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Crafting a Unique Anniversary or a Memorable Honeymoon Italy Itinerary

Updated: Dec 7, 2023

Embracing La Dolce Vita – Why Choose Italy?

Italy is a natural choice for a romantic vacation. There are fantastic resorts and spas in the mountains and the coast and endless opportunities to delve into shared interests, whether history, food, wine, hiking, or skiing. Italy is also home to a multitude of classic images associated with romance – waking up under the Tuscan sun or snuggled up together for a gondola ride through Venice's canals whether you’re a young honeymooner or returning to travel for the first time in many years to celebrate a milestone anniversary, there are a million ways to celebrate your unique connection in Italy.

Crafting An Off-The-Beaten Path Itinerary: From Rome to Tuscany

honeymoon italy itinerary

Starting in Rome: The Eternal City

Thanks to the movie Roman Holiday, sites like the Spanish Steps and Trevi Fountain are associated with romance. Given that Rome is home to one of Italy’s two international airports, it’s likely your flight will be landing there. Begin your Italian honeymoon journey in Rome with famous sites like the Colosseum and reservations at classic Roman restaurants like Piatto Romano or Armando al Pantheon. If you stay in Rome for a week, you may want to stay in a Trastevere, Testaccio or Monti, but if you have just a few days, choose a hotel directly in the city center.

Amalfi Coast & Capri

Exploring the Amalfi Coast & Capri

The Amalfi Coast is the number one wedding and honeymoon destination in Italy and among the top romantic destinations in the world. The winding coastline offers breathtaking views, and the photo opportunities are endless. If you choose the Amalfi Coast, book a resort like the Caesar Augustus or Le Agavi, as a luxury hotel is the only way to ensure you will have the experience you dream about. The vision of hidden Amalfi Coast beaches and quiet villages is one rooted in the past – the Amalfi Coast has been fully conquered by mass tourism. The swell of travelers there, thanks to Airbnb and day trippers from the major cruise lines, makes the crowds and the traffic intolerable in high season. To enjoy Capri, Positano, or Ravello, you will need a larger budget, but you will also enjoy 5-star luxury and hospitality in one of the most scenic places on earth.

Expert insight: If you want to enjoy luxury but can’t afford the high price of a 5-star resort, go during the first two weeks of April or the last two weeks of October. The resorts will just be opening/closing then, and not only will there not be any crowds, but the staff won’t be burned out from the high season stress. Without the crowds in the shops and restaurants, you can stroll hand in hand and enjoy a romantic time together.

Off-the-Beaten-Path: A Detour to Cilento

Off-the-Beaten-Path: A Detour to Cilento

If you’re looking for the Amalfi experience without the crowds and high prices, go just a bit farther south to Cilento. Unseen by mass tourism, the Cilento region offers an experience of authentic traditional Italian culture with a fantastic tourism infrastructure.. Known for its pristine coastline and mountain villages where traditional Italian life persists, it is truly a hidden gem. Here, you can experience authentic coastal Italy, away from the bustling crowds and in tranquility.

Expert insight: If you’re a member of the “Before Sunrise” Generation and you’re returning to travel for the first time in twenty years, Cilento is perfect for you.

Wine and Dine in Tuscany

Wine and Dine in Tuscany

If wine and views are what you seek, Tuscany is among the most beautiful and classic destinations you could choose. I recommend spending several days in Florence to see the major sites, shopping in the artisan shops for jewelry and leather, going on a food tour, and booking at least one high-end restaurant experience. Stay in the Oltrarno neighborhood, away from the fake handbags and bad steak restaurants that proliferate around the San Lorenzo Market. Then, transfer to a resort in the Tuscan countryside for romance and luxury. Tuscans are known throughout Italy for their attention to detail and ability to offer services to tourists at a very high level, making it an ideal honeymoon or anniversary destination.

Expert insight: The northwest corner of Tuscany around Lucca is less touristy and offers a classic Tuscan landscape paired with the seaside. Explore contemporary art in Pietrasanta, do a jeep tour of the Carrara marble quarries, or spend a few days on the island of Elba. You could also do a day trip to the Cinque Terre from this part of Tuscany – just be sure to check Cruise Dig ahead of time to ensure there aren’t too many cruisers in port at La Spezia on the day you plan to visit.

Experiencing More Extraordinary Scenery: Venice to Sicily

Wine and Dine in Tuscany

Venice: The City of Canals

Venice is magical, and if you want your vacation to enhance the ineffable feeling of romance, there is no better choice. The problem is that Venice is crowded, but if you plan well, you can enjoy the city well. First, stay for at least three nights – Venice is a different city when the day trippers leave. 2) Stay in the best hotel your budget will allow. 3) Book activities that will enhance the magic of Venice, like a nighttime tour of the cathedral of San Marco or a catamaran ride of the Northern Lagoon at sunset.

Expert insight: Venice is a sophisticated city, and the best experiences include dressing up, boutique shopping, wine bars, and art galleries and museums. If that doesn’t sound like your scene, I recommend taking Venice off your list.

Puglia: The Maldives of Italy

Puglia: The Maldives of Italy

Puglia, a gem in the heel of Italy, is perfect for couples who wish to escape mainstream tourism and enjoy some of the world’s best beaches. The Adriatic Coast has clear water and a rocky coast, while the interior, facing the Ionian Sea, is known as the Maldives of Italy for its turquoise waters and white sand beaches. If your vision of the Amalfi Coast is white-washed villages and quiet beaches, you more accurately imagine Puglia. Base yourself in Monopoli or Ostuni to be on the coast, or in Locortondo to be slightly island and to more easily drive all around the heel of Italy’s boot. Or

Expert Insight: if you want to be active, stay in Otranto and rent bikes to ride south to Santa Maria di Leuca, where the Adriatic and Ionian Seas meet. Because the terrain is flat, car rentals are recommended for getting around the region.

Sicilian Romance

Sicilian Romance

Sicily is a world unto itself, with a stupefying cross-section of culture, history, food, and wine. It can also be a challenging place to travel, with a lack of 3 and 4-star hotels, and reliable Wi-Fi, so detailed planning is essential. The White Lotus effect is real – Taormina which was already a popular destination and a cruise port, is teeming with people who want to stay at the San Domenico, a former convent turned Four Seasons hotel property that stood in for the fictional White Lotus.

The top two reasons to visit Sicily are food and archaeology. If you love history, Sicily has the temples at Agrigento, the mosaics at Piazza Armerina, and the amphitheater at Siracusa, and that’s only the beginning. The many cultures that have conquered Sicily all left their culinary imprint, making it a fascinating destination for serious foodies.

Expert Insight: If you’re committed to swimming on the beaches you saw in The White Lotus, they’re not actually in Taormina rather they filmed those scenes in Cefalù.

Planning Your Dreamy Escape: Essential Tips

Italy Essential Tips

Deciding the Best Time to Visit

You can have a fantastic experience in Italy whenever you go, but you must choose your destinations well. If you’re committed to the most famous places including Florence, Venice or Rome, go in the winter. If can only travel during high season, make sure your budget can accommodate nicer hotels, and also plan on some less crowded options. (Think Ischia instead of Capri.) Always plan with experience as your top priority.

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"We had a brilliant time and really enjoyed your suggested itinerary. We especially enjoyed our wine tour in Irpinia with Sarah and the family, it was a highlight. The other tours and tour guides were also wonderful. The whole process was fun and easy with only a few hiccups due to weather, but these were easy enough to navigate. Thank you!!!"

Ilana & Brooke, October 2023

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