Maybe you’re feeling this way now. I hope I can be the friend to help you along your journey of starting the process. This was my order of operations for the first few decisions.

1) Budget and Priorities 2) Location 3) Date 4) Planner 5) Venue 6) Dress 7) Experience


Bailey’s engagment ring from Trey.


Step 1 - Wedding Budget and Priorities

Let’s be real! The first step in wedding planning is zooming out and figuring out what your all-in budget is. Are you paying for your wedding yourself? If so, is there time needed to save up? Are your parents covering the cost? Have a clear, open conversation with them about their contribution. It’s so important to discuss upfront so you have a number to work with.

Next comes an honest chat with your fiancee. List out all of the categories within a wedding celebration on two separate sheets of paper (ex: venue, planner, florals, fashion, guest count, stationary, food/drink, music, photo, video, day before/after event, etc.). To avoid influence, each of you circle your top 3 before talking about it. Then, see if you align on any of your top 3. If so, that jumps up to your first priority. If not, debate your case and see if you can land on a combined top 5. 

Have this priority list accessible during your planning process. It’s not necessarily an order of where to spend the most time, but it is a way to help you prioritize where to spend more of your budget and where you choose to save.

photo of italy where the wedding was looking over a cliff

Viewpoint from Bailey’s wedding in Italy.


Step 2 - Wedding Location

Next in the process after getting engaged is choosing a location. Notice, venue selection is later on my list. We knew we wanted to have a faraway destination wedding, so location for us meant a country. Maybe for you it’s a state, a city, or a region? 

Travel was a major part of our relationship’s beginnings. We did long distance temporarily, so our first date was in Nashville, second date in Toronto, third date in Niagara Falls, and fourth date in Boston. We both always knew a massive ballroom wedding wouldn’t feel true to who we are. We wanted something intimate and a distance from home, where everyone in attendance was out of their everyday routine, enjoying a slower pace and creating their own memories somewhere spectacular beyond the wedding celebrations. 

Coming to a conclusion on this decision wasn’t difficult for us, but it did take a bit of research. Trey and I knew we wanted to begin our honeymoon wherever our wedding took place. Europe was our focus. We researched different countries and regions and landed on Southern Italy.

Italian wedding details with tomato themed tablescape for destination wedding

Destination Italian wedding highlighting the local culture

Step 3 - Wedding Date

This step is negotiable. At this point we chose our time of year, rather than an exact date. Your time of year can be affected by both the weather and seasonality of the location you choose as well as your budget. That’s why it’s important to know these two things before thinking about your date. Maybe for you, there’s a special month or symbolic number to keep in mind. For us, it was important to choose a month with beautiful weather that was not too hot and to choose a time of year that was less busy with tourists in our region. That combination is tricky! We were deciding on September or May and landed on May, which can be cool, but tends to be before the rush of travelers.


Step 4 - Wedding Planner

Planner or venue? The chicken and the egg! Since we had landed on a region based on our research, we had a list of venues. We were unable to travel overseas to venue hunt and scout out the cities, so we selected our planner prior in order to help us narrow down our venues.

I am so happy with this decision! The planners we chose were ideal for several reasons. The Amalfi Experience is a group of women who each do part of the process, but work together as a term. They’re each experts at the part they handle and bring it together effortlessly. Jacquie, the lead planner, manages it all broadly and is originally Australian (despite living in the region for over 20 years with her Italian husband). Communication was clear and from the start, they sent me videos of the venues I was debating as well as sharing details that I would have never known from their websites. Our planners had done many events at each of our proposed venues, so their insight was extremely valuable when it came to making that decision.

Guide to destination wedding planning in Italy featuring the wedding venue and orange, pink floral hues.

Wedding Planning Guide featuring Bailey’s wedding in Southern Italy. Her wedding had beautiful, soft details of pink, yellow, and orange hues.

Step 5 - The Wedding Venue



If you’re not a creative, I can totally see how this part is a bit challenging. Can you see past however the venue is set up when you see it on a tour or the emptiness of the photos the venue sends you? Trust the process! Are you getting married in a back yard? Are you leaning towards a church ceremony? Will you dine in an art gallery or a museum? 

Ask your venue about accessibility for your guests. Do they have somewhere for you to get ready? What all is included? Don’t be afraid to ask questions about how you can utilize and transform the space.

For us, getting married on a weekday made so much sense. Once you’re overseas, day of the week matters less, but this choice helped not only in lowering the price of venue, but also in vendor availability.

In her ines di santo wedding dress standing on the balcony with her wedding flowers. the wedding dress has butterflies in it.

Bailey dressed in her Ines Di Santo wedding dress she found at The Bridal Finery in Orlando, FL

Step 6 - The Wedding Dress

I was honored to go wedding dress shopping with both my sister for her wedding and my friend for hers long before getting engaged. For my sister, we flew to Charlotte to this dress store with a massive amount of wedding dresses including a large selection of dresses from the designer my sister was set on. It worked perfectly for her! She knew the designer she wanted, this place had the largest collection, and she found her dress. I enjoyed every moment as her MOH, but I knew I would probably feel overwhelmed in an environment with so many options. For my friend's dress shopping day, she and her mom booked appointment after appointment all in one day. To be fair, they are from out-of-town, but the day was exhausting and ended with her confused about her favorites at each store.

From driving by for years and reading the reviews, I knew The Bridal Finery was where I wanted to start my dress shopping journey. I booked my first appointment there with my only expectations being a sweet experience with my mom, sister, and baby niece.

The personalization of the appointment made the process feel so special. About a week before, they reached out over text for confirmation, but also to learn more about my dream dress. I had screenshotted and thrown in an album some photos of dresses I had seen over the past few years. I sent them all and told them I wanted to try a variety because I didn’t have a clue what I wanted!

When we arrived, Tali introduced herself to us and we sat down for a chat. I loved that it felt so relaxing and most importantly, FUN! She truly cared about getting to know me. The stylists do this everyday with a variety of brides, but it truly felt special that Tali took the time to ask me questions about myself, my relationship, and my wedding, but beyond that, she took the time to get to know my guests and how they would each describe my everyday style.

Though I hadn’t realized it, Tali noticed that the images I sent in (that I thought were all over the place) actually had a lot in common. The overall feel of the dresses in the inspo pics was similar. 

Tali had picked out dresses for me based on those images, but after our chat she pulled a few more, and she had me, my mom, and my sister pick some too! I was so pleased that they had such a lovely variety. I found several I loved on the hanger, and there were just the right amount displayed.

Next, I went into the dressing room and tried them all on! It was such a blast to see myself in all different types of dresses. It was lighthearted and every time she opened the curtain we would talk about things we loved and things we didn’t love about each dress. I’m a pretty decisive person when it comes to what I wear, so I quickly would say “keep it in the mix” or “not it”.

Funny enough, I narrowed it down to two and my sister started crying when I put on THE one!

I knew it.

However, I had committed the wedding dress shop owner’s cardinal sin. I had already booked another appointment afterwards.

We ate a quick lunch in the car and went to the second appointment. From the non-attentive service to the low quality of the gowns, all that appointment did was cement my choice from that morning. 

The experience at The Bridal Finery felt like home. It felt like an expert stylist, who also became a friend, was there for you as you figured it out. From the lighting to the music, the environment was perfect for my appointment. 

We called them immediately and bought the dress!

Black and white photo of couple on the streets of italy getting married.

The newlyweds on their wedding day in their wedding attire.

Step 7 - The Wedding Day Experience

So many weddings I’ve attended have looked and felt similar. Regardless of the size of the budget, many brides choose to follow the same script for the day. Often it seems that planners are used to operating this way over and over, so they may automatically think you would want your day-of schedule to look just like everyone else's. 

In my opinion, you should never do something “just because everyone else does”. A wedding that looks and feels like YOU is one that will not only be memorable, but will also make you feel the best all day long!

Since our wedding was a destination for all of our guests, it was immensely important to me that our wedding would honor where we were and not be an American wedding in Italy. For example, our produce-inspired Welcome Dinner (instead of a traditional dress rehearsal because we only had 50 people), was held at a Trattoria. We had a fresh mozzarella maker when guests arrived, we gifted our guests local custom ceramics that we worked with the artist to create, and we gave back to the small town by donating the produce we used as decor for the evening. 

It wasn’t a traditional night-before, but it was a special night that established where we all were, brought us together before the big day, and featured casual, family-style food to encourage conversation between all!


As you enter this special season of your life, I’ll leave you with two pieces of advice.

Do it your way. Wear the chunky necklace. Swap the cake for banana splits. Hire an onsite poet. Make your own bouquet with wildflowers from around town. Sing karaoke with your guests. Whatever feel the most YOU!

Enjoy every second of the creative process. Society has created the idea that wedding planning is stressful. If boundaries are in place correctly, it’s enjoyable! Don’t be scared, don’t worry, it will all come together and it will be a super fun process!

Bailey’s Wedding Vendors:
Planning & Design @the_amalfi_experience
Venue @belmondhotelcaruso
Photo @lizandolinaphotography
Video @luigidegregorio
Hair & Make-up @alessandromancinostudios
Dress @inesdisanto @thebridalfinery
Celebrant @comolakecelebrant
Flowers @malafrontefiori
Stationery @beccaberensonstudio
Lighting @antares_events
Music @elanartists @lauracvolin @pianobyelie
Logistics @ravellobackstage

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