Over The Moon’s La Dolce Vita Honeymoon Guide to Italy

By Shayna Seid

Summer is Over The Moon’s peak wedding season, which also means, honeymoons are in abundance. And while flocks of newlyweds will no doubt make us drool with envy as they head to Italy to bask in their post-I do glow, navigating a La Dolce Vita trip isn’t as blissful as it may seem. As one of the most popular honeymoon destinations in the world, planning travel there has become increasingly difficult. Enter Wedaways, a luxury honeymoon travel advisor, which helps couples navigate the dos and don’ts of planning an Italian itinerary—and we’re sharing ours with you to copy and paste as you please. For our dream honeymoon, we’re starting in Rome then traversing the coast to Sorrento, before ending in the Amalfi Coast.

First things first, it’s ideal to start planning a honeymoon in Italy as far out in advance as you can. For an August Roman holiday, starting to plan in February was *chefs kiss.* Hot Tip: If you have your eye on Le Sirenuse in Positano—as we all do—rates become available about a year in advance. There’s also the national holiday Ferragosto on August 15 to keep in mind, when a majority of restaurants and shops will be closed.

When to Go

The Amalfi Coast is “open” from the end of March through October, similar to Tuscany. Wedaways Lead Travel Advisor Pamela Goldman says her favorite times to visit are in April, May, September, and the beginning of October because it’s not too hot and the hoards of people are mostly gone. We’ve also personally braved the heat and crowds in late August, and to our surprise, it was still highly enjoyable.

Where to Stay

We start our journey in Rome—to channel our inner Audrey Hepburn in Roman Holiday, of course, and because Rome’s airport is easy to get to. Once you’ve gotten through customs, take a taxi (or have Wedaways arrange a luxe car service) to Hotel de la Ville, right above the famed Spanish Steps. The five-star Rocco Forte property, which is also an 18th-century palazzo, puts you in the perfect position to navigate the city with ease and a luxurious touch. You must take in the views at Chef Fulvio Pierangelini’s rooftop restaurant, Cielo. We highly suggest beating the jet lag, finding the best Roman carbonara, and recharging in The Eternal City before heading to Sorrento.

OTM Travel Tip: Have Wedaways arrange a car service from Rome to Sorrento—and maybe even stop on Mount Vesuvius and in Pompeii (if you or your partner love history). The drive is around three-and-a-half hours, but trust us, it’s best to sit back and be comfortable with an experienced local driver than clench the wheel with white knuckles as you try to navigate the cliffs in a rental. 

Once by the coast, check in to Bellevue Syrene. The five-star hotel is the crown jewel of Sorrento and is open all year. When we last visited, we witnessed a proposal and wedding party in one night. And it’s easy to see why, the romance is unbeatable with cliffside views of the ocean, spectacular service, and that iconic seaside Italian design.

OTM Bride Chang Liu on her wedding day at Villa Cimbrone. Photo: David Bastianoni

After a few nights in Sorrento, head to up the mountain to Ravello. One of our favorite wedding venues, Villa Cimbrone, also makes for a wonderful honeymoon spot. The 12th-century residence features the famous Terrace of Infinity, which you can see in OTM Bride Chang Liu’s wedding feature. Stay in one of the hotel’s 19 guest rooms before traveling through more of the Amalfi Coast.


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In total, there are 13 towns in the Amalfi Coast. We found that it’s best to make camp in one of them and then do day trips to the others. We chose Positano—stay with us, we know it’s controversial. As one of the most popular areas, one may think that it’s too overdone for a romantic honeymoon. But they just don’t know where to stay. As we mentioned earlier, Le Sirenuse is on everyone’s mind each season—and it didn’t disappoint. From the exclusive feel to the colorful design and the food—don’t even get us started on the food—the boutique hotel should be on everyone’s bucket list. With that said, it does have a three-night minimum, books up quickly, and is priced at market value. We say, make a three-night stay at Le Sirenuse an experience on your Over The Moon Registry and see what happens, frankly.

Le Agavi

However, should Le Sirenuse not work out for whatever reason, we have a five-star “IYKYK” hotel in Positano that we’re no longer gatekeeping. Hotel Le Agavi Positano was outstanding, and we wouldn’t have found it without the guidance from Wedaways. Built into the cliffside just a few meters away from the bustle of the Positano port, this hotel is tranquil with views that sirens would sink ships for. Each room features private terraces, where you must have breakfast in terrycloth robes together. And the private beach club is heaven on earth. When you’re ready to embrace the town, take the Le Agavi private shuttle five minutes into Positano’s center for shopping or a beachside meal.

OTM Bride Daisy Bishop walking down the aisle at Caesar Augustus Hotel. Photo: Bottega53

Lastly, if Capri is on the itinerary, we recommend staying on the island for a few nights or taking a private boat out to visit. (A day trip via ferry to explore Capri on foot isn’t for the weak and patience was tested). One of our favorite hotels is the Caesar Augustus Hotel, where OTM Bride Daisy Bishop hosted her destination wedding.

Pierluigi’s vermicelli all vongole.

Where to Eat

Mamma mia, let’s get into the food. Starting in Rome, make a reservation for Pierluigi. In the ’90s, it became a pioneer in the Roman culinary scene, particularly in the preparation of fresh fish and seafood. Get a table outside and order the vermicelli all vongole.

OTM Travel Tip: Have Wedaways make as many restaurant reservations as possible, as they have a local team who can call in Italian and get it done. We got a prime La Sponda reservation thanks to them. More on that later. 

Poldo e Gianna Osteria’s carbonara.

Poldo e Gianna Osteria is a must. You have to order the carbonara—we don’t make the rules. Made with pork cheek, it is creamy and delectable, and you’ll need a light evening walk afterward.

La Pergola at Bellevue Syrene.

Once in Sorrento, the most romantic reservation one can make is at La Pergola at Bellevue Syrene—and the food is as delicious as the view is breathtaking. Sit down right before sunset, take all the pictures, and then maybe even witness someone a few tables over pop the question—like we did.

O’Parrucchiano la Favorita

Immersed in a lemon grove, O’Parrucchiano la Favorita is a great spot for lunch with a huge menu that will please even the pickiest eaters. Founded in 1868 by Antonino Ercolano, the restaurant claims to be the inventor of the cannelloni dish. And hey, they also do weddings in their large space!

L’Antica Trattoria’s spaghetti cacio e pepe.

For one of the best meals you’ll have in Italy, book a table at L’Antica Trattoria—the spaghetti cacio e pepe is unlike anything else with goat cheese, black pepper, and beef and pork ragout. It will live in your head rent free forever.

La Sponda’s cacio e pepe tortellini.

A tie for the best meal is at La Sponda at Le Sirenuse. This restaurant has everything: atmosphere, live music, views, romantic design, elegant people, excellent service, delicious pasta. Even the website notes that proposals here are aplenty, and we can personally attest to that. And if there’s a cacio e pepe tortellini dish with truffle on the menu, order it.

Ristorante Da Teresa’s homemade seafood pasta.

To see where locals go, stop at Ristorante Da Teresa in Amalfi, which also hosts weddings! Part beach club, part restaurant, it’s the best place to fuel up during a boat day, and the pasta is super fresh and light.

The Trevi Fountain

What to Do

Let us preface this by saying, it’s you honeymoon, you do you. You don’t have to do anything, but if you’d like to, we have thoughts. . .If you haven’t been to the Vatican City, might as well check it off your list. As one of the most known works of art in the world, you may want to skip the Sistine Chapel; that would be a mistake. It is overwhelmingly special and close to a spiritual experience. We recommend booking the first morning semi-private tour with Wedaways. If you’re in Rome for a bit, also check out the Colosseum, the Trevi Fountain, and the Spanish Steps. You’ll get way more than your recommended 10,000 steps in.

OTM Travel Tip: Wedaways can arrange semi-private or completely private tours of tons of excursions. Let them pick for you or browse their vast library of options across the country. Pamela can also take care of any ferry tickets—her instructions were super clear and we traveled without a hitch. 

On the way to Sorrento from Rome, why not visit Pompeii? Buried by the volcanic eruption of Mount Vesuvius in 79 AD, it is one of the most incredible archeological sites. And in the spirit of a honeymoon, it’s worth mentioning that the citizens of Pompeii really liked to get it on and dedicated several frescoes and sculptures to it.

The Nonna Flora kitchen.

Once in Sorrento, take a private cooking class at Nonna Flora with Anna Maione. Whether you’re a Michelin-starred chef or barely know how to use a microwave, Anna will lead you and your partner through a delicious multi-course meal. You’ll learn how to make fresh pasta and end the evening with homemade tiramisu.

One of the highlights of any trip to the Amalfi Coast is doing a boat day. Wedaways will arrange a private speed boat for a romantic tour of the coastline from the water. Our captain from Amalfi Sails had hosted Dua Lipa, so we knew we were in good hands. He knew all the spots where we could safely jump in the water and even let us take the aux cord.

Arienzo Beach Club

If your hotel doesn’t have a private beach club, or you’d like to change up the scenery, head to the Instagram-famous Arienzo Beach Club with its unmistakable striped orange umbrellas. Fair warning, they price by how close each row of chairs is to the water—it really made no difference being further back—and American accents will one hundred-percent be heard here, whether you miss them or not. It’s a great vibe, and it now feels like trips to the Amalfi Coast are incomplete without lounging on an Aperol Spritz-colored chair.

The OTM Exclusive: Lori Tote.

What to Pack

Now that you’ve been sold on the location, it’s time to pack for a honeymoon in Italy with our Summertime Travel Edit of swimwear, fashion, accessories, and more.