Romantic Destinations of Italy and Spain Itinerary

Spain, Andalusia, Seville, foreshortenings of the architectures of Plaza de Espana.
A 14 day trip to Italy & Spain 
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Walk hand in hand through the best of Italy and Spain on a handcrafted getaway designed just for two. Exquisite destinations set the scene, from historic cities to artisanal towns to Mediterranean villages of color and cobbles. Celebrations revolve around new experiences such as tapas hopping, Chianti vineyards, and driving a vintage Fiat 500. There’s also plenty of space and time for romance to thrive in Florence, Cinque Terre, Lake Como, Madrid, and Seville.

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Most tours are customized for private travel.

General Information

Detailed Itinerary

Places Visited 

Florence, Florence Cathedral, Uffizi Gallery, Ponte Vecchio, Palazzo Vecchio, Tuscany, Chianti, Siena, San Gisignano, Lucca, Pisa, Vernazza, Cinque Terre, Monterosso, Corniglia, Riomaggiore, Milan, Santa Maria delle Grazie, Milan Cathedral, Galleria Vittorio Emanuele II, Bellagio, Lake Como, Madrid, Prado Museum, Segovia, Cordoba, Mosque of Cordoba, Andalusia, Seville, Alcazar, Seville Cathedral, Giralda

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Florence – Landing in Tuscany

When you touch down in Florence, domes will set the scene for your vacation. So many churches and cathedrals stand proud across the city, and their summits glow in the afternoon light. Beneath them, you will find piazzas, places where local people take a stroll or congregate on terraces. You can smell the espressos down narrow lanes and sense the inimitability on a first walk through Florence’s old urban core. This is a city built upon the beauty of the Renaissance, and it’s a particularly inspiring place to be from late afternoon to sunset. At this time of day, you don’t need a guide. You can go out exploring, just the two of you in Italy’s most romantic city.

What’s Included: airport transfer, accommodation

Day 2: Florence – Vineyards and Southern Tuscany

Wake up late and spend the morning relaxing while the sounds of Florence flutter onto your verandah. A guide will escort you into the hills, south toward Chianti and Siena. Towns cling to hilltops. Vineyards cascade down the hills and mix occasionally with olive groves. Stone farmhouses peek out from the green, their facades luminous in the morning light. Stop first in Siena to hear the footsteps on cobbles as you explore the old city of Palio fame. Then travel to Chianti, where a cellar-master takes you on a tour of a vineyard before a healthy tasting session. The cellar-master will introduce the two of you to Tuscan gastronomy as they open vintage wines and pairing drinks with food. Then you’ll be left on the terrace with your partner, great wine, and endless views.

What’s Included: accommodation, tour, breakfast

Day 3: Florence – A Vintage Fiat 500 Through the Hills

Today, you’ll drive a vintage Fiat 500 perfect for tackling hilly roads that lead out from Florence. It’s an iconic vehicle, and the photos will be memorable with the two of you surrounded by different pieces of Italian history. A guide leads the way, and you travel in convoy, stopping at two villages and an olive farm. From the Fiat 500, you get an unobtrusive look into rural Tuscany, without needing to always be in the company of a guide. Like yesterday, return to Florence in the late afternoon. So take a walk, grab a coffee, dine on the piazza, and listen for those telltale church bells.

What’s Included: accommodation, tour, breakfast

Day 4: Vernazza – Relaxing on the Cinque Terre Coast

A tower leans and its porticoes shoot off at a strange skyward angle. A cathedral stands straight and true, crafted from the same white stone. A baptistery and university continue the architectural harmony, showing you more of the 12th century. This is Pisa, a convenient and charming little stop on the road to the coast. Take a walking tour, eat some lunch near the tower, and arrive in Cinque Terre around mid-afternoon. You’ll stay in the village of Vernazza, which appears to have come from a romantic dream. There are colorful townhouses around the harbor, dramatic castle remains, and cobbled alleyways and staircases that lead to another square or church. The guide will give you a quick brief of the area then you will spend the day at leisure with a hotel based in the most beautiful of all the Cinque Terre villages.

What’s Included: accommodation, tour, breakfast

Day 5: Vernazza – Small Seaside Villages of Color and Charm

There are five villages in total that dot the Cinque Terre coast. The classic experience is to take a train between them and stop to explore Corniglia, Riomaggiore, Manarola, and La Spezia. You can also walk, a delightful journey across the cliffs as the sea shimmers brightly far below. However, you don’t need to see every village to get the full experience. Just pick and choose as you create a personal adventure in this colorful corner of the continent. Enjoy pizza and espresso at a small cafe, fine wines as sunset colors fill the sky, and taking a turn down a narrow lane to find spectacular views. When you’re somewhere like Cinque Terre, there’s not much need to plan in advance. Just wake up and see how you feel, then allow Italy’s coastline to work its magic.

What’s Included: accommodation, tour, breakfast

Day 6: Bellagio – Da Vinci and the Lake

This morning, you will leave the coast behind and travel north to Milan, a city with three unforgettable experiences. First, you’ll see Da Vinci’s The Last Supper, an enormous mural that’s tucked away in a Milanese convent. Then, visit Milan’s cathedral, a dramatic structure that took over 600 years to build. Finally, tour Galleria Emanuele Vittoria II, a glamorous late 19th-century shopping mall where you can stop for a glass of wine and a pizza. Continue your journey to Lake Como, where you check in to one of Italy’s finest hotels. Draped along the waterfront and with a history that whispers from every wall, the hotel has been used by many a celebrity or royalty on honeymoon.

What’s Included: accommodation, tour, breakfast

Days 7 – 8: Bellagio – Romantic Downtime On the Water

Lake Como ripples softly, singing a little lullaby. Morning sunlight bounces back off its surface, as enlivening as a morning cappuccino. Boats occasionally saunter into the harbor to pick up passengers before they head off to nearby shores. Sometimes you will hear them, and sometimes you hear the excited hum of people who have just disembarked. Mostly, you will only hear the water, as Bellagio is a tiny town tucked away from the rest of the world. Take a stroll here to find opulent experiences from boutiques and fine dining restaurants to lakeside cafes and wine bars. Walking is the only way to get around, as most of Bellagio is completely closed to vehicles.

Lake Como has always been a romantic destination. There is no guide, no interference, no need to plan anything until you arrive. A ferry pass is provided, so you can easily travel to any other village or town on Lake Como. These ferries run regularly throughout the day and are far quicker than any journey by road. Dotted across the lake, you’ll find villas and gardens, along with residences owned by royalty and celebrities. Most of all, you’ll find tranquility and space for romance to thrive. Settle into the hotel, toast to life, and spend time with your significant other.

What’s Included: accommodation, tour, breakfast

Day 9: Madrid – Savoring Spanish Flavors

Today, a guide will transfer you back to Milan for your flight to Madrid. The atmosphere is relaxed in the Spanish capital with broad boulevards that lead you toward grand plazas and an old quarter that comes alive at dusk. Check in to the hotel and head out on a private food tour. Madrid is home to migrants, like all capital cities, and those migrants have brought their own flavors. Stop in a Galician tavern to taste Galician octopus. Then, visit a small Valencian bar to try paella before you taste wine from La Rioja and Penedes at a quirky bistro. Your food tour will conclude with chocolate and churros from an establishment with over a century of history. With food as a focus, the tour will explore the heart of Madrid, including the figures and stories that have made it what it is today. End on the Plaza Mayor, an idyllic place to watch the world pass by you.

What’s Included: accommodation, tour, breakfast

Day 10: Madrid – Discovering Segovia

Spend the morning sleeping in and taking your time to get ready for the day. There’s no need to rush a romantic tour and the local guides will adjust timings to your interests. When you’re ready for the day trip, step into Segovia’s walls and 2000 years of history. More than 160 Roman arches run through the center, and an aqueduct built without a mortar extends through the main plaza. The cathedral is Gothic in style, dominated by cupolas and fine stained glass. Churches point to differing eras, and this single city shows the contrast between Romanesque, Renaissance and Gothic architectural styles. Travel back to Madrid and the evening will be at your leisure, with the guide able to suggest restaurants based on your tastes.

What’s Included: accommodation, tour, breakfast

Day 11: Seville – Old-World Moorish Enchantment

Today you’ll take a high-speed train to Cordoba, where whitewashed Moorish walls entice you into a pre-medieval realm. Meet a guide and leave your luggage securely at the railway station. When you wander into the city, the streets will get narrower and narrower. They grow more exotic, full of peculiar calligraphy and Byzantine relics. Soon you’ll be at La Mezquita, one of the great Islamic buildings. Walk through the columned prayer hall, admire all the mosaics, find a Renaissance-styled Catholic nave, and exit through archways of gilded gold. There will be other Moorish highlights here, examples from an artistic world that struggles to get the recognition it deserves. Go in search of these with your guide before you re-board the train in the late afternoon.

When you arrive in Seville, you’ll enter into one of the world’s largest old quarters. Smells emanate from small taverns and palm trees rise around cobbled plazas. The cathedral stands majestic and acts as your compass point. Your hotel will be within this old quarter, in a section of streets that are mostly pedestrianized. After undergoing significant restoration in the 21st century, Seville is starting to look like the world leader it once was. Back in the time of New World discovery, almost all the Spanish ships returned through Seville, bringing with them wealth and treasure. Today, the streets are reliving that glamorous period, making Seville one of Spain’s most amorous destinations.

What’s Included: accommodation, tour, breakfast

Day 12: Seville – The Fiery Beauty of Spain’s Most Amorous City

Seville is a city full of fiery passion in the heart of Andalusia. It’s a city where old-world beauty meets the lively energy of today, a city that’s quick to pull you into its rhythm. Today you will explore with a guide, traveling the old quarter to see legendary pieces of history. Like the cathedral, this area of the city is stupendous in size and memorable for its details. Next, see the ceramic tiles of Plaza de Espana before you visit the Royal Alcazar and all its architectural glory. After a day of visiting the sites, you will have some time to experience Seville’s energy, as various city quarters make for a romantic night amid history.

What’s Included: accommodation, tour, breakfast

Day 13: Seville – Flamenco and Tapas

On your last day in Spain, you will enjoy two authentic local experiences. Tapas originates in this city and you will hop between bars with a local guide leading the way through the early part of the evening. At the more authentic bars, you will order a drink and wait for the chef to bring a celebratory snack from the kitchen. Next, attend a late-evening flamenco performance to bring this romantic journey to a close. A dress twirls while feet tap and the guitarist plays softly and improvised acoustic guitar rings through the room. Finally, a haunting voice emerges that conveys the emotion of the song and transcends any language barrier. Flamenco came from a small district in Seville and the world’s best performers still hang out here. So you don’t watch a tourist show that starts early in the evening. You follow the flamenco in a small atmospheric tavern, just the two of you and a performance from a distant age.

What’s Included: accommodation, tour, breakfast

Day 14: Seville – Departure

Enjoy a final morning in Spain before you depart the country that has given you so much over the last few days.

What’s Included: airport transfer, breakfast


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.