The Lifestyle Itinerary
- Kimberly DiMascio
- Sep 5
- 2 min read
Updated: Oct 2
Villas, yachts, hotels, and your second home—designed to move as one.
Travel, Elevated
Every element of a WellConcierge journey is curated to move effortlessly. From private villas in St. Kitts and Islamorada to member-only hotel offers in the Caribbean, each stay is designed with continuity in mind. Add in yachts that carry you from Anguilla to Antigua, or a convertible drive through the Keys, and travel becomes less about logistics and more about flow.
Through IATAN accreditation and partnerships with the Travel Advisor Resource Center (TARC), my clients access global booking systems, private-rate programs, and a vetted network of specialists. In practice, that means the right private villas, hotels with VIP considerations, yachts and charters when water is the way, and the ground transport that stitches it all together—quietly.
For Owners: Monetizing While You Travel
Second homes are more than escapes — they are lifestyle assets. Owners in Florida and the Caribbean can align their properties with WellConcierge to generate income while away, with full guest services and curated concierge experiences managed end-to-end. It’s a dual opportunity: explore the world while your home works for you.
Destinations, Connected
Upcoming features show how these worlds overlap—from Nevis villa stays and second-home tours to Islamorada properties with dockage, South Florida developments with hotel-level amenities, and St. Barth itineraries that pair regatta season with villa living.
The Art of a Life Well Lived
This Lifestyle Itinerary isn’t about checking boxes — it’s about creating continuity.
Villas, yachts, and second homes aren’t separate chapters; they’re part of the same story.
By connecting them seamlessly, WellConcierge designs experiences that feel intentional, indulgent, and entirely your own.
Next Step
Tell me your dates and party size—I’ll confirm availability and handle the setup.
Four Seasons Yachts page for those following the yachting updates.
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