The Best of Florence and Venice

September 10, 2019 2 Comments

Category: Personal
Tags: Europe, Florence, Must dos in Florence, Must dos in Venice, Travel, Venice, What to eat in Florence

We recently got back from one of the most memorable trips we’ve been on, so I wanted to share some of our favorite experiences and recommendations from Florence and Venice.

A Surprise to Remember

My mom and her husband, Rick, planned a trip to Italy to celebrate her BIG birthday but little did she know that the biggest surprise would be waiting for her when she got there… My brother, Bill and I left the kids at home and hopped on overnight flights from DC and Chicago and met them in Florence for 3 days of memorable celebrations.

We ate, we drank, we toured… but most importantly, we laughed so much and had such a great time together. Nothing is better than being with family!

Planning customized itineraries for our trips is one of my favorite hobbies, so I thought I’d share some of the highlights of our trip below. I like to do a lot of research and planning in advance and aim to find culturally authentic dining, tours and experiences to really soak in the place we visit. We love touring by foot if we can, so our plans always include a walking tour with a local expert to really understand the background and history of the city we’re in.


Florence at sunset

Overall takeaway: Florence is a city I could go to time and time again. It was beautiful, walkable and full of delicious restaurants, lively squares, great shops and lots to do. I would love to go back and spend more time there, especially within the Tuscany region, as we focused mostly on the heart of the city.


L’Osteria di Giovanni

L’Osteria di Giovanni – This was my favorite restaurant of the trip – not just because the food was delicious but because it was such a lively atmosphere and really made me feel like we were in Italy. The restaurant owner even stopped at our table, chatted with us and gifted us the most delicious biscotti and desserts.

La Leggenda dei Frati – Sophisticated, upscale Michelin-starred restaurant with spectacular view of Florence. Meant for special occasion though since it’s fancy!

Enjoying a beautiful evening outside at Frescobaldi

Frescobaldi – Delicious, authentic Italian meal within the square of Palazzo Vecchio. Perfect for any night of the week. Great for people-watching and sitting outside. We loved it so much we went twice (the truffle pasta was to die for!)

Tasting Menu at Cum Quibus

Cum Quibus – If you want to get outside of the city for a day trip, consider San Gimingano and this very cozy Michelin-starred restaurant. The garden courtyard in back only seats only 6 tables so it felt very intimate but not intimidating. We typically do not opt for uber-fancy, tiny plate tasting menus (we like to eat!) but did this for my mom’s actual birthday and it was actually the most delicious tasting I’ve had. Truly incredible restaurant experience.

Views from the top of the Westin Excelsior

The Westin Excelsior for a drink – Beautiful view of the city. Get a table to watch the sunset before you have dinner (Note: They do have a restaurant but the menu / atmosphere wasn’t our style.. felt too touristy but perfect for an amazing view and a drink)


The Mall – There is an outdoor luxury discount mall about 30 minutes outside of Florence that’s amazing

Guided Florence Tour – We took a walking tour with Paola and she was great. She’s very knowledgeable especially with art history (we had the most thorough tour at the Accademia Gallery Museum that featured many of Michelangelo’s famous sculptures, like David) and she also took us to the Duomo, Palazzo Vecchio etc. Great experience if you’re interested in a personalized experience / tour of the city and its history. She also offers a private boat ride / tour on the Arno River, which is the perfect way to kick off your evening and see the sunset before dinner. It’s only an hour or so and you can even BYOB! Info:

San Gimingano

Day trip to San Gimingano– If you’re looking for a day trip from Florence that’s not one of the popular, busy spots like Chianti or Siena, check out this small, quaint medieval town. It’s a small town on top of a hill, built within walls, and has an interesting history. We ate at Cum Quibus which was amazing (see above) and then toured local wineries in the area after.




Overall takeaway: Such a beautiful place to visit! We had a wonderful time and I am so glad I got to see it but it’s not somewhere I’d rush to go back to. I think once you’ve been, you’ve seen it!

Likes: The beauty of the city and touring it by water and foot, the picturesque views at every turn, the architecture of the homes, bridges buildings was so unique, and it’s a perfect place to walk around and get lost

Dislikes: It felt over-populated by tourists by day from the cruise ships – literally people were shoulder to shoulder, too many trinket / touristy shops, harder to find an authentic restaurant and nice glass of wine (most places felt very generic!)


Enjoying the meal and beautiful views at Lineadombra

Lineadombra – Beautiful views of Venice can be seen from this picturesque restaurant. It is upscale but warm and welcoming. Make sure you request a table from the view outside and bring a coat.. gets very chilly!

Al Covo – Very small and intimate authentic restaurant (only 8 tables or so in one room). Option of ordering a la carte or you can get a pre-fix menu. This was where we sat across from Hilary Clinton! Note: You must book in advance, credit card required to hold.


Take a walking tour of Venice with Antonella, a lovely, knowledgeable local. You can do either a 2 or 3-hour walking tour and even add on a 1-hour boat tour by private water taxi. Info: Antonella –, +39 340 2933 701

Gondola – So cheesy and overpriced (80 euros for 30 min) but fun to say you did it.

Gritti Place for a glass of champagne – There’s no place quite like the Gritti Palace.. it’s a gorgeous historical hotel that really makes you feel like you’re in old world Venice. Staying at this luxury hotel is very pricey but go have a drink or lunch to walk around and soak it in. It’s an experience in itself just being there.


Consorzio Venezia Futura Water Taxi was an incredible experience in itself!

Consorzio Venezia Futura Water Taxi – This private water taxi can pick you up at either the train station or airport. Convenient and easy way to get to/from to your hotel but best of all, you also get a boat ride to see Venice.
Info: +39 342 106 8412;


Bill and I at the St. Regis Venice

St Regis Venice – This hotel was less than 2 weeks old when we stayed there and we selected it because it was new and modern (which is very different than every other traditional Venetian hotel). We splurged on it but it was one of the absolute highlights of the trip. Amazing courtyard patio for drinks, directly on the water and less than 5 min walk to St. Mark’s Square.

Hope this was helpful if you decide to book a trip in the future! Let me know if you have any questions.

More memories of our trip are below



2 thoughts on “The Best of Florence and Venice

  1. Avatar for Angie Rose Randall


    Beautiful photos!

  2. Avatar for Angie Rose Randall


    Thank you for sharing Angie!!!

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