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The human species has a yearning for exploration as evidenced by the extensive historical ocean voyages and expeditions which have led to a massive advancement in the scientific and geodetic knowledge about planet Earth. These global explorations via the oceans have also had strategic, economic, cultural and religious implications and impacts, which have drastically changed the state of humanity and its condition. The transportation network created by ships traveling across the oceans has been supplemented by other transportation networks on land and in the air, creating a global economy that, in general, has improved the human condition leading to better health, longer lives, lower child mortality, better education, political freedom, higher gross national product (GNP) and improved hygiene. The logical extension of this societal trend is to extend the transportation network and human civilization into outer space, beyond the cradle of planet Earth. Our solar system contains vast amounts of natural resources which can be harnessed and used to bootstrap a space economy and related infrastructure by using advanced technologies. Sailing journeys from hundreds of years ago required large vessels and large crews, (in comparison with today’s space capsules). Modern sailors of today are able to complete large voyages, in small vessels, with a minimal crew, comparable in magnitude to modern space travel. This paper will use a systems engineering approach (e.g. using the NASA Human Integration Design Handbook (HIDH), NASA-SP-2010-3407, 2010 and the “Advanced Life Support Baseline Values and Assumptions Document, (BVAD)” NASA-CR-2004-208941, 2004.), to examine and compare the logistics and sustainability aspects of a small crew traveling on Earth's oceans in sailing vessels versus humans traveling in space. The “Mālama Honua Worldwide Voyage” of the Hokule’a, a replica of an ancient Hawaiian double hulled sailing canoe, will be used as a case study. This is the best comparison case since the Polynesian exploration of the vast (and virtually empty) Pacific Ocean is the closest analogue to modern space travel. “"Both are voyages of exploration.” –Shuttle astronaut Lacy Veach. Minimizing waste and maximizing re-use and re-cycling will lead to more efficient logistics and sustainability. In addition, In-Situ Resource Utilization (ISRU) strategies, based on successful Earth based strategies used for many years by sailors will be considered and evaluated for their usefulness. For example, human logistics for a typical space mission are shown in Table 1 and Table 2 (Lopez et al, 2015). Studies show that typical human water consumption in space is projected to be 3.2 kg/day per crew member as shown in Table 2. Data from human sailing voyages around the globe will be examined. Anecdotal evidence indicates that knowledgeable and well-equipped modern sailors, who conserve water, can comfortably live using 1.5 to 5 kg/day per person. This paper will investigate key logistics and sustainability aspects of living in space and compare them quantitatively to similar aspects of living on ocean faring sailing vessels on Earth. Mutually beneficial observations, advanced technologies and modern considerations will be applied within confines of a remote sailing environment, which could be of immense value to both the space faring community and the ocean sailing community.