Packing for Italy in Vogue with The Next Chapter Travel

My Instagram friend, Martha Stockhausen with The Next Chapter Travel, has another incredible trip coming up on October 3-13 called “Italy in Vogue: Como, Portofino & Milan.”

Her lucky group of travelers will head to Italy in style beginning in Lake Como, stopping next in Portofino and finally, Milan. I can confidently speak to the perfection of this itinerary having done it myself last summer. You can read all about my trip including details on each location here, here and here.

Funnily enough, Martha and I have never met in person but we are connected by our love of travel, and apparently of the same destinations! Not only did we plan the same Italy itinerary without consulting each other; she just returned from a trip to Spain and Portugal, and I am headed there in November. One of these days we will overlap!

While summer was an incredible time to visit this part of Italy (primarily to experience this), I can imagine that Fall will be completely magical.

As for shopping and packing ideas, she timed the trip perfectly as it is prime Fall shopping season – my inbox is flooded with suggestions for boots, sweaters and jackets as I’m sure yours is as well.

We’ve partnered again on a packing list – I had a lot of fun putting it together and thinking about what I would want to wear on each of the different days. There’s a cooking class, a boat tour, dinners, lunches, sightseeing, hiking, etc. etc. If you are lucky enough to be on the Next Chapter Travel trip, here are a few suggestions to take with you based on the daily itinerary.

And if not, I hope you enjoy wherever you are traveling to this Fall. I can’t wait to follow along on Martha’s adventures – you can follow The Next Chapter Travel here !

Find the collection below HERE and my entire shopping guide HERE.

ITALY IN VOGUE: COMO, PORTOFINO, & MILAN
Join The Next Chapter Travel for an extraordinary 10-day journey through northern Italy’s most sophisticated destinations. The legendary shores of Lake Como beckon, where ancient Roman nobility once retreated and today’s Hollywood elite still flock. The adventure continues in Portofino, the crown jewel of the Italian Riviera, and culminates in chic Milan, the world’s undisputed capital of fashion and design. This all-women small-group trip offers an unparalleled experience of Italian culture and class. Known for its breathtaking landscapes, culinary excellence, and spellbinding sophistication, northern Italy provides the perfect setting for a luxury adventure that combines cultural immersion with luxurious experiences.
The Next Chapter Travel

I hope the Next Chapter group can sneak in a visit to The Passalacqua in Lake Como.

TRIP VIGNETTE TRAVEL ESSENTIALS

My Favorite Suitcase
the best moisturizer (carry-on friendly)
The best crossbody for sightseeing & airport navigating
Good socks and Good sneakers
A set of adapters
A hint of color strawberry chapstick
Portable charger for your phone
Good quality cosmetic bags
A stylish rain coat and a packable umbrella
A Lightweight Backpack
Adidas sneakers
Comfortable pajamas
Wireless headphones
Sunglasses

DAY ONE, Travel Day from Milan to Lake Como, Check into Hotel
DAY TWO: Villa Balbianello, Villa Carlotta – Villa and Garden tours, Lunch at Tremezzo
After breakfast, we’ll discover the cinematic beauty of Villa Balbianello, where the magnificent villa and its romantic gardens have served as the backdrop for films including Star Wars and Casino Royale. We’ll explore both the historic villa and its spectacular terraced gardens overlooking the lake. For lunch, we’ll enjoy the elegant atmosphere of Hotel Tremezzo’s T Bar with its stunning lake views. In the afternoon, we’ll visit Villa Carlotta to explore the botanical splendor of its twenty-acre gardens, featuring an extraordinary collection of ancient camellias, rhododendrons, and exotic plants. The evening is yours to dine at one of Villa d’Este’s exceptional restaurants or explore the charming local dining scene.

These flattering and fun striped cotton pants by the newly popular brand La Veste would make a great sightseeing outfit with a button down or t-shirt and sandals or sneakers. See how Alison Loehnis with Net a Porter styled them below to drop her son off at college. Casual and comfortable but elegant.

Alison Loehnis, London-based former President of Net-a-Porter

Barbour Jacket with pink detail – I would pack a couple of lightweight jackets – this new version of the Barbour jacket with pink collars and sleeves would be great.

J. Crew Ruffle-Collar Button Down would pair well with stripes.

Love this lime green version. Would also look great with a t-shirt and cardigan.

J.Crew Club Collar Shirt – The green and white stripes and light blue would be a fun combination.

Pack this basic cotton rib jersey shirt to wear with leather pants or jeans

Adidas sneakers – perfect for sightseeting and travel days

These Isabel Marant sneakers would work with a lot of different outfits too.

another good option is this lightweight colorful jacket by Ugg

You could also pair them with the perfect white t-shirt.

DAY THREE: Private Boat Tour of Lake Como
This morning, we’ll embark on a private boat tour of Lake Como’s glittering waters, one of the most spectacular ways to experience this legendary destination. We’ll glide past hidden waterfalls and centuries-old palatial estates that have welcomed everyone from Roman emperors to Hollywood royalty. Our journey includes visits to the enchanting village of Bellagio, known as the “Pearl of Lake Como,” where you’ll have time to explore its charming streets and sophisticated boutiques. We’ll continue to the picturesque village of Varenna, where you’ll have stunning lake views and can explore its romantic waterfront promenades. Lunch will be at your leisure in one of these beautiful lakeside villages. This evening we’ll gather for dinner at The Grill at Villa D’Este, an informal yet chic setting in which to share the day’s discoveries.

This pretty J. Crew yellow poplin dress would be perfect on a boat ride with a jacket or cardigan.

love the look of this J.Crew Stone Snake Chain Necklace

I would pair it with gold sandals and a jean jacket or cardigan.

Very versatile Cashmere Travel Wrap – this is such a great investment as you can use it on the plane, out to dinner, in cold trains and cars, etc.

DAY FOUR: Como Private Tour, Leisure Activities
This morning offers your choice of rejuvenating activities: embark on a scenic hike through the surrounding hills to the Swiss border to invigorate your senses, or indulge in luxurious spa treatments at the resort’s world-class wellness center to restore and refresh. Lunch will be at your leisure on property or at one of the many lakeside restaurants. In the afternoon, we’ll uncover Como’s remarkable legacy as the world’s silk capital during a private walking tour through the city’s elegant streets, where centuries of luxury textile heritage come alive. You’ll have some free time to explore this sophisticated lakeside town. Returning to Villa d’Este, we’ll dine like locals at Il Gatto Nero, an intimate restaurant that offers authentic Italian charm, and celebrate our time in this extraordinary corner of Lake Como.

Lake Como Cycling — One of the very best experiences of our trip last summer was this incredible 28 mile bike ride (electric bikes, mind you) through the Lake Como region up into Switzerland. I cannot recommend it enough. You can read all about my experience here.

ScreenshotLove this elegant yet casual dress for a boat day with a jacket and scarf.

Never travel without my Clare V crossbody.

Il Gatto Nero – my husband and I had a wonderful dinner there last summer.

This White & Warren cashmere travel wrap is a great investment – you can wear it on the plane, to dinner, on a boat or on a long car ride.

This is a pretty long sleeved dress for colder nights.

DAYS FIVE AND SIX : Cinque Terre
Today we’ll journey through the UNESCO World Heritage villages of Cinque Terre, experiencing the dramatic beauty of this rugged coastline. We’ll visit the colorful villages of Vernazza, Monterosso, and Riomaggiore, each offering its own unique charm and spectacular seaside views. Our adventure includes a memorable lunch at Belforte, perched dramatically on the rocks with panoramic ocean views. To complete the experience, we’ll also enjoy a private boat tour along this stunning coastline, appreciating the villages from the sea. The evening is yours to enjoy the amenities of Hotel Splendido or dine in charming Portofino.

You’ll need comfortable clothes and layers for today’s itinerary that includes a lot of walking and exploring – pair this Cashmere Striped Crewneck with jeans and a button down.

Embellished J.Crew Button Down – button down with rhinestones

Another versatile option is this J. Crew Ruffle Collar Sweater T-shirt

DAY SEVEN: Ligurian Cooking Class, Leisure Time
This morning, we’ll learn the secrets of authentic Ligurian cuisine during a hands-on cooking class, mastering the art of traditional pesto. Lunch is at your leisure, and the afternoon is your choice of an invigorating hike through the surrounding hills to San Fruttuoso Abbey, relaxing spa time at the hotel’s Dior Spa, pizza-making if you want to continue the culinary exploration, or simply wandering the beautiful streets of Portofino to discover hidden corners and charming boutiques. Tonight we’ll gather for dinner at La Terrazzo at Belmond Splendido, savoring the exceptional cuisine and wine that make this region a culinary destination.

Does not get any more fun that the piano bar at The Splendido – my husband can be spotted in this photo singing “Sweet Home Alabama” to me on my birthday with a group of Spanish travelers that he met at the bar. Cue me mortified but secretly loving.

Put a few lightweight sweaters in your suitcase like this one: lightweight cashmere henley sweater

Pair the sweaters with these Veronica Beard cropped corduroys and your Isabel Marant sneakers.

This lightweight Rag & Bone blazer is perfect to travel with.

And I love these New Veronica Beard jeans

These are the most comfortable boots I have ever worn. Would be great for walking around and wearing with jeans. They are a fun brand to follow – I wrote all about them here, including all about the founder’s incredible Parisian weddding.

My husband and I took a boat ride while we were in Portofino and one of our stops was the little fishing village of Camogli. There isn’t much to see there but we walked around and stopped at this pastry shop, Revallo…only because there was a line out the door and I wanted to see what all the fuss was about. The shop was the Italian pastry version of The Soup Nazi and honestly the best pastry I have EVER tasted in my life. I did not share one bite and enjoyed every delicious satisfying bite. They also had slices of pizza (I also bought a slice of pizza and did share that – I’m not a complete monster), bread, cookies and other treats and it was very entertaining to watch the customers interact with the bakery staff. No one spoke any English so I resorted to a lot of embarrassing pointing at different things. I hope Martha and her group get the chance to stop by and experience and taste it.

DAY EIGHT: Transfer to Milan, Last Supper
After breakfast, we’ll journey to Milan, Italy’s fashion capital, where we’ll check into the exquisitely restored 19th-century Rocco Forte House in the heart of the fashion district. Located at the prestigious corner of Via Manzoni and Via della Spiga in the Quadrilatero della Moda, these sophisticated accommodations combine historic charm with modern luxury. You’ll enjoy lunch at your leisure, followed by a skip-the-line visit to see Leonardo da Vinci’s masterpiece, The Last Supper. After a memorable dinner together, you can choose to attend an optional evening performance of Rigoletto at the legendary Teatro alla Scala.

A comfortable outfit for travel day from Portofino to Milan – Gap Wide Leg Ankle Jeans and Adidas sneakers + one of the sweaters above.

Definitely take the climb to the top of the Duomo – it is an easy climb and the views are amazing.

Last Summer at The Last Supper. Tip – there is a cute little café called Ottolina with great coffee and snacks just to the right of where I am standing.

Definitely worth stopping in for a snack or a coffee while you’re waiting to go in the museum.

DAY NINE: Duomo Tour, Fashion District
This morning, we’ll experience the magnificence of Milan’s stunning Duomo with a skip-the-line tour, exploring its intricate Gothic architecture and breathtaking views from the rooftop terraces. For lunch we’ll savor the simple yet exceptional cuisine of La Goia, one of Milan’s most celebrated restaurants. This afternoon, we’ll step into Milan’s dazzling fashion world as our expert guide reveals the stories behind legendary houses like Prada, Versace, Armani, and Dolce & Gabbana during our Milan Fashion Tour. Tonight, dinner will be at your leisure in this stylish city, allowing you to discover Milan’s vibrant café culture or sophisticated restaurants.

I love this La Ligne cotton crochet dress for a night out to dinner – pair with flats, a jacket or a blazer.

I’ve written about this black off-the-shoulder Rohe dress before and that’s because it is a great travel dress. Made of jersey material, it looks elegant and doesn’t wrinkle.

DAY TEN: Bespoke Perfume Workshop, Cooking Class
Today we’ll immerse ourselves in two quintessentially Milanese crafts – perfumery and cuisine. This morning, we’ll create our own signature scent during a bespoke perfume workshop in a hidden atelier, crafting a personalized essence that captures the sophistication of Milan and becomes a one-of-a-kind keepsake of your Italian journey. Lunch and the afternoon are at your leisure to explore this vibrant city. This evening, we’ll immerse ourselves in a culinary master-class. From crafting hand-made pasta to preparing traditional sauces and desserts, you’ll discover the secrets behind the sophisticated flavors that have made Northern Italian cusiine legendary. We’ll enjoy the results of this culinary exploration as our farewell dinner, the perfect culmination of an unforgettable journey through Italy’s most stylish destinations.