My sister took me on an unforgettable nine-day trip to Italy and I want to share the places we visited and recommend. Normally I’m the planner for trips, but this time my sister Maddie—who has visited the Amalfi Coast several times—organized an itinerary of her favorite spots. It was a perfect highlight tour.
We traveled in early August during peak season. While the islands were busy, it didn’t negatively affect our experience. If you go in July or August, book restaurants, beach clubs, and hotels well in advance. For example, Maddie reserved La Fontelina months ahead. The weather was hot and slightly humid—nothing a quick jump in the sea couldn’t fix. Tip: keep a change of lightweight clothes in your carry-on to swap into at the airport if needed.
We stayed four nights in Capri, two nights in Amalfi, and one night in Positano. One week is plenty to experience the highlights and make lasting memories. If you’re considering a sister trip (or any getaway with friends), do it.
Where to fly into / Transportation
We flew into Naples Airport. A private transfer organized by our first hotel met us at baggage claim, carried our bags to the car, and took us to the port for the ferry to Capri. At each transfer point, company staff met us and escorted our luggage. The total cost from the airport to the hotel was around €160 and was well worth the convenience and peace of mind.
Alternative: Fly into Rome for more frequent and often cheaper flights from the U.S., then take a train to Naples (about 1 hour 10 minutes) and continue by private car or taxi to the ferry. Our hotel also offered a full transfer from Rome (about 2.5 hours by road).
Where to stay on Capri
Caesar Augustus: We stayed here and loved it. Located in Anacapri, it feels boutique and family-run. Perched about 300 meters above sea level, the hotel offers panoramic views of the Bay of Naples and the Amalfi Coast, a double-level infinity pool, garden-grown ingredients in the restaurant, and an exceptional breakfast buffet. Amenities include a gym, spa, concierge, and one of the best sunset views on Capri. Even if you’re not staying here, consider visiting for sunset and a peach bellini.
Other recommended hotels on Capri:
- Quisisana: Central, steps from the Piazzetta, five-star service and iconic Faraglioni views.
- Capri Tiberio Palace: Stylish hotel in the heart of Capri.
- La Minerva: Excellent boutique option.
- Punta Tragara: Superb panoramic views.
- Capri Palace Jumeirah: Five-star luxury in Anacapri.
Where to eat on Capri
Da Paolino (The Lemon Tree Restaurant): Famous for lemon pasta and lemon sorbet served inside a lemon.
La Fontelina: The classic lunch spot—try the caffé shakerato, zucchini pasta, and grilled fish. Reservations are required well in advance and often come with a multi-day commitment.
La Terrazza (at Caesar Augustus): Fresh, garden-grown ingredients and thoughtful tasting menus.
Da Giorgio: Casual, family-style dining in the center of Capri.
Il Riccio: Beach club and seafood restaurant below the Dior Bar in Anacapri. Open for lunch and dinner, with ocean access and rentable beach chairs. Taxis back can be scarce and expensive, so arrange pickup in advance.
What to do on Capri
- Spend the day at La Fontelina: Book far ahead, especially in high season. The restaurant often requires a multi-day reservation commitment. Consider arriving early to avoid crowds and remember that the return walk up can be steep—keep water handy or take a boat taxi.
- Explore the Piazzetta: Enjoy an Aperol Spritz, people-watch, and browse designer boutiques that sometimes sell Capri-exclusive pieces.
- Evening Cocktails: Aperitivos at Quisi Bar (Quisisana) are great for people-watching.
- Boat ride around the island / Blue Grotto: If you have time, take a boat tour to see Capri from the water and visit the Blue Grotto.
Note: Taxis on Capri can be expensive—expect €20–€40 per ride.
Transfer to Amalfi
We chose a private boat transfer with Capri Boat Tours and asked to stop near Positano for a short swim en route to Amalfi. It was a splurge but a highlight and helped avoid seasickness on longer ferries. The transfer took about 1.5 hours including the swim stop and dropped us at our Amalfi hotel dock.
Where to stay in Amalfi
Hotel Santa Caterina: A standout stay right on the water with excellent service, an elevator to the restaurant and pool, a gym, and fresh cuisine. It’s close to Amalfi town and felt both luxurious and welcoming. I enjoyed Amalfi’s atmosphere and activities, and this hotel made the stay especially memorable.
Where to eat in Amalfi
De Gemma: Charming town restaurant; great food and atmosphere—try to arrive early without reservations if possible.
Al Mare (Hotel Santa Caterina): Fresh, well-prepared dishes. We enjoyed salads, pizza, and pasta made with high-quality ingredients.
What to do in Amalfi
- Try lemon sorbet served in a lemon.
- Visit the Amalfi Cathedral in the town center.
- Shop and stroll along Ruga Nova Mercatorum for local boutiques and cafés.
Transfer to Positano
We hired a driver from Santa Caterina to Le Sirenuse in Positano; the drive took about 35–40 minutes.
Where to stay in Positano
Le Sirenuse: Iconic and worth the splurge. The hotel offers exceptional service, beautiful rooms with sea views, a lively pool area, an outstanding breakfast, and spa amenities including a cold plunge and steam room. We spent a peaceful afternoon by the pool and enjoyed sunset cocktails at Aldo’s.
Other notable accommodations in Positano include Villa Boheme, Il San Pietro, and Villa Tre Ville.
Where to eat in Positano
Pool Restaurant at Le Sirenuse: Exceptional lunch if you can secure a reservation.
Chez Black: Family-run, extensive menu, and reliable for groups. Book in advance.
La Sponda, Ada’s Oyster Bar, Aldo’s Cocktail Bar: Great options for dinner, oysters, or sunset drinks.
What to do in Positano
- Rent a boat for the day to cruise the Amalfi Coast or visit Capri—Luccibello boat tours comes recommended.
- Walk down to the beach for gelato and seaside views; the area is very touristy, so be prepared.
- Rent lounge chairs at the beach to swim with Positano’s iconic cliffside backdrop.
Our 7-Night Itinerary (summary)
Day 1: Arrival to Capri — Hotel: Caesar Augustus. Late lunch at Il Riccio / Dior Bar. Sunset at hotel terrace. Dinner at La Terrazza di Lucullo.
Days 2–4: Capri — Hotel: Caesar Augustus. Daytime visits to La Fontelina, explore the Piazzetta, dinners at Da Giorgio, Da Paolino, and Il Riccio across the evenings.
Day 5: Transfer Capri → Amalfi — Private boat transfer. Hotel: Santa Caterina. Afternoon at the hotel beach and Al Mare restaurant. Dinner in town at De Gemma.
Day 6: Amalfi — Hotel: Santa Caterina. Hotel beach and town exploration. Dinner at Al Mare.
Day 7: Positano — Hotel: Le Sirenuse. Pool and hotel dining, sunset cocktails at Aldo’s, dinner at Chez Black.
If you have any questions about planning a similar trip, ask below and I’ll do my best to help. — Rachael