For travelers who crave remarkable experiences, the first half of 2026 is packed with unforgettable opportunities. From glamorous red carpets and ancient traditions to legendary music festivals and high-profile sports, this curated calendar highlights the world’s most compelling events in stunning global destinations.
Whether your passions lie in film, food, fashion, or culture, these moments are designed for those who seek more from their travels. Plan your journey around the places where luxury, excitement, and authenticity come together.
Here are the top luxury travel events to experience between January and June 2026.
January
Venice Carnival – Venice Italy | January 23 – 25, 2026
This legendary celebration transforms Venice into a living work of art. Expect candlelit masquerade balls, ornate costumes, and gondola parades along quiet canals. The entire city becomes a stage for elegance and tradition.
Inspirato Hotel:
Nolinski Venezia – A 13th-century palace reborn as a refined, art-filled sanctuary just steps from the Grand Canal, offering the perfect setting to immerse yourself in the elegance and spectacle of Venice Carnival.
Napa in Cabo – Cabo San Lucas, Mexico | January 15 – 18, 2026
This four-day event brings Napa Valley’s top winemakers and chefs to the coast of Baja. Expect beachside tastings, gourmet dinners, and live entertainment in one of Mexico’s most beautiful seaside destinations. Set against the backdrop of the Sea of Cortez, guests can enjoy exclusive wine pairings, oceanfront culinary showcases, and intimate gatherings that blend the best of Napa’s refinement with Cabo’s relaxed coastal charm.
Inspirato Home:
Casa Mandarina – Perched above the Sea of Cortez in the prestigious Pedregal enclave, this contemporary cliffside estate offers sweeping ocean views and serene seclusion, just minutes from the culinary and wine experiences of Napa in Cabo.
X Games — Aspen, Colorado | January 23 – 25, 2026
The ultimate showcase of winter sports, music, and mountain culture. Watch the world’s best athletes compete in skiing, snowboarding, and snowmobiling, all set against the snowy peaks of the Colorado Rockies.
Inspirato Home:
Bear Paw – Tucked into Aspen’s peaceful West End, this mountain-modern retreat blends alpine charm with refined comfort, offering a quiet haven just a short ride from the electrifying energy of the X Games.
Sundance Film Festival | January 22 – February 1, 2026
Discover breakout films, attend thought-provoking panels, and explore the creative edge of cinema. Park City becomes a hub of energy and culture with snow-lined streets, pop-up lounges, and star-studded screenings. Beyond the theaters, the town buzzes with exclusive events, après-ski gatherings, and opportunities to connect with filmmakers and tastemakers from around the world.
Inspirato Hotel:
Waldorf Astoria Park City – With ski-in, ski-out access and sophisticated alpine style, this slopeside retreat pairs five-star luxury with effortless proximity to Sundance Film Festival screenings, events, and après gatherings in downtown Park City.
February
Carnival of Viareggio — Tuscany, Italy | Throughout February
This seaside celebration features massive paper-mâché floats, elaborate masks, and lively parades. It is one of Europe’s most extravagant and artistic carnivals, set in the vibrant coastal town of Viareggio.
Inspirato Home:
Villa Collina – Set among the rolling hills of Tuscany, this restored stone farmhouse offers timeless countryside elegance and a tranquil escape within easy reach of the vibrant artistry and grand parades of the Carnival of Viareggio.
Winter Olympics – Milan & Cortina, Italy | February 6 – 22, 2026
The Olympic Winter Games return to Italy with events hosted in both stylish Milan and the alpine town of Cortina. Expect a mix of world-class competition, Italian hospitality, and picturesque winter settings. From high-fashion streets to snow-dusted slopes, the 2026 Games promise a uniquely Italian celebration of sport and culture.
Inspirato Hotel:
Nemi Milan – Located in the heart of Milan’s chic Brera district, this sleek and stylish residence offers a sophisticated home base for experiencing the fashion, culture, and Olympic excitement unfolding across the city.
Envision Festival — Uvita, Costa Rica | February 23 – March 2, 2026
A fusion of music, art, movement, and sustainability set between the rainforest and the sea. From morning yoga to beachfront concerts under the stars, Envision offers a soulful, immersive experience in one of the most biodiverse places on earth.
Inspirato Home:
Pizote – Tucked into the wild beauty of Costa Rica’s northwestern coast, this modern hillside villa offers panoramic ocean views and tranquil luxury, making it an ideal place to unwind after the energy and artistry of Envision Festival in Uvita. Traveling with a group? We have multiple homes in this location so no one feels left out while still enjoying their own space.
March
Charleston Wine + Food Festival – Charleston, South Carolina | March 4 – 8, 2026
An epicurean gathering that celebrates Southern cuisine, local ingredients, and coastal hospitality. Events range from grand tastings and chef collaborations to intimate dinners in historic Lowcountry settings. Guests can expect immersive culinary experiences, engaging panels with renowned chefs, and vibrant energy that fills Charleston’s charming streets.
Inspirato Home:
Rigney – Set in the heart of one of America’s most historic and charming cities, these elegant homes provide a refined retreat just moments from the culinary energy and coastal flair of the Charleston Wine + Food Festival. Bringing friends or family? We offer multiple homes nearby so your group can stay close while enjoying the comfort of their own space.
SXSW – Austin, Texas | March 12 – 18, 2026
A dynamic convergence of music, film, technology, and culture. South by Southwest is known for launching global trends and showcasing boundary-pushing creativity across downtown Austin’s venues and stage.
Inspirato Hotel:
Archer Hotel Austin – Located in the vibrant Domain Northside district, this stylish boutique hotel offers upscale comfort and easy access to the creative energy, live performances, and cultural events of SXSW.
April
Coachella – Indio, California | April 10 – 12 and April 17 – 19, 2026
One of the world’s most iconic music and arts festivals, Coachella returns to the California desert with two weekends of high-energy performances, immersive art installations, and an eclectic lineup that spans genres and generations. Held at the Empire Polo Club in Indio, Coachella is as much about the scene as the sound. Expect celebrity sightings, trendsetting fashion, and cutting-edge culinary offerings, all set against the sun-drenched backdrop of the Coachella Valley.
Inspirato Home:
Paloverde – With bold mid-century design and a private pool surrounded by desert scenery, this chic Palm Springs retreat offers a stylish and serene escape just a short drive from the music, art, and energy of Coachella.
Monte-Carlo Masters — Monte Carlo, Monaco | Mid-April, 2026
Set along the glittering Mediterranean coastline, the Monte-Carlo Masters is one of the most prestigious tennis tournaments on the ATP Tour and a springtime tradition for fans of the sport. Held at the Monte-Carlo Country Club, the event combines elite athleticism with Riviera elegance, drawing tennis stars and stylish spectators from around the world. With the scent of sea air and panoramic coastal views as your backdrop, this is tennis at its most refined.
Inspirato Home:
Apartment Orfèvre – Tucked within the winding streets of Mougins’ historic village, this thoughtfully designed apartment blends local charm with contemporary comfort, just a short coastal drive from the Monte-Carlo Masters. Traveling with friends or extended family? With multiple Inspirato residences nearby, everyone can stay close and enjoy the experience together while still having space to relax and recharge.
May
Masters 1000 Tennis – Rome, Italy | April 28 – May 17, 2026
Held at the historic Foro Italico, the Masters 1000 in Rome is one of the most prestigious clay-court tournaments leading up to the French Open. The atmosphere is electric as top-ranked players compete beneath the towering umbrella pines and classical Roman architecture. Beyond the matches, spring in Rome offers blooming gardens, al fresco dining, and world-class art at every turn—making this a sophisticated and culturally rich way to experience elite sport in the Eternal City.
Inspirato Hotel:
Rocco Forte House Rome – Overlooking the iconic Piazza di Spagna, this refined city residence offers tailored luxury and timeless Roman style, perfectly situated for exploring the city’s cultural treasures and attending the world-class matches of the Masters 1000 Tennis Tournament at Foro Italico.
Kentucky Derby – Louisville, Kentucky | May 2, 2026
Each May, Louisville comes alive with the refined pageantry and spirited energy of the Kentucky Derby. Set against a backdrop of rolling bluegrass hills and centuries-old horse farms, the Derby is more than a race—it is a Southern tradition steeped in elegance, style, and celebration. From mint juleps and bold hats to thoroughbred triumphs, Derby weekend offers a uniquely American blend of sport and spectacle.
Inspirato Experience:
2026 Kentucky Derby Experience – Inspirato’s exclusive Derby package offers access to premium grandstand seating, luxury accommodations, curated culinary events, and private celebrations, all seamlessly planned with personalized service for an unforgettable weekend in true Southern style.
Cannes Film Festival – Cannes, France | May 12 – 23, 2026
A pinnacle of international cinema, the Cannes Film Festival draws filmmakers, celebrities, and cinephiles from around the world. The French Riviera becomes the epicenter of red-carpet glamour and cinematic prestige.
Inspirato Home:
Villa Grain d’Orge – Tucked into the hills of Mougins, this elegant Provençal estate offers a peaceful escape with lush gardens and sweeping views, just a short drive from the red carpets, screenings, and seaside glamour of the Cannes Film Festival.
June
Pride 2026 – New York City, San Francisco, and Chicago
Celebrate Pride 2026 in three iconic cities where LGBTQ+ history and culture shine. Chicago kicks things off with its Pride Parade on June 21, filling the streets with music, color, and celebration. One week later, New York City and San Francisco host their legendary parades on June 28, honoring decades of activism and community. From the birthplace of Pride to the heart of the West Coast, each city offers its own unforgettable way to show up, stand proud, and celebrate love.
Inspirato Hotels:
The Langham, Chicago – Overlooking the Chicago River in the heart of downtown, this sophisticated urban sanctuary pairs timeless elegance with easy access to the parades, festivals, and celebrations of Chicago Pride.
Faena New York – Set in the heart of Midtown Manhattan, this striking new residence combines bold design with elevated comfort, offering a luxurious home base for experiencing the vibrant energy and historic spirit of NYC Pride.
Cavallo Point – Nestled at the foot of the Golden Gate Bridge, this serene retreat blends historic charm with modern luxury, offering a peaceful escape just minutes from the vibrant energy of San Francisco Pride.
U.S. Open Golf Championship – Shinnecock Hills, Southampton | New York June 18 – 21, 2026
The 2026 U.S. Open returns to one of America’s most storied courses, Shinnecock Hills, set among the rolling dunes of Long Island’s East End. Known for its challenging layout, historic pedigree, and dramatic seaside winds, Shinnecock offers a true test of championship golf. Spectators can expect four days of elite competition in a refined coastal setting, just a short drive from the culture and charm of the Hamptons.
Inspirato Hotel:
Inspirato SoHo at The Dominick — luxury Inspirato-branded accommodations at The Dominick offer stylish, sophisticated suites with sweeping Manhattan and Hudson River views in the heart of SoHo’s vibrant Lower Manhattan.
Calcio Storico – Florence, Italy | June 24, 2026
A fierce and ancient game that combines soccer, rugby, and historic pageantry. Played in Florence’s Piazza Santa Croce, it is one of Italy’s most dramatic and unique sporting events, steeped in local pride and tradition. Each match is a powerful display of strength, strategy, and centuries-old rivalry between the city’s historic neighborhoods.
Inspirato Home:
Foresteria Firenze – Set in the heart of Florence’s historic center, this elegant city residence offers a front-row seat to the pageantry and passion of Calcio Storico, just steps from the iconic Piazza Santa Croce.
A Year to Remember, A Lifetime of Luxury
Explore them all through the handpicked locations featured on our Inspirato destinations page—where every stay is curated for comfort, style, and unforgettable memories.
Discover these events and more across our handpicked collection of destinations, or let our team design the extraordinary vacation you’ve been dreaming of.
Discover luxury travel with Inspirato, with access to exclusive homes and personalized service that elevates every trip. Schedule a tour to explore how an Inspirato membership can change the way you vacation forever.
