"A Taste of Tuscany" Raffle

As part of the upcoming "Under the Tuscan Sun" auction, we are raffling off a 5-night all-inclusive trip for two to Tuscany. It's a win-win—a great prize for a great cause!  Here's how it works:

  • 200 tickets are being sold at $100 a ticket. THE ODDS ARE GOOD!
  • To purchase a ticket, contact one of our ticket sellers by clicking on their name listed below. 
  • Do you have friends, family, neighbors or colleagues who might be interested? Great! The raffle is open to the public. Spread the word!
  • The raffle will take place at the "Under the Tuscan Sun" Auction on Saturday, April 6, 2019. The winner does not need to be present at the event in order to win.  
  • The total value of the prize is $7,500 which includes a trip value of $5,700 and $1,800 in taxes which Tower will cover.

In case you're not sold yet, imagine yourself with your spouse or best friend "Under the Tuscan Sun" -- sipping espresso in the piazzas and wine in the vineyards, taking in the unrivaled architecture and historic sights, noshing on gelato and savoring Italy's legendary cuisine. Stone and Compass offers an all-inclusive tour but can tailor the trip if you're looking for more time on your own vs. personalized tours. 

So what are you waiting for? Grab a ticket and start dreaming of Italy! 


Raffle tickets are $100 each and there are only 200 tickets being sold! Click on a name below to purchase your ticket from one of our ticket sellers. 

Tess Bauta '90--SOLD OUT
Deirdre Bertrand--SOLD OUT
Kate Bracken '92--SOLD OUT
Kerri Burr--SOLD OUT
Meredith Carter--SOLD OUT
Stefanie Conahan--SOLD OUT
Jocelyn Cook--SOLD OUT
Paige Hamilton--SOLD OUT
Jessica '95 and Jon Hyde--SOLD OUT
Loretta Lang--SOLD OUT
Joelle and Greg Lydon '91--SOLD OUT
Sam Maxted--SOLD OUT
Alethea McCormick '89--SOLD OUT
Pat Milner--SOLD OUT
Angie Munro '91--SOLD OUT
Beth and Henry Peabody--SOLD OUT
Maki and Brad Robie '88--SOLD OUT
Carrie Rosenman--SOLD OUT
Alison Spring '95--SOLD OUT
Amanda and Matthew Velluto--SOLD OUT
Emily Zotto-Barnum--SOLD OUT


Tower is proud to partner with a local boutique tour company, Stone & Compass, to offer this unique tour of Tuscany. Stone and Compass "serves as an incubator for sustainable cultural entrepreneurship projects through our tours and programs that connect, educate, and inspire round the world." Learn more...


Below is a sample itinerary of the vacation being offered. Stone and Compass will work with the raffle winner to make this trip an experience of a lifetime! 



The capital of Tuscany, Florence is like an outdoor museum. The incredible architecture invites visitors to meander through its streets and let go. In the morning we will visit the Accademia Gallery and gaze upon Michelangelo’s David. After lunch in a traditional café, we will head out on a walking tour of this incredible city visiting Piazza’s and Basilica’s along the way. Late in the afternoon take time on your own to relax and enjoy this Tuscany dream city. Dinner will be a special treat as we head to one of Florence’s greatest restaurants Pensavo Peggio!


After a great night sleep we awake to a wonderful breakfast. It is then time to head off to the wine region as we embark on an incredible journey. Visiting the Gaiole region in Chianti we take in a wonderful wine tasting and stroll through the vineyards. But wait…it gets even better. We actually get to spend the night in a historic winery and hotel. After a traditional Italian dinner relax out on the veranda and stroll the manicured Tuscan gardens as you watch the sunset.


Today we leave the rolling vineyards and head back in time 1000 years as we visit Sienna. Listed as a UNESCO world cultural heritage site, the city boasts one of the largest medieval squares in the world the Piazza del Campo. Since the 1300’s the square has been the centerpiece of the city and an active market place with the famed fountain Fonte Gaia located here. In the afternoon there is time to take a relaxing walk through the city. For those who are adventurous you can try ascending the Torre del Mangia! Take the 400 steps to the top and you won’t be disappointed as the views of the city below are simply breathtaking. You can also visit the cathedral, the complex of Santa Maria, or simply meander in and out of the many café’s and shops that line the streets.


After a wonderful breakfast in Siena we head to the famous town of Pisa. Of course we will visit the leaning tower, but there is also so much more to do in this incredible Tuscan city. Pisa, famous for its artisan shops, antique shops, and markets is sure to delight any visitor. You can walk along Corso Italia the main shopping district area, stroll along the cobble streets and pop in and out of churches and historic sites along the way. On this evening we have a special treat planned as we conclude our stay by taking in a show at the famous Verdi Theater!


In the morning we return to Florence and begin our journey home but the memories will last a lifetime. Extension trips begin on this day if you choose to take one. For those who wish to extend your European Vacation to a full 10-day trip Stone & Compass is also offering four extended excursions at a special discounted rate as a thank you for being part of the Tower School auction. Extension trips and prices are as follows (flights included):

  • Sicily extension (4 days) 1150.00 per person
  • Croatia extension (4 days) 1250.00 per person
  • Paris extension (4 days) 1250.00 per person
  • Bosnia extension (4 days) 1150.00 per person


The trip is all-inclusive. Stone & Compass has no extra fees associated with any trip. All flights (from/to any major east coast airport), lodging, food, site seeing, guides, and insurances are covered in our cost. The only extra cost to our travelers is money for gifts and maybe an extra gelato or two!

Trip must be taken before December 31, 2021.

Trip will be booked directly between winning ticket holder and Rob Goodwin of Stone and Compass.