Steve Sallion
With parents from St. Vincent and Grenada, I’ve always felt a deep connection to the Caribbean—the rhythm of the islands, the warmth of the people, and the sense of belonging that comes every time I return. Over the years, I’ve often thought about the possibility of retiring in the Caribbean or owning a second home to escape New York’s winter chill for the balmy breezes of the islands.
Each year, I make it a point to attend Carnival in Trinidad, which has become both a cultural pilgrimage and a personal motivator. It gives me something to look forward to through the winter months, keeps me inspired to stay in shape, and reminds me why I work so hard—to create the freedom to enjoy life, travel, and celebrate the vibrant cultures that shaped my roots.
In these interesting times, many of my friends, clients, and family have shared similar thoughts—talking about having a “Plan B”: a place that offers stability, lifestyle, and opportunity. That curiosity inspired me to take my own personal journey to better understand the real options for living, investing, or even obtaining a second passport in the Caribbean.
What I’ve discovered is that the Caribbean isn’t just about turquoise waters and white-sand beaches—it’s a dynamic real estate market that blends lifestyle, investment, and long-term financial planning. Whether for retirement, short-term rental income, or a generational family property, it’s a region that rewards thoughtful exploration and the right guidance.
Market Sentiment
Demand is steady for turnkey villas and condos near beaches, marinas, and airports. Carnival celebrations on every island provide reliable high-occupancy peaks for short-term rentals. Professionally managed properties are commanding premium nightly rates, while buyers looking for lifestyle are prioritizing communities with security, amenities, and wellness options. I chose a few of my favorite destinations to profile in this article, including Barbados, USVI, Grenada, Jamaica and Antigua & Barbuda.
Financing Options
Barbados: Regional banks provide USD mortgages to non-residents (larger down payments required).
USVI: Lending terms mirror U.S. mainland, making it a familiar process for Americans.
Grenada & Jamaica: Mortgages available but expect stricter documentation and 30–50% down payments.
Antigua & Barbuda: Cash purchases and developer financing common in Citizenship by Investment (CBI) projects.
Taxes & Structuring
Capital Gains Taxes: Absent in Antigua, Barbados, Grenada, and Jamaica. The USVI applies U.S. tax law, including capital gains and depreciation recapture.
Other costs: Transfer duties, property taxes, and stamp fees apply across the board.
Short-Term Rentals: Each island requires some form of licensing or registration, plus tourism or occupancy taxes.
Cross-Border Planning: U.S. citizens should consider holding through LLCs or trusts to align U.S. reporting and local requirements.
Lifestyle & Local Considerations
Antigua & Barbuda: Famous for “365 beaches,” sailing, and relaxed living.
Grenada: Eco-friendly, spice markets, waterfalls, and a quieter pace.
Barbados: Upscale coastal lifestyle, excellent dining, golf, and a strong expat community.
USVI: Convenient for Americans—U.S. laws, currency, and integration.
Jamaica: Vibrant music and culture, larger cities, and world-class natural attractions.
Safety & Weather Considerations
Safety: Grenada and Barbados rank among the safest; Antigua is secure in tourist/gated areas; Jamaica requires neighborhood awareness; USVI has localized crime concerns—neighborhood selection is critical.
Weather: All islands experience hurricane season (June–Nov). Barbados and Grenada, being further south, see fewer direct hits; Antigua, Jamaica, and the USVI are more exposed—factor in insurance costs.
Island Summaries
Antigua & Barbuda
Lifestyle: “365 beaches,” sailing culture, and expat-friendly communities.
Market: Condos ~$350K+; villas $1.2M–$3M+. CBI options available.
Strengths: Great for boaters; Carnival season spikes rental demand.
Considerations: Hurricane-prone; limited healthcare (med-evac often used).
Grenada
Lifestyle: The “Spice Isle”—eco-living, waterfalls, chocolate festivals, and a tight-knit community.
Market: Condos ~$250K+; villas $1M–$2.5M+. CBI eligible.
Strengths: Safest of the region; rare hurricane activity; expat/student base via SGU.
Considerations: Smaller scale market; quieter lifestyle.
Barbados
Lifestyle: Cosmopolitan island with polo, golf, fine dining, and beach clubs. Strong infrastructure.
Market: Condos ~$400K+; luxury villas $2M–$5M+.
Strengths: No CGT; foreigner financing available; expat-friendly.
Considerations: West Coast prime real estate commands high prices.
U.S. Virgin Islands
Lifestyle: U.S. territory convenience. St. Thomas is lively, St. John is eco-focused, St. Croix more residential. Sailing and diving are major draws.
Market: Condos ~$300K+; homes $900K–$2M+.
Strengths: Familiar U.S. tax/legal systems; no currency exchange.
Considerations: Higher hurricane exposure; localized crime; insurance is costly.
Jamaica
Lifestyle: Cultural hub with reggae, waterfalls, and resort destinations like Montego Bay and Negril.
Market: Apartments ~$200K–$400K; villas $700K–$2M+.
Strengths: Strong tourism demand; diverse property mix.
Considerations: Safety varies widely; hurricane-prone; STRs must be licensed.
Retirement Lens
Healthcare infrastructure is strongest in Barbados and Jamaica, while Grenada and Antigua offer reliable but more limited facilities (medical evacuation insurance recommended). Expats enjoy social integration through golf, marinas, community clubs, and fitness hubs. Direct flights from U.S. gateways make visits simple.
Brokerage Support
Brokerages provide:
Property sourcing, negotiation, and valuation.
Legal, tax, and financing introductions.
STR licensing and management setup.
Full-service property management and rental operations.
Advisory for retirement planning and resale strategy.
Why Sotheby’s International Realty
Sotheby’s International Realty has offices in over 80 countries, with deep expertise across the Caribbean region, including: Jamaica, Cayman Islands, Bahamas, U.S. & British Virgin Islands, Puerto Rico, Turks & Caicos, Barbados, Dominican Republic, Bermuda, Antigua & Barbuda, St. Kitts & Nevis, and Aruba.
This global reach combined with local expertise ensures buyers benefit from both market insight and international exposure when acquiring or reselling Caribbean property.
Final Word
I chose a few of my favorite Caribbean destinations to profile in this article, but I hope to share my personal view and experiences in future editions of this newsletter. Each island has its own rhythm, opportunity, and charm—and I look forward to diving deeper into what makes them unique.
Caribbean ownership is more than a purchase—it’s a lifestyle choice with investment upside. With the right strategy and guidance, you can balance yield, enjoyment, and security, while creating a legacy that extends beyond borders.
Ready to Explore Your Caribbean Move or Investment?
Contact: Steve Sallion, Global Real Estate Advisor, Sotheby’s International Realty
I maintain direct relationships with Sotheby’s offices throughout the Caribbean, ensuring clients receive immediate local expertise and seamless referrals. I’ll be your quarterback—guiding you end-to-end through property selection, financing, licensing, tax coordination, and property management so you can invest with clarity and enjoy the lifestyle upside. Steve can be reached at [email protected], or follow him on IG at steve.sallion.
For additional information and current listings in Antigua & Barbuda, Grenada, Barbados, the U.S. Virgin Islands, Jamaica or other Caribbean destinations, visit:
👉 www.sothebysrealty.com
