The heel of Italy: Puglia, Italy Wine Club Tour March 2020

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Two Wine Clubs / Two different dates  

~Bjornson wine club: fly out March 28 – April 7, 2020 

Bjornson trip is sold out.

~Left Coast wine club: fly out April 17 – 27, 2020 

Left Coast trip is sold out.

10 days/ 9 nights

9 nights four-star resorts, wine tasting, 10 lunches and dinners (some wine-paired), Michelin restaurants, two half-day easy bike tours through the countryside, walking tours in 5 ancient villages, cooking class, winery / vineyard tour and tasting, tour and olive oil tasting at 2,000 year old olive grove, more.

from $2,817


boats small

Verdant blue waves of crystal blue waters lap onto Adriatic shores.

flowers olives s

And deep green Roman – Empire olive trees still thrive and produce.

locorotondo pano s

Ancient hilltop-towns soar above

 vineyards full of Negroamaro grapes

truli grp flowers s

mingled with 500 year old trullis, hobbit-like houses existing only here.

deb memo sea 2 s

A friendly people with smiling faces

monopoly boats 2 s

because they know they live in one of the most beautiful regions in all of Italy.

truli flowers s

A land so rich in colors,

lecce col s


gravina aquaduct shistory

ostuni pizza s

and food

sea bike s

it does not appear to be even possible. 

This is Puglia 

Join Dan and Deb in one of their favorite places in Italy for a 10-day tour with your wine club. 

This is one of the reasons we have done  this business for 35 years: exploring marvelous places with friends old and new.

Bonus: Puglia (poo lee ah) is small and we will never have a drive longer than one hour during the entire journey.

from $2,817

Click for Puglia logistics page.

We highly recommend you protect your trip with a Trip Insurance policy.  CLICK for details.

Included in this outstanding travel value:

~9 nights  4-star hotels with daily breakfast, 6 nights are in 500 year old masserias (old farm fortresses).

     They have been transformed  into beautiful  modern properties.

~Seven dinners included – three of these at a Michelin restaurant. One of the Michelin dinners will be wine-paired 

~ Private Italian cooking class 

~ Culinary walking dinner tour of Altamura’s local restaurants

~ 2 half-day-guided bike tours in the countryside. Option to upgrade to electric bike. Tour ends at hilltop town of Locorotondo with a wine-paired lunch.

~ Guided private walking tours of Gravina, Matera, Lecce, Ostuni, and Alberobello

~Wine-paired lunches in Ostuni, Locorotondo, and Alberobello

~ Two private wine tastings

~ Olive oil tasting at a Roman Empire era farm amidst 2500 year old trees   

~ALL ground transportation on our own private chartered bus

~ Our luxury Masseria hotels are truly stunning. UPGRADE to various levels of suites for an extra cost. 

~ As with every one of our tours, Dan and Deb will be right there with everyone eating, wine tasting, and enjoying la dolce vida. 



     Puglia is a breath of fresh air… something completely unexpected… a balm for the spirit…a respite from the crowds …a break from the touristic… a rabbit hole which transports you back 30 years. Puglia is the heel of Italy. For those fortunate enough to visit, it connects to simpler times and a natural landscape that is increasingly difficult to find. No hype, no hordes of tourists… just natural wonders, great wine and food,  and fascinating history.

          If you want to experience how Italy used to be,  join us on our wine and food tasting journey through Puglia. 


See below for the many exciting details of this Puglia journey. Take the time to read the descriptions of the itinerary. Be sure to look at the numerous linked photo galleries. If you do, you will understand our enthusiasm for this region Italy’s heel.

IMPORTANT  NOTE: We have limited space for this exclusive tour. For the two stays at the 4-star masseria hotels, there are several upgrade room choices and limited base-level rooms available. Rooms assigned on first-come/ first-served basis. Once the base rooms are gone, it will be necessary to upgrade to another room class at additional cost. The upgrade rooms are assigned on a first-come, first-served basis. It is critical to read the Puglia Logistics page carefully to understand all of these options.

Click for Puglia logistics page.



DO NOT book any air until the trip has been declared a “go” by us!  Once we reach our minimum participants threshold, we will give the go-ahead for you to purchase air. 

 Bjornson trip: Book your flight to arrive in Bari, Italy any time on March 28th. Taxi from airport to hotel not included, 10 minute ride.  At end of tour: You will be transported  to the Bari airport on the  morning of April 7. Please do not book any return flight before 10 AM.

   Left Coast trip: Book your flight to arrive in Bari, Italy any time on April 17. Taxi from airport to hotel not included, 10 minute ride.  At end of tour: You will be transported  to the Bari airport on the  morning of April 27. Please do not book any return flight before 10 AM.

Day one ~  Arrive Bari, Italy airport (BRI) and hire a taxi for the 10 minute ride to Nicholas Hotel in Bari. 


Day two  and three lodging: Your first Masseria ~ 

Move to Masseria Pitti. We are on our way to what will be your first masseria experience. Masserias were farm/fortresses from the 1600s. Olive oil and wine was produced in caves under the properties. The defensive fortress-like estates were constructed to ward off pirate attacks. Our two masserias for the next three nights will be the Laudati and the Luoghi di Pitti.

Both properties are 5 minutes apart. Both are family-run gorgeous hotels. The package includes the 3-star Laudati and the Pitti is an upgrade. Two of the included dinners will be at the Pitti with the third being a 3 hour walking dinner tour in Altamura. Best of all: we will be the ONLY people in the masserias…all ours!  

CLICK for photo gallery of Masseria I Luoghi di Pitti.

Deb and Orazio touring the gorgeous stone hall.

Deb and Orazio tour Masseria di Pitti. 


This is what Masseria San Giovanni looked like 12 years ago!

             This is what I Luoghi di Pitti looked like 12 years ago

                          Masseria Laudati


Day 2 ~ 

Gravina – walking tour of this unique and historic village with underground olive oil and wine making facilities that date back many centuries. There will be free time to explore and have lunch. We will visit Gravina on our way to our first night at the Masserian Pitti. 

Click for Gravina photo gallery.

Gravina is in a spectacular setting, rich in history above and below the ground. We will tour both.

Gravina is in a spectacular setting, rich in history above and below the ground. We will tour both. 


Day 3 ~ 

Get ready to be stunned. Matera, an ancient hilltop town that features 2,000 year old cave homes under the modern city, will be our tour for the day. Free time to explore and have lunch.

        Matera is a hilltop town that is now the location of many movies.

Click for Matera for photo gallery.

Late afternoon return to our masserias for free time. Our dear friend Orazio, Maître d at Luoghi di Pitti has organized a walking dinner/wine-paired tour of his home town, Altamura. This ancient town is charming. We did this walking dinner tour on our last trip to Puglia and it was a big hit. It helped to walk a bit between restaurants. It is a three hour food and wine extravaganza!

              Dan and Orazio


Day 4 ~  

Alberobello, a Unesco site. This town has more trullis per square foot than anywhere in the world. A short guided walking tour followed by a wine-paired lunch. Free time after lunch. 

                Trulli capitol of the world… Alberobello is a marvel.


Day 5 ~

Move to Masseria Cervarolo. We will visit Ostuni, the White City, for a short walking tour followed by a wine-paired lunch.  

         Ostuni wine-paired lunch with a view.

Click for Ostuni photo gallery.

 Masseria Cervarolo is located in a pastoral country setting and only 10 minutes from Ostuni. This property is a centuries-old farm/fortress that has been beautifully restored. Many of the rooms are trullis! Replete with a beautiful pool area, full-service spa, and a Michelin restaurant. Cervarolo is perfectly located and within short driving distances of all the sites we will visit. 

On our first night at Masseria Cerverola, you will have a double treat in store. First, a Puglian cooking class in the late afternoon. A 4 course wine-paired dinner at the Cervarolo’s Michilen restaurant follows. Bonus: A local som will be there during the entire meal to share notes about each wine! As with our other masserias, we will be the only guests in the hotel…all ours! 

                                                              Click for photo gallery of Masseria Cervarolo.

                      Masseria Cervarolo… a “trulie” unique hotel



Day 6 ~ 

A half-day-long bike ride along an easy pathway that winds through vineyards, olive trees, trullis, and panoramas you will never forget. All gear is provided, electric bike upgrade available. We will finish our ride in the hilltop town of Locorotondo with a 2 hour wine paired lunch at a restaurant with great panoramic views of the valley we will have just rode through.

                                                               Click for photo gallery of bike ride day.

OUr day ride to hilltop Locorotondo is full of trullis, vineyards, olive groves, and natural beauty. Along a smooth path, anyone can do this ride.

     Our day ride to hilltop Locorotondo is full of trullis, vineyards, olive            groves, and  beauty. 


Day 7 ~ 

Lecce: one of the best-preserved baroque cities in the world. Two hour walking tour followed by free time and lunch on your own. 

                                 Deb in central piazza of old Lecce

Click for Lecce photo gallery.

Depart Lecce, visit  a local vineyard and winery for a tour and tasting at Cantina San Donaci.   After that a guided visit to  Masseria Brancati for a short tour of an olive grove that hosts tress planted in the first century by the Romans. There is  tree that is 2,500 years old and is still producing. Olive oil tasting. 


Day 8 ~ 

Half-day bike ride, Parco della Dune Costiere… The ride takes us through the Ostuni countryside with panoramas of the Adriatic coast and the Puglian landscape. Electric bike upgrade possible.

                                                   Biking by the sea.

Click for photo gallery of Parco della Dune bike ride

Late-afternoon wine tasting. Dinner in Ciglie Messapica, a nearby village. Zitto y Manga is a family-run authentic Puglian trattoria. It’s name translates “Shut up and Eat!”.. and you will!

                                 Zitto y Manga… Shut up and eat!

 Click for Ciglie photo gallery. 


Day 9 ~  

Depart for Monopoly. On the way we will visit Polignano a Mare, a village dangling over a high sea. It was home to Domenico Modugno who wrote and sang “Volare”. There is an incredible restaurant here located in a sea cave. 

One of the most spectacular settings for a restaurant, the Cave at Pulignano is a marvel.

                                                                      Amazing cave restaurant


eb takes a break on a bike ride with the breathtaking Pulignano a Mare in the background.

                                                    Polignano a Mare..a lovely stop on our way to Monopoly

Click for Pulignano a Mare and nearby coastal region photo gallery.


Monopoli  has been inhabited since 500 B.C. It is a seafront town with plenty of piazzas and restaurants. Our hotel is in the heart of the old city near a castle built in 1086.

  Click for Monopoli photo gallery.


Skiman's favorite Monopoli photo. He passed Go and got $200 for this one!

         Dan’s favorite Monopoli photo…. a nice town to wander at night.


 Last Morning

Morning depart for the Bari airport


 For all air  details, UPGRADED room options and costs, deposit/cancellation details, Click  for  Logistics Page.