top of page

Last minute sign-up~ Only 4 spaces left!

*Buy 1 get 1

1/2 off!!

Food &Wine Tour

Cortona Italy

May 11-18, 2019 

Nourish your soul with a Taste of Tuscany!

Dreaming of eating (and drinking) your way through Italy?
Let us take you on a rich cultural journey 
 of Italian Passion, Beauty 
 Food and Wine

Your week in Tuscany

Tuscany is a food and wine lovers dream. Together we'll experience the food and wine specialties of the region, the perfect way to get to know Italy. 

The Val D ’Orcia in Tuscany with its rolling hills covered in vineyards dotted with hill top medieval villages and art cities full of history, will be our playground. 


If you've been dreaming of Italy and savoring it's delicious food and wine, while enjoying the most scenic Tuscan routes... then this gastronomic and visual feast is for you! 


This fun tour of Italy will encompass the feeling of hospitality the Italian culture does so well.  We'll visit small family run vineyards where you'll get to share an intimate experience with the owners.

At the end of our time together you will have made new friends, and know why the Italian culture is so loved, 

because you will have lived it.

Your Tuscan Adventure 

You'll discover beautiful villages and off the beaten path experiences in the jewel towns of Tuscany while taking  in the breathtakingly picturesque scenery of the Tuscan countryside. This is where the magic of Italy is.

This is a semi all-inclusive trip and there will be some fun surprises for you during our week together. See below for a list of what's included in your holiday Under the Tuscan Sun.  

Olive oil mill visit in Cortona

We'll start the day at a Frantoio (olive mill)  where we'll learn about the process of making olive oil and walk through ancient terraced olive groves. We'll spend the morning tasting oils and delicious balsamics while learning of their health benefits. Later we'll enjoy a typical Tuscan meal and have plenty of time to explore this famous little hill town.

This is just a taste of what's to come!

While we'll definitely have fun exploring nearby towns we also suggest you take time to slow down, immerse yourself in the quiet beauty

of Italy and simply enjoy life

under the Tuscan Sun

Get ready for an amazing week 
under the Tuscan Sun 

So excited to welcome Janell Pekkain 

From Olive This Olive That

in San Francisco's Noe Valley!

She brings not only her knowledge of delicious olive oil to the table, but also her fun sassy attitude to inspire connection, support, well-being and friendship as my fabulous assistant during our amazing week in Tuscany! 


Chianti is another one of the most beautiful areas in all of Tuscany and the perfect spot for lovers of fine red wine. Here we'll enjoy a winery and garden tour followed by a beautiful farm to table lunch with the winemaker. You'll sample her delicious wines and prosecco during this very special afternoon in Chianti.

She may even demonstrate how to uncork a bottle of prosecco with a sword! This technique is known as “sabering” or “sabrage.” 

Pienza and Montalcino 

Enjoy cheese tasting at a local Pecorino farm followed by a delicious farm to table lunch in Pienza.

Afterwards we'll head to Montalcino, a picturesque hill top medieval village with views of the rolling hills. After enjoying some free time exploring we'll meet up to visit a very special winery just outside of town. Here you'll meet Annabale the winemaker, enjoy a personal tour and tasting with his family and sample Brunello di Montalcino, currently the most appreciated Italian wine in the world.

If time permits there will be an opportunity to visit the Abbazia di Sant'Antimo, a former Benedictine monastery famous for Gregorian chants. Unfortunately the monks have been called back and no longer reside at the Abbey.  

Spending quality time enjoying life is

extremely important for your health, well being and happiness.  Ready to take care of you? 

Special Events
happening during our week

Trip package only


* Sign up by  May 1st and save $1847.50!  

on a companion  

with our last minute Buy 1 Get 1, 1/2 off special!!


*airfare not included

 *click here for trip details

Wine and shine showcase.jpg
You're invited to an exclusive event

A special evening of food, entertainment and fun!

We'll kick things off enjoying Prosecco sprinkled with gold flakes while participating in an exclusive "jewelry tasting" where you'll choose your favorite handcrafted piece to borrow and wear for the evening. This red-carpet visit to DelBrenna Jewelers will no doubt be a special highlight of the evening.

Afterwards we'll savor Cortona's local cuisine paired with a fine array of vintages from famous wine regions throughout Italy.

This is a perfect opportunity to indulge your passion for food, wine and beautiful things. The atmosphere is casual but elegant with a focus on living La Dolce Vita. We'll get to toast some bubbly with Megan and Sebastian, and hear stories of jewelry making and life in Tuscany!

Photo Credit: Delbrenna Jewelers, Cortona  


Photo Credit: Andrea e Marta Photography 

The 2019 Mille Miglia
is scheduled May 15 – 18


Last year this historic race passed right through Cortona! OThursday, May 17, they will be passing through Tuscany.  Though the exact route hasn't yet been announced, its a fun

opportunity for any car enthusiast to be here during this week. There are many great spots to view the race along the route even if they don't pass directly through Cortona.

They will be passing through Siena which could be a fantasic option for anyone who's interested in witnessing this event. 

What is the Mille Miglia? It's a four day 1000 km classic car road show that loops through Italy, starting and ending in Brescia. This tradition dates back to 1927, when four friends from Brescia started it together after the grand prix was moved from their home town. Per tradition, the race is set for one-week before the Monaco Formula One Grand Prix. 

For more fun information about this race click here.  

 Indulge in the wonderful cuisine of Tuscany

Eating a delicious meal is one of the great pleasures in life. 

Italians are very passionate about food and the quality of ingredients they use.

Everything is locally sourced, fresh, and simple.

Local chefs will indulge your senses with the authentic flavors of Tuscany during some very special excursions and events that are sure to be among your favorite highlights of Italy!

Most people visit the big cities when they go to Italy, but they miss out on the magic you find in the small hill top villages, which is exactly what I want to share with you! 

So, be ready to taste all the sensory delights Italy has to offer from extra virgin olive oil, balsamic vinegar, authentic regional cuisine, cheeses, and of course Vino!

And don't worry... we'll walk it all off when we head out exploring the rest of what bella Toscana has to offer!

We'll be staying right in the heart of  Cortona this time so you'll have the freedom to explore on your own when we're not out enjoying  awesome adventures together

cortona view.jpg

Our Home in Tuscany

You'll be staying in a beautiful boutique hotel right in the center of the historic medieval hilltop town of Cortona Italy, made famous by Frances Mayes book Under the Tuscan Sun, and movie of the same name with Diane Lane. The backdrop to this unrivaled location is southern Tuscany known as the Val di Chiana, in the province of Arezzo. It's a region with unique art, history, culture, traditions and cuisine.

Lobby cortona hotel.jpg
bar cortona hotel.jpg

Our boutique hotel has a beautiful garden area to enjoy coffee or an apertivo, as well as a stunning family area to gather as a group or relax and read a book. Breakfast is included daily, as well as a several other meals included in your semi all-inclusive Italy tour  

Hotel double in cortona.jpg
outdoor seating bar cortona.jpg
breakfast in cortona.jpg

What's Included: 

  • Welcome dinner, wine included

  • 7 nights accommodations in Boutique Hotel dbl occupancy (a roommate will be assigned if you are traveling solo, in twin room)

  • Daily breakfast included

  • Transportation during our excursions  

  • Olive oil tasting and experience

  • Chianti wine tasting excursion with lunch

  • Excursion to Pienza for cheese tasting tour followed by a Farm to table lunch with wine, 

  • Brunello wine tasting in Montalcino

  • Special wine dine and shine event/dinner

  • Fun surprises

  • Pizza party farewell dinner  

  • Total of 7 breakfasts, 3 lunches,  3 dinners 

  • Transportation to/from Camucia train station to/from hotel *at designated time only. Time to be announced once the train schedule is available. 

**Want to add on an extra night or two in Rome or Florence?  Just ask and I'll be happy to help you book flights and hotels.

Reminder: USA flights arrive in Italy 1 day later than your departure date!

What's not included:

  • Your round-trip airfare from home

  • Transportation to train station (meeting point) in Camucia Cortona  

  • All dinners and lunches not mentioned in the itinerary 

  • Personal Alcoholic beverages, other than whats provided in itinerary   

  • Other non-included items: souvenir shopping, tips, spa services, personal taxi fare when venturing out on your own, etc.

  • Personal, medical or trip cancellation insurance

  • Optional excursions. 

*Please inquire if there is a place you'd like to go during one of the two free days, or before/after our week together and I'll help you arrange it!

Meet your hosts

Ann Marie Packard

Your Host, and event planner

Hello! I'm so excited to share my favorite country with you this upcoming Spring 2019!

I have some really amazing things lined up for us and I can't wait to experience them with you. 

I became very passionate about travel and helping people live their dreams after my father passed away in 2007 without ever having realized his. We had a bucket list trip planned for when he retired without any thought that he wouldn't live to see any of those beautiful places. 

It was then that I realized life is for living and experiencing now, not waiting for a someday that may never come or be too difficult to enjoy at an older age. 

It has become my mission to share the gift of travel by creating amazing trips so you don't have to stress about details. There is so much beauty and culture to be explored, why not give yourself permission to enjoy it? Come awaken your wanderlust spirit, this is your one life... come live it! 

Janell Pekkain

Co-Host, Olive oil expert and passionista!

Janell's love of travel, food, connection and community led her to open Olive This Olive That in 2012, an olive oil retail shop in San Francisco. Janell graduated from the International Tour Management Institute in 1996 and lived abroad for 12 years. It's her passion for travel and connecting with people that makes Janell a wonderful co-host for our week in Tuscany.

Her deep knowledge and passion for extra virgin olive oil and gastronomy is a big bonus as well! Janell has become an active member of the California Olive Oil Council and its sensory panel. She judges olive oil in competitions and certifies hundreds of California produced olive oils through the panel every year. One of her greatest joys is witnessing the a-ha moment and connection someone has when they understand freshness and diversity of olive oil for the first time. It will be a special treat to have her along as we explore the tastes of Italian extra virgin olive oil. 


Please reload

Under the Tuscan Sun




dbl occupancy

(airfare not included)

Space is limited to 12 participants 

       A non-refundable deposit of $695 is due at the time of registration to secure your space

Deposits can be made through PayPal, Visa, Check or Cash






All remaining balances due by March 1st 2023

There is a 3% fee for credit card and PayPal payments, payment plan options available

For general questions about this trip please email

Ann Marie



Reservation/Refund and Cancellation Policy:

A $695 non-refundable deposit is due at the time of registration. Your spot is not reserved until we receive your deposit. Second payment of $1500 due by January 15th, 2023. All remaining balances due in full by March 1, 2023. If you need to cancel anytime between 30 days to 60 days prior to the trip 50% of the payment, less the deposit, will be refunded. We are not able to provide refunds for cancellations less than 30 days prior to the trip. We reserve the right to cancel the trip if it is not meeting the trip minimum (if we do your deposit is refunded in full). Trip cancellation insurance is always recommended whenever making travel plans, a "cancel for any reason" policy is highly recommended. Insure my trip  online insurance is one company we know and trust, you can choose from several policy options.

Contact Us
Dolce Vita retreats

San Francisco, California

bottom of page