Getting There from San Diego: How I Did It
If you’re in CA, you’ve got a few options for getting to Italy: Fly from San Diego International (SAN) - you’ll usually connect through hubs Dallas, ATL, CHI. The Drama: My original United flight got messed up last minute (classic). I ended up rebooking to fly out of LA- honestly worth it for a direct overnight to Rome. My Route: I love an adventure (and avoiding airport parking fees), so I took the Amtrak train from San Diego up to Union Station in LA. From there, the FlyAway Bus goes straight to LAX- super easy and pretty affordable. Travel Tip: If you book Economy Light on Norse Airways or similar budget-friendly airlines, watch for sneaky carry-on fees! They’ll charge you extra $80 for a standard-sized carry-on, so plan ahead.
Florence: Walkable Streets, Wine Windows, Shops & Pasta
Why Florence is a vibe: Florence is so walkable- you’ll stroll everywhere on cobblestone streets, pass Renaissance churches on accident, and pop into boutiques for bags and sandals you didn’t know you needed. Arrive in Rome (FCO) Follow the signs to the train station in Terminal 3 and took the Leonardo Express a smooth, non-stop ride that got me to Roma Termini in just 32 minutes. From there, try to catch the Frecciarossa high-speed train to get to the heart of Florence in 90 minutes. The Drama My 2 friend's checked bags got lost in their rebooked flights. I waited at the airport with them and we missed the last high speed train. There were limited options late at night, so we got to a smaller station on the local 3 hour train to Florence.
Shopping: Ponte Vecchio is the famous bridge lined with jewelry shops, boutiques, and artisan stalls. Even if you don’t buy anything, it’s an iconic stroll.
First Glass wine window ring the bell to get mini bottles to go or sit inside to get a glass, some AC and use the restroom.
Sunset: Piazzale Michelangelo - bring a bottle of wine, climb the stairs just above San Niccolò, and watch the sun hit the red rooftops.
Happy Hour Drinks: View on Art rooftop- great Duomo views, spritz in hand.
Dinner: Osteria Pastella - pasta tableside in a cheese wheel, so save your appetite!
Do the classics: Climb to the top of the Duomo, see the replica David at Piazza della Signoria, wander the tiny streets and find a wine window. take a pasta making class.
Vivoli Gelato was one of my favorite foodie stops, where I lined up early for their famous affogato: espresso poured over a scoop of creamy gelato & pistachios that tasted like absolute heaven in a cup.
Capri: Lemon Groves, Beach Clubs & Warm Wedding Nights
Why Capri is different: Capri is magical. Think cliffside hotels with old-school glamour, blue grottos, hidden beaches, lemon trees everywhere, and family-run restaurants that have been around for generations. It’s smaller and more intimate than Positano. Capri is super chic but laid back if you know where to go.
Take the train to Naples (~2.5 hrs from Florence) Take ferry to Capri (~30 mins).
Shuttle to and from Hotel Weber Ambassador -classic cliffside spot with views of Marina Piccola.
Dinner: Da Paolino - the one with lemon trees everywhere. It’s so dreamy at night. Worth the late (11 PM) reservation.
Rooftop sunset at Luna Hotel, dinner at Pulalli - tiny terrace right next to Capri’s main piazza clock tower. Lemon risotto here is the move.
Take the chairlift from Anacapri up to Monte Solaro: the highest point on the island. It’s a peaceful 12-minute solo ride up in an open-air chair, gliding over lemon groves and terracotta rooftops with 360-degree views of the sea, cliffs, and boats below. At the top: Stunning panoramic views of the Faraglioni rocks, Mount Vesuvius, and the whole Bay of Naples and a row of cute little shops selling handmade sandals, ceramics, linen sets, and the best lemon-themed souvenirs
White Welcome Party: La Capannina - old-school Capri, tucked away in town, known for classic Capri bites like fried zucchini flowers and fresh local mozzarella. Wedding Day: La Zagara: In Anacapri (the quieter side of the island)- lush gardens, lanterns, the works. Capri knows how to do romance.
Capri Beach Clubs
Luigi Al Faraglioni
Luigi ai Faraglioni Beach Club: Family-run, blue and yellow umbrellas, right by the famous Faraglioni rocks. These clubs usually include your beach chair, umbrella, towel service, and sometimes a light lunch option like 60 Euro credit to the restaurant. Always check what’s included! Most spots serve up fresh salads, seafood pasta, or sandwiches, plus a bottle of local white wine or rosé is a must.
I had Spaghetti alla Nerano! It’s the iconic Capri (and Amalfi Coast) dish: spaghetti tossed with thinly sliced fried zucchini, fresh basil, lots of grated local cheese (usually provolone del Monaco or Parmigiano), and often finished with butter or a bit of the starchy pasta water for that silky, creamy texture.It was invented in the little village of Nerano (between Sorrento and Positano) and you’ll see it everywhere in Capri. Every beach club or family trattoria does their own twist, super simple, super fresh, super summer.
Bagni Tiberio
Bagni Tiberio: A bit more casual than Luigi - green umbrellas, an easy vibe. Free boat shuttles run to Marina Grande every 15 min. Order lunch at your sunbed and you’re living the dream. Fresh fruit, buckets of ice water, Peroni beer and panini sandwiches were our go to's for the day. We brought floats for relaxing in the Mediterranean sea.
Boat Day: Champagne, Saxophones & Too Much Pasta
One of the absolute highlights of the trip was our Boat Day- because Capri from the water is its own kind of magic. swim under the Faraglioni, pop prosecco, maybe see the Blue Grotto (touristy but iconic, bummed it was choppy so we couldn’t see it). We spent the day sunbathing, swimming through hidden coves, and anchoring off the coast for a long, way-too-big lunch at Conca del Sogno - a dreamy restaurant tucked into a secret cove near Nerano.
Here’s how it went down: We pulled up on our boat and they shuttled us in on a little dinghy -barefoot, salty hair, and me… with a barf bag in hand running to the bathroom. As I sat down and began nibbling on some bread I heard the server say family style? And before this sea sick girlie's Zofran dissolved under her tongue...we suddenly had platters of food- salads, appetizers, whole fish ...flying onto our table. Pasta? Of course! We had Spaghetti alle Nerano (the famous zucchini pasta), Spaghetti alle Vongole, tomato gnocchi, lobster linguine -because why choose just one? Everyone was slightly hungover, a little bit seasick, and 100% not ready for round two- until the surprise Limoncello show hit. The bride and groom had secretly arranged a whole scene: A saxophone player appeared out of nowhere and started playing Italian remixes right in the middle of lunch. The staff came out with whistles, headbands, and began stretching their bodies for the massive pitcher of Limoncello, they were about to force us to drink. Then they brought out champagne guns- literally spraying bubbles across our table down our throats while the entire restaurant cheered, filmed, & joined in clapping & dancing.
What started as “Should I just order a salad?” turned into a full-on dance floor.
This day was proof that on the Amalfi Coast, you’re never too hungover for a Limoncello moment.
If you’re planning your own boat day, Conca del Sogno is the move: arrive by boat, order too much pasta, and let the Amalfi Coast do the rest.
Positano: Cliffside Views, Speakeasys & More Lemon Everything
Why Positano is different: Positano is iconic- a vertical village spilling down to the sea. Chic hotels, colorful umbrellas, more bustling than Capri, more lively than Florence. Expect stairs and expect to fall in love with them and the Porters who carry your bags up and down said stairs.
Ferry Capri to Positano (~1 hr). Airbnb check-in at Kings View: the views are exactly what you imagine.
Dinner: Lo Guarracino cliffside with classic Positano pastas (& Vegetarian options!)
Dinner: Miskaki Sushi: Positano’s Japanese spot for when you’re over pasta (just for a sec). They have an entire vegetarian menu with gyoza, crispy rice, and specialty rolls.
After: Don’t Worry Bar at Le Sirenuse Hotel: a speakeasy hidden inside the most famous hotel in town.
Go Out: Music On The Rocks, Positano’s legendary cliffside nightclub.
Chez Black- iconic beachfront pizza + pasta. Must dress nice.
Hike the Path of the Gods: epic cliff views, 3+ hour hike. (We didn’t have time.)
Arienzo Beach Club: Cliff Jumps, Limoncello + a Wild Show
If you’re in Positano, Arienzo Beach Club is the spot for a true Amalfi Coast beach day. Unlike the more polished main beach in town, Arienzo feels a bit more local - a pretty pebbly cove tucked just past the cliffs, reachable by boat or a lot of steep steps. The beach itself is rocky (yes, bring sandals) and full of hidden treasures: we spent forever picking up tiny bits of beach glass polished by the waves. And unlike some Amalfi beaches, Arienzo actually has waves that crash in… which felt so refreshing after days jumping into bodies of water.
We made a whole day of it- cliff jumping into the deep blue, sunbathing under orange umbrellas, sipping cold spritzes, popping bottles of Veuve, then regrouping for the famous Arienzo lunch. (Beach club day packages here usually include a reserved beach chair, umbrella, towel service, and a multi-course meal. Ours came with an appetizer, a main, and one bottle of rosè.)
But the real highlight? The Limoncello show. Picture this: Everyone at the club is a few spritzes deep, the DJ turns the music up, and the staff suddenly appears with my friends carrying huge signs, big frozen bottles of Limoncello. They picked my friends to be the stars- they had to sit in special beach chairs and hold up the signs while the beach club crew danced around them. Then… chaos. They poured cold Limoncello straight into their mouths, over their shoulders, down their backs, all over the chairs. Everyone on the beach was cheering, filming, chanting “Limooooooncello!” It turned into this hilarious, messy, over-the-top party moment right there on the pebbled beach… exactly what you want from a Positano beach club day.
By the time we packed up, we were sticky from the sun and Limoncello but zero regrets. If you want to get the full Amalfi vibe: jump off a cliff, swim it off, then let the beach club crew pour icy Limoncello all over you…because you’re only in Positano once.
Arienzo Tip: Reserve early (seats sell out fast), bring extra cash for boat taxis, and don’t wear anything you don’t want covered in Limoncello.
Rome: Big, Bustling & All the BEST Food
Why Rome is different: Rome is big and full of huge piazzas, ancient ruins around every corner, buzzing local neighborhoods. It’s less walkable than Florence but so worth exploring. Pick a few areas to wander each day.
Ferry back to Naples then train to Rome (~1 hour).
Airbnb check-in: extra space, fridge for Aperol and snacks, more local vibe than a hotel.
Evening: Explore Trastevere- charming, boho neighborhood packed with bars, restaurants, cobblestone streets, and locals out late. This is where I stayed this time and enjoyed so much more than my first weekend trip here.
Breakfast near the Pantheon- stunning ancient temple, early morning = fewer crowds.
Hit the Trevi Fountain (early!) and the Spanish Steps- grab a coffee and people watch.
Travel Tip: Connect to the wifi outside of the designer stores to see where your crew is and ask Chat GPT to take you on a walking tour with interesting stories along the way.
Lunch in Piazza Navona - fountains, street artists, pasta al fresco.
Dinner Dar Sor Olimpio al Drago - classic Roman trattoria
Foodie highlight: Rome is the carbonara, cacio e pepe, and Fettuccine Alfredo capital so don’t skip a true Alfredo experience. Alfredo alla Scrofa, the birthplace of the original Fettuccine Alfredo- impossibly rich, creamy, and made candlelit table side with just butter and Parmigiano.
Tiramisu, Two Sizes is the best quick stop they offer two sizes of tiramisu to go.
Gelato at Giolitti the real Roman deal. Add whipped cream on top. Pay first then order.
Wander Campo di Fiore market for fresh fruit, flowers, people yelling (in the best way).
Sunset at Janiculum Terrace- city views forever.
Night: Court Bar, the chic cocktail bar at Palazzo Manfredi that overlooks the Colosseum. So moody, so Rome. It was listed in The World's 50 Best Bars for top tier cocktails and views. Dress code is smart-casual (think crisp pants, cute dresses. Steer clear of flip flops and guys wear pants.) Reservations are a must for the view.
Cocktails at Jerry Thomas Speakeasy
Quick breakfast at Antico Forno Roscioli : pastries to go for the airport ride.
Metro (or Uber) to Train to go to Fiumicino Airport. I was pleased to know I could walk to the Trastevere Train station after my Ubers kept canceling on me.
Arrivederci! If you’re dreaming of an Italy trip, save this post- because you could be the Type A queen with the spreadsheet, the beach club loungers reserved, and the extra carry-on full of linen sets and snacks. Bring your crew, splurge on the sunset spritzes, and say yes to a different gelato everyday!
Now I’m back to work teaching and already dreaming up where Après Sweat should meet next. Got recs?