Some trips are all about the views. I planned this one partly for myself, since my birthday fell on our second morning in Capri. I couldn’t imagine a better place to wake up a year older than on an island surrounded by the bright blue water near Naples.
Here’s how our two days on Capri went: Oscar, the boys, and I hauled our bags across half of southern Italy to get there, and it turned out to be completely worth it. If you’re considering Capri with teenagers and wondering if it’s too fussy, too fancy, or too far, let me show you exactly what we did.
Getting There: It’s a Journey, and That’s Okay
Capri is not a quick trip, and I think it helps to know that going in. From Montepulciano, here’s the full chain of how we got there: a four-hour train to Naples, then a taxi to the Beverello ferry terminal, then the ferry across to Capri, and finally a taxi up to our hotel in Anacapri.
It sounds like a lot, and it is, but each part of the trip is short. There’s actually something fun about the whole process, especially if your teenagers enjoy a bit of a logistics adventure. Buying our ferry tickets through Ferryhopper made that part easy—I highly recommend it. The site is simple, the schedules are clear, and there’s no last-minute rush at the port. If you remember one practical tip from this post, make it this one.
A note on the two sides of the island: Capri town is the glamorous, buzzy, see-and-be-seen side, while Anacapri, higher up the mountain, is quieter, more laid-back, and (in my opinion) lovelier for families. We based our first night there on purpose.
Night One: Anacapri and a Sunset Dinner
We spent our first night at Hotel Carmencita, a charming little spot in Anacapri. It had just the relaxed, simple atmosphere I was hoping for—a perfect way to unwind after a long day of travel.
For dinner, we went to Da Gelsomina Ristorante and made sure to arrive at sunset. I’d do it again in a heartbeat. The food was delicious, the view stretched over the island and the sea, and, as you might guess, there was more seafood. By this point, “more seafood” had become our family’s unofficial motto. Watching the sky turn gold and then pink over the water while the boys enjoyed plates of fresh fish is a memory I’ll hold onto for a long time.
Day Two: The Big Island Tour
This was our full day, and we made the most of it. If you only have one full day on Capri with teens, this plan really works.
We started with the Blue Grotto, or Grotta Azzurra, and it was my first time seeing it after years of waiting. You climb into a small rowboat, the boatman has you duck down to fit through the tiny cave entrance, and then you’re inside, floating on water that glows with an unreal electric blue. The boys were so amazed they went silent, which, if you have teenagers, you know is the best review possible. It’s touristy and the line can be long, but it’s absolutely worth it. Go early.
Next was the chairlift up Monte Solaro. From Anacapri, we took the single-seat chairlift to the top, and it quickly became a teen favorite. You ride up alone, gliding quietly over gardens and rooftops, and at the top, the whole island opens up below you: Capri, the sea, the faraglioni rocks, and the mainland in the distance. It’s a little thrilling, completely beautiful, and perfect for photos.
For lunch, we stopped at Le Arcate. It was the perfect midday break—just the kind of relaxed, generous meal you want during a busy day of exploring.
In the afternoon, we visited the Gardens of Augustus (Giardini di Augusto), beautiful terraced gardens with one of the island’s most famous views: looking down over the Via Krupp’s switchbacks to the sea and the faraglioni. It’s a short, easy stop, which makes it perfect with teens—big reward, little effort.
We ended the day with a boat tour around the whole island, and I’d put this near the top of any must-do list. Seeing Capri from the water—the grottoes, the cliffs, the Faraglioni up close, and the hidden coves—gives you a whole new perspective. It’s the kind of activity that makes everyone happy, no matter their age. The teens enjoyed being out on the water, I loved the views, and Oscar appreciated that no one was asking for the Wi-Fi password.
Night Two: CapriWine and One More Seafood Dinner
On our second night, we switched to the CapriWine hotel, which was absolutely beautiful—a real treat and a lovely place to spend the night before my birthday. We had dinner at Ristorante Vergin and, as usual, ordered more seafood. By now, the boys had become quietly skilled at choosing from a menu of grilled fish and pasta, which felt like a small parenting win.
My Birthday, and the Slow Way Home
On Thursday, I woke up a year older on Capri, and we did the most luxurious thing you can do while traveling: nothing, and we did it slowly. We enjoyed a long, relaxed breakfast at the hotel with no rush and no schedule. Then we packed up, headed down to the ferry, and started our long, happy journey back to Montepulciano.
It was, hands down, one of the best birthdays I can remember.
Teen-Tested Tips for Capri
- Buy ferry tickets through Ferryhopper. Easiest part of the whole trip.
- Base yourself in Anacapri for a calmer, more family-friendly feel — especially for your first night.
- Do the Blue Grotto early to beat the lines, and don’t let the touristy reputation talk you out of it.
- The single-seat chairlift up Monte Solaro is a teen favorite. It’s a little bit thrilling and offers an unbeatable view.
- A boat tour around the whole island is a great equalizer. People of every age truly enjoy it.
- Build in one slow morning. With this much travel, a leisurely hotel breakfast is a gift.
Is Capri Worth It? I Think So
Getting to Capri takes some effort and patience with all the connections. But in return, you find an island that can surprise even the hardest-to-impress traveler in your group. On a sunny birthday morning, with my boys, my husband, and the bluest water I’ve ever seen, Capri gave me a day I’ll always remember.
If you’re weighing Capri with teenagers: go. Take the trains and the taxis and the ferries, order the seafood, ride the chairlift, and let the island do the rest.
