This chapter reads the Mediterranean as a terraqueous space of fluidity where a dialectics of hospitality/hostility (whence Derrida’s term hostipitality) is constantly played out between host and guest. It shifts the emphasis away from the limited notion of hospitality as a simple act of welcoming the guest, and toward the emergence of an enabling opening in the act of hospitality. To argue for such a reconfigured notion of hospitality as enabling, it addresses the Mediterranean as a fluid space receptive to change, movement, multiplicity, and the other/guest which finds resonance in the literary spaces that tackle the Mediterranean. As an extension of such a Mediterranean literary space, this chapter has recourse to Virginia Woolf’s Orlando (1928), whose eponymous hero/ine undergoes life-changing and transformative experiences via Mediterranean hospitality in Constantinople and Broussa. By drawing parallels between the volatile spaces of the Mediterranean and hospitality, both of which oscillate between hospitality and hostility, it further argues that the Mediterranean hospitality explored through Orlando’s encounters with two hosts (Constantinople and the Gypsies in Broussa) not only de-spatializes the inherently delimited space of hospitality but also de-temporalizes the essentially temporal standing of hospitality by dispersing and (str)etching its effects beyond the hic et nunc. By problematizing the critical discussions of hospitality, where the stress mostly falls on the structural hostility and violence embedded in hospitality, this chapter demonstrates that the hostipitable Mediterranean spaces in Woolf’s Orlando bring forth and accentuate the enabling and transformative power of Mediterranean hospitality, which irrevocably changes Orlando’s life and point of view by providing her with a fresh pair of eyes to re-view her values and perspective.