The Most Expensive Islands to Visit: Billionaire-Backed Real Estate Acquisitions

Dream vacations often involve escaping to pristine tropical paradises, but what if your fantasy included actually owning a private island? The world’s wealthiest individuals have transformed this dream into reality by investing in some of the planet’s most exclusive island properties. These ultra-premium acquisitions showcase not just spectacular natural beauty, but also the ambitions and vision of their owners in developing island communities and creating luxury destinations.

Lanai, Hawaii: The 141-Square-Mile Oracle Vision

When Oracle co-founder Larry Ellison acquired approximately 98% of Lanai, it wasn’t simply for personal seclusion. Instead, Ellison’s acquisition strategy centered on island development and infrastructure enhancement for the benefit of over 3,000 island residents. The transaction reportedly valued at approximately $500 million positioned Lanai as the largest privately controlled island in the United States, with an impressive coastline spanning nearly 50 miles.

The island’s transformation has included the development of multiple Four Seasons luxury resorts, allowing visitors to experience its pristine beaches and verdant landscapes without requiring a personal introduction to Ellison. For travelers seeking upscale accommodations combined with natural splendor, Lanai represents one of the most accessible gateways to experiencing the most expensive islands to visit in North America.

Caribbean Dreams: Bonds Cay’s Multi-Artist Collaboration

Located 120 miles from Florida’s eastern coast, Bonds Cay represents an unconventional ownership model—a collaborative venture between musician Shakira and two other artistic collaborators, including Roger Waters of Pink Floyd and Spanish musician Alejandro Sanz. The trio’s $16 million investment secured control of 700 acres featuring five pristine beaches, immaculate white sand, and three natural salt pond lakes.

Rather than pursuing conventional luxury development, these owners have committed to transforming the property into an eco-conscious retreat and artistic sanctuary. This approach reflects a growing trend among wealthy investors in positioning island acquisitions not merely as personal holdings but as venues for creative and environmental initiatives.

Quebec’s Fairy-Tale Escape: Île Gagnon’s Architecture

Celine Dion’s approach to island ownership took a decidedly different direction, focusing on architectural grandeur rather than geographical warmth. Her residence on Île Gagnon on Quebec’s Rivière des Mille Îles featured a mansion designed in French Norman chateau style, accessible via a private gated bridge that enhanced its storybook aesthetic.

Unlike Dion’s legendary vocal career, her tenure as island owner proved temporary. The property found new ownership in 2016 when it sold for $25.5 million, demonstrating that even celebrity-owned island properties remain subject to market dynamics and changing personal priorities.

Skorpios Island, Greece: When Billionaires Don’t Get Their Way

The desirability of Skorpios Island tested the acquisition power of some of the world’s most influential figures. Despite interest from tech billionaires, fashion titans, and music icons, the 74-acre Greek island ultimately went to a different buyer altogether.

This historically significant property—famous as the wedding location of shipping magnate Aristotle Onassis and Jacqueline Kennedy—commanded extraordinary premium pricing. Ekaterina Rybolovlev, daughter of Russian billionaire Dmitry Rybolovlev, secured the property along with its neighboring Sparti islet for $150 million, establishing a record for island acquisitions and highlighting the intense competition among ultra-high-net-worth individuals for trophy properties.

Puerto Rico’s Largest Private Island: Cayo Norte’s Ecosystem

Google co-founder Larry Page’s investment strategy has encompassed multiple island acquisitions, reflecting his diversified approach to luxury real estate. In 2018, through an investment vehicle called U.S. Virgin Island Properties, Page acquired Cayo Norte—Puerto Rico’s largest privately owned island—for $32 million.

This tropical asset features distinctive natural attributes including coral reef systems, white-sand beaches, and an ecosystem that provides critical habitats for endangered sea turtles and diverse wildlife. For investors viewing island acquisitions through an environmental stewardship lens, Cayo Norte represents the intersection of personal luxury and ecological responsibility—qualities that increasingly define how the world’s most expensive islands to visit are developed and managed for both contemporary enjoyment and long-term conservation.