COMO Castello del Nero
Luxury HotelA 12th-century castle in the bull's-eye of Chianti, reimagined by COMO Hotels as a design-led retreat with one of Tuscany's most considered wellness programs. The estate covers 740 acres of vineyards, olive groves and woodland in Tavarnelle, 30 minutes from Florence and 40 minutes from Siena.
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Borgo Santo Pietro, Tuscany
Tuscany Luxury HotelA 13th-century estate on 300 acres of organic Tuscan farmland near Chiusdino, combining a 22-room boutique hotel with a working farm, Michelin-starred dining and an on-site skincare laboratory. The property was a healing stopover for medieval pilgrims on the Via Francigena, and that sense of restorative purpose still runs through it.
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Rosewood Castiglion del Bosco
Tuscany Luxury HotelA 5,000-acre private estate in the Val d'Orcia, built around a medieval borgo near Montalcino and operating as one of the most complete rural retreats in Italy. The estate has been inhabited continuously since the 12th century and includes working vineyards producing Brunello di Montalcino, an 18-hole private golf course and a village of restored stone buildings at its center.
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Villa d’Este
Lake Como Luxury HotelA 16th-century cardinal's palace on the western shore of Lake Como, operating as a hotel since 1873 and still one of the most recognizable addresses in Italian luxury hospitality. Built in 1568 and set within 25 acres of landscaped grounds in Cernobbio, Villa d'Este has the scale and grandeur that most historic hotels only gesture toward.
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Passalacqua
Lake Como Luxury HotelOne of the most celebrated small hotels in the world, set in an 18th-century lakeside villa on the western shore of Lake Como above the village of Moltrasio. Passalacqua was built as a private retreat for friends, leisure and the pleasures of the table, and that ethos has never really left.
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Hotel Santa Caterina (Amalfi)
Amalfi Coast Luxury HotelHotel Santa Caterina has been in the same Gambardella family for more than four generations, its Art Nouveau villa built into a cliff face above the sea on the Amalfi Drive, surrounded by Sfusato Amalfitano lemon groves. All 66 rooms and suites have sea or garden views, with hand-painted majolica floors from Vietri, marble bathrooms, and early 20th-century family furniture throughout.
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Castello di Casole, A Belmond Hotel, Tuscany
Luxury HotelA thousand-year-old hilltop estate in the Sienese countryside, restored to become one of Tuscany's most cinematic retreats. Set across 4,200 acres of vineyards, olive groves and oak forest, Castello di Casole carries real historical weight. This was once a self-sufficient hamlet, and the landscape still reflects that heritage.
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Le Sirenuse (Positano)
Amalfi Coast Luxury HotelGrand Hotel Tremezzo has held its position on the western shore of Lake Como since 1910, its Liberty-style facade one of the most recognized on the lake, facing directly across the water to Bellagio. The hotel closes each winter and reopens fully refreshed, a detail that shows in rooms that never feel tired.
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Grand Hotel Tremezzo
Lake Como Luxury HotelGrand Hotel Tremezzo has occupied the same stretch of Lake Como's western shore since 1910, its canary-yellow Liberty facade facing directly across the water to Bellagio. The family-run hotel closes each winter and reopens fully refreshed, which shows. Ninety rooms and suites are dressed in period antiques, oil paintings, and marble bathrooms, with the upper rooftop category adding private Jacuzzi terraces and views that stretch from Punta Balbianello to the Grigne mountains.
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Bulgari Milan
Luxury HotelThe Bulgari Hotel Milano occupies a converted eighteenth-century palazzo and former convent on a quiet residential street between the Brera arts quarter and the Via Montenapoleone shopping district. The address is central by any measure, yet the hotel's 43,000 square feet of private gardens create a sense of remove from the city that most Milan hotels at any price point cannot come close to matching.
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Il Sereno
Lake Como Luxury HotelIl Sereno is one of Lake Como's most distinctive properties: a 40-suite hotel in Torno designed by Patricia Urquiola, where floor-to-ceiling glass puts the lake at the center of every room. The hotel takes a deliberately contemporary stance on a destination more associated with belle-epoque grandeur. Urquiola's interiors work earthy materials, natural patterns, and exclusively designed fabrics into a palette that feels rooted in its surroundings without deferring to them.
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Bulgari Hotel, Rome
Rome Luxury HotelBvlgari Hotel Roma brings the jewelry house's Italian legacy to its most powerful address: Piazza Augusto Imperatore, in the historic heart of Campo Marzio. The 106-room hotel draws its design from the imperial grandeur surrounding it, working travertine and marble into large-format contemporary interiors that look out directly over the Mausoleum of Augustus. Rooms and suites follow a palette calibrated to ancient Rome, blending historical weight with precision craftsmanship.
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Armani Hotel Milan
Luxury HotelThe Armani Hotel Milano occupies the upper floors of a 1930s Rationalist building on Via Manzoni, one of the most quietly prestigious addresses in the city. The entrance is deliberately discreet, the lift takes you to the seventh floor, and the hotel begins properly there: reception, bar, and restaurant all looking out over the Milan skyline in a space that feels less like a hotel lobby and more like a very well-edited private apartment.
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Luxury Gay Honeymoon in Italy: Rome & Amalfi Coast
Tailor-made VacationItaly is one of the best destinations on the planet for a honeymoon. Rome comes first: four nights in a city where ancient history and exceptional restaurants occupy the same street. Then the Amalfi Coast for five nights, where the agenda shifts to boat trips, cliff-top dinners, and endless views over the Mediterranean. The itinerary runs nine nights across two bases, with private transfers connecting every stage.
8 days tailor-made from $9,110 per person View trip
Luxury French Riviera: Nice, Monaco & Saint-Tropez
Tailor-made VacationThe French Riviera blends coastline, culture, and an upwardly mobile social scene that feels unmistakably European, moving from the relaxed of Nice to the wealth of Monaco and the beach clubs of Saint-Tropez. This itinerary is designed to flow naturally, with just two bases and enough time in each to settle in properly. Expect private transfers, carefully timed experiences, and reservations that make the difference between a good trip and a seamless one.
8 days tailor-made from $8,925 per person View trip
Six Senses, Rome
Luxury HotelSix Senses brings its wellness-first philosophy to the historic heart of Rome, steps from the Trevi Fountain, Pantheon, and Colosseum. The brand's first Italian address occupies a quietly commanding position in the centro storico, with 96 rooms and suites rooted in Roman heritage and finished with courtyard or cityscape views. Signature Suites add private terraces for guests who want the city on their own terms.
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Emily in Paris Tour: Versailles, Champagne and the Riviera
Tailor-made VacationNine days following the show's most iconic locations, from the rooftops of Paris to the vineyards of Champagne and the glamour of the Riviera. Emily in Paris arrived on Netflix in 2020, during a period when most of the world couldn't travel anywhere, and the timing was not incidental to its success. The show offered something people were acutely missing: Paris in full color, the food, the fashion, the arguments, the light.
From $10,115 per person View trip
LGBTQ+ Cultural Tour of France: Paris, the Riviera and Provence
Tailor-made VacationSpend eight days tracing the LGBTQ+ artists, writers, and thinkers who shaped French culture, from Gertrude Stein's Paris salon to Jean Cocteau's painted chapel on the Riviera. Paris has been a refuge for gay artists and writers since the 19th century, drawn by a city that was, by the standards of the time, remarkably tolerant.
8 days tailor-made from $8,965 per person View trip
La Réserve Ramatuelle, St Tropez
St Tropez Luxury HotelLa Réserve Ramatuelle occupies a private garrigue estate above the Saint-Tropez peninsula, looking out over one of the most beautiful bays on the French Riviera. La Réserve Ramatuelle sits within a vast private domain in the Provençal garrigue, a few minutes from Saint-Tropez but removed from the noise and crowds of the village itself.
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We plant trees for every booking
For every booking made with Out Of Office we commit to planting trees in your name to help reduce the impact of travel on future generations. You'll even get a link to see where your trees are planted in the world via our partner Ecologi.
We donate to Rainbow Railroad with every booking
Rainbow Railroad helps LGBTQ+ people escape state-sponsored violence and persecution. A donation goes with every trip we sell, funded by us and never added to your price.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of traveling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
One named specialist, first inquiry to homecoming. No call center, and nothing is charged until you decide to book.