Dreamy Italy Hotels
A curated collection of dreamy stays in Italy for special occasions. Featuring design-led boutique hotels, rustic masserias, and seaside villas throughout Italy’s varied regions.
21 Places • 18 Saves • ago
Free
🛏 Masseria Potenti
@Chelsea
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Palazzo Daniele
@Chelsea
Set in a historic palazzo near the southern tip of Puglia, Palazzo Daniele artfully juxtaposes minimalist decor with neoclassic grandeur. This intimate, nine suite boutique hotel features a pool and spa, orange tree garden, and a secluded space for private dinners.
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🍽🛏 Le Sirenuse*
@Chelsea
Chances are you’ve seen photos of this upscale hotel featuring scenic views of the surrounding coastline and architecture. If you stay elsewhere, consider visiting for a romantic dinner at La Sponda or drinks at the champagne bar. Book well in advance, and note that some rooms don’t have a view.
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🛏 Borgo Egnazia
@Chelsea
This lavish, village-like property made of tufo stone boasts three restaurants, three pools, a spa, and a private beach club. As elaborate as it is, it reflects the character of Puglia with a charming and romantic feel. The town of Savelletri is well positioned to visit both the countryside and the coastline, and the amenities at Borgo Egnazia make it an ideal option for families. Rooms in the hotel are adults only, while the small townhouses and larger villas sprinkled throughout the grounds are for groups and families. There are two beaches (one sandy, one rocky with a beach club and plenty of activities) a few minutes away that the hotel drives guests to.
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🛏 Palazzo Avino
@Chelsea
Luxurious, family-owned hotel set in a historic villa known as the "Pink Palace" in Ravello, a hilltop town with stunning views of the surrounding coastline. Palazzo Avino offers the best of both worlds with a clifftop location and private beach club down below. Note: Most of the rooms here feature coastal views, but the ones facing the mountainside are less expensive. Perfect for travelers looking for a high-end hotel experience at a more affordable price point.
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Mezzatorre Hotel & Thermal Spa*
@Chelsea
While Ischia's comuni offer rustic Italian charm, this hotel oozes elegant allure. Located in a secluded cove amid chestnut forests and volcanic rock, Il Mezzatorre benefits from a private bay, beach and a spa housed in a 16th-century watchtower. An indoor thermal spa, seawater pool, and direct access to swimming in their private cove, as well as world-class dining, make this a resort you'll never want to leave. oozes Italian beach sophistication. If you could distil la dolce vita and 1950s Italy, it would look like the Pellicano Hotels group. It’s right on the bay, so book a room in the tower by the sea. Breakfast is amazing—a million pastries and 10 kinds of mozzarella from Naples. Have the lobster spaghetti by the pool for lunch. At the beach, ask for Giorgio: I always tip him in advance, and he saves the best chairs for me.
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🛏 Sextantio Le Grotte Della Civita
@Chelsea
Sextantio Le Grotte Della Civita is made up of 18 caves and a common space in an ancient rock church. Located in the oldest part of the Sassi overlooking the Gravina stream and Murgia Park, the setting is dreamy and perfect for a special occasion.
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🛏 Palazzo Margherita
@Chelsea
Francis Ford Coppola’s hotel in his grandparents’ former hometown.
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🛏 Villa Cora
@Chelsea
Opulent hotel brimming with frescos and ornate decor. First floor rooms are recognized by the Italian government as historically significant. Stately 5-star boutique hotel near the Boboli Gardens, on a garden estate in the hills just outside the city center. Features elegant rooms and a beautiful outdoor pool area. $550+/night Highlights: Villa Cora is a stunningly elaborate hotel that feels more like a Tuscan resort than an urban hotel, despite being only 10 minutes from the city center. Tips: They have a beautiful outdoor pool, perfect for the crew to relax after an active day exploring Florence. Keep in mind: This hotel checks the box for a range of folks, whether groups, families, or couples who flock here for the sense of place and historic details.
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🛏 Grand Hotel Tremezzo*
@Chelsea
Luxurious renovated Art Nouveau resort in the village of Tremezzo next to the famous Villa Carlotta gardens, with rooms overlooking either the lake or mountains. The interior is infused with traditional Italian design details, but the overall vibe here is more modern than most of the classic properties in Lake Como. It's also family friendly with plenty of connecting rooms (book well in advance) and a few suites for up to 4 people. There's an 8 bedroom villa that can be taken over for groups or large family stays. Guests will have access to a range of amenities including two pools, a beach club, five dining options, tennis courts, and boat tours with lunch. If you're here for a special occasion, splurge on a top-floor suite with a private hot tub. Non-guests can visit T Bar for pre-dinner drinks with views after visiting Villa Carlotta.
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🛏 La Posta Vecchia
@Chelsea
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Hotel Il Pellicano
@Chelsea
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🛏🍷 Villa San Michele
@Chelsea
Situated 15 minutes from the city, Villa San Michele feels like its own destination with verdant gardens, scenic views, and stylish interiors. Guests can also take a class at the on-site cookery school, plus a separate one for kids. If you’re staying elsewhere, consider coming for drinks. The hotel can be reached by taxi, private transfer, or a courtesy shuttle bus for guests that runs to the city center multiple times daily. $825+/night, stunning luxury hotel on a hilltop overlooking Florence and the hills of Chianti. A bit outside the city center, but great for a romantic honeymoon experience. Highlights: Villa San Michele is honeymoon-approved! Located up in the hills overlooking Florence, the views from your room will be unmatched. Tips: The hotel is located 25 minutes outside of the city center, so avoid placing clients who want to do a lot of touring and need proximity to the city here. Keep in mind: Villa San Michele is not a year round destination, the best time to visit would be between Easter and October.
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Villa Cetinale
@Chelsea
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🛏 Castello di Vicarello
@Chelsea
Luxurious estate set on a vast property in the Maremma featuring organic vineyards, olive groves, and farmland.
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🛏🧖🏻‍♀️👩🏻‍🍳 Borgo Pignano
@Chelsea
One of Tuscany’s most dreamy stays with its thoughtfully decorated interior, panoramic pool, and on-site wellness center. Though it’s luxurious, Borgo Pignano retains a sense of connection to the land and emphasizes sustainable practices. The on-site restaurant serves Tuscan dishes using fresh and organic ingredients from the garden. Acitivities and experiences include spa treatments, cooking and fitness classes, wine tastings, yoga, horseback riding and more. Check their website for more details (links below). Book experiences in advance, namely spa experiences. If prices are too expensive, I recommend taking full advantage of the pool (try to spend magic hour here at least once!) and visit Villasanpaolo for a spa day instead.
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🛏 Hotel Splendido
@Chelsea
More than a few VIP's (the Duke and Duchess of Windsor, Catherine Deneuve) have signed the visitor's book at this Portofino hotel. Originally a 16th-century monastery, the property was transformed into 69 guest rooms (16 at the more affordable Splendido Mare), three restaurants, and two bars. Guests can relax on the hotel's Chris-Craft Corsair 36 while enjoying champagne and canapés. Splendido can arrange a sunset cruise on their small yacht, which anchors in the San Fruttuoso bay for Champagne and snacks. Even if you don’t stay overnight, it’s worth a visit for a panoramic lunch. For a more exclusive experience, guests of the Belmond Hotel Splendido can book the hotel’s chic boat for an evening cruise to San Fruttuoso, followed by a private open-air concert in the Abbey’s enchanting courtyard.
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Reschio
@Chelsea
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🏨 Villa Sant'Andrea
@Chelsea
Luxurious hotel by the seaside. The original villa was constructed in the 1830s and has been lovingly restored down to the tropical plants in the surrounding gardens. The crowd is a complete mixed bag, but you're guaranteed to find many Americans and Brits, primarily of older age, as quiet is the order of the day. the additions of a gym, a small spa, and complimentary boat tours (with swimming) of the surrounding islands and inlets are all pluses. You'll find beautiful rooms and suites — most with flower-filled balconies and sea views — as well as the most picturesque patio for breakfasts that can last for hours. People don't come here to work out, but if you must sweat, the adequate small gym features several cardio machines. The spa does excellent in-room or outdoor massages. WiFi is available throughout the property, including at the pool and in the hotel's private beach cabanas. Be sure to request a room away from the service elevator, which kicks in very early in the morning. Breakfast on the covered terrace is the highlight. Skip dinner as it is wildly expensive and not very charming. Perfect for Couples and families with extremely well-behaved, older children. A shuttle whisks guests up to Taormina proper
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🛏 Dimora delle Balze
@Chelsea
Comprised of 11 rooms (each named after a piece of art, film, literature or music by a Sicilian artist), this restored 19th-century masseria is a haven for creatives and romantic types alike. Situated among lush, hilly countryside Dimora delle Balze stylishly mixes old and new - its handmade cementine tiles and super-comfy Simmons beds sweeten the deal. Guests can lounge by the saltwater pool or in any of the three large courtyards — or wander the 60-acre grounds filled with lavender, olive trees and an organic vegetable garden that supplies the compound’s kitchen.
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🛏 Ca' P'a Casa Privata*
@Chelsea
Casa Privata is a design-forward boutique hotel set on an idyllic property by the sea in laid-back Praiano. This is my top pick!
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* * *
CURATED BY
California based travel designer for the design minded + culturally curious. With professional experience in the luxury travel industry, I specialize in designing custom travel experiences that get to the heart of a place and its local culture through the lens of design and food. I’m here to help you travel in good taste with the perfect balance of high luxury and local flavor. My destinations of expertise include Italy, France, Mexico and the US, but I'm always expanding my destination knowledge and love taking on requests in other places. Shop my curated travel guides or check out my custom travel design services to elevate your experience and minimize the stress of travel planning. Let’s get designing!
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Dreamy Italy Hotels
A curated collection of dreamy stays in Italy for special occasions. Featuring design-led boutique hotels, rustic masserias, and seaside villas throughout Italy’s varied regions.
21 Places • 18 Saves • ago
Free
🛏 Masseria Potenti
@Chelsea
Add to
Details
Palazzo Daniele
@Chelsea
Set in a historic palazzo near the southern tip of Puglia, Palazzo Daniele artfully juxtaposes minimalist decor with neoclassic grandeur. This intimate, nine suite boutique hotel features a pool and spa, orange tree garden, and a secluded space for private dinners.
Add to
Details
🍽🛏 Le Sirenuse*
@Chelsea
Chances are you’ve seen photos of this upscale hotel featuring scenic views of the surrounding coastline and architecture. If you stay elsewhere, consider visiting for a romantic dinner at La Sponda or drinks at the champagne bar. Book well in advance, and note that some rooms don’t have a view.
Add to
Details
🛏 Borgo Egnazia
@Chelsea
This lavish, village-like property made of tufo stone boasts three restaurants, three pools, a spa, and a private beach club. As elaborate as it is, it reflects the character of Puglia with a charming and romantic feel. The town of Savelletri is well positioned to visit both the countryside and the coastline, and the amenities at Borgo Egnazia make it an ideal option for families. Rooms in the hotel are adults only, while the small townhouses and larger villas sprinkled throughout the grounds are for groups and families. There are two beaches (one sandy, one rocky with a beach club and plenty of activities) a few minutes away that the hotel drives guests to.
Add to
Details
🛏 Palazzo Avino
@Chelsea
Luxurious, family-owned hotel set in a historic villa known as the "Pink Palace" in Ravello, a hilltop town with stunning views of the surrounding coastline. Palazzo Avino offers the best of both worlds with a clifftop location and private beach club down below. Note: Most of the rooms here feature coastal views, but the ones facing the mountainside are less expensive. Perfect for travelers looking for a high-end hotel experience at a more affordable price point.
Add to
Details
Mezzatorre Hotel & Thermal Spa*
@Chelsea
While Ischia's comuni offer rustic Italian charm, this hotel oozes elegant allure. Located in a secluded cove amid chestnut forests and volcanic rock, Il Mezzatorre benefits from a private bay, beach and a spa housed in a 16th-century watchtower. An indoor thermal spa, seawater pool, and direct access to swimming in their private cove, as well as world-class dining, make this a resort you'll never want to leave. oozes Italian beach sophistication. If you could distil la dolce vita and 1950s Italy, it would look like the Pellicano Hotels group. It’s right on the bay, so book a room in the tower by the sea. Breakfast is amazing—a million pastries and 10 kinds of mozzarella from Naples. Have the lobster spaghetti by the pool for lunch. At the beach, ask for Giorgio: I always tip him in advance, and he saves the best chairs for me.
Add to
Details
🛏 Sextantio Le Grotte Della Civita
@Chelsea
Sextantio Le Grotte Della Civita is made up of 18 caves and a common space in an ancient rock church. Located in the oldest part of the Sassi overlooking the Gravina stream and Murgia Park, the setting is dreamy and perfect for a special occasion.
Add to
Details
🛏 Palazzo Margherita
@Chelsea
Francis Ford Coppola’s hotel in his grandparents’ former hometown.
Add to
Details
🛏 Villa Cora
@Chelsea
Opulent hotel brimming with frescos and ornate decor. First floor rooms are recognized by the Italian government as historically significant. Stately 5-star boutique hotel near the Boboli Gardens, on a garden estate in the hills just outside the city center. Features elegant rooms and a beautiful outdoor pool area. $550+/night Highlights: Villa Cora is a stunningly elaborate hotel that feels more like a Tuscan resort than an urban hotel, despite being only 10 minutes from the city center. Tips: They have a beautiful outdoor pool, perfect for the crew to relax after an active day exploring Florence. Keep in mind: This hotel checks the box for a range of folks, whether groups, families, or couples who flock here for the sense of place and historic details.
Add to
Details
🛏 Grand Hotel Tremezzo*
@Chelsea
Luxurious renovated Art Nouveau resort in the village of Tremezzo next to the famous Villa Carlotta gardens, with rooms overlooking either the lake or mountains. The interior is infused with traditional Italian design details, but the overall vibe here is more modern than most of the classic properties in Lake Como. It's also family friendly with plenty of connecting rooms (book well in advance) and a few suites for up to 4 people. There's an 8 bedroom villa that can be taken over for groups or large family stays. Guests will have access to a range of amenities including two pools, a beach club, five dining options, tennis courts, and boat tours with lunch. If you're here for a special occasion, splurge on a top-floor suite with a private hot tub. Non-guests can visit T Bar for pre-dinner drinks with views after visiting Villa Carlotta.
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Details
🛏 La Posta Vecchia
@Chelsea
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Hotel Il Pellicano
@Chelsea
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🛏🍷 Villa San Michele
@Chelsea
Situated 15 minutes from the city, Villa San Michele feels like its own destination with verdant gardens, scenic views, and stylish interiors. Guests can also take a class at the on-site cookery school, plus a separate one for kids. If you’re staying elsewhere, consider coming for drinks. The hotel can be reached by taxi, private transfer, or a courtesy shuttle bus for guests that runs to the city center multiple times daily. $825+/night, stunning luxury hotel on a hilltop overlooking Florence and the hills of Chianti. A bit outside the city center, but great for a romantic honeymoon experience. Highlights: Villa San Michele is honeymoon-approved! Located up in the hills overlooking Florence, the views from your room will be unmatched. Tips: The hotel is located 25 minutes outside of the city center, so avoid placing clients who want to do a lot of touring and need proximity to the city here. Keep in mind: Villa San Michele is not a year round destination, the best time to visit would be between Easter and October.
Add to
Details
Villa Cetinale
@Chelsea
Add to
Details
🛏 Castello di Vicarello
@Chelsea
Luxurious estate set on a vast property in the Maremma featuring organic vineyards, olive groves, and farmland.
Add to
Details
🛏🧖🏻‍♀️👩🏻‍🍳 Borgo Pignano
@Chelsea
One of Tuscany’s most dreamy stays with its thoughtfully decorated interior, panoramic pool, and on-site wellness center. Though it’s luxurious, Borgo Pignano retains a sense of connection to the land and emphasizes sustainable practices. The on-site restaurant serves Tuscan dishes using fresh and organic ingredients from the garden. Acitivities and experiences include spa treatments, cooking and fitness classes, wine tastings, yoga, horseback riding and more. Check their website for more details (links below). Book experiences in advance, namely spa experiences. If prices are too expensive, I recommend taking full advantage of the pool (try to spend magic hour here at least once!) and visit Villasanpaolo for a spa day instead.
Add to
Details
🛏 Hotel Splendido
@Chelsea
More than a few VIP's (the Duke and Duchess of Windsor, Catherine Deneuve) have signed the visitor's book at this Portofino hotel. Originally a 16th-century monastery, the property was transformed into 69 guest rooms (16 at the more affordable Splendido Mare), three restaurants, and two bars. Guests can relax on the hotel's Chris-Craft Corsair 36 while enjoying champagne and canapés. Splendido can arrange a sunset cruise on their small yacht, which anchors in the San Fruttuoso bay for Champagne and snacks. Even if you don’t stay overnight, it’s worth a visit for a panoramic lunch. For a more exclusive experience, guests of the Belmond Hotel Splendido can book the hotel’s chic boat for an evening cruise to San Fruttuoso, followed by a private open-air concert in the Abbey’s enchanting courtyard.
Add to
Details
Reschio
@Chelsea
Add to
Details
🏨 Villa Sant'Andrea
@Chelsea
Luxurious hotel by the seaside. The original villa was constructed in the 1830s and has been lovingly restored down to the tropical plants in the surrounding gardens. The crowd is a complete mixed bag, but you're guaranteed to find many Americans and Brits, primarily of older age, as quiet is the order of the day. the additions of a gym, a small spa, and complimentary boat tours (with swimming) of the surrounding islands and inlets are all pluses. You'll find beautiful rooms and suites — most with flower-filled balconies and sea views — as well as the most picturesque patio for breakfasts that can last for hours. People don't come here to work out, but if you must sweat, the adequate small gym features several cardio machines. The spa does excellent in-room or outdoor massages. WiFi is available throughout the property, including at the pool and in the hotel's private beach cabanas. Be sure to request a room away from the service elevator, which kicks in very early in the morning. Breakfast on the covered terrace is the highlight. Skip dinner as it is wildly expensive and not very charming. Perfect for Couples and families with extremely well-behaved, older children. A shuttle whisks guests up to Taormina proper
Add to
Details
🛏 Dimora delle Balze
@Chelsea
Comprised of 11 rooms (each named after a piece of art, film, literature or music by a Sicilian artist), this restored 19th-century masseria is a haven for creatives and romantic types alike. Situated among lush, hilly countryside Dimora delle Balze stylishly mixes old and new - its handmade cementine tiles and super-comfy Simmons beds sweeten the deal. Guests can lounge by the saltwater pool or in any of the three large courtyards — or wander the 60-acre grounds filled with lavender, olive trees and an organic vegetable garden that supplies the compound’s kitchen.
Add to
Details
🛏 Ca' P'a Casa Privata*
@Chelsea
Casa Privata is a design-forward boutique hotel set on an idyllic property by the sea in laid-back Praiano. This is my top pick!
Add to
Details

* * *
CURATED BY
California based travel designer for the design minded + culturally curious. With professional experience in the luxury travel industry, I specialize in designing custom travel experiences that get to the heart of a place and its local culture through the lens of design and food. I’m here to help you travel in good taste with the perfect balance of high luxury and local flavor. My destinations of expertise include Italy, France, Mexico and the US, but I'm always expanding my destination knowledge and love taking on requests in other places. Shop my curated travel guides or check out my custom travel design services to elevate your experience and minimize the stress of travel planning. Let’s get designing!
Send A Tip
Support Chelsea Papa’s work.
Select your tip amount
$5
$10
$20
$50
Or type in other amount
Powered by Thatch
The home for unique & authentic travel
Powered by Thatch: Where great trips are made.
© Chelsea Papa Privacy Terms