Multi-Island Master: The Right Islands, Your Way

Beach Bumming with my Girls

Between Greece’s 227 inhabited islands, the Hawaiian Islands' very different personalities, and French Polynesia’s scattered archipelago of Tahiti, Moorea, Bora Bora, and beyond, the hardest part of a bucket-list, multi-island trip usually isn’t picking a destination — it’s picking the right islands, in the right order, without losing two days of your vacation to a missed ferry or an inconvenient flight connection. That’s the part I handle. I design multi-island journeys built around real beach days, real culture, and the occasional splurge that’s actually worth it — sequenced so the logistics fade into the background and the experience takes over.

Whether it’s a couple finally getting a real break from being “mom” and “dad” for a week, retired couples checking a bucket-list island off the list at their own pace, or a family navigating four kids’ worth of opinions about which beach is “the best one,” the same principle applies: the right islands, sequenced well, and crafted to you make the difference between a trip that feels like vacation and one that feels like a transit schedule with a beach attached. As a wife and mom myself, I build in real time to reconnect, whether that’s a couple’s quiet dinner on the beach or a family’s whole day with nothing planned.

French Polynesia alone has a dozen islands worth considering beyond Bora Bora — Moorea,Tahiti, Taha’a, and Rangiroa each offer something different, and the right combination, and the right number of nights in each, is where most self-planned itineraries go wrong. The same is true in Greece, where 227 inhabited islands mean the difference between a trip that flows an done that spends half its days on ferries headed the wrong direction. I do the sequencing work so you don’t have to.

What Island-Hopping Done Well Looks Like: Flying into Tahiti, spending three nights easing into island time in Moorea, then continuing on to Bora Bora for the overwater bungalow you’ve been picturing for years — each leg timed so you’re never losing a full day to transit. Or island-hopping the Cyclades by ferry, spending just enough time among Santorini’s whitewashed cliffs before the crowds arrive, then continuing to a quieter island like Naxos or Paros for the pace shift that makes the whole trip feel unhurried instead of rushed. Or skipping the Cyclades altogether for Crete’s Minoan ruins, a few days in Corfu’s Venetian old town, or the medieval streets of Rhodes — Greece rewards going beyond the postcard islands, too. In Hawaii, that might mean starting in Oahu for culture, big city energy, and history, and then moving to Maui or Kauai once you’re ready to slow down and just be on a beach.

The islands do the work; the logistics masterminding is mine to solve — which flights connect, how to sequence the islands, and how many nights each one truly needs before the next leg makes sense. Yet the trip itself is uniquely crafted around you.

The Islands I Highlight:

• Greece — 227 inhabited islands mean endless options and easy missteps; I build itineraries across the Cyclades (Santorini, Naxos, Paros, Mykonos), the Ionian (Corfu),the Dodecanese (Rhodes), and Crete — each island group entirely different from the next
• Hawaii — island-hop across Oahu, Maui, Kauai, and the Big Island, sequenced so each island gets the right amount of time, not an after thought
• French Polynesia — beyond Bora Bora: Moorea, Tahiti, Taha’a, and Rangiroa each bring something different, and I help you choose, and connect, the right combination

Why choose me:

• Deep expertise in multi-island sequencing — which islands, in what order, for how long, so you spend your vacation experiencing islands, not commuting between them
• Destination expertise in Hawaii, Greece, and French Polynesia, including personal visits, in-destination partners and suppliers, and certification through the respective Tourism Boards for each location
• Equally suited to couples and families — a milestone trip for two, a child-free escape for parents who need it, retired couples finally checking off the bucket list, or a multi-generational group of eight
• Real logistics management across inter-island flights and ferries, leveraging in-destination partners, so a missed connection never costs you a day of your trip
• Cultural immersion built into every itinerary — market visits, hands-on workshops, and local traditions, not just a landmark checklist
• An eye for the splurge that’s actually worth it — the overwater bungalow, the private boat day, the custom-tailored day trip that feel like one

Based in Glen Carbon, IL (St. Louis Metro Area) • Serving island-hopping dreamers in the Midwest and beyond