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 when Bridger and I travel—he shows up and I handle logistics, restaurants and reservations—but this time Maddie planned everything. She’s been to the Amalfi Coast several times and knows the best spots. She put together a highlight itinerary for me and it truly felt like a curated dream trip.
We traveled the first week of August, during peak season. If it’s your first time in Italy, you might not notice the crowds as much, but I do recommend booking restaurants, beach clubs and hotels well in advance for July and August. For example, Maddie reserved our spot at La Fontelina months ahead. The weather was hot and a bit humid, but the ocean was always refreshing—just pack a change of clothes in your carry-on for the airport if your travel day is long.
We spent 4 nights in Capri, 2 nights in Amalfi and 1 night in Positano. In one week you can see a lot, make lasting memories, and still feel relaxed. If you’re considering a sister trip—or a getaway with friends—definitely do it.
Where to fly into / transportation:
We flew into Naples. A private transfer arranged by our first hotel met us at baggage claim, handled our luggage and drove us to the port for the ferry to Capri. At each step—airport, port and arrival on Capri—someone from the transfer company assisted with luggage and tickets. The full transfer cost was €160 and removed all the stress of figuring out logistics; I highly recommend using a trusted transfer service if your budget allows.
Alternative: fly into Rome for more flight options from the U.S. then take a train to Naples (about 1 hour and 10 minutes) and continue by private car or taxi to the ferry. Some hotels also offer direct transfers from Rome by car, which can take around 2.5 hours.
Where to stay on Capri:
Caesar Augustus: We stayed here and loved it. Located in Anacapri, about 300 meters above sea level, the hotel offers panoramic views of the Bay of Naples and the Amalfi Coast. It has a tiered infinity pool overlooking the sea, a restaurant that uses ingredients from the on-site garden, a generous breakfast buffet, spa and gym. The hotel has a warm, family-run feel and is one of the best spots on the island to watch the sunset. Even if you’re not staying there, visiting for sunset and trying their peach bellini is worth it.
Other notable hotels: Quisisana (central Capri, steps from the Piazzetta), Capri Tiberio Palace (stylish, central), La Minerva (best boutique hotel), Punta Tragara (best overall views), Capri Palace Jumeirah (luxury in Anacapri).
Where to eat on Capri:
Da Paolino: Also known as the Lemon Tree Restaurant. Order the lemon pasta and finish with lemon sorbet served in a lemon.
La Fontelina: A classic lunch spot on the water. Try the caffè shakerato, zucchini pasta and grilled fish. Reserve well in advance; they require multiple-day commitments in high season.
La Terrazza: Restaurant at Caesar Augustus using garden-fresh ingredients. The tasting menus, including vegetarian options, are excellent.
Da Giorgio: Casual family-style cooking right in the center of Capri.
Il Riccio: Beach club seafood restaurant below the Dior Bar in Anacapri. They offer lunch and dinner plus small dessert selections. It’s an ocean-access spot if you want to swim, but taxis back to central Capri can be scarce so plan transportation ahead.
What to do on Capri:
- Spend a day at La Fontelina: Book early during high season. They offer combined restaurant and beach reservations; no-shows can be charged. Arrive early to enjoy quieter hours. Walking there from Capri town is a trek downhill and back uphill—bring water or take a boat taxi if preferred. Reward yourself with gelato from Gelateria Buonocore or a granita from Chiosco Tizzano on the return walk.
- Explore the Piazzetta: The main square is perfect for an Aperol Spritz, people-watching and designer window shopping—Capri-exclusive items are common in local boutiques.
- Evening drinks: Enjoy an aperitivo at Quisi Bar in Quisisana for prime people-watching.
- Boat ride: Rent a boat to circle the island and visit grottos; make time for the Blue Grotto if possible.
Note: taxis on Capri can be expensive and frequent short rides add up, often costing €20–€40 each way.
Transfer to Amalfi:
We opted for a private boat transfer with Capri Boat Tours to avoid sea sickness and to stop for a swim near Positano. The trip was about 90 minutes including the swim stop and delivered us to our hotel’s dock. It was a splurge but one of the trip’s highlights.
Where to stay in Amalfi:
Hotel Santa Caterina: A favorite—right on the water with excellent service, great food and easy access to Amalfi town. The hotel offers elevators to terraces and dining areas, an ocean pool, and a lovely beach area. I enjoyed staying in Amalfi as much as, or more than, Positano for the relaxed atmosphere and variety of activities.
Where to eat in Amalfi:
De Gemma: Charming spot in Amalfi town. We arrived when they opened and enjoyed a table overlooking the town paths—great local cooking.
Al Mare at Hotel Santa Caterina: The hotel’s restaurant served fresh salads, pizzas and pasta. Service was accommodating and ingredients felt exceptionally fresh.
What to do in Amalfi:
- Enjoy lemon sorbet—served in a lemon—for a local treat.
- Visit the Amalfi Cathedral in the town center.
- Shop along Ruga Nova Mercatorum for boutiques, cafes and souvenirs.
Transfer to Positano:
We arranged a driver through Santa Caterina for the 35–40 minute drive to Positano, which was straightforward and comfortable.
Where to stay in Positano:
Le Sirenuse: An iconic hotel and a splurge worth making at least once. Exceptional service, beautiful rooms with sea views, a lively pool area and outstanding dining. The spa and breakfast were highlights—there’s a lemon sorbet cart and thoughtful touches throughout. If you can, book more than one night.
Other notable Positano options: Villa Boheme, Il San Pietro, Villa Tre Ville.
Where to eat in Positano:
Pool Restaurant at Le Sirenuse: Excellent food and atmosphere—try to reserve if possible.
Chez Black: A well-known, family-run beachfront restaurant with a huge menu and reliable dishes; reservations are advised during high season.
La Sponda and Ada’s Oyster Bar are other standout dining choices, while Aldo’s cocktail bar at Le Sirenuse is perfect for sunset drinks and small plates.
What to do in Positano:
- Rent a boat to cruise the Amalfi Coast or visit Capri—local operators such as Luccibello offer half- and full-day options. Ask to stop at the popular swimming spot near Positano’s main bay.
- Stroll along the beach, grab gelato and enjoy the seaside ambiance. Mornings can be crowded and locals are protective of certain photo angles, so be mindful.
- Rent lounge chairs at the beach and swim with the postcard Positano cliffs as your backdrop.
7-Night Sample Itinerary
Day 1 — Arrival to Capri. Hotel: Caesar Augustus. Late lunch at Il Riccio/Dior Bar. Sunset at the hotel terrace. Dinner at La Terrazza.
Days 2–4 — Capri. Stay at Caesar Augustus. Spend days at La Fontelina (book ahead), explore the Piazzetta, and dine at Da Giorgio, Da Paolino and Il Riccio on different evenings.
Day 5 — Transfer to Amalfi. Private boat transfer with a swim stop. Hotel: Santa Caterina. Afternoon on the hotel beach and dinner at De Gemma in town.
Day 6 — Amalfi. Relax at the hotel beach, explore Amalfi town, enjoy lemon sorbet and visit the cathedral. Dinner at Al Mare.
Day 7 — Positano. Hotel: Le Sirenuse. Pool and restaurant time, sunset cocktails at Aldo’s, dinner at Chez Black.
If you have questions about planning, timing, reservations or tips for any of these places, ask and I’ll do my best to help. xx Rachael