The Perfect 10-Day Italian Honeymoon Itinerary

After you arrive in Milan, check into your hotel and either take a quick nap to help with some jet-lag or immediately set off to explore the city! Once you embark on your explorations, head straight for the iconic Duomo di Milano. After taking in the beautiful Gothic architecture, head over to the Galleria Vittorio Emanuele II, a luxurious shopping gallery where you can enjoy a cappuccino in one of its historic cafes or grab an aperol spritz at the Terrazza Aperol, where you can view the Duomo from up higher!

Spend the afternoon strolling the charming streets of the Brera district, where you can pop into a variety of boutiques, art galleries, and cafes. Visit the renowned Sforza Castle, a historic fortress that now houses several museums and art collections, including the Pinacoteca, which displays works by Michelangelo and Leonardo da Vinci.

As the sun sets, head to the vibrant district of Navigli. Known for its picturesque canals and lively atmosphere, Navigli offers many world-class dining options. Enjoy a romantic dinner along the water at Ristorante Belé Navigli while watching the reflections of the city lights and savoring your first night of fine Italian cuisine.

Have breakfast at your hotel and grab a cappuccino for the journey--today you're taking the train to Lake Como! Just about every hour, there is a train departing Milano Centrale Station to Como S. Giovanni in Como. The train ride takes approximately one hour.

Once you arrive in Como, it is highly recommended you get a rental car for the length of your stay. Taxis are very expensive, Ubers are non-existent and the bus system is unreliable. Also, if the bus gets full before you get on, you will likely have to wait an hour or more for the next bus! After picking up your rental car, head to your accommodations and check in! Grab lunch at the hotel and admire the beauty of the lake.

After lunch, head over to Villa del Balbianello, one of Lake Como's most iconic villas. It is recommended to buy tickets in advance that correspond with a late afternoon entry time--you can choose to either have a 45-minute guided tour of the villa and gardens (23€) or a self-guided gardens-only ticket (12€). To get there, you can either park and walk there (the walk there is mostly uphill!) or boat shuttle from Lenno (~8€ roundtrip). Keep in mind the boats are on a first-come-first-served basis, so give yourself plenty of time just in case there is a wait!

After spending the late afternoon strolling the marvelous gardens of Villa del Balbianello, grab dinner at the nearby Hotel Tremezzo for an upscale evening dining on the waterfront (reservations highly recommended).

Today is all about the art of relaxation, or dolce far niente, as the Italians would say. After grabbing breakfast at your hotel (or room service, if you're looking for a lazy morning), spend the afternoon lounging by the pool. In the late afternoon, grab a few drinks at the hotel or pool bar as you embrace the Italian custom of aperitivo!

For dinner, you can opt for continuing the casual vibes with pizza from Pizzeria Il Sagittario in Laglio, stay close to home and grab dinner at your hotel or get dolled up for a romantic waterfront dinner at Ristorante Imperialino.

After a day of rest and relaxation, get ready for your final day of exploring Lake Como! Today, get ready to explore Bellagio--Lake Como's most famous town. Start your morning with breakfast at your hotel, or get a head start exploring Bellagio with breakfast at Nenè Bellagio. Spend the morning wandering through the narrow cobblestone streets and discovering local shops and boutiques.

Next, visit the iconic Villa Melzi Gardens, a picturesque estate with beautiful gardens overlooking the lake--tickets are 10€. Stroll through the beautifully maintained grounds adorned with sculptures, exotic plants, and serene pathways. Take in the breathtaking views of Lake Como and the surrounding mountains.

After working up an appetite, grab lunch at Ristorante Bilacus in their beautiful garden setting before heading off for your last Lake Como adventure--a late afternoon boat ride on the lake. Como Classic Boats will pick you up from any town with a dock, or your hotel if there is a dock! From there, spend a few hours on your private boat tour exploring the majestic waters of Lake Como. As the sun begins to set, pop a bottle of Prosecco and cheers to this romantic evening! This may be your last night in Lake Como, but your honeymoon is truly just getting started!

Next up, you're headed to the rolling hills and vineyards of Tuscany. After breakfast/checking out of your hotel and dropping off your rental car, you'll take a train from Como S. Giovanni to Florence. It's likely that you will need to transfer at Milano Centrale (but good news, you're already familiar with that station!) The total trip from Lake Como to Tuscany will take about three and a half hours. I recommend pre-booking all of your train tickets before heading to Italy. It is easy to book city-to-city train tickets on ItaliaRail and booking ahead is usually cheaper! For your honeymoon, I recommend booking first-class fares. This way, you'll have dedicated luggage storage space, comfortable seats next to each other and first-class tickets also come with free welcome snack amenities, including a snack box, water, and a free drink!

If you have enough time during your transfer at Milano Centrale, pop out of the station and head to All’Antico Vinaio (a two min. walk from the station) and grab some focaccia sandwiches for your journey!

I also recommend booking a driver service for your transportation in Tuscany. While renting a car is also an option, your stay in Tuscany will be focused more on relaxation than adventure--and what better way to kick back and relax than knowing your transportation is taken care of by a well-respected and knowledgeable driver? I recommend checking out Bellini Bruno. Once you get to Florence, your driver will be waiting for you as soon as you step off the train, ready to whisk you away to your next romantic location!

For your stay in Tuscany, you'll head to a boutique hotel near San Gimignano, about an hour south of Florence. I recommend staying in a hotel with a winery/dining on-site, such as Locanda le Piazze so you can relax and enjoy the beauty and culture of Tuscany without ever having to leave your accommodation!

Once you arrive, grab a glass of wine and head down to the hotel pool overlooking the hills of Tuscany. Spend the late afternoon relaxing, knowing dinner reservations are just a few steps away at the hotel restaurant! You could get used to this...

Today, you can choose to either spend the afternoon relaxing at the hotel pool after a day of travel, indulging in a wine-tasting at your hotel winery (or one of the many nearby) or heading into town to explore the medieval village of San Gimignano. Whichever you choose, you can choose to either extend your stay if you have longer than 10 days for your honeymoon and do one option per day, or try to squeeze in all three in one day!

If you choose to explore San Gimignano, have your hotel arrange a taxi service to pick you up! Ask your driver to drop you off at the top of the walled city, so as you explore you can make your way down through the entire village and get picked back up at the main entrance on your way home. Some highlights of San Gimignano are Gelateria Dondoli for award-winning gelato and be sure to grab either lunch or dinner at Ristorante Bel Soggiorno for beautiful panoramic views and delicious traditional Tuscan cuisine. With almost 30 restaurants on the Michelin guide, San Gimignano will have plenty of amazing dining options for you to check out!

If you extend your honeymoon beyond 10 days, I strongly recommend spending 1-2 more days enjoying the Tuscan countryside. However, if you only have 10 days, today, you will embark on your last leg of the journey to the Amalfi Coast! Have your driver pick you up with enough time to take you back to the Florence train station (~1 hour drive), where you will embark on your final train journey to Naples. Once again, book your tickets ahead of time and choose first-class seats for dedicated luggage storage space, a welcome snack and beverage, and comfortable seats. The trip from Florence to Naples will take about three hours. I also recommend booking a private transfer from the Naples train station to your accommodation in Positano. Often, your accommodation concierge will be able to recommend and book private transfer services for you. While there are other ways of getting to Positano that include busses, ferries, and/or renting a car and driving yourself, they are not recommended! Each either takes many transfers and lots of time, can be very crowded, or involves stressful cliffside driving along windy roads--why stress on your honeymoon? Leave the driving to the professionals so you can kick back and relax. The drive from Naples to Positano takes about 1.5 hours, meaning you will likely arrive in Positano in the early evening. Once you check in, spend some time exploring your accommodation, and then leave plenty of time for your walk to dinner so you can explore a few boutiques along the way. Opt for some pre-dinner drinks at Franco's Bar and catch the sun setting over Positano. Then, have dinner at the romantic La Sponda next door at the iconic Hotel Sirenuse.

Today, you will embark on a day trip to Capri Island! You can choose to either book a private boat tour ($$$) or a shared small-group boat, which is more affordable. Either way, you will enjoy an afternoon of sailing along the beautiful Amalfi Coast, swimming in the crystal blue waters and viewing iconic spots like the Faraglioni Rocks and the grottos. Keep in mind, tours of the Blue Grotto are often separate activities and dependent on the water levels for safety. Once you dock in Capri, take the funicular tram to the top of the island, where you can spend the afternoon exploring Capri Town, shopping in the many high-end stores and boutiques, grabbing lunch, or adventuring through the Gardens of Augustus and Via Krupp. If you have time, you can even opt to take the chairlift to Monte Solaro in Anacapri, which has beautiful panoramic views of the islands and the coastline. Once it's time to head back to the boat, spend the rest of the late afternoon sailing back and enjoying the sunshine and coastal views. After a day in the sun, opt for a more casual dinner at spots like Misaki Sushi or pizza at Saracena d'Oro.

For your final full day in Italy, spend the day soaking up the Italian sun at a Positano beach club! My personal favorite is La Scogliera, which is the most exclusive beach club in Positano and offers the best views of town while you swim in the clear blue waters! Or, you can opt for classics like Arienzo Beach Club or Da Adolfo, both of which offer complimentary boat shuttles to their private beach areas. After spending the afternoon lounging in the sun, enjoying fresh seafood, and drinking some aperol spritzes at the beach club, head back to the hotel to freshen up for your final romantic dinner in Positano! Make reservations for your final evening at one of Positano's most romantic spots, like Il Tridente, Ristorante Adamo ed Eva, or Zass (*you will need to arrange transportation here as it is not walkable from Positano.)

For your final morning in Positano, depending on your flight time home, grab breakfast at Casa e Bottega and spend some time ambling through the streets for some last-minute keepsake shopping. Don't forget to bring home some limoncello, hand-crafted ceramics, or classic Italian linens to remember this once-in-a-lifetime trip! After breakfast, check out of your hotel and head to meet your private driver for your homeward-bound trip to the Naples airport. Ciao Italia!