- A Glut of Fiberglass—Moxie Marlinspike first turned me on to idea that almost all the production fiberglass boats built since the late 1950s are still with us, and they aren't going anywhere. This has resulted in many, many good, durable, plastic sailboats on the used market for comparatively, and increasingly, cheap prices. There is now a cruising boat out there for every family's budget.
- Communications Technologies—Nothing has shrunk this planet like advances in communications. The Internet is increasingly available and employers are increasingly willing to accommodate folks working from afar—even if afloat.
- Workplace Mobility—Forbes reports that, "job hopping is the new normal," and that workers stay with an employer an average of 4.4 years. This mobility presents opportunities to turn a transition into a cruising itinerary.
- Sailboat Technologies—Advances in sail-handling and navigation systems reduce the demands on all crews. For a cruising family on a boat big enough to house a family, and with one parent often managing the needs of smaller crew, these steps forward are a boon.