Three new ways to make history together

Iconic sports moments and Portugal’s coast, reserved for you

April 30 - May 3

The Kentucky Derby 2026

Step into the tradition of the world’s most exciting two minutes in sports and a Derby weekend like no other. With Club SI premium hospitality at Churchill Downs, savor gourmet dining, private betting windows, and paddock views for Oaks and Derby Day. Stay at Hotel Distil in downtown Louisville and enjoy curated Inspirato touches, like shopping with The Hat Girls.

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July 8-12

Pinnacle of Soccer 2026

Feel the thrill of the world’s biggest soccer stage with Trophy Club seats for the Quarterfinals in Boston and Miami. Stay at The Newbury Boston and Miami Beach EDITION, enjoy curated Inspirato gatherings, premium match hospitality, and stress-free transfers with a private flight between cities. The ultimate way to witness soccer history with fellow Inspirato members.

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September 19-27

Portugal in Motion 2026

Embrace active luxury on Portugal’s dramatic coastlines and storied trails. Discover Porto, Lisbon, Sintra, Évora, and the Algarve with guided outdoor adventures at your pace. Complement your days with kayaking, wine tastings, and authentic cultural experiences. Each night, relax in boutique hotels and share fine dining with like-minded Inspirato travelers.

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