Caribbean News – Driftwood Capital Eyes Caribbean Expansion with New Luxury and Lifestyle Division

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Led by industry expert Alinio Azevedo, the new platform will pursue high-end hotel and residential deals across the Caribbean and beyond.

Driftwood Capital is sharpening its focus on luxury and lifestyle hospitality, with the launch of a new division dedicated to high-end hotels and branded residences. At the forefront of this initiative is Alinio Azevedo — a seasoned hospitality leader with deep experience at Four Seasons, Loews Hotels, and Aspen Hospitality.

Azevedo has been tasked with building the platform from the ground up, launching a new investment fund and overseeing luxury properties already in Driftwood’s portfolio. But significantly, he’s also leading the charge into the Caribbean market — where Driftwood is already seeing growing investor interest and strategic potential.

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Boutique Hotel & Restaurant on the East Coast

A Strong Caribbean Connection

Driftwood’s leadership has long-standing ties to the region. Founder Carlos Rodriguez Sr. and COO Carlos Rodriguez Jr. are both originally from Costa Rica, where the company currently owns two hotels. This familiarity, along with strong relationships with Latin American family offices, positions Driftwood well for Caribbean expansion.

“We are very comfortable and interested in Costa Rica, the Dominican Republic, and Mexico,” Azevedo shared. “These markets have strong fundamentals and are aligned with our growth strategy.”

Now, Driftwood is also turning its attention to Europe — with Portugal and Spain on the radar — but the Caribbean remains a central focus due to its consistent tourism demand, favorable development costs, and investor appeal.

High-End Strategy for the Region

The new division will target properties that can be acquired, renovated, or built from the ground up. Azevedo emphasized Driftwood’s commitment to quality, noting that each deal will be selected based on factors like airlift, seasonality, and overall revenue potential — all essential ingredients in key Caribbean destinations.

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Beachfront Hotel – Silver Sands DEVELOPMENT OPPORTUNITY

“Whatever we do will involve either renovation or brand-new construction,” he said. “That’s a key differentiator for us — we look to enhance or completely reimagine the asset.”

Twelve properties from Driftwood’s existing portfolio have already been rolled into the new luxury arm, including:

  • The Scottsdale Resort and Spa (Curio Collection by Hilton)
  • Hilton Cocoa Beach Oceanfront
  • Hotel Rumbao in Puerto Rico (a Tribute Portfolio hotel)

The goal is to build a strong portfolio and track record ahead of fundraising, which is expected to begin later this year.

Investors Seeking Island Luxury

Over the past decade, Driftwood Capital has built a base of more than 1,200 investors, many of whom are actively seeking luxury and lifestyle opportunities — especially in high-demand markets like the Caribbean.

“Investor appetite for high-end travel and hospitality is growing,” said Azevedo. “Our strategy is to meet that demand with thoughtful investments that deliver long-term value.”

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Ocean 15 Hotel: 23 room, St Lawrence Gap, Christ Church

He also acknowledged global challenges, including inflation and geopolitical uncertainty, but sees this period as an opportunity to prepare.

“This environment has allowed us time to structure the team and get everything in place,” he said. “The long-term trends for luxury travel — particularly in the Caribbean — are very positive.”

A New Chapter in Upscale Hospitality

Driftwood Capital is no stranger to large-scale hotel management. Its portfolio includes 80 hotels in the U.S. and Puerto Rico, ranging from limited-service to upper-upscale properties. But this new luxury and lifestyle platform marks a distinct evolution in its strategy — one that places greater emphasis on elevated guest experiences, iconic locations, and premium returns.

As Azevedo puts it: “We’re building a strategy that aligns with where travel is heading — and the Caribbean is a key part of that vision.”

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