Itinerary of the perfect birthday weekend in Santa Ynez

A JD Agency Experience Client Case Study 

Travel is the best gift. So true.  

It’s what inspired our client, Carolina to give her friend Lori the perfect birthday weekend getaway trip this year. 

Carolina along with 3 of their friends wanted to surprise Lori with a 3-day weekend filled with wine and dinner parties.

It doesn’t get better than that, am I right?

Challenge accepted. 

With 9 weeks before the trip, I happily took the task of making this happen for Carolina, Lori, and their friends. After all, it’s what we do best; a stress-free and memorable experience for your loved ones. 

This was a well-planned trip. Like any of my other clients, I had to tailor-fit this whole trip according to their likes and dislikes. I carefully chose the house they stayed in, the wineries they went to, and the food we prepared for them.

What Our Client Wanted

From the get-go, our client was clear, she wanted this trip to be a celebration. This was after all, her friend Lori’s 40th birthday. She wanted a fun, wine-filled weekend and dinner parties.

Lori’s Birthday Dinner Party Plans

Carolina wanted an intricate dinner party for Lori. We decided on a garden-themed dinner birthday party. I managed everything we needed to execute this event from rentals, florists, and the cake. 

I planned this with ease thanks to my experience designing and carrying out luxury dinner parties for JD Little Soirée.

My very talented chef, with fine dining expertise, prepared a 5-course meal for this dinner. 

Everything was accounted for. I looked out for anything that may or may not go as planned and made sure I was there to fix it – Perks #1 of hiring a travel planner.

The Santa Barbara Birthday Weekend Getaway Itinerary

Carolina was involved in mapping out the itinerary. I gave her lots of options and once it was approved, I made all the reservations! Easy-peasy.


It was time to find a place where Carolina, Lori, and their friends could stay for the weekend. we scored for the nicest, chic-est houses in Airbnb because I had the perfect idea for Lori’s birthday dinner – more on that later. 

The first house I booked in Los Olivos got canceled, 10 days before they were supposed to stay there. Luckily, we found a much bigger, stylish, and cheaper place in Buellton. See, everything happens for a reason.

Because the reservation was changed, everything else had to be adjusted.  

Perks #2 of hiring a travel planner. You never have to worry about this. I’ll be more than happy to do it for you. 

There are so many wineries in Santa Barbara and I started picking out the best ones to call for reservations. I was able to reserve 6 winery tours with wine tastings for the entire weekend. 

I also arranged reservations and transportation to and from the best restaurants in town.

To ensure we followed Covid protocols, I had to make all these reservations ahead of time. 

Day 1 – Friday

5:55AM – Departing San Diego

One of the first things I did for the ladies on this trip was to set up a group chat. This way we stayed in constant communication for anything and everything they needed. It eventually became a great place to share photos and videos while on the trip.

The ladies aboard the train enjoyed Pac-Man lunch boxes filled with goodies. It had a personalized puzzle photo of Lori they worked on while on the way to the destination. 


Meanwhile, I got to the house in Buellton ahead of time to decorate and check everything out. I filled the fridge with snacks and drinks for the entire weekend. 

I also put together a welcome basket for them. It had a bottle of wine, a wine cork holder, matching hoodies & caps, bath bombs, and a copy of the itinerary for the weekend.

I asked the ladies what they wanted for lunch through our group chat. They wanted sandwiches which I happily ordered for them.

12:45 – 1:20PM 

Shortly after the ladies arrived at the house rental, I drove them up to Los Olivos Pedego Electric Bikes. They picked up their lunch and off they went on their first winery tour. Yes! On their bikes. 

Side note: I called the wineries to make sure it’s okay to bring food. Perks #3 of hiring a travel planner. 

Los Olivos 

Los Olivos is a quaint town located in the exquisite Santa Ynez Valley. It is home to about 20+ wine tasting rooms showcasing the best of Santa Ynez Valley wine. The ladies spent about 4 magical hours biking through 3 of the best wineries in the area on their first day. 

2:00PM – The Brewer Clifton 

3:30PM – The Brander Vineyard 

4:30PM – Roblar Winery & Vineyards 

6:00PM Pick up at Los Olivos Pedego Bike Rental 

8:00PM Dinner Reservations at FIRST & OAK in Solvang, California 


Solvang is known for its Danish-style architecture, authentic Danish bakeries, and laid-back atmosphere. It’s a 10-minute drive away from Buellton and a charming town with lots to offer. 

And for the ladies’ first night, I made a reservation at one of the best restaurants in the area: FIRST & OAK. 

They were awarded a MICHELIN Plate rating in 2019 by the renowned Michelin Guide for their delightful place and excellent cooking.  

It was an exceptional first day filled with wine and good food. The next day was even more remarkable. 

Day 2 – Saturday

TWO affairs happened on this day. 

A surprise luxury lunch picnic at one of the wineries and the MAIN EVENT – Lori’s garden-themed birthday dinner party. 

Both were planned and executed beautifully, if I say so myself. 


My chef and I arrived at the house where the ladies stayed. We made preparations for everything we needed that day. 


The ladies’ limo service, I booked, arrived on time to take them to their first winery tour of the day. 

10:00AM – Brave & Maiden Estate 

12:00NN – Luxury Picnic Lunch & Wine Tasting at Rideau Vineyard 

It was a lovely day. I arranged a surprise luxury picnic for them at an exclusive area at Rideau Vineyard. I designed their picnic table down to the last smallest detail- something that I take pride in doing for my clients. 

My chef made a scrumptious meal making sure to also accomodate the pescatarians. The spread included a charcuterie board with hummus and truffle salami and homemade focaccia bread. 

Perks #4 of hiring a travel planner: We get access to exclusive areas because of our connections.  

The ladies had so much fun they went overtime on one of their wine tours I had to reschedule the one that was coming next.

Jessica to the rescue! Perks #5 of hiring a travel planner.

1:30PM – Wine Tasting at Sunstone Winery

My chef and I prepped for Lori’s garden-themed birthday dinner back at the rental house while they were on winery tours for the rest of the afternoon. 


After a day of wine tasting, the ladies were back at the house. Around this time, we (my chef and I) were still working on the preparations for the birthday dinner. 

And while they waited, we served them some tortilla chips, homemade guacamole, and salsa. PLUS! A fresh fruit platter. 


Finally, they had an extraordinary dinner to celebrate Lori’s 40th birthday. 

My goal was to give them a fine dining experience.

From installing a chandelier, making balloon garlands, fabulous floral arrangements, to the plush table setting. I did it all. 

As someone who pays attention to even the tiniest details, this is my cup of tea! 

The ladies enjoyed a 5-course meal, carefully prepared by my highly talented chef: 

Amuse Bouche 

Foie gras macaron

Caviar and creme fraiche blinis


Garden Salad, herbs, flowers olive soil 


Smoked champagne gelee, black raspberry granita 

Main Course

Squid ink risotto, herbs, scallops, crab, fennel


Birthday cake

It was indeed a day to remember. 

Day 3 – Sunday


The ladies had an early day because they needed to catch the train going back to San Diego at 9 am.

My chef made them a to-go breakfast – yogurt parfait with homemade granola and green juice. 

Aside from its authentic Danish-style architecture, Solvang is also famous for its pastries. And so, I can’t let them leave without giving them fresh and traditional Danish pastries from The Solvang Bakery. 

9:27AM – Amtrak 

3:28PM – Arrival in San Diego 

It was truly a fun weekend getaway. One for the books! 

Behind The Scenes 

To ensure Carolina, Lori, and their friends had a stress-free weekend, I worked hard behind the scenes. 

These are what JD Agency Experience did to make it happen: 

  1. I arrived at the rental house in Buellton before my clients. I did an ocular inspection of the house we rented for the weekend. 

I needed to make sure everything was in order and they felt comfortable. 

  1. Running errands for my clients is part of my job as their travel planner. On this trip, in particular, I had to get one of the ladies a bottle of Tequila since she doesn’t drink wine. 

Or if they forget some things from the house rental, I happily go back and get it for them, whatever it is. 

It’s the little things you do for them that make them more appreciative of your service. 

  1. A thorough check on their reservations on the daily. I spent time calling every winery to brief them about my clients. Especially on identifying who the birthday celebrant was from the group. 
  1. I get them the best areas or the best tables in the restaurants through my connections. A promise of VIP treatment is what I aspire to at all times because all my clients are very important. 
  1. Constant communication with my clients before and during the trip is essential for doing good business. 

I encourage them to contact me for anything they may need throughout the trip. In turn, I also gently remind them about the schedule for the day so they all get ready in time for their reservations. 

Overall, Carolina, Lori, and their friends had a magical time. They went there to celebrate and they did just that and more! 

No details were left behind. Everyone left Santa Ynez Valley refreshed and happy. 

How do you know if you spent the best weekend of your life? When you still talk about it days later. That’s how it was for my clients. 

But you don’t have to take it from me. Here’s what she has to say about it: 

Jessica was absolutely amazing and hiring her for my friend’s 40th birthday celebration in Santa Barbara was the best decision! We didn’t have to worry about a single thing because Jessica thought about everything.  Her connections made our experience so magical! I highly recommend working with Jessica.  She’s professional, thoughtful, organized and so sweet.

~ Carolina Vivas 

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