Next October we're heading to the southern coast of Italy for our art retreat! We are going to paint and practice self-care, enjoy delicious homemade Italian food, explore through excursions, and immerse ourselves in nature!
October 25-November 1, 2026
Italy Art Retreat waitlist!
Email questions
- The Quick Facts:
- Retreat cost: 3,300-3,700
- $800 deposit to hold your spot
- Duration: 7 nights, 8 days
- Trip is non-refundable; travel insurance is required to help cover expenses for interruptions or if you need to cancel
- Cost includes:
Meals
Excursions + transport
Airport transfers
Happy to discuss questions!
"I went home with beautiful memories of our week in Italy"
It was an amazing week! Picture the most beautiful venue, the best food, the sweetest people taking care of the venue, a beautiful classroom to paint and the most supportive group of people you can imagine to paint with! So much fun to try different techniques, paint stuff around the venue and to do plein air sketching and painting. I went home with beautiful memories of our week in Italy, new friends from all over the world and more painting skills. It was the best!
Rika
What my students are saying
"I loved the simplicity of the venue and the commitment of the owners"
This retreat experience was exceptional. Tammy brought, not only her watercolour expertise, but also warmth, kindness, humour and passion that energized the group and made each day special.
I loved the simplicity of the venue and the commitment of the owners to creating an environmentally sustainable space. It was very special.
Ann
"The group that gathered was so supportive and fun."
Tammy's art retreat was a perfect combination of learning, excursions, shared meals and fellowship. The group that gathered was so supportive and fun.
Having a dedicated space for relaxing, painting and adventures was perfect.
Thank to Tammy and her wonderful friends to pulling this all together.
Kristin
You're in the right place.
How would you like to spend a glorious week painting, exploring, swimming, dining in the gorgeous and peaceful countryside of the south of Italy, off the coast of the Mediterranean sea?
During this relaxing art retreat, we will be staying in a beautifully restored historic Italian farmhouse overlooking the Sea. The venue and grounds are reserved for our group and you will have full access to explore the gardens, roof-top terraces, and open spaces.
We won’t be rushed but we will be enjoying many activities in this incredible place as we experience what the calmer side of Italy has to offer. In addition to 7-8 painting sessions together, we will embark on exciting excursions and also savor our free time. Choose to swim in the warm sea, relax on one of the rooftop terraces with a good book, bike to the lake or sea, or maybe even take a nap :)
"Travel is more than the seeing of sights; it is a change that goes on, deep and permanent, in the ideas of living"
-Miriam Bird
Prices include all retreat amenities: Accommodations, food, excursions, transportation, and painting classes with me.
Double Occupancy - $3,700 per person
Venue Accomodations
Triple Occupancy - 3,300 per person
Spacious and beautifully decorated room has both a queen and a twin bed and its own bathroom. Rooms come with soap, shampoo, and a hairdryer. Each room has wifi access and AC and heating as needed.
"This experience was unforgettable"
This experience was unforgettable. The staff was amazing and very accommodating. Tammy was the best and taught me some new techniques that I can’t wait to go home and share with my painting group!
Sandy
What my students are saying
"Tammy's painting retreat in Italy was a magical experience"
Tammy's painting retreat in Italy was a magical experience. It was such a joy to be able to absorb the wonderful scenery, make new friends, enjoy the most wonderful vegetarian meals and take part in the art sessions knowing Tammy had taken care of every detail. I also loved that mindfulness was built into the daily art sessions. The location itself is spectacular, a painter's dream! Transfers to and from the airport were seamless. The staff at the Masseria were exceptional. All in all a five star experience.I loved the simplicity of the venue and the commitment of the owners to creating an environmentally sustainable space. It was very special.
Anonymous
" Everyone should take this chance of a lifetime opportunity"
Tammy Kaye‘s retreat was amazing. The venue was in a perfect location in the content of her class was exactly what I needed. We had a lot of fun painting, laughing, eating together, and getting to know one another. I’ve made some lifelong friends. Everyone should take this chance of a lifetime opportunity. Having a dedicated space for relaxing, painting and adventures was perfect.
Thank to Tammy and her wonderful friends to pulling this all together.
Anonymous
- Art classes, tuition, and painting demonstrations with Tammy Kaye (7-8 scheduled, but can be subject to change)
- Accommodations at the Masseria Specula
- Exclusive usage of the venues and grounds, retreat rooms, gardens, terraces, etc. during the retreat
- Rooms have AC/heat, and Wifi
- Meals are vegetarian and are lovingly prepared by local chefs Rosanna and Franca with fresh ingredients. This is part of their strong committment to the sustainability of their venue (as well as planting more than 500 trees, solar panels, etc).
- Excursions including: A painting and shopping trip to local towns and an additional outing, to be determined. We will also have some additional fun activities to immerse ourselves in the culture. Private transportation to all excursions will be provided
- Bikes, beach chairs, and umbrellas are provided by the venue, as well as paper towels and glass water jars for painting
- Complimentary cappuccinos, coffee, and tea will be available
- Local taxes, as well as state and provincial taxes are included in the price of this trip
- Private WhatsApp group to share details of our upcoming plans where you can ask questions and connect with your fellow travelers
- 1 scheduled courtesy transfer from the airport and 1 scheduled courtesy transfer to the airport at assigned times
What's Included:
What's Not Included:
- Airfare
- Travel insurance - This is required for covering medical expenses, travel interruptions, and personal cancellation to cover anything that might require cancellation or a change in travel arrangements
- If you are not able to schedule your flight within the recommend flight times for arrival and departure, you will miss the scheduled courtesy transfer and will find transportation on your own
- Lunch during our shopping trip(s)
- Tips for staff (not required, but a kind gesture if you desire to do so)
- Other expenses you may incur on your own
***This is an example schedule - based on our last retreat. Things may be changed around based on availability of excursions, transportation, etc.
Class content may also change, at the artist's discretion ***
Sunday
Afternoon: Arrive at the BRINDISI airport (around 2:30 PM) and prepare for the transfer to the venue. There will be only one transfer included in the retreat costs but if you need another time, that can be arranged ahead of time with the venue on your own or you can get an airport taxi. After arriving and settling into our rooms, we will enjoy a fruity welcome drink with some free time until dinner.
What to expect for classes and excursions:
Monday
Morning: Watercolor basics, loose florals with real flowers or references
Afternoon: Wet-on-wet vs wet-on-dry florals
Tuesday
Morning: Sketching and painting objects from around the grounds
Afternoon: Excursion to the city of Lecce
Wednesday
Morning: Floral sketching and adding watercolor
Afternoon: Excursion and wine tasting in Grottaglie
Thursday
Morning: Watercolor landscapes
Afternoon: Watercolor landscapes on location at the sea
Friday
Morning: Painting objects from excursion reference photos
Afternoon: Free paint, based on the class’s desire
Saturday: Morning and afternoon:
Our painting classes will be complete, and on your last day in Italy, we will focus on relaxation and immersing ourselves in our surroundings. Saturdays are personally my Sabbath days of rest, and I will be looking forward to relaxing and appreciating nature :)
What’s included in this day: If you choose to stay at the venue, all meals will be served to you that day. One of the scheduled events will be a hands-on class on how to make fresh pasta at the venue. Some other options to consider include: Walking or biking to the flamingo lake or swimming in the sea, quality time with friends or on your own, going on an excursion of your choice, which you would book on your own (not included in the cost), or staying in and painting, etc. You can even take a short bikeride into the small town to get some gelato :)
Sunday:
Brunch: 10 am
Leave for the airport: 12 pm
Sample Schedule
Sample Schedule
1. Do you have to have experience with watercolor to go on this trip?
Frequently Asked Questions
3. This trip is non-refundable so what if the trip is canceled by Tammy Kaye or the Italian Venue?
2. How much will we really be painting versus exploring Italy?
Although this is a watercolor painting retreat, you don't have to have previous experience with the medium! The way I teach is inclusive of all skill levels, whether you are a beginner, experienced, or just starting out with me in Italy! My big focus is to let go of the need for perfectionism in our art, using simple self-care techniques when we paint to learn to enjoy every step of our session, not just the end result. There is great joy and peace from putting brushstrokes on paper!
As I have listed in my sample schedule for the week, I have 7 painting sessions planned, each of which will probably last 2 hours a piece (last year students stayed longer after class because they wanted to finish pieces). There are several days where we have a morning and afternoon sessions and the other days we have one painting session and one excursion planned. But as we begin our trip together, we can be flexible on the length and amount of classes. The most important thing to me is that we are relaxing, don't feel rushed, and experience joy together by balancing painting with Italian fun :) We must have room for chill time and swimming.
Travel insurance is required to attend this trip and it will cover cancelations and interruptions, including the trip being cancelled by myself. If this happens, insurance should cover all expenses that you have paid out. If not, I will be glad to reimburse what is not covered.
- A non-refundable deposit of $800 to hold your spot
- 50% of your remaining balance is due May 1, 2026 and finishing your balance is due August 1, 2026
- Feel free to pay your fees in full, if you desire and no processing fee will be charged
- Payment options include: Personal or cashier's check or money order if in the United States. If you will pay via electronic payment such as Paypal, Venmo, etc, there is a $40 fee per payment to cover credit card fees.
- If you are overseas, you can use Wise, which you connect to your bank to make your payments. If you will pay via electronic payment such as Paypal, Venmo, etc, there is a $40 fee per payment to cover credit card fees.
Payment Info
Cancelation policy
- Once you have put down your deposit, you have confirmed your participation in the trip and it is non-refundable.
- We require you to purchase travel insurance to cover medical expenses, travel interruptions, and personal cancellation to cover anything that might require you having to cancel or make a change in travel arrangements. We will require proof of your insurance 30 days after you book your flight.
Contact me if you have any questions!
Ready to Make Your Dream trip Happen?
lets do this.