Start your first morning with an espresso and sfogliatella at Caffè Gambrinus, then head to the atmospheric lanes of the Spanish Quarter for a walking introduction to everyday Neapolitan life and street art. Continue to the hilltop Castel Sant'Elmo for sweeping views over the Bay of Naples and a short wander through the adjacent Certosa di San Martino museum to get oriented with the city's art, history, and skyline.
After a morning of panoramic views, spend the afternoon exploring the heart of Naples starting with a guided walk through Via Toledo and the elegant shopping arcade Galleria Umberto I, where you can sip a leisurely aperitivo. Meander down to the waterfront to visit the imposing Castel Nuovo (Maschio Angioino) and then stroll along the Lungomare Caracciolo, pausing for a seafood lunch at Trattoria da Nennella or a scenic gelato with views of Vesuvius to set the tone for an evening in the historic center.
As dusk falls, wander into the atmospheric lanes of Piazza del Plebiscito to admire the lit facades, then take a short walk to the elegant Teatro di San Carlo for an evening tour or-if available-a short concert to feel Naples' operatic heartbeat. After the performance, savor a classic Neapolitan dinner at Pizzeria Sorbillo (Via dei Tribunali branch) or choose a cozy seafood trattoria in Santa Lucia while enjoying views across the bay toward the illuminated silhouette of Castel dell'Ovo.
Wake up to sea breezes and begin with a leisurely breakfast of lemon granita and brioche at Bar Ercolano, then wander the cliff-top Villa Comunale park for postcard views over the Bay of Naples and a quiet photo stop. From there, follow the scenic coastal promenade toward Marina Grande, where you can watch fishermen mend nets, browse stalls selling local limoncello, and enjoy a mid-morning seafood tasting at Ristorante Da Emilia before continuing your exploration of Sorrento's winding lanes.
After a relaxed morning by the sea, head to the charming hillside neighborhood of Piazza Tasso for people-watching and a light lunch at Ristorante O'Parrucchiano beneath its lemon groves, then wander down to the dramatic clifftop Valle dei Mulini lookout for atmospheric ruins and photo ops. Follow the scenic footpath to Marina Piccola to catch a short boat trip to the secluded Bagni della Regina Giovanna tidal pool for a refreshing swim, finishing with a tasting of artisanal limoncello at Limonoro before sunset.
As twilight falls, settle into the intimate seaside ambiance of Marina Grande's waterfront for aperitivo and watch fishing boats bob under the cliffs, then stroll up to the panoramic Terrazza Vittoria for sweeping night views of the Bay of Naples and distant lights of Vesuvius. For dinner, dine on fresh seafood and homemade pasta at the family-run Ristorante Il Buco, followed by a digestif tasting at the cozy, aromatic I Giardini di Cataldo to round out a relaxed Sorrento evening.
Begin with a sunrise drive along the scenic SS163, stopping at the cliffside Belvedere di Sponda for sweeping sea views and morning light on the pastel villages; follow with a relaxing breakfast of sfogliatella and espresso at Bar Internazionale in Praiano overlooking the water. Afterward, take the short ferry from Praiano to Positano's Fornillo Beach for a gentle swim or a stroll past boutique shops, then climb the ceramic-lined stairways to visit the family-run Franco Senesi Ceramics workshop to watch artisans at work and pick up a handmade keepsake.
After a cliffside morning, continue eastward with a leisurely lunch in Ravello's Piazza Vescovado, sampling fresh pasta with Amalfi lemon at Trattoria Cumpa' Cosimo while enjoying cathedral-side people-watching. Then explore the terraced gardens of Villa Rufolo for sweeping views down the coast, descend to the turquoise cove at Atrani for a quiet beach stroll and espresso at a waterside café, and wrap the afternoon with a scenic drive along the SS163 toward Amalfi's Duomo to arrive in time for late-afternoon light on its Byzantine façade.
As the sun softens, unwind with a sunset aperitivo on the terrace of Il Capitano in Praiano, watching the pastel houses glow and fishing boats drift below. Later, head to Ristorante Marina Grande in Amalfi for classic seafood risotto and a slice of local lemon tart, then finish the night with a leisurely digestif at the cozy seaside Bar Nettuno while listening to the waves against the quay.