Five days on the island of Capri — a lemon grove dinner, a cliffside hike to a lighthouse, kayaking through sea caves, and a day trip to Positano.
Just off the coast of Naples, Capri is the kind of place that makes you rethink your relationship with slowing down. The island offers something for every kind of traveler — cliff hikes, sea kayaking, boutique wandering, boat trips to neighboring Amalfi coast towns, or simply a porch with a view and a good book. This post covers five days of all of the above, with every practical detail you need to actually get there and make the most of it.
Getting to Capri
Arriving into Naples by train came with a surprise — skyscrapers. To reach Capri, you take a boat from the main port, Molo Beverello. The taxi to the port weaved through Naples traffic an inch from other cars; the driver was light-hearted, which made it more fun than stressful, but he also charged extra "for the traffic" — €30 total for a 15–20 minute ride.
The port is easy to navigate. Tickets were €25 one way, and buying on-site cost the same as online. The ride was a breeze (seasick friends, bring Dramamine), with bathrooms, tables and free WiFi. Expect to part with heavy luggage at the entrance and collect it on the way out — a little chaotic, but the only option.
Up the Mountain to Anacapri
Sit on the left side of the boat for a stunning view into the port. Offloading is crowded — one sidewalk, hundreds of people coming and going. Weave to the ticket office on the right for a handful of public bus tickets, then queue for Anacapri. The bus scales the side of a mountain on roads tight enough to high-five passing cars, with no maps or signs onboard — luckily most people get off at the main Anacapri stop.
The Airbnb host met at a church and led the way down a winding path to a gated, absolutely dreamy space (booked in September for May, about $100/night).
Evening — Dinner in a Lemon Grove
La Zagara, pinned during Pinterest research, was close by and sounded too incredible to pass up. Every single thing about this meal was perfect: a glass of red wine, rich beef-stuffed pasta, and complimentary housemade bread. Bellissimo.
Cappuccino & a Cliffside Road
A cappuccino and pastry at a great café in Anacapri (about €10), then a bus to the center of Capri. On the bus, a couple from Brazil shared their hotel map of the island — snap a photo of any map you can — and together we went looking for Via Krupp, a road built into the cliffside in the early 1900s.
The Faraglioni
The gardens overlooking Via Krupp were closed for weather, so the map led to an alternative viewpoint instead. Many steps and steep hills later, the reward was an excellent view of the Faraglioni.
Lunch on the edge of the overlook in the center of town waited out a downpour. The view was perfect; the food was overpriced and not very good — enjoy the view, eat elsewhere.
Limoncello in a Giant Lemon
Back in Anacapri, an afternoon wandering the shops ended at Casa Orlandi, which serves limoncello inside a giant lemon. Even as someone who isn't a massive limoncello fan, it felt like a once-in-a-lifetime experience.
Rain in May is uncharacteristic for Capri, according to the locals — an apartment with a view made it bearable. When the sun finally showed its face, it was time for a quest: the Faro di Punta Carena lighthouse, on foot (you can also take a bus).
The route starts on an inconspicuous road next to the Anacapri chairlift. The area feels rural, with houses surrounded by grapevines and homegrown gardens, and the road ends at an overlook called Belvedere della Migliara.
Finding the Trail
From here, the path on the map becomes very unclear. A right turn by a cluster of houses dead-ended in a yard of high grass; what looked like a dirt driveway turned out to be the trail. Rocky, wild, and very hobbit-like.
After a second field of high grass came the most insane set of stairs — straight down, with a view of the lighthouse the whole way. It's hard not to think about how many generations ago these steps were built, and how many thousands of people have used them since.
The stairs surprisingly end on a busy road, with a walk along the gutter around a bend (a second trail may connect to the forts around the island — unconfirmed). The road ends with a spectacular scene: the lighthouse straight ahead, and a path to Lido del Faro for a perfect drink in hand.
The Ferry to Positano
Choosing one Amalfi coast town for the day was hard — Positano's charm won. Arrive at Capri's port early, and sit on the left side of the boat for the best view of the coastline. Positano's port is small, so expect to wait in the water 30 minutes to an hour; the rocking gets intense.
Positano is surprisingly small and easy to navigate — only a few paths, so it's hard to get lost. A few hours of wandering between pinned restaurants ended with lunch at Casa e Bottega, a fresh, farm-to-table spot. Not especially Italian, but a dish worth eating weekly.
Anacapri's Best-Kept Secret
Back in Anacapri to rest tired feet, Pizzeria Aumm Aumm delivered perfect pizza and the most affordable meal on the island (€8). Follow it with a Sorbetto di Limone from Bar Grotta Azzurra.
Back to Via Krupp
The rain pushed the kayak trip to the last day, which left the morning free to return to Via Krupp — deep blue water and an ingenious path down the steep cliff to reach it. Lunch was a mouth-watering meal overlooking the ocean.
Kayaking the Caves
Loaded up on sunscreen and took the bus down to Marina Piccola di Capri for the kayak trip with Capri Hydro. Dozens of people were camped on the beach with towels and swimsuits. The guides led the group through caves along the coast — and it was fun to spot the lunch restaurant from the water.
Meatballs & Goodbyes
After all that rowing, meatballs were a must: L'Angolo del Gusto, a sweet corner spot near the Airbnb. The last meal in Anacapri was bittersweet — just starting to feel settled after five days, while missing home more and more. Then back to Naples for a few more days of pizza and pasta.
Good to know before you go:
Capri was the most expensive stop of the whole Italy trip — everything has to be imported to the island, and it shows in the prices. Book stays early (the Airbnb was booked eight months out). May weather can surprise you, so leave flexibility in boat and kayak plans. Ferry luggage isn't really secured, so lock your suitcase if you can.
A Place for a Sabbatical
Leaving Capri, one thought stuck: this would be the perfect place for a sabbatical. The island offers incredible rest, incredible views, and loads of adventure.
Trails & Boats
Many overlook points connect through old forts built to protect the island — grab a photo of a trail map, and remember these are mountains, so the terrain isn't light. Boats run to Positano, Sorrento and more, with rentals for self-guided or guided excursions.
How It Compares
Surrounded by water, Capri felt unique compared to every other stop: a lot slower paced, still full of beauty and delicious food — and the most expensive, which makes sense when import fees and paying workers fold into everything.
