Rooted in the Islands. Built on Real Relationships.
A more personal way to experience Caribbean travel and island living.
We founded Always Sunny to help others experience the Caribbean the way we fell in love with it: up close, unfiltered, and unforgettable.
After spending over a decade living and working in the British Virgin Islands, we built deep connections in hospitality, real estate, and local communities. Always Sunny is our way of sharing that network - and our passion - with people who want to explore the islands more personally and meaningfully.
Considering a change of latitude?
The People Behind Always Sunny
Who We Are
Why We’re Different
Why We’re Different
We’re Always Sunny — Alexander and Morgan Dobbs.
Both born and raised in Michigan, our paths didn’t cross until we each independently moved to the British Virgin Islands after college. What started as a shared leap toward island life turned into something much bigger.
We met during a memorable happy hour at Saba Rock (if you know, you know)
We’re Always Sunny — Alexander and Morgan Dobbs.
Both born and raised in Michigan, our paths didn’t cross until we each independently moved to the British Virgin Islands after college. What started as a shared leap toward island life turned into something much bigger.
We met during a memorable happy hour at Saba Rock (if you know, you know), and quickly fell in love...not just with each other, but with the rhythm, beauty, and community of the islands. The Caribbean became home, and over the next decade it shaped both our personal lives and professional paths.
Our experience spans luxury hotels, curated travel experiences, residential developments, and high-end Caribbean real estate—totaling more than $100 million in property transactions across the region. Along the way, we built deep relationships and firsthand knowledge that only come from truly living it.
Today, Always Sunny is our way of sharing that world with others. We offer insider access, trusted connections, and a genuine love for island living that guides every recommendation we make—whether you’re planning a visit, exploring ownership, or simply curious about life in the Caribbean.
Why We’re Different
Why We’re Different
Why We’re Different
We’ve actually lived (and loved) this lifestyle ourselves, and we stay closely connected to the people who make these islands what they are.
Would you rather have your vacation planned by someone with 100+ clients who has visited the islands just once? Or a couple with only a select number of clients, and 10 years of island living under th
We’ve actually lived (and loved) this lifestyle ourselves, and we stay closely connected to the people who make these islands what they are.
Would you rather have your vacation planned by someone with 100+ clients who has visited the islands just once? Or a couple with only a select number of clients, and 10 years of island living under their belts.
Our approach is hands-on, thoughtful, and refreshingly honest - more like advice from a friend who knows the ropes than a pitch.