Wine & Culinary Tour of Tuscany & Cinque Terre | 2019

$2,750 per person based on double occupancy
$325 single occupancy upcharge

Price includes all breakfasts, all lunches, all dinners, all beverages (except optional happy hours), six nights of hotel accommodations, all winery tours and tastings, luxury bus transportation with an on-board restroom, and unlimited boat travel for one day within Cinque Terre. Air and taxi fare is not included.


Your choice of 2 tour dates (all are Sunday through Saturday)
TOUR #1 ~ May 5-11, 2019 ~ SOLD OUT
TOUR #2 ~ May 12-18, 2019 ~ 13 seats available

Each tour maxes out at 54 guests as that's how many seats are on the bus.

>>> Please SCROLL DOWN for the hour-by-hour itinerary below, but here’s an overview of the highlights. This will be a comprehensive, week-long wine and culinary tour of Tuscany including Florence, Chianti, Montepulciano, Montalcino, Montecucco, Maremma and Bolgheri with the finale in Cinque Terre.

The tour will start in Florence and end in Porto Venere. Porto Venere is on the coast of the Italian Riviera and is the gateway to Cinque Terre. I thought it would be an awesome place to end the tour as many of you will want to extend your stay in this gorgeous paradise. Those of you who need to get back to Florence right away (or any other place in Europe for that matter) can easily take the train out of nearby La Spezia. So here's the itinerary:

We'll meet at Hotel Croce di Malta in the old part of Florence where we’ll spend the night. (And yes, I will make arrangements for discounted group rates for those of you who want to come in a day or two early, or return here and stay a day or two longer.) The hotel building dates back to Roman times and was a convent up until the mid-1800's before being converted into a hotel. It’s remodeled on the interior but kept the charm of the era on the exterior. For those of you taking the train into town, the hotel is an easy three blocks walking distance from the train station. For those of you flying into Florence, taxi fare from the airport to the hotel is a fixed price of 24 euros per taxi. The taxi ride takes about 20-30 minutes. Many taxi drivers do not take credit cards so be prepared with cash.

After a meet ‘n’ greet orientation in the hotel bar, we’ll walk as a group over the Arno River to All'Antico Ristoro di Cambi, a famous bistro located in an over 500-year-old building that used to be a convent. Here we'll enjoy "bistecca alla fiorentina" (the mother of all steaks and the local specialty of Florence) along with a seemingly endless supply of side dishes and plenty of local wine. Then we'll walk back to the hotel for the night.

Our bus will pick everyone up at the hotel in the morning and we'll head south into the heart of Chianti. First stop will be at Badia a Coltibuono, a top-notch Chianti producer located in an ancient monastery. We’ll tour the extensive gardens and cellars, and then enjoy a tasting of four Chiantis. We’ll start with their current release regular Chianti followed by their current release Riserva Chianti. Then owner Roberto Stucchi has graciously agreed to provide a couple of older, not-available-to-the-public vintages of Riserva. This will be a rare opportunity to experience firsthand how well these wines age after a decade or so.

Next we’ll go to what I think is hands down the best restaurant in Gaiole in Chianti, Ristorante Le Contrade. My friend Andrea Oppo is the extremely talented chef/owner of this out-in-the-middle-of-nowhere restaurant with sweeping views of the countryside and ancient villages. We’ll start with a quick visit to the gardens with an obligatory Rosemary Gin Tonic in hand. Then we’ll sit down for a unique, cold plus hot fantasy of seasonal trios that will be different for each tour. When I last visited he prepared tea smoked duck breast salad + sea beans with beet puree and gorgonzola ice cream + a cappuccino (the foam was whipped parmesan and the coffee froth was grated truffle) for the cold fantasy trio. Then out came the hot fantasy trio with crispy lasagna with sun-dried tomatoes + oversized semolina gnocchi with grated truffles + quail stuffed with foie gras. I know everyone is going to love this place and I’m already concerned about how I’m going to get everyone to leave!

Next stop will be Tolaini Winery in the southern part of Chianti. After leaving his native Tuscany over fifty years ago to start one of the largest trucking companies in Canada, founder Pier Luigi Tolaini returned to pursue his true passion of making great wine. With his mechanical background Pier created a state-of-the-art production system with unique, two chamber fermentation tanks that I’d never seen before. He even made his own custom tractors that fit between the rows of their tightly spaced vines ... which you’ll get to drive if you’d like! After the tour we’ll adjourn to the cellar for a tasting of their wines with local olive oil, cheeses and salamis.

After Tolaini we'll check into Hotel Montaperti just outside of Siena which will be our hotel for the next two nights. Since many folks will be just getting over jet lag, I thought we’d take it easy this first full day and have an early dinner at the hotel so everyone can catch up on some sleep.

After breakfast we’ll explore a couple of wineries that are actually within the walled village of Montepulciano. There’s no way a bus can get through the narrow streets of this hilltop village but fortunately there’s a parking lot relatively close to the wineries where we’ll be dropped off and picked up. It’s still a bit of a steep hike though so start taking the stairs instead of the elevator to get those thighs and calves into shape!

First stop will be Talosa Winery. We’ll enter their unassuming, tiny front entrance only to descend four stories down (sorry, no elevators) to their spacious 16th century cellars. Here we’ll have a private tasting of their Rosso, Vino Nobile, and Vino Nobile Riserva paired with some bruschetta and Italian cold cuts. After hiking back up (to work off the cold cuts!) we’ll walk over to De’Ricci.

De’Ricci Winery is laid out very similar to Talosa in that you enter from a small entrance on the top level and then descend about five floors into a cellar cathedral dating back to 1337. Walking through this underground stone cathedral with thirty-foot high ceilings and packed with massive wine barrels is an awe-inspiring, almost sacred experience. Once we exit the cathedral, we’ll enter a giant dining room where we’ll have a cooking demo hosted by a local cooking instructor. We’ll start with some bruschetta appetizers and salamis while she demonstrates how to make pici, the local hand-rolled pasta. Then she’ll show us how to make aglione sauce, a traditional spicy garlic-based sauce for the pici. Then we’ll eat the Pici all'Aglione! All of these courses will, of course, be paired with their wines. Finally, owner Enrico is going to bust out some older Vin Santo from his personal stash for dessert which he’ll pair with some local blue cheese from nearby Pienza, some cantucci (local biscotti) for dipping, and some nuts and local chocolate pieces. After lunch we’ll have an hour or so of free time for you to explore the village before hiking back to the parking lot where the bus will be waiting for us.

Next stop will be Avignonesi, a biodynamic winery about a half hour outside of the walled village. Here we’ll take short trek to see their experimental circular vineyards and then visit their historic cellars. Finally, we’ll visit their famous Vin Santo aging room similar to a miniature version of a Kentucky Bourbon rickhouse. And, similar to Bourbon, Vin Santo barrels do not get topped off so there’s a whole lot of “angel’s share” floating around in that room. Producing old Vin Santo is a risky and expensive business ... sometimes when a barrel is finally tapped a decade later over 80% has evaporated to the “angel’s share,” leaving a paltry 20% left to bottle. But oh, what a delicious 20%. After the short tour we’ll sample their high-end wines and have a few appetizers to tide us over until dinner.

Dinner will be in a private castle tonight! About halfway between Montepulciano and the hotel is a beautifully restored castle, parts of which date back to the 800’s. Father and son team Salvatore and Antonio Gangale (that would be the original Salvatore of Salvatore’s restaurant in San Diego!) spent over twenty years meticulously restoring Castello delle Serre to its original splendor and converting it into a high-end B&B. Once we arrive, they’ll give us a tour of the historical grounds before serving an elaborate multi-course dinner of traditional Tuscan appetizers, pasta and osso buco in the castle cavern. After dinner we’ll get back on the bus for the short twenty-minute drive back to the hotel for the night.

After breakfast we’ll pack up and leave Hotel Montaperti to explore wineries in the Montalcino area. It’s Brunello di Montalcino time! First stop will be way off the beaten path to visit the iconic Silvio Nardi winery. We’ll do a quick tour of their vineyard and cellars but then we’ve got a special post-breakfast, pre-lunch treat in store for you. Their resident chef is preparing a trio of savory cheesecake + lasagna + cinghiale meat balls for us to pair with their premium wines. The tasting will be on their outdoor patio but owner Emilia Nardi has graciously offered us the use of her private great room (she lives on site) in case the weather doesn’t cooperate. We’ll also enjoy their excellent Vin Santo paired with a small dessert tasting before bidding good bye.

Next stop will be Ciacci Piccolomini Winery about 45 minutes south. This winery has a fascinating history of successive ownership beginning as a palace in the 17th century. Then it was auctioned off and subsequently resold in the late 1800’s. Then an interesting turn of events occurred: In 1985 the countess who owned it bequeathed the entire property to a farmer who had worked the land for many years. He built up the winery and dramatically increased both the quantity and quality of the wines produced there. After he passed over a decade ago his son and daughter, Paulo and Lucia, took over the business and continue to produce exceptional wines. Paulo is also an accomplished cyclist and those of you interested in cycling will especially enjoy the unique tasting area filled with racing bikes. Anyway, here we’ll take the short trek up the hill to visit the cellars before returning to the private tasting area below to sample their wines and olive oil and enjoy some Tuscan cold cuts and cheeses.

Final stop of the day will be another 45 minutes south at ColleMassari Winery which conveeeeniently has a resort-like hotel and restaurant on sprawling grounds overlooking the Tuscan countryside a mere five minutes away. First stop will be at their winery for a quick tour. (We’ll forego the tasting at the winery and have it for a pre-dinner reception back at the resort after everyone’s had a chance to check into their rooms and freshen up.) The owners of ColleMassari are Swiss (so that should tell you something about the precision and cleanliness of the facility!). I’ve obviously seen a lot of wineries before but this one had not one, but two new techniques that I’d never seen before: a totally enclosed (to prevent oxidation) automated punch down system plus a CO2 (the sometimes deadly by-product of fermentation) recovery system that automatically evacuates the gas from the sealed tanks through a sealed line that’s actually the top rail of the safety hand railing around the tanks. Leave it to the Swiss!

After the winery we’ll head five minutes up the road to their “hotel.” I use the word “hotel” loosely because this is not your ordinary hotel. While the construction is new, the original stone buildings in place for centuries were meticulously disassembled and then meticulously rebuilt so that the exteriors look original but the interiors have all of the modern amenities. Since our group is so large we’ll be taking over the entire property ... plus an additional (equally nice) estate another five minutes down the road. (To put it in perspective, rooms here would easily go for $400-500 a night stateside ... if they existed.) After everyone’s had a chance to check into their room and freshen up, we’ll meet for a reception to taste the wines that we missed on the winery visit. This will be a nice opportunity to relax, walk around the grounds, admire the views, and chat it up with your new friends before dinner. Dinner will be a multi-course, seasonal menu based on locally sourced Tuscan ingredients paired with plenty of wines. And, of course, there will be Vin Santo with dessert and Grappa afterwards before everyone heads back to their villas for a refreshing night of comatose sleep.

After breakfast we'll leave the hills of Tuscany and head west towards the coast. (After all the bistecca and cold cuts y’all are getting ready for some uber fresh seafood now, right?!) First stop will be at the halfway point in Maremma to visit the architecturally amazing Rocca di Frassinello winery. Located in the middle of 3,000-year-old Etruscan ruins (I’ll spare you visits to the tombs but you can see videos of them in their museum if you’re interested), this is an exceptional winery out in the middle of nowhere. We’re now moving out of Sangiovese land and moving towards the coast where the Bordeaux varietals of Cabernet and Merlot are stand-alone stars or are blended with Sangiovese to create “super-Tuscans.” Rocca di Frassinello typically blends these three varietals to create their high end wines which have been featured in Wine Spectator’s Top 100. It’s a spectacular property with a mobile crush pad on the winery roof deck that drops the grapes one level below for fermentation, and then one level below that to their one-of-a-kind barrel room amphitheater. Make sure you’ve got plenty of battery life left as you’re going to want to take lots of photos here. After the tour we’ll have an informal tasting of their wines along with a light lunch of panzanella, cold cuts, cheeses and pasta salads. (We’ve got a lot of ground to cover today so we won’t be stopping for a formal lunch; instead we’ll have two light lunches at two wineries. You will thank me later when we have our seafood dinner feast on the Ligurian Sea in a few short hours!)

After Rocca di Frassinello we’ll head straight to the coast to Bolgheri. This is where some of the finest triple-digit price tag wines in all of Italy come from. Our one and only stop here will be with none other than Bolgheri wine pioneer Michele Satta. (Michele’s first vintage was 1983; the Bolgheri DOC was established in 1984.) Michele is one of the most passionate winemakers I know, and his passion is contagious when you meet him. He will personally take our groups on a short trek through the vineyards next to his winery to briefly explain his farming techniques and the impact that the sea has on the vines before bringing us back to his new tasting room on top of his winery. There we’ll taste his wines and enjoy light pairing lunch #2 of crostini, Tuscan tomato soup, pesto pasta, cheese, and vegetables dressed with his olive oil. Should be just enough to tide everyone over until dinner.

From Bolgheri we’ll settle in for the two-hour bus ride up the Italian coast. We’ll pass by Pisa and Cararra where you’ll see the famous Cararra marble quarries before hitting La Spezia, the beginning of the Italian Riviera. From La Spezia it’s a jaw-dropping, thirty-minute scenic drive overlooking the cliffs to the ocean below before we get to Porto Venere, our final destination and home for the next two nights. Since the village of Porto Venere is so small, there’s not one single hotel that can accommodate our entire group but I was able to contract with two equally beautiful hotels one block away from each other. We’ll check into our rooms, freshen up, and then meet for an optional no-host cocktail hour at the hotel’s ocean view terrace bar. Then we’ll walk the short distance down the hill to the harbor where we’ll take over Ristorante Elettra where we’ll have the first of several seafood inspired meals to come. Looking over the harbor from our private terrace room while enjoying seafood caught from the waters below promises to be a relaxing finale to a day that covered three wine regions. Whew! And yes, I will have an after dinner grappa, thank you! After dinner we’ll make the ten-minute walk up the hill back to the hotel and call it a night.

Today is Cinque Terre day! Aside from lunch in Monterosso at 1:00 and dinner back at the hotel in Porto Venere at 8:30, the day is yours to do as you wish. I will provide everyone with a one-day unlimited boat pass to the villages of Cinque Terre. (On rare occasion, the seas are too rough for the boats to sail. If that happens, I will shuttle everyone to the La Spezia train station and buy everyone a one-day unlimited train pass to the villages of Cinque Terre. Unfortunately. the train does not stop in Porto Venere so you’ll have to cross your fingers that the boats will be running in the afternoon and that you can take a boat back ... or you’ll have to take the train back to La Spezia and taxi back to Porto Venere. Either option will set you back about 15 euros.) I know this sounds terribly complicated but once we get there, I’ll explain the options thoroughly and it will all make sense. In the meantime, I highly, highly, highly (whenever I use the same word three times in a row that means to take heed!) recommend that you google Rick Steve’s YouTube videos of Cinque Terre to get a better feel for how special this isolated part of the world is. It’s definitely on many folks’ bucket list so I thought it would be an amazing place for the tour finale.

Anyway, we’ll have lunch at Hotel Pasquale in Monterosso at 1:00. Monterosso is the fifth and northernmost village of Cinque Terre. On the way there (by boat) you'll see Riomaggiore (the first and southernmost village), followed by Manarola (village #2), followed by Corniglia (village #3), followed by Vernazza (village #4) before arriving to Montorosso (village #5). Pasquale is located literally at the end of the boat dock as you enter the village so is very easy to find. There will also be an optional complementary pesto making class just before lunch if you’re interested. Lunch will be an amazing seafood fest including lobster and other local delicacies. And, of course the deliciously crisp yet rich local Cinque Terre white wine (the only white I’ve ever had that can stand up to lemon) will be free flowing.

But I got ahead of myself. As most of you may already know (or will know after you’ve done your “homework” of watching those Rick Steves YouTubes!), Cinque Terre is a hiker’s paradise. For those of you who want to burn off some calories before lunch, I’ll take whoever wants to join me on the 8:45am boat out of Porto Venere that will put us in Monterosso in just under an hour. From there we’ll either take the train (5 minutes) to Vernazza and then hike back to Monterosso ... or hike to Vernazza and then take the train back to Monterosso in time for lunch. This hike will take one-and-a-half to two hours and has elevation changes equivalent to a 65-story building.

For those of you who would prefer a more leisurely start to the day, there are boats leaving Porto Venere at 10:00, 10:30 and 11:00 that will all get you to Monterosso in plenty of time for lunch. I’ll point out the boat dock on the way to dinner the night before but it’s less than a five-minute walk from the hotel.

For anyone wanting to hike some more after lunch I’ll take whoever wants to go (via train) to Corniglia and then we’ll hike back to Vernazza and take the boat from there. This hike is about the same length and difficulty as the first one. (Hiking passes are about five euros and an unlimited train pass is about twenty euros but the train pass includes a hiking pass. Here again, I’m sure it sounds complicated now but it will all make sense when we get there!) Unfortunately the trails from Corniglia to Manarola, and from Manarola to Riomaggiore were closed when I was there in May of 2018 and it is unlikely that they will be reopened in time for our tours. Please keep in mind that if you do want to do these trails, they are extremely rigorous and somewhat dangerous. Please make sure you’re in excellent shape and wear the appropriate footwear. (No flip flops ... not even for me!)

And for those of you who would prefer not to do the after lunch hike, you’re on your own to explore the villages. They are all quaint and beautiful and each has lots to offer. The boat has frequent service to all of the villages (except Corniglia which is only accessible by train or hiking trail) so you can hop-skip your way down the coast and visit as many or as few as you want. The train is quite a bit faster and runs more frequently so another option is to purchase a train pass and then take the boat back to Porto Venere. The last boat of the day arrives back to Porto Venere at 6:50pm so just make sure you consult your boat schedule so you don’t miss it; otherwise you’ll have to take the train to La Spezia and then taxi back to Porto Venere. (It’s not the end of the world if this happens ... but it is a little inconvenient and will cost you a bit more.)

Once back in Porto Venere for the night we’ll all meet up at the hotel’s terrace bar overlooking the ocean before dinner for another optional no-host happy hour and then have our finale dinner at the hotel. Dinner will, of course, be a seafood fantasy of whatever was freshly caught that day. It should be an amazing way to end the tour and yet another great dinner for the record books!

After dinner you’re free to go upstairs and call it a night or, for anyone wanting to extend this final night a bit longer, we’ll adjourn to the terrace bar for a nightcap or two.

The tour is officially over after breakfast Saturday morning but I suspect many of you will want to extend your stay in this enchanting area for another day or two. (And yes, I will make arrangements for discounted group hotel rates for those of you who want to stay longer.) Those of you who need to head back to Florence (or anyplace else in Europe) can easily take a shuttle, taxi or bus to the La Spezia train station about thirty minutes away and then make your connections there. If you’re going back to Florence there are many daily trains. The train takes just under three hours and costs less than twenty euros. Options are unlimited at this point as you can pretty much take a train anywhere in Europe from La Spezia. Whatever you do though, have fun! If commitments back home allow, I definitely recommend taking advantage of this opportunity to do some additional exploring.

Here's the hour by hour (subject to modification) itinerary.



Fly or take the train into Florence on your own any time before evening (or a day or two before)

Check into Hotel Croce di Malta any time before evening

05:00pm meet at Hotel Croce di Malta in Florence for orientation

06:15pm dep Hotel Croce di Malta (15 minutes on foot)

06:30pm dinner at All'Antico Ristoro di Cambi

08:45pm dep All'Antico Ristoro di Cambi (15 minutes on foot)

09:00pm walk back to hotel for the night


07:30am breakfast at hotel

09:00am dep Florence

10:30am arr Badia a Coltibuono for tour and tasting

12:30pm dep Badia a Coltibuono

12:45pm arr Restaurante Le Contrade di Vinci for lunch

03:00pm dep Restaurante Le Contrade di Vinci

03:30pm arr Tolaini for tour and tasting

05:15pm dep Tolaini

05:45pm arr Hotel Montaperti (check in for 2 nights)

07:00pm optional no host pre-dinner cocktails at the hotel

07:30pm dinner at the hotel

09:00pm spend night at the hotel after dinner


07:30am breakfast at hotel

09:00am dep hotel

09:45am arrive parking lot #7 in Montepulciano; walk to Cantina Storica Fattoria della Talosa

10:00am arr Cantina Storica Fattoria della Talosa for tour and tasting

11:30am dep Cantina Storica Fattoria della Talosa; walk to De’Ricci

11:45am arr De’Ricci for tour, cooking demo lunch with paired wines

01:30pm dep De’Ricci; free time in Montepulciano; walk back to parking lot #7

02:30pm dep parking lot #7 in Montepulciano

03:15pm arr Avignonesi for tour, tasting and very light snacks

05:00pm dep Avignonesi

05:45pm arr Castello delle Serre for castle tour and cocktails

07:00pm dinner at Castello delle Serre

09:00pm dep Castello delle Serre

09:30pm arr Hotel Montaperti for the night


07:30am breakfast at hotel

09:00am dep hotel

10:00am arrive Silvio Nardi for tour and food pairing

12:45pm dep Silvio Nardi

01:45pm arr Ciacci Piccolomini for tour, tasting and light snacks

03:15pm dep Ciacci Piccolomini

04:15pm arr ColleMassari Winery for tour only

04:45pm dep ColleMassari Winery

05:00pm arr ColleMassari Hotel & Restaurant; check in

07:00pm pre-dinner reception at the hotel

07:30pm dinner at the hotel

09:30pm spend night at the hotel after dinner


07:30am breakfast at hotel

09:00am dep ColleMassari Hotel

10:00am arr Rocca di Frassinello for tour, Etruscan tasting experience, and wine tasting with light lunch

12:00pm dep Rocca di Frassinello

01:00pm arr Michele Satta for vineyard trek, tour, and wine tasting with light lunch

03:15pm dep Michele Satta

05:30pm arr Hotel Belvedere and Hotel Paradiso in Porto Venere (check in for two nights)

07:30pm optional no host pre-dinner cocktails at the hotel

08:15pm walk to Elettra for dinner (10 minutes on foot)

08:30pm dinner at Elettra

10:30pm walk back to hotel for the night


08:45am early boat departs Porto Venere

09:50am early boat arrives Monterosso

10:00am early hikers train to Vernazza and trek back to Monterosso

11:00am late boat leaves Porto Venere

12:20pm late boat arrives Monterosso

12:45pm optional pesto making class at Pasquale

01:00pm lunch at Pasquale in Monterosso

03:00pm free time in Cinque Terra with boat or train passes

06:50pm last boat arrival to Porto Venere

07:30pm optional no host pre-dinner cocktails at the hotel

08:30pm finale dinner at the hotel restaurant


07:30am Breakfast at Hotel Paradiso and Hotel Belvedere in Porto Venere (tour over)