Italy is one of those places that somehow lives up to every expectation—from the rolling hills of Tuscany to the quiet drama of the Amalfi Coast. But if there are two spots that really capture that effortless mix of beauty, energy, and indulgence, it’s Capri and Positano. Both sit along the coast in southern Italy’s Campania region, and together they make for the kind of trip that feels equal parts cinematic and completely easy to fall into.
Capri is a small island in the Gulf of Naples, accessible by ferry from Naples or Sorrento, and it immediately feels like its own world. It’s known for its natural beauty, but also for that slightly glamorous, slightly chaotic energy that makes the island so fun. One of the best ways to take it all in is heading up to Monte Solaro—the highest point on the island—where the views stretch out over the sea in every direction. From there, you can make your way to the Blue Grotto, a sea cave known for its glowing blue water that you can only reach by boat.
Back in town, Capri shifts from nature to something a little more polished. The streets are lined with boutiques—from Prada to Gucci—and wandering through them feels like part of the experience. Via Camerelle is the main stretch, but it’s just as much about the atmosphere as it is the shopping. When it comes to food, Capri leans into long, lingering meals in beautiful settings. Da Paolino, set in a lemon grove, is one of those places that feels almost surreal, while Il Riccio offers a more dramatic, cliffside setting with views that are hard to beat.
From Capri, you can head back to the mainland and make your way along the Amalfi Coast to Positano—either by ferry or by driving one of the most scenic coastal roads in Italy. Positano is instantly recognizable, with its colorful buildings cascading down the cliffs toward the sea. It’s the kind of place that feels almost unreal at first, but quickly becomes somewhere you don’t want to leave.
At the center of it all is Chiesa di Santa Maria Assunta, with its iconic tiled dome just steps from the beach. From there, it’s easy to spend the rest of the day moving between the beach, long lunches, and slow walks through town. Restaurants tend to lean into simple, fresh seafood and homemade pastas—La Tagliata is a great example, set a bit higher up with sweeping views over the coast. And if you have time, getting out on the water is worth it—the coastline looks completely different from a boat, with hidden coves and dramatic cliffs you won’t see any other way.
Capri
How to get there: To get to Capri, you can take a ferry from Amalfi, Naples, Positano, Sorrento, Ischia, Procida, or Salerno. The island has two main areas: Capri (the main town) and Anacapri (quieter, higher up). You can take a taxi up, or hop on the chairlift for one of the best views on the island.
To Eat:
- *Da Gelsomina – (on Anacapri!) Hands down my favorite dinner on the island. It’s tucked away in Anacapri and feels super local—you’ll actually need them to pick you up because the roads are too narrow to reach it yourself. Start with sunset drinks at Hotel Caesar Augustus, then have them grab you from there—it turns into one of those perfect, low-key nights.
- Villa Verde – Right in the center of Capri and always buzzing. It’s lush, a little chaotic, and somehow turns into a full night without you planning it. Come for dinner, stay for the energy—it’s very “Capri after dark.”
- Da Giorgio – A classic, no-frills Capri institution that’s all about the view and simple, traditional food. The terrace overlooks the sea and feels especially good on a warm night when you want something a little slower. Not trendy, but that’s kind of the point.
- Ristorante La Fontelina – This is one an iconic Capri lunches you plan your day around. Set right on the water with the Faraglioni in front of you, it’s equal parts beach club and restaurant. Book ahead, get a chair, and settle in for a long, very Capri afternoon.
- Da Luigi ai Faraglioni – Another legendary beach club, just as iconic but slightly more low-key than Fontelina. Go in the morning, swim, order lunch, and don’t rush it—this is an all-day situation. It’s one of those places that feels like old-school Capri in the best way.
- *Conca del Sogno – A must for lunch, but you’ll need a boat to get here (it’s technically in Nerano, not Capri). The setting is unreal—tucked into the rocks with bright blue water—and the food completely lives up to it. One of those meals you’ll talk about long after the trip.
- Restaurant Al Caprì – Right near the Piazzetta and perfect when you want something easy and central. It’s relaxed, open-air, and doesn’t feel overly formal, which is nice after a long day on the island. A good “we didn’t plan this but it works” kind of spot.
- Casa Tua Capri – Intimate, polished, and slightly under the radar in that “if you know, you know” way. Dinner here tends to turn into drinks without you realizing it, and the crowd leans stylish but low-key. A good option if you want something that feels a little more curated.
- Mare by Casa Tua – If you want a beach club that feels a little more curated and less chaotic than the classics, this is a good option. It’s at Marina Piccola and leans more polished, with a slightly more low-key crowd. A nice alternative if Fontelina feels like too much.
- FUOCO by Casa Tua – This is the newer Capri energy. Set on top of Hotel La Palma, it’s all about sunset, cocktails, and a more international crowd—feels a bit like fashion week landed on the island. Come early for drinks and stay into dinner.
- Aurora Capri – A more polished, dressed-up dinner option right in town. It’s chic without trying too hard, and a good choice if you want something that feels a little more refined than the usual Capri chaos. Great for a later dinner before heading out.
- Zuma Capri (on Anacapri) – Not traditional Capri at all—in the best way. It’s a rooftop Japanese spot with insane sunset views and a very global, fashion-forward crowd. Feels more like London or New York dropped into Anacapri.
- Pedro Capri – Smaller, more modern, and a bit under the radar compared to the big names. The food leans seafood-forward but with a more contemporary feel, and it’s a nice break from the more tourist-heavy spots. Feels like a newer addition to the island’s scene.
To Drink:
- The Piazzetta – Not one place, but the place. Grab a table anywhere around the square, order a drink, and stay longer than you meant to. It’s the easiest, most effortless night on the island. Favorite place to grab drinks in the town square and people watch!
- J.K. Place – This hotel is a top-notch stay overlooking the harbor. The dinner was an experience, but would be ideal to go at sunset to enjoy their house specialty, an Aperol Spritz on the terrace!
- *Hotel Caesar Augustus – (on Anacapri) An absolute must for afternoon/sunset drinks. The views from the terrace overlooking Capri are simply stunning.
- Quisi Bar – Classic aperitivo spot at the Grand Hotel Quisisana. Sit outside, order something simple, and people-watch—it’s old-school Capri at its best.
- Il Riccio – More of a daytime-to-sunset drinks situation, especially if you’re near the Blue Grotto. It’s dramatic, a little over-the-top, and perfect for a long, lingering afternoon.
- Taverna Anema e Core – This is where the night goes off the rails—in the best way. Live music, dancing on tables, everyone packed in together. It’s chaotic, iconic, and very Capri.
- La Palma Capri – Recently reimagined and now one of the chicest places on the island. Even if you’re not staying here, it’s worth stopping in for a drink—the whole place feels very “new Capri.”
To Do:
- Boat rental – This is a must.
- Grotta Azzurra
- Eat lunch at Conca del Sogno
- Hang at the Fontelina Beach Club
- Explore the ruins of a grand Roman palace at Villa Jovis
- Take bus up to Anacapri –
- Hike to see the Archo Naturale
- Walk along the Via Kruup in the Augustus Gardens
- Chiesa di San Michele Arcangelo
- Visit the Villa San Michele Museum
- Explore the Parco Filosofico in Ana Capri
- Scenic sunset at the lighthouse of Faro di Punta Carena
Stay:
- Capri Wine Hotel – Run by a lovely couple that combined two of their passions, wine & hospitality, they opened this boutique hotel in 2013. The grounds overlook the gulf, there’s a garden, and the whole hotel has a quaint feel. It’s a 10-minute walk to the town square – it’s hilly though, so bring comfy shoes!
- Grand Hotel Quisisana – An old (built in the mid-1800s) and famous Capri spot, this hotel is what Italian dreams are made of. There’s an old-world charm, a beautiful pool, and people watching that cannot be beaten. Lots of shopping and stores around this area, too. This is a good place to stay if you want something lively with lots of Italian history.
- La Minerva – This smaller hotel is an upscale option and is known for its beautiful property and relaxing vibes. If you’re looking for luxury and maybe something romantic, even though all of Capri feels romantic, it would be a great spot
- Airbnb – Always a great option, if that’s more your style!
Positano:
How to get there: If you’re coming from Capri, the easiest option is to take a ferry directly to Positano—it’s quick, scenic, and by far the best way to arrive. From Naples, your best bet is booking a private driver (usually around €110–€160), which you can arrange through your hotel or online ahead of time. If you’re coming from Sorrento, you can take the the “SITA” bus ( Around €8) bus for a budget-friendly option, or opt for a private car (around €70) if you’re traveling with luggage and want something a bit easier.
To Eat:
- *Ristorante Max – Tucked just off the main streets, this one feels a bit more intimate and under the radar. The food leans more elevated Italian, and the setting is cozy but still polished. Good for a quieter night.
- *Da Vincenzo – Grandpa Vincenzo founded the inn over 50 years ago and today, the nephew with the same name has taken the helm himself. A small spot that’s become one of the hardest reservations to get in town. It’s warm, busy, and feels very authentic—simple pasta, fresh ingredients, and great service. One of those places people return to every trip. Make a reservation for this spot at least 3 days in advance and ask to sit outside on the OTHER side of the street (so you’ll have a view of the town and ocean)
- da Gabrisa – Loved everything about this place and this view was amazing, but the best part is that it’s a little out of the way of all the chaos so it’s got a more intimate and less-touristy setting (but still has a view). Go before it gets dark so you can watch the sunset from your dinner table! And be sure you’re able to sit at one of the tables outside if possible!
- Bruno – Local cuisine, from seafood to classic pastas! Try and snag a spot outside with a view!
- *La Sponda at Le Sirenuse Hotel – Check to see if you can dine here without being a guest! But I’d recommend coming for sunset drinks and staying through dinner on the terrace! It’s of the most beautiful settings in Positano. It’s refined, romantic, and perfect for a slower, dressed-up dinner overlooking the town. Not casual—but worth it for the atmosphere alone.
- *Da Gabrisa – Gorgeous spot serving upscale local favorites! The inside is beautiful, but their outside seats are located on the edge
- Latteria Mini Market – For quick goods, this place was just down the road from us and came in clutch! I loved the little hack I would do here: get their coffee-flavored ice cream and ask them for an espresso on top – it was such a great move!
- Il Tridente – Set higher up in town, so you get that full panoramic view looking down over Positano. It’s a great mix of relaxed and polished, especially around sunset. A good option if you want something slightly removed from the beach crowds.
- Zass Restaurant – Located at Il San Pietro just outside of town, and one of the most beautiful restaurants on the coast. It’s more of a destination dinner—quiet, refined, and very elevated. Worth the trip if you want something memorable.
- Lo Scoglio – Not technically Positano, but one of the best lunches on the coast and worth the boat ride. Super fresh seafood, right on the water, and very relaxed in that effortless Italian way. This is the kind of place you plan a whole day around.
To Drink:
- *Franco’s (part of Le Sirenuse Hotel) – even if you’re not staying here, it’s worth making a reservation and going for sunset drinks and/or dinner. Incredible views and where you want to be!
- *The Terrace bar at Hotel Il San Pietro di Positano – A must for sunset drinks. It’s an 8-minute drive east of Positano, and had great views on the terrace looking back at the city!
- Music on the Rocks – Full-on club with a great outdoor area looking back over the city
- Chez Black – Right on the beach and great for a more casual drink. It’s busy, a little chaotic, and perfect after a day in the sun. Easy, fun, and always lively.
- Aldo’s Cocktail Bar – A bit more tucked away and less chaotic than the main beach spots. It has a clean, modern feel and is great if you want something slightly more curated. Good cocktails and a nice break from the crowds.
To Do:
- Play a few matches of tennis at Tennis al Settimo Piano Positano
- Rent a private boat
- Go have lunch and enjoy the beach at Da Alfo
- More touristy, but could go to Bagni d’Arienzo Beach Club for lunch & beach as well
- Spend a day at the beach!
- Take a cooking class at Casa Mele
- Or hike to a more private beach, Spiaggia Fornillo!
- Hike the Path of the Gods – This is a popular hike that is about 3 hours long. You’ll need to take a bus to the trailhead! We kind of hacked this hike, and just did the good part! What a friend and I did was walk from Positano to the end of the hike, and then go up the back-way. It’s much shorter to reach the rock formation that everybody takes a photo at, then we turned around!
Stay:
- Hotel Polzaao Murat – Set in an 18th-century palazzo surrounded by botanical gardens, this palatial hotel is a 5-minute walk from a sandy beach
- Villa Franca – The 5-star Hotel Villa Franca features stunning views of the sea and of Positano from its hilltop position. Offering 2 restaurants, it also comes with an outdoor pool, a spa, and a bar. Free shuttle rides to/from the town center are available.
- *Le Sirenuse – Le Sirenuse is a charming family-owned hotel located in the heart of Positano. Opened in 1951 by the Sersale family who converted their summer house into a hotel with 12 rooms. The hotel has grown since then with the acquisitions of two neighboring houses to 59 rooms and suites.
- *Airbnb – I ended up staying in an Airbnb and it was a wonderful experience!
Capri and Positano are the kind of places that feel almost unreal at first—and then somehow even better once you settle into them. Between the views, the food, and the rhythm of days that stretch from the water into long dinners, it’s an easy place to fall into and not want to leave. It’s one of those trips that stays with you long after you’re home.
Stay Risky,
– John
