Curated by: Lucas Santos & Ben Dumas
Travel Period: May 2014
Traveled With: Five other couples
Typical Weather: Around 70 during the day and 50’s at night. 
Getting There: NYC – Florence, connecting in London.  Total travel around 10.5 hours and flight cost $750. 
Getting Around: We rented a van for transporting the crew around (side note, very hard to get an automatic transmission large vehicle, so learn stick!)


  • Castello Di Reschio: We were lucky enough to stay at a friend’s unbelievable family home while in Italy, just on the border of Tuscany and Umbria.  The villa was located within the Castello Di Reschio estate, true historic-castle-style-living but will all the modern amenities, with an infinity pool overlooking vineyards and olive groves.  This was a uniquely fortunate experience, and we’re including it in this list more as a way to provide context to our photos vs. being a reasonable “stay” option for most.
  • Portrait Firenze: If you’re looking to really treat yourself and splurge on the room, this is the spot.  The location is as perfect as the views of the Arno.  Rooms have a modern look but you still feel like you’re in Italy!
  • Il Salviatino: If you’re willing to be a bit more secluded but still have access to Florence sites, this 15th century villa, turned boutique hotel, is the perfect spot.  With an amazing pool area overlooking the Tuscan hills and views of Florence, this is the perfect place to get away from the action. 



  • Piazzale Michelangelo: Not too far of a walk from the center of Florence, just South of the Arno, Piazzale Michelangelo offers stunning panoramic views of the city.  Bring up some wine and cheese and it’s the perfect sunset spot.  Amazing photos and good times guaranteed.  Best of all, free!
  • Museums:  Uffizi Gallery & Galleria dell’Accademia are probably the two most popular museums in Florence, and not to be missed if that’s your thing.  If that’s not your thing, we’d recommend heading to Palazzo Vecchio, overlooking Piazza della Signoria, which contains an exact copy of Michelango’s David statue outside in the square, so you can beat the lines at the museum and still check “David” off your list. 
  • Villa La Pietra: Home of NYU’s Florence campus, but also home to one of the most spectacular gardens in Florence.  They offer tours of the gardens and villa grounds on Friday afternoons (when all the kids leave campus).  Maybe I’m partial because I went to school here, but I think it’s worth a stop. 


  • San Gimignano: About and hour from Florence, this tiny walled medieval town is a great stop on a drive through Tuscany and makes you feel like you've gone (way) back in time.  There is a bunch of cute little shops, casual lunch spots, and gelateria's.
  • Siena: Just over an hour from Florence, Siena seems like a smaller and sleeipier version.  It's central square, Piazza del Campo, is a great place to sit down with a glass of wine and relax.  We unfortunately missed it, but each year on July 2nd and August 16th they have the Palio horse race through Piazza del Campo which is a high-energy medieval revival of an very old tradition.  
  • Tartufi Bianconi: About 1.5 hours drive from Florence, this day of hunting and eating truffles was one of our best in Italy.  First you go out in the woods with a very informed older Italian guide and his truffle hunting dog to search for the goods.  The 3-4 hour tour also came with a truffle cooking demonstration, tour of the Bianconi farm, and ended with a delicious truffle filled lunch and wine pairing in what felt like the owners personal dining room.  120€ each, but well worth it.


Dinner & Cocktails

  • La Giostra: This is my hands-down favorite restaurant in Italy and a must-try for anyone passing through Florence.  It has a cozy and authentically-Italian vibe with a rich history, founded by (actual) princes with a passion for food.  Each of my visits to La Giostra included not only the most amazing meal (Bistecca all Fiorentina and gorgonzola gnocchi were my favorite) but also a visit from the charismatic owner and sons who make the dining experience all the more special.  From the greeting with a glass of prosecco to talking through the menu with the owner himself, this is a place the makes you feel at home and leaves you feeling fat and happy. 
  • Il Palagio: This fine dining Michelin star restaurant at the Four Seasons Hotel is amazing for a fancy dinner out.  They also have a nice patio and outdoor seating perfect on warm night. 
  • Gusto Osteria Piazza Santo Spirito: This place is away from the crowds of central Florence, just south of the Arno in Santo Spirito.  Is has a more local and laid back feel, with hand written menu’s and the most delicious lasagna ever!
  • La Terrazza: This chic rooftop bar perched on top of a medeieval town at the Continentale Hotel is a great pre-dinner cocktail spot to watch the sun go down over the Arno.
  • Da Delfine: Just a few miles outside of Florence in old stone farmhouse, this place feels like grandma’s house, serving up delicious Tuscan dishes.  Get a table on the large terrace to take in Tuscan views.

Casual Lunch & Snacks

  • Gusto Panino: This little sandwich shop just south of the Arno is worth a visit.  Simple but quality ingredient’s and affordable panini’s make this a great lunch option if you’re in Santo Spitito, my favorite piazza with a more local vibe.  Grab a panini and glass of wine and sit out on the church steps to take in what feels like authentic Italy.
  • Pizzaman Via Dell’Agnelo:  Located in Santa Croce, this is the our favorite pizza in Florence, a must try!
  • Carabe Gelato:  You really can’t go wrong with Italian Gelato, but this place was definitely one of best – and trust me we tried a lot of gelato. 
  • Mercato Centrale: This market is a great spot to grab fresh pasta, cheese, wine, prosciutto, and whatever else you’re craving, and to take it out onto the streets to enjoy.   

Below Pictures by: Lauren Richardson