Please ensure Javascript is enabled for purposes of website accessibility

A Journey Awaits You

Sip stellar wines at estates still in harvest activities, indulge in vineyard estate culinary experiences and tour the sights and countryside of bucolic Tuscany. A journey personally curated by winemakers, Gabrielle & Wayne O’Connell with insider connections from Michael Mastrocola, a native of Tuscany and owner of MillenniuM Travel.

Please join us! Reserve today.

Contact MillenniuM Travel at (831) 659-0151 or

Oct 3, Sun: Arrival Florence Airport (D) 
Upon arrival at the Florence Airport, you will clear customs and meet your driver and van outside your baggage claim area. A group transfer will be provided to our ​Villa Curina Estate Hotel​. ​Airline flight info is required in advance.
Welcome to Tuscany! Enriching, ​fun​ , informational 4-night stay in the Tuscan Countryside. Private car transfer is available on request for an additional fee (contact us for pricing).
7:00p: ​Meet Gabrielle and Wayne O’Connell in the hotel lounge before dinner.
8:00p:​ Welcome Tuscan Wine Dinner at hotel.


Each morning we will awake to an included hot cooked breakfast with fresh baked pastries, fruit, cheese, cereal and steaming cappuccino and tea. After breakfast we ​board our private motorcoach at 9am for a day trip to historic Siena, home of the famous Palio horse race. We arrive in Siena at 9:30am, likely Italy’s loveliest medieval city. Siena’s heart is its central piazza known as Il Campo, known worldwide for the famous Palio run here, a horse race run around the piazza two times every summer. Movie audiences worldwide can see Siena and the Palio in the James Bond movie, Quantum of Solace. Siena is said to have been founded by Senius, son of Remus, one of the two legendary founders of Rome, thus Siena’s emblem is the she-wolf who suckled Remus and Romulus ​(statue is located in the Capitoline Museum in Rome)​ . The city sits over three hills with its heart the huge, concave, Piazza del Campo, where the Roman forum used to be. Rebuilt during the rule of the Council of Nine, a democratic group from 1287 to 1355, the nine sections of the fan-like brick pavement of the piazza represent the council and symbolizes the Madonna’s cloak which shelters Siena. The Campo is dominated by the red Palazzo Pubblico and its tower, Torre del Mangia. Along with the Duomo of Siena, the Palazzo Pubblico was also built during the same period of rule by the Council of Nine. The civic palace, built between 1297 and 1310, still houses the city’s municipal offices much like Palazzo Vecchio in Florence. Its internal courtyard has entrances to the Torre del Mangia and to the Civic Museum. If you feel energetic, a climb up the over 500 steps will reward you with a wonderful view of Siena and its surroundings. The Museum, on the other hand, offers some of the greatest of Sienese paintings. The Sala del Concistoro with ceiling frescoes of allegories on the virtues of Siena’s medieval government, the Sala del Mappamondo and the Sale della Pace that hold the palaces highlights: Simone Martini’s huge Maestà and Equestrian Portrait of Guidoriccio da Fogliano and Ambrogio Lorenzetti’s Allegories of Good and Bad Government, once considered the most important cycle of secular paintings of the Middle Ages. We will depart at 11:30.

After a guided tour and free time for shopping, we continue by motorcoach to one of the ​Antinori Family Wine Estates with an arrival time of 12:30. The Antinori family has a history of wine-making for over 6 centuries, since the year 1385. We will enjoy an afternoon learning of the vast Antinori wine estates of the world, while touring and tasting from their collection, and enjoy a fine-wine dining experience perfectly paired with the best of Chianti. Early evening we return to our countryside estate for a free night ​(​Villa Curina Estate ​details & room options​ page 6​).


After breakfast we ​board our private motorcoach at 9am ​to visit the foundation of the charming village of ​San Gimignano that dates back to ancient times. According to legend, in 63 B.C. two brothers, Muzio and Silvio, two young patricians escaping from Rome after their implication in the conspiracy of Catiline, sheltered in Valdelsa and built two castles: the Castle of Mucchio and the Castle of Silvia, which would develop in the future San Gimignano. With its forest of towers spiking the horizon, San Gimignano is one of the most recognizable and iconic destinations in all of Tuscany. In every part of the world there is someone dreaming about this ancient hilltown in the Val d’Elsa, for to be there is to dive into an image of medieval times. A World Heritage Site since 1990, San Gimignano owes its name to the incredible number of towers that look up over the town rooftops: 65 of them, no less, when the city was at its height. Thirteen of these magnificent towers survive today, and they still shape a skyline that is without a doubt unique. A visit to San Gimignano does not end by just looking upwards. The cathedral, completed in 1148, is also a must-see, considered one of Tuscany’s most precious. Built around three naves, this cathedral is a true anthology of frescos from the Florentine school. Also of interest is the Palazzo Comunale, which today is home to the town museum and art gallery, where you can admire the works of artists like Pinturicchio, Benozzo Gozzoli, Filippino Lippi, Domenico di Michelino and Pier Francesco Fiorentino. You can also visit the palazzo’s sala di Dante (Dante’s room), which contains a Maestà by Lippo Memmi, and climb the Torre del Podestà (or Torre Grossa, meaning ‘fat tower’), whose 54 meters have made it San Gimignano’s tallest tower ever since it was built in 1311.

At ​11am​, we will depart San Gimignano to make our way to meet the 13th generation of family wine-making, from 1720 to 2020, at ​Tenuta di Torciano Wine Estate​. Pierluigi Giachi is owner and winemaker of Tenuta Torciano and carries on the centuries-old tradition together with his wife Luciana and their children, Emanuele and Vittoria. Tradition, passion, instinct and love are the principles of the success of the Giachi family. In 2020 they celebrate its 300 years of wine-making, during which the art of wine has been handed down from father to son for 13 generations. Today we will share the private vineyard and estate with the family, visit its cellars to taste a few of the hundreds of labels of Brunello and other ​Tuscan wines​. We ease into the afternoon enjoying the convivial hospitality with an outdoor wine-paired lunch with their special wines and savor their estate grown olive oil. Early in the evening we return to our countryside estate for a free night to enjoy it’s amenities.



Today will be dedicated to the discovery of the ​Brunello wine​, and ​estate Olive Oi​l. After breakfast we will depart at 8:30am to visit Montepulciano ​at 9:30am. Montepulciano is located in the Val di Chiana of Tuscany, near Val d’Orcia, one of the most attractive hills towns in Tuscany. It is built on a ridge of Monte Poliziano in the province of Siena. It is the ancient Etruscan city of Nocera Alfaterna, which in 308 B.C. made an alliance with Rome against the Samnites. In the Middle Ages it was under the control of Florence, but was conquered by Siena in 1260. The main street of Montepulciano stretches for 11.5 kilometers from the Porta al Prato to the Piazza Grande at the top of the hill. The cathedral was built in 1619, from plans by Scalzo and until the 18 C it held the tomb of Bartolomeo Arragazzi, secretary of Pope Martin V, a work of Michelozzo. The church of the Madonna di San Biagio was planned by Antonio da Sangallo (1518-37).

We depart at 11am to head to the Frescobaldi Winery at 12n for wine-tasting and a fantastic lunch at the Castelgiocondo estate​, producers of the famous Brunello di Montalcino. Todays’ lunch menu will be paired with more Brunello wine at the estate restaurant. The history of the Frescobaldi family starts over a thousand years ago and is closely connected with the history of Tuscany. At the high point of medieval Florence, the Frescobaldi’s spread their influence as bankers, earning the title of treasures to the English crown. A little later, with the flowering of the Renaissance, they became patrons of major works in Florence, such as the construction of the Santa Trinita bridge and the Basilica of Santo Spirito.

The village of Castelgiocondo overlooks the historic estate of the Frescobaldi’s in Montalcino: an ancient stronghold built in 1100 to defend the road leading from the sea to Siena. The property is one of the first 4 to begin producing Brunello di Montalcino in 1800, and its historic importance is represented on the label of Castelgiocondo by the figure of a candottiere from a celebrated fresco of the Sienese artist Simone Martini. The Artist’s depiction shows Guidoriccio da Fogliano, commander of the troops of Siena who in 1323 led the attack on the Montemassi castle; an historic moment that coincided with the initiation of the Frescobaldi family’s centuries-old adventure in the world of wine.

After Lunch we will head to ​Trequanda to experience the manufacturing of the virgin olive oil at the ​OLIVIERA SANT’ANGELO​. In 1970 Giorgio Bindi, known as Doriano, bought with his wife, Mariella Mancini, the estate Podere Sant’Angelo. Composed of an old farm house and 12 hectares with 500 olive trees, it represented a dream which Doriano had since the days in which he worked as gamekeeper. With the passing of the years the number of olive trees grew until they doubled and finally, in 1983, with the opening of the press, the dream came true. Today Doriano is no longer with us, but there is Mariella with her sons Nilo and Paolo, also devoted to their father’s passion for olive growing. Here we will sample the finest golden & emerald green Tuscan Olive oil, tasting spicy-fruity with aromas of artichokes, fresh trimmed grass and green olives.

On the way back to our hotel – time permitting – we will visit the village of ​Montalcino. The castle of Montalcino construction began in 1361 on the southern vertex of the 13C city walls, incorporating the fortified towers of S. Martino and the S. Giovanni. Il Castello di Montalcino looks much like a classic castle enclosure, based on a pentagonal plan with towers at the five angles. The walls and tower machicoulis are stone, supported by rows of brackets shaped like inverted pyramids. The northern towers are open on the side facing the courtyard. The castle also incorporated a little ancient basilica that became the chapel of the fortification, & its remains are still visible near the northeast tower. On the south side is the mighty Medicean rampart, added by Cosimo in the mid-16 C. At the end of a very satisfying day in the Brunello region of Tuscany we return for our last night stay.



8am: After breakfast and check-out, we embark on a bespoke journey to our ship in ​Civitavecchia​, the port of Rome. Enroute we will stop in the quaint village of ​BOLGHERI at 10:30am where we have arranged a rare opportunity to taste and purchase the elite Super Tuscans: Ornellaia, Sassicaia and Solaia ​(extra fee). These beautiful wines are considered top cult wines of the world. Bolgheri is a charming intimate village for those that prefer to shop for local crafts instead of the wine-tasting. We depart at 11:30am.

Next, we visit Guado al Tasso at 11:45am, another flagship vineyard of Piero Antinori and his three daughters, Albeira, Allegra and Alessia. We will share an aperitivo at this lovely countryside wine villa set amidst vineyards and farm, before sitting down to a savory 4-course wine-paired Tuscan style lunch. Guado al Tasso estate’s vineyards are set in a geographic amphitheater, encircled by rolling hillsides that faces the Tyrrhenian Sea – with an optimal microclimate with nocturnal breezes to cool down the vines. These climate conditions give the grapes pronounced aromas and a perfect ripening of the berries.

A ​Wine-paired lunch at Osteria al Tasso​ will satisfy your sophisticated and wildest appetite. After lunch, we will depart at 1:45pm and continue to the port Civitavecchia harbor by 4pm to board our 5-star ship. ​After boarding, we will gather again at 7:15pm to meet others in the group for a ​Welcome reception and O’Connell Family Wine-paired Welcome Aboard Dinner.


Villa Curina Estate Resort​: Tuscan countryside – Oct 3-7, 2021, 4 nights

Villa Curina Estate ResortThis peaceful villa, surrounded by vineyards and olive groves, dates back to the 16th century, and transformed during the 18th century, between 1776 and 1780. There is a small Italian garden, an architectural jewel located at the entrance of the Villa. The oratory of Curina is called “the little Sistine Chapel of Chianti”. Wooden floors, decorative painted walls, romantic 4-poster beds, antique furniture and the Sienese craftsmanship, help to create an atmosphere of charm and warmth typical of a country farmhouse. Modern amenities include a swimming pool, tennis court, bicycles, and a fine dining restaurant for breakfast (included), and dinner.
You may choose between a Classic room or upgrade to a Junior Suite. ​Both rooms include: Heating and air-conditioning, Safe, Wi-Fi, Room service, Minibar, Telephone, Hair dry Electric Tea kettle, Private bathroom with shower & or bathtub, Satellite TV and SKY satellite, Make-up mirror and Pool towels. ​These rooms are both located in the Villa and Scuderia annex with private entrances for maximum privacy.

Classic Room, Included in Price ​(180-220 sq ft) 
Classic bedrooms in Tuscany country style with wooden beams, antique furniture and walls decorated in relaxing colours. The style of these rooms which respects tradition in the furnishing and decorations, will award you with an authentic and genuine experience without sacrificing modern comforts. The beautiful bathrooms, some with bathtub and others with shower, are spacious and decorated with hand painted majolica tiles.

Junior Suite ​(320-430 sq ft) Optional ​ Upgrade: Add $150 pp for 4 nights 

Spacious and well-lit rooms, each different from the other with their own personality and style. Furnished with antique furniture and finely decorated; more spacious they come with a welcoming sitting room. Some are bilevel with two floors with a charming loft where the bed is located. The beautiful bathroom with hand painted majolica tiles have hydromassage showers.

O’Connell Tuscany Pre-Cruise Extension: October 3-7, 2021, 4 nights
Pricing $2,395 per person based on Double occupancy *

*Upgrade to Junior Suite for only $150 per person total ($2,545pp)

$2,395 per person​ Pricing Includes:

  • 4 nights accommodation at Villa Curina Estate in a Classic Room.
  • Group arrival transfer from the Florence Airport to the Villa in Tuscany ​(Private car available for a fee). Please provide flight details at least 45 days prior to service.
  •  Wine-paired meals included throughout the journey:
    • Hot cooked Breakfast​ daily x 4
    • Welcome Dinner ​at Hotel with wine
    • 4-course Wine lunch at Antinori Estate in Chianti Region with paired wines (e.g. Tignanello)
    •  4-course Wine Lunch at Tenuta di Torciano ​with paired wines
    • 4-course Wine lunch at Frescobaldi estate ​with paired Brunello wines
    •  4-course Wine paired lunch at Antinori Guado al Tasso, Bolgheri​(e.g. Guado al Tasso)
    •  Olive oil tasting
    • Wine tasting at Antinori Chianti – Tenuta Torciano – Frescobaldi winery + Guado al Tasso
  •  English-speaking Tour leader​ for the entire stay.
  •  Private motorcoach at the groups disposal from October 4 to October 7th with, Drivers and Parking fees, road fees, tolls, city & harbor access fees are included.
  •  Local English speaking guides in ​Siena and San Gimignano, Montalcino and Montepulciano, plus entrance fees – Headset for visit where available.


  •  Oct 7: Optional opportunity to taste & purchase Super Tuscans as Ornellaia, Sassicaia & Solaia. ​Extra fee of $TBA per person for a rare tasting opportunity.
  •  Local city tax: ​3 to 6 Euros per person, per day, to be paid locally at Villa Curina Estate
  •  Gratuities​ to tour leader, guides, porters.
  •  Items of personal nature.
  •  Everything not included in the “Price includes” list here above.

Please provide your room preference at the Villa Curina Estate (Classic Room or  Junior Suite), and advise if you would like to participate in the Super Tuscan Tasting  on October 7 (Ornellaia, Sassicaia & Solaia).

Terms & Conditions:
Prices are based on a minimum of 16 guests. Prices are in USD and are based on double occupancy. Tariff exchange rates prevailing as of the date of this proposal and thus price is subject to change without notice. Your initial deposit does not protect your price from the fluctuation of currency and quote is subject to currency rate at time of final payment. Price is subject to the final number of guests participating and may change closer to departure. Extra nights, Single and Triple rates on request based on availability. Guests must make reservations through MillenniuM Travel to participate in program activities. Advance reservation and prepayment is required. Hotel rooms are subject to availability at the time of reservation, and deposit does not guarantee availability. RSVP and deposits after June 15, 2021 will incur a $25 per person late RSVP fee. ​Final Payment due: July 1, 2021. Please provide your flight details by July 1, 2021 so that we can arrange your arrival transfer. MillenniuM Travel’s Terms & Conditions apply.

Cancellation Schedule:
Full refund if cancelled by April 1, 2021
Loss of deposit if cancelled between April 2 – June 1, 2021
50% fee of total if cancelled by July 15, 2021
75% of total if cancelled by August 16, 2021
No refund if cancelled after August 16, 2021

Travel Insurance is highly recommended.
For quotes please contact ​

DOWNLOAD THE FLYER: Exclusive O’Connell Family Wines Tuscany Pre-Cruise Program