Lifestyle Travel

Five Family Members, Two Italian Coasts—Here’s How They Navigated a Cross-Country Trip

Without too much gelato bribery.
child overlooking Positano, Italy
“Our kids loved being at the beach so much that we didn’t really need to bring anything to entertain them,” says Seth Smoot. “They collected sea glass and worn pieces of tile to keep as souvenirs.”

We may earn revenue from the products available on this page and participate in affiliate programs.

The centuries-old towns of southern Italy have all the makings for an epic playground, from hidden seaside caves to winding hilltop streets. That’s what San Francisco–based photographer Seth Smoot and his wife, Kendra, an art director and stylist, found when they decided to point their compass to the iconic area last October—and bring their kids Stella, Imogen, and Truman along for the ride.

three kids on boat in Amalfi
The sculptural rock formations of Faraglioni, a speck of land off Capri, provide the perfect choose-your-own-adventure.

“Their imaginations were running wild, pretending everything was a castle or a secret lair,” says Kendra. Starting in buzzy, tourist-favorite Positano, then meandering across the boot to serene Puglia, the family of five essentially split their holiday into two coastal adventures. “There are so many things to do in Positano, while Puglia has a slower pace, and it was easier to blend in and live like locals,” Seth explains. Each place may have a different vibe, but the Smoots’ daily outline remained the same, according to Kendra: “Our structure felt inspired by the Italian phrase dolce far niente—the sweetness of idleness.”

4 Packing Essentials for Family Trips

Kendra Smoot in doorway
a tree in Fasano
  1. Durable plastic shoes like Natives, Crocs, and Smoot-approved Birkenstock EVAs help kids (and adults) better navigate rocky shorelines.
  2. Bring a watercolor set to share during the trip. “It’s fun to paint postcards to send back to friends and family,” says Kendra.
  3. A roomy, lightweight tote folds down to nothing, holds towels and lunch for everyone, and can be an extra carry-on on the way back.
  4. Make Airbnbs feel like home with palo santo sticks or a small candle. (Bonus: A comforting scent works wonders come bedtime.)

Where to Stay and What to Do in Amalfi

Marina Cacciapuoti, founder of travel consultancy and Italian lifestyle brand Italy Segreta, shares her top spots on both coasts.

Positano's cliffside cityscape
“We chose to stay in the northern section of Positano, in the area of Fornillo Beach, which is about 400 steps up! Most of the homes open out to the sea via terrace doors. It’s quite lovely,” says Kendra of the epic cliffside views.

Agricola Fore Porta

A beautiful enclave away from the crowds, where you can hike through lemon groves and waterfalls, then enjoy a homemade meal outside. Open mid-March through November. Via Paradiso, 22, Amalfi

Casa Privata

This very charming hideaway feels more like a stylish private home than a luxury hotel (the discreet staff is available via WhatsApp). Via Rezzola, 41, Praiano 

Don Alfonso 1890

In the sleepy town of Sant-Agata, high up in the Amalfi hills, this boutique hotel also has a Michelin-starred restaurant and organic farm. Corso Sant’Agata, 11/13, Sant’Agata Sui Due Golfi, Massa Lubrense

shells lined up on kids' legs on beach
Kendra Smoot and her three kids

La Bottega di Brunella

You can buy lovely linen clothing here, all made in Italy, from fabric to finished product. Via Pasitea, 72, Positano

Conca del Sogno

This cliffside nook has been known as the land of the mermaids since ancient times and is a destination for Sunday lunch. Via Amerigo Vespucci, 25, Massa Lubrense

MAR Positano Villa Romana

The area’s archaeological museum is housed in an ancient Roman villa with mosaic floors and walls painted with brightly colored frescoes. Piazza Flavio Gioia, 7, Positano

rock formation on the Amalfi Coast
“It’s amazing to take in the view of Positano from the ocean and see how these towns are literally built on cliffs with just a road or two snaking through them,” says Kendra.

Pasticceria Pansa

The bakery’s sfogliatella Santa Rosa and delizia al limone are musts! Piazza Duomo, 40, Amalfi

Trattoria da Armandino

A local favorite, this family-run trattoria has some of the best seafood on the coast. Try the sardines and frittura mista. Via Marina di Praia, 1, Praiano

Where to Stay and What to Do in Puglia

the beach in Polignano a Mare
Polignano a Mare, a 15-minute drive north, may be rocky, but “the kids loved exploring all the tunnels,” says Seth.
the blue-green water in Monopoli

Agriturismo Da Marta

There’s no menu, but you will most likely be able to try Marta’s excellent melanzane ripiene and fried fiori di zucca. Via Orte, Otranto

Borgo Egnazia

Puglia has many beautiful places to stay, but only one Borgo Egnazia, a magical village with overflowing bougainvillea, limestone interiors, olive groves, and two private beach clubs. Strada Comunale Egnazia, Savelletri, Fasano

Caffè Alvino

Head to this bakery for pasticciotto (a typical baked good packed with custard) and superb rustico (traditional pastry filled with tomato and mozzarella). Piazza Sant’Oronzo, 30, Lecce

the beach in Polignano a Mare
“It’s a special experience to be inside that picture you see so much,” says Seth of the oft-photographed Polignano a Mare.

Caseficio Torre Sant’Emiliano

Puglia is known for its excellent cheeses, and you can find amazing ricotta here. Litoranea Otranto, Porto Badisco


The vibe at Cibus is laid-back and warm, and the must-order is spaghetti with cherry tomatoes and stracciatella, a local specialty. Via Chianche di Scarano, 7, Ceglie Messapica

side street in Monopoli, Italy
“It feels like a walk back in time,” says Kendra of the town of Monopoli. “You’re surrounded by this incredible, timeless architecture. It’s so pretty; even the copper drainage pipes are cute!”
clams dish
Spaghetti alle vongole in the town of Fasano (where “nobody spoke English so we ended up overordering—it was all phenomenal”), a stroll through the olive groves, and a lazy afternoon round of cards checked off the family’s Italian-style must-dos.

Farmacia Balboa

All the drinks are made with organic ingredients from nearby farms. And the location, overlooking the piazza, is the perfect backdrop for a post-beach aperitivo. Piazza Giuseppe Pisanelli, 24, Tricase

Lighthouse of Santa Maria di Leuca

Climb to the top—accessed via a 254-step staircase—to enjoy an extraordinary view. On clear days you can see the Greek island of Corfu. Via Francesco Pireca, 5, Santa Maria di Leuca

glassware on blue-painted ground
“The flea market in Ostuni, known as the White City, was a place we really loved,” says Seth.
kids playing cards on blanket
“We found a few treasures,” he adds—like a vintage pack of cards (something the family always has on hand when traveling) that will come along for the next trip.

Porto Badisco

Don’t miss a trip to the port, where you can eat sea urchins directly from the fishermen’s docked boats. 

The Towns of Grottaglie and Lucugnano

Both are must-visits for ceramics lovers—lined with artisanal stores selling traditional handmade vases and plates whose designs (like the flower-dotted patterns and schizzato-splattered paint technique) date back centuries.

How to Get Around, by Land or by Sea

moher and two kids on boat in Amalfi


Many ancient Italian towns come with equally ancient streets: steep, cobblestone, narrow—which is to say, not very stroller-friendly. If you’re traveling with an infant or toddler, bring a lightweight, easily foldable stroller (like Babyzen Yoyo) for flatter terrain and a sturdy carrier for hillier locales.


A hard-side wood boat requires a captain or person with a boating license, but anyone can commandeer an inflatable boat, which Seth did. Positano’s main pier has a number of boat companies. All rentals come with the option of both child- and adult-size life jackets and cost $500 to $600 a day.


Kendra and Seth’s approach to road-tripping with three kids in the back seat was to limit car rides to a maximum of three hours and, whenever possible, bookend them with active time for a better chance of in-transit napping. If your children are car seat–age, lighten your load and rent one in Italy with your vehicle.

How Seth and Kendra Travel With Kids

Lose the Structure

“We’re very anti-itinerary,” says Kendra of their approach to holidays. They take friends’ recommendations into account, plan days loosely, and never focus on being results-driven, so “everything feels like a discovery.”

mother and child embracing in bathing suits
“There was a lot of piggybacks and gelato bribery, but the kids did great with all the walking and stair climbing that come with some of these towns,” says Kendra.

Skip the Hotel

Beyond having access to a kitchen and closed bedrooms, an Airbnb or home rental connects you to local hosts, who “always have the best tips and are excited to share what makes their region so special,” says Kendra.

Positano as seen from the water

Consider Shoulder Season

If exploring a new destination with your kids while contending with throngs of tourists raises your stress level, avoid the summer months. In Italy, autumn sees sustained warm temperatures and not as many people.

Go Solo

“Have alone time when traveling together,” says Kendra, “for sanity’s sake, but also to experience a place in a different way than when you’re in a big pack.” The couple alternates taking the odd solo outing.

This story was originally published in our Summer 2020 issue with the headline “A Tale of Two Coasts.”