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Italian Adventure

Trip details:

Hello Rochelle!

I read your great reviews and am looking forward to having some help in planning my vacation. I am 33 years old and will be travelling with my girlfriend to Italy for 11 days. We will be flying from the US and arrive into Milan at 8am on the 19th. We are trying to see as many places as possible but at the same time don’t want to be overly rushed. My initial thoughts were we would go straight from the airport to the train station and catch a train over to Venice. I was thinking that we would spend 2 nights there and then leave on a train to Florence the morning of the 21st. I figured we could spend a few days there and then leave on 23rd. From there I was thinking that we could rent a car and spend a few days exploring Tuscany (Chianti, Montepulciano, ect) before we head to Rome for our last two days. That itinerary might be overly ambitious so I would love to hear your thoughts and any ideas you may have as this will be our first time in Italy.

My girlfriend and I really love to eat, drink and experience new things. We are pretty adventurous people and love anything outdoors and anything off the beaten path. We are not huge museum people but would like to hit all a few of the major spots but don’t have to spend a ton of time at them. 

Our budget is probably about average as we are not extravagant but want to stay in places that are clean and friendly(hotels or Air BnB's). I do have a ton of hotel rewards and will most likely splurge on the St. Regis in Florence for two days using points. All of the other hotels I would like to keep around $100 a night but can go up to $150 for the right place. I would prefer to spend more money on food(no dietary restrictions), drinks and activities than the accommodations.

Thanks for your help and I am looking forward to hearing your thoughts.

Thank you,


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Day 1 :

  • Arrive in Milan at 8 am

  • Breakfast and taxi to the train station

  • Train to Venice around noon (in case of delays with flight or luggage)

  • After a 2.5 to 3.5 hour train ride, arrive in Venice. Rides vary on whether or not you plan to take the express train or a regular route. Click here for more info.

  • Arrive in Venice by approximately 3:30 p.m. depending on train route

  • Hotel/Airbnb check-in

  • Dinner and an unforgettable gondola ride while being serenaded by a Venetian musician. My favorite restaurant here is Trattoria Da Silvio. Really great wine and fresh salmon, other fish, and Italian cusine with fresh ingredients. They do not have a website but here is the address:

    • Calle S. Pantalon, 3748/3818, 30123 Sestiere Dorsoduro, Venezia VE, Italy

    • No reservation needed

  • Other restaurant options:

    • Alla Madonna near the Rialto Bridge  - Traditional dishes. Locals eat here. (No reservation needed; average prices)

    • Boccadoro: away from the crowds at Rialto and St. Mark’s Square. Boccadoro is a well-lit, elegant and roomy restaurant without “faux” Venetian details, and it mainly attracts locals. The host, Luciano, offers super-fresh fish served with vegetables he grows himself on the island of Sant’Erasmo, in the north lagoon (don’t bother looking at the menu and just ask what he recommends). Outstanding fresh pasta,
      like the black tagliolini with scallops and artichokes; good wine list. This restaurant is a favorite among artists and people involved in the Venice Biennale. (Reservations recommended)

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Day 2 (Morning) - Venice:

After breakfast at your hotel take a walk to the Alilaguna pier in front of the Royal Gardens (Giardinetti Reali) at San Marco to begin your 9:30 a.m. or 10:30 am off the beaten path tour to Murano, Burano, Torcello for $43 total. (lasts 4.5 hours)


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Visit Torcello, Murano and Burano—three islands in the Venetian Lagoon—on this tour from Venice by motorboat. With a guide, you’ll watch glass being blown at a Murano glass factory, see historical cathedrals on Torcello and admire exquisite handmade lace on Burano. This is a great way to see more than just the central sights of Venice and enjoy a cruise on the water. Select a departure time when booking. Your tour from Venice to Murano, Torcello and Burano begins as you board your motorboat and set off across the Venetian Lagoon to your first stop, the island of Murano, which is actually several small isles dissected by a wide canal. Disembark the boat to walk around Murano with your guide. Visit a glass factory, where you’ll watch a glass blower creating beautiful pieces of glassware, a Murano tradition that dates back to 1291. Hear a bit about the island’s history from your guide, who tells you about Murano’s prosperity in the 1400s and 1500s, when it was the center of glassmaking in Europe. Then go admire other sights like churches decorated with mosaics and other ornamental details. Next, visit Torcello, an island established between the 5th and 6th centuries, to see its ornate palaces and churches. Highlights include the Cathedral of Santa Maria Assunta, founded in the 7th century, and the excavated remnants of the baptistery in the Church of Santa Fosca. Then head to your third stop, Burano, an island known for its lace production, which dates back to the 16th century and was once the best in Europe. While you visit local shops and a museum to admire high-end lace on display, admire the island’s brightly colored fishermen’s houses. Your tour then ends with the return boat ride to Venice.


Read more about Murano, Burano and Torcello Half-Day Sightseeing Tour - Venice | Viator at:

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Day 2 (Afternoon) Venice:

Take a walk from the pier to Saint Mark's Basilica and St. Mark's Square (Entrance to the Basilica is free; Admission until 4:45 p.m.)


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Walk 7 minutes to the Rialto Bridge to cross the Grand Canal.


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During your walk, once you are ready for dinner there are several restaurants along the water once you cross the bridge. You will also notice several shops to buy souvenirs, leather, and other crafts to take back with you.

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Day 3 - Venice to Florence:

Train around 9 a.m. to Florence (2.5 hours). Book here.

Arrive in Florence around Noon or earlier.

Check into hotel.

This afternoon, have lunch in Piazza della Signoria where you can choose a restaurant and sit outdoors while you enjoy your meal and take in all the views of your surroundings. After lunch, take a stroll through the streets near your hotel. Some things to see are:

    • The Duomo - admission is free to tour this beautiful cathedral and 15 euro if you shoose to climb the 463 steps up the dome to experience a beautiful view of Florence.  

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    • Enjoy the surrounding shoppes for souvenirs or a hand-carved pinocchio, and maybe enjoy a mocha latte at a nearby cafe while you people watch or a nice dinner at one of the many restaurants in the area.

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Day 4 - Florence:

After breakfast drive a scooter: 


  • Duration: 3-4 hours

  • Departures 2017: pick your date!

  • Departing from: our Florence office at 9:30 am 

  • Ending in: our Florence office at 13:30 pm


Follow our locally-based guide up and over Mugello, to the Northern side of the Arno river on small, quiet roads rather than the usual busy routes. Our ride takes us on lovely country roads through small hamlets and villages nestled beneath the Mugello mountains. San Piero a Sieve is our first destionation, and we can admire its imposing Medieval walls and Medici-style architecture, then we continue on to a winery for a visit and tasting (not too much!). You can learn to taste your wine and look for specific fruits and grapes taste in it: many grapes will also show a spectrum of possible fruit scents that help you to identify the growing conditions—cool climate, moderate or very warm—of the vineyard. After the wine tasting, we will hop back on our Vespas for a ride to the lovely village of Fiesole, affording breathtaking views over downtown Florence... but not only that! Fiesole is an old Etruscan town, with a stunning cathedral and even a Roman theater, so, whether you would just like to stop for a few minutes to sip a cappuccino or for a more in-depth visit of the monuments, Fiesole will surprise you with its typical Tuscan charme. One final twisting descent takes up back to Florence.

Combine the freedom and exhilaration of touring by scooter with the amazing food, wine, and beauty of Tuscany. Book here.

After the tour, take a walk to Ponte Vecchio. This was by far my favorite part of Florence. The pituresque views, scenery, shoppes, and architecture are breathtaking!

    • Image result for Ponte Vecchio 

      Next, explore the San Lorenzo Market area and shop in or near Mercato Centrale:

      Whether you are looking for an activity for the whole family, a Tuscan meal, hunting for those local ingredients to try your hands at a Florentine dish or for a souvenir to bring home, the San Lorenzo Market is the place for you. The market is actually comprised of two separate markets, an indoor market, known at the Mercato Centrale, or Central Market, home to all things food and the outdoor section that lines the surroundings streets of the large Mercato Centrale building, selling leather, clothing and many souvenirs. This outdoor market (and the indoor one as well) is a great addition to your sightseeing. The indoor market is a great place for food!

      Image result for san lorenzo market area


      For dinner, I recommend Terrazza 45. This off the beaten path Florence restaurant is in Fiesole, the Etruscan town located in the hills just over the city.

      If you're looking for a romantic place to dine Terrazza45 is one of the best and highly recommended. From this rooftop terrace there is a view right onto the Florence Duomo and all of the city center, stunning!

      Terrace with view of Florence from Fiesole at Terrazza45

      The atmosphere is laid back and peaceful and candles are lit at night to enhance the mood.

      And the food? Very good: classic dishes (Tuscan meats, bistecca, homemade pastas) and some avant-garde recipes too for the more daring diners.  You'll find a few foreign influences on the menu too, like huge burgers and warm apple crumble!

      where: Fiesole, piazza Mino da Fiesole, 45 (the main square) 

      phone: 055 59 72 59 (place is small so must book)

      cost: about €30-35 a person 


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Hello By Rochelle B.
Replies (+)

Rochelle B. wrote:  

Hi Nathan! 

Thank you for all of the information! I will start by planning your trip with the details you mentioned and then you can tell me if you think it is too rushed or if you want to add more activities. Please give me until Friday evening to get back to you with an initial itinerary. 


Thank you! 

Rochelle B. wrote:  


I am still working on your itinerary. I apologize for the delay. I will send everything to you tomorrow. 


First Draft Itinerary By Rochelle B.
Replies (+)

Rochelle B. wrote:  

Hi Nathan,

My apologies for the delay. I have completed the first draft of your itinerary! Please let me know if you like what you see so far. If you are okay with this plan I can add hotels/airbnbs near the activities and sites, maps, and more restaurant ideas. I know you already mentioned wanting to stay at St. Regis in Florence, I will help you find other reasonble accomodations in the other parts of Italy you plan to visit as well. Talk to you soon.

Thank you!


First Draft By Nathan Glumac
Replies (+)

Nathan Glumac wrote:  


I apologize for the delay but thank you so much for the itineray. Everything looks amazing and you did a great job! I would love to hear what airbnb/hotel and restraunt suggestions that you may have. I haven't booked the St. Regis yet so I wouldn't mind hearing your idea on where to stay in Florence as well. If you have any winery suggestions that would be nice too. Also I am not sure if reservations need to be made ahead of time for any restaurants or wineries or if I am able to just show up.


Thank you!!


Rochelle B. wrote:  

Hi Nathan!

I am happy that you like it! I am researching Airbnb's/hotels and more restaurant options for you. The wineries I added initially were in the Chianti region, do you want me to search for more there or in the other parts of Italy you will travel to? Let me know. I will also find out if you need reservations at any of the restaurants or wineries. Talk to you soon!