Summer 2026

Strawberry Sky is a travel technology company that makes planning a trip feel fun, not overwhelming. The platform combines thoughtfully curated destinations with live flight pricing, hotel availability, and an AI-powered travel advisor called Strawberry Sky Oracle. Users enter their origin city, dates they’re available, and choose a collection curated by Strawberry Sky to receive a carefully packaged edit of meaningful travel options. If it’s not in the Strawberry Sky Collection, users can as Oracle to create the trip they want using text, image, or links. Together, Strawberry Sky distills a cluttered booking landscape into a small set of meaningful choices.

Strawberry Sky is currently in First Light, a fully functional friends and family preview. Though essentially a beta version, users can search, edit, and book complete trips while receiving founder level support and early adopter perks. 

Alongside the consumer platform, Strawberry Sky Studio provides high-touch travel planning for museums, fairs, galleries, artists, and collectors. Together, they pair modern technology with the care and judgment of an art, culture, and travel professional.