A trip of a lifetime sounds cliche, but it’s exactly how I feel about the past twelve days of July across Italy with my family. We knew our time would be limited and our desire to see as much of the country at once was high — so we spent months maximizing an itinerary that would fulfill that very wish.

I’m here to spill all the details for you. If I don’t hit something you’re curious about, feel free to leave a comment or message me on Instagram!

How did you plan the trip?

Ever since rebooking this trip (originally planned for February 2020 when visiting my sister abroad), the uncertainty of the trip hung over our heads. We had flights booked and itineraries outlined, but until Delta’s COVID-free flights were announced, we had no idea what would even be possible.

My sister Julia gets total credit for the city order and broad itinerary of activities and excursions. Because she was immersed in the Italian culture as a student in Florence last January/February before being sent home due to COVID-19, Julia learned the ropes quickly. She understood how to navigate transportation throughout Italy and was very confident in the train system, which we loved and recommend.

Second, Julia is a total planner like me and had already made detailed arrangements to travel to cities including Venice, Rome, Milan, and the Amalfi Coast. Because these trips were planned for later in the Spring 2020, she never made it there. But, luckily for us, we already had an outline of how to get there, what to see, and (of course) where to eat. Her network of abroad friends shared top restaurant recs and opinions on hotels/tours, so we were in an advantageous place to curate something truly special based on already-vetted itineraries of friends.

I didn’t want to share plans prior to experiencing them in case details fell through — however, every day exceeded our expectations, and I’m so excited to share our highlights with you.

Where in Italy did you travel?

We traveled to Rome, the Amalfi Coast, Florence, Venice, and Milan. If possible to book flights that arrive to and depart from different Italian cities, I recommend it — it forces you to see more and not feel too tied to one home base!

Here is our broad city-to-city timeline by day. I’ll drill down into the details later if you keep scrolling!

Day 1: Rome
Day 2: Rome
Day 3: Naples/Pompeii (arrive/sleep in Positano)
Day 4: Positano
Day 5: Sorrento/Ravello (sleep in Positano)
Day 6: Capri
Day 7: Florence
Day 8: Florence
Day 9: Venice
Day 10: Murano and Burano
Day 11: Milan
Day 12: Milan

How did you determine the timing/order of these cities?

Looking at a map, this order made perfect sense for us. We arrived in Rome, a fairly centrally-located city, and immediately headed South to Amalfi before making our way back up and departing from Milan. If we had more time, we would have kept going to Lake Como, Cinque Terre, or Turin.

None of us had been to the Amalfi Coast before, which is a vacation in itself, in essence. I’m happy we bookmarked those leisurely days with jam-packed sightseeing.

Two nights seemed to be the sweet spot for each location. Our time in Amalfi was precious; but had we not programmed our days, we would have regretted the length. Four nights feels more appropriate for a honeymoon or totally resort-focused stay.

Note: The demand appears to have skyrocketed now that travel is opening back up. We booked our flights and hotels months and months ago, so our rates do not reflect what is currently shown.

Did you make reservations everywhere for meals and activities?

Of course, I love a good day or two of agenda-less adventuring — but with a group of seven, spontaneity was less feasible. We kept afternoons fairly open for free time but ensured no meal or activity would go unplanned otherwise!

Restaurants appreciated the reservations for planning purposes (especially for a table for seven), but advance notice is not necessarily mandatory.

My advice: lean on your hotel concierges! Once you book a hotel stay, the concierge team is at your disposal at no extra cost — even prior to arrival. I had difficulty calling restaurants from the States to inquire, but I then learned that emailing the hotel concierge was pure magic! They can book your excursions, restaurants, and even transportation for you. They are trusted sources and will become fast friends!

How was traveling with COVID protocols?

Italy was hit incredibly hard in the early days of COVID-19, as we all remember. The Lombardy region was essentially ground zero of the pandemic. Their economy is still crushed, but their people and populations are now healthy, vaccinated, and safe. We were some of our drivers’ and tour guides’ first American tourists. Wearing a mask in Italy is not a debate; it’s simply what everyone does as a part of daily life. No measure felt “overdone” or under-considered; it was a perfectly at-ease environment.

Delta and Italy** updated their COVID policy the week before our flight (July 1), allowing a vaccine card as standalone satisfactory proof for entry onboard. Prior to July 1, you needed to show a negative PCR COVID test regardless of vaccination status. We went ahead and got a negative COVID test since we had already made appointments — and just in case we ran into an issue. Looking back, the PCR test in Memphis was not necessary, but it was nice for peace of mind!

Currently (as of July 17, 2021), the United States requires a negative COVID test within three days of re-entry. Marriott had an online reservation platform to book rapid tests at the hotel in Venice. While the tests were not free, we were informed that submitted receipts to our health insurance once back home could ensure reimbursement. Our results were emailed to us within an hour, and the concierge printed copies to take with us to Milan and back home. It was a seamless process. Delta required the paperwork during check-in with our passports. You can’t get away with this step, so don’t risk it!

**Note: Every country has a different protocol for travel. This is specifically our experience with Italy during July 2021. I cannot speak for other destinations!

How did you travel between cities?

Julia introduced us to Italo, a high-speed train service around the country. It was phenomenal. We purchased “Primo” ticket levels, which were not first class but felt like it. Clean, well air-conditioned, friendly staff. We were provided with wipes, free Wi-Fi, drinks and snacks while on board. The train reaches 300 km/hr, so our trains were less than 2 hours each.

Our family is full of early risers, which was key to maximizing our time in each place. We took morning trains to arrive to each destination by lunch time. You can nap on the train if you need to — but the earlier, the better!

Upon arrival in each city in Italy, if you’re traveling with less than four people, taxis (or water taxis, in Venice!) are clean and safe to get you from place to place. Train stations in these major cities are centrally located, so we would find our trips to take less than 10 minutes.

Our only exception to trains was navigating the Amalfi Coast. You must take a train to Naples and arrange private transportation to reach your Amalfi destination. I recommend Rainbow Limos! Because Capri is an island, you must navigate by boat. We had a private boat for the day from Positano to Capri (more on that below). To leave Capri the next morning, we took the SNAV high-speed hydrofoil from Capri to Naples. I was very impressed.

Again, if you have any concerns or questions about transportation, lean on your hotel concierges.

How did you pack?

It’s hot in Italy in July! I recommend light, airy dresses or linen shorts (don’t forget a shoulder covering for the basilicas!) for every single day. Sneakers during the day and flat sandals at night are all you need. I wish I could have reworn outfits, but I’d sweat too much from walking, ha! Hotels offer laundry services if you stay long enough. I’ll be sharing outfit links soon, to those who asked!

Now, let’s recap each city.

ROME

Landing in Rome is perfect. The history and awe-inspiring architecture encapsulates you immediately upon arrival. Plus, the history and tour-focused city keeps you on your feet when you’d otherwise prefer a post-plane snooze. We went straight through the day after landing at 9am, and while I would’ve fallen asleep if seated for more than 2 minutes, the Coliseum and squares kept us moving.

Rome Hotel: Westin Excelsior (With some exceptions, we enjoyed sticking with Marriott Bonvoy hotels and were very pleased across the board.)

Rome Sites/Activities:

Coliseum
Piazza di Spagna / Spanish Steps
Piazza Navona
Pantheon
Trevi Fountain
Vatican City Museums & Sistine Chapel
St. Peter’s Square / Basilica

Rome Standout Meals:

Armando Al Pantheon — Order the Rigatoni all’Amatriciana and have them pair wine for you.
Da Enzo al 29 — They open at 7 p.m. with a long line. Arrive by 6:40 and you’re set for the first seating. Italians eat late, but you want to make sure you have a spot! Order their chalkboard specials and award-winning Carbonara.

AMALFI COAST

The Amalfi Coast is magical. While less “historic” compared to Rome and other major cities, its views and overall atmosphere are medicine for the soul. I am so happy we picked Positano as our home base, as we were able to see the entirety of the coast within arm’s reach.

As explained earlier, we took an Italo speed train from Rome to Naples. A private driver took us from the Naples train station to the ruins of Pompeii just 45 minutes away. After a jaw-dropping walk around Pompeii, we continued 45 minutes further to Positano.

Amalfi Coast Hotels:

Hotel Villa Franca (Positano) — Could not recommend this hotel enough. I think it was my favorite of our entire stay. The hour-long complimentary breakfasts, concierge service, immaculate rooms and pool/amenities were beyond all expectations. It literally sits at the top point of Positano with the greatest view imaginable, and a complimentary shuttle every 30 minutes can take you down to town or pick you back up until midnight.
Capri Tiberio Palace (Capri) — Exquisite, large, colorful rooms with Sophia Loren inspiration. A fantastic pool and view of the Capri coast. Perfectly situated next to restaurants and shops.
Unpopular opinion: We only stayed one night and didn’t feel the splurge was worthwhile for just one night. Unless you’re interested in sitting by the pool and walking to shops in total vacay mode for a week, I don’t find it to be worth it as an overnight destination, particularly for the price. Positano is much more central and allows you to see the full coast (and Capri within reach!) at your leisure.
Hotel Caruso (Ravello) — We did not stay here but I wish we had! We dined here, and I’m pretty sure it’s heaven on Earth. The gardens are absolutely immaculate. I haven’t seen the rooms, but I would be outside at the infinity pool or camped out in the gardens’ lounge seating during every waking hour.

Amalfi Coast Sites/Activities:

Ruins of Pompeii (en route from Naples to Amalfi Coast)
Spiaggia Grande beach (Positano) — Reserve chairs at L’Incanto Beach Club
Cooking Class with Foodies from Sorrento — Gio and Sancha were such a highlight! Gnocchi alla Sorrentina and Scialatielli Cacio e Pepe were on our custom lunch menu. The kitchen is immaculate and totally “Instagrammable.” We had the greatest time and learned so much!
Villa Rufolo (Ravello) — An absolute must-see. We had a private car take us from Positano through Ravello (with an hour stop to roam here) before dinner.
Blue Grotto (Capri) — Wild! You have to lay flat in a canoe to enter the Blue Grotto. The five minutes inside are unforgettable.
Private boat (Positano to Capri) — Greatest day we could have asked for. Ask your hotel concierge for a recommendation of a private boat service, as there are many. The skipper will take you to caves, hidden gems around Capri, and can even arrange lunch for you. We put all of our luggage on the boat, making it a seamless vehicle from Positano to Capri.

*Hotel Villa Franca is the white building at the very tip top!*

Amalfi Coast Standout meals:

Ristorante Max (Positano) — Magical outdoor setting in the heart of Positano. Order the Tagliolini Scampi and veal — and save room for dessert.
Da Adolfo (Lunch) (Positano) — The restaurant sits in a secluded hut about 10 minutes from Positano’s main beach, and its character will carry you away for the day. You can only access it by boat! Get a reservation through your hotel concierge. Look for the Da Adolfo boat at the Positano port to transport you to lunch complimentary. Order the grilled mozzarella on lemon leaves, fresh catch, tuna carpaccio, and lobster pasta.
Ristorante Belvedere at Hotel Caruso (Ravello) — Best negroni of my life. Go for apertivo and then enjoy a meal under the stars overlooking the coast. The meal felt a bit too pretentious (perhaps due to our waiter), but the food was excellent. Each pasta was better than the last.
Il Riccio (Lunch) (Capri) — During our private boat day, we docked here for lunch. The prices are outrageous, but you can’t beat the freshness of the seafood. I enjoyed a scallop dish with uni and caviar. The prawns by the kilo were the best we had all trip. It sits next to an insane Christian Dior Capri showroom and is literally 10 feet from the Blue Grotto entrance.
Aurora (Capri) — Order the truffle cacio y pepe and veal with truffle and mustard. Best all-around meal of the trip. I love that they serve zucchini fries to the table to get the meal started!
Unpopular opinion: La Tagliata’s scenery was so memorable, but the food was not! We did not realize we’d be limited to pre-made, pre-fixe family-style courses. The staff/owners were so kind and lovely, but when giving me the kitchen tour, it was confirmed they pre-make all of their food in big chaffing dishes.

FLORENCE

Florence was Julia’s “home” and the only Italian city I had visited before, so it felt like a beautiful reunion.

Once we arrived, Julia guided us to her old apartment on the way to the Duomo. We passed a wine bar, where Julia had befriended the entire staff. Armando, a waiter at the wine bar, saw Julia — and it was the most touching reunion I had ever witnessed! Everyone was so worried about each other during the COVID-19 lockdown. We had a beautiful catch-up and were so relieved to learn everyone was healthy and recovered.

Florence Hotel: Westin Excelsior — Right along the water but perfectly set five minutes away from the noise of the Ponte Vecchio, this Westin location has beautiful rooms and the best rooftop for apertivo in town.

Florence Sites/Activities:

Duomo
Accademia Gallery (Michelangelo’s David)
Pitti Palace/Boboli Gardens — Start your day here in the gardens!
Gucci Garden — Impressive exhibit of Gucci’s history and collections over the decades
Florence Outlets (if you’re in the mood to shop!) — Take a cab 30 minutes to immaculate outlet malls with deep discounts on designers.
Leather market
Central market
Ponte Vecchio
Tuscany — We did a vespa/farm and winery tour with Private Tuscany Tours and absolutely loved it. Our guides were fantastic. While winery hopping could be fun, I thought this was a perfectly curated opportunity to see the sprawling hills, eat and drink authentic Tuscan delicacies, and get to know the area in just a half day.

Florence Standout meals:

A'll’Antico Venaio (Lunch) — The hype is real. Paninis bigger than your head and fully loaded with the most delicious toppings! Try the truffle spread and artichoke spread as a base.
La Giostra — Order the pear ravioli and filet. The dark setting with candles and twinkling lights is so romantic!
Osteria Delle Tre Panche — They’re known for truffle, and the truffle ravioli is next-level! However, unpopular opinion: The truffle entrees essentially take their pasta truffle sauce and pour it over chicken, beef, veal, etc. I should have ordered differently, as the redundancy was too overwhelming for me!
Sbrino Gelateria: Order the cookie butter gelato. Insane.
My sister has so many other recs from living there — we just didn’t have enough time!

VENICE

Venice was the surprising highlight of our trip. Our entire family agreed it was a top two destination from our itinerary — of course, everyone differs on their favorite city! Venice, Murano and Burano can be seen as tourist traps traditionally, but we felt incredibly lucky to experience a pure, quiet, clean (not smelly, I promise!) version of the city on water. We laughed at my rookie mistake of booking dinner “5 minutes away” on Google Maps without realizing a 50 Euro water taxi was required. But alas, we learned so much about the city’s history while there and leaned into the renowned history-meets-fashion and arts attributes of the area.

Venice Hotel: St. Regis Venice — Absolutely gorgeous and worth every penny. The restaurant and garden patio sits right on the water. The rooms were beautifully appointed, and the lobbies were breathtaking. The concierge was very helpful with our COVID tests as well as navigating the windy streets of town.

Venice Sites/Activities:

Jewish Ghetto + Synagogues + Jewish Museum — The history begins long before the Holocaust, and it’s incredibly important to learn and experience.
San Marco Square
St. Mark’s Basilica
Murano — Known for its gorgeous glass-blown creations
Burano — Known for its lace, whimsical shops and colorful buildings
Gondola ride — What’s a trip to Venice without it?
After-dark water taxi on the Grand Canal — Private homes keep their lights on and windows open, boasting beautiful chandeliers and fresco ceilings that you can see from the water.

Venice Standout meals:

Lineadombra — An outdoor breathtaking scene on the water with Michelin-appointed seafood. The salt-crusted seabass for the table was outstanding.
Ristorante da Raffaele — We happened across this Venetian spot near our hotel for lunch and absolutely loved it. Order the Maltagliati with prawns and pesto.
Gio’s at St. Regis — We opted for a final meal on the water at our hotel, which did not disappoint. A female chef from Sicily heads the kitchen with gorgeous presentations and techniques. Order the gnocchi with clams, fried prawns and avocado, and slow-cooked short ribs.
Al Covo — We had to cancel this lunch reservation last-minute since we were stretched for time, but I’ve read wonderful reviews.
Trattoria al Gatto Nero (Lunch) (Burano) — What a gem. Elegant, whimsical dining with witty conversations led by restaurant owner Max. The pappardelle with prawns, fried king prawns, and seabass with cherry tomatoes and wine were all outstanding.

MILAN

Our time was brief, but we managed to see as much as we could in a day. I find Milan to feel more like a London/New York with metropolitan mannerisms. It arguably made me miss the traditional Italian charm!

Milan Hotel: Westin Palace — Literally 3 minutes from the train station and situated near beautiful parks.

Milan Sites/Activities:

Duomo + Duomo Museum — Don’t just tour the interior of the Cathedral; go to the roof! Walking above the cathedral is arguably the neatest viewpoint of Italy I’ve ever experienced.
San Siro Museum — If you’re a football fan, you can see one of the largest and most renowned soccer stadiums in Italy. Alex absolutely loved it, especially days after Italy was crowned champion of Euro 2020!
Golden Goose Lab — The HQ is one of the original design labs for personalized sneakers. I had so much fun picking out my pair.

Milan Standout Meals:

Paper Moon — I felt like I was in Paris! A stunning garden welcomes tables filled with fresh pastas, meats and seafood. The large menu will accommodate any diner.
Rataná — If you’ve seen Stanley Tucci’s Italy series, this lunch spot was on his Milan episode. Next to a beautiful park and gardens in the Financial District, we tried traditional Milano staples and artful appetizers like beet hummus, crudo, and a raw tomato soup.

A Trip of a Lifetime: Twelve Days in Italy (July 2021)