Find your travel escape
A starting point, not a catalog. If somewhere you love isn’t listed, ask — it almost certainly still gets planned.
The Caribbean
The easiest first cruise there is, and still the one repeat cruisers keep coming back to. Eastern sailings lean toward beaches and duty-free ports; western sailings toward ruins, cenotes and snorkeling. Southern itineraries go further, stay warmer later in the year and hit the islands most people never reach.
- Sailings from Florida, often with resident and drive-to rates
- Ship matters more than itinerary — we’ll match you to the right one
- Balcony versus interior is a bigger decision than most people expect
Mexico & the Riviera Maya
Cancun, Playa del Carmen, Tulum and the Riviera Maya cover an enormous range — from adults-only adult-beverage territory to genuinely excellent family resorts with waterparks and kids’ clubs. The gap between the best and the merely acceptable resort at the same price point is wide, which is exactly where an advisor earns their keep.
- Adults-only, family-friendly, or split-property resorts
- Swim-up suites and club-level upgrades worth paying for
- Low deposits and payment plans on most properties
Aruba & the ABC Islands
Outside the hurricane belt, dry, breezy and reliable — Aruba is the answer when someone wants a guaranteed-weather beach week. Curaçao brings color and better diving; Bonaire is for people who’d rather be underwater than at the swim-up bar.
- Swim-up suites and beachfront high-rise or low-rise
- Consistently good weather year round
- Easy to pair with a Southern Caribbean sailing
Japan
Independent tours are the sweet spot here: your hotels, transfers and rail sorted in advance, but your days left open. Tokyo and Kyoto anchor most first trips, with Hakone, Osaka or Hiroshima slotted in depending on how much train time you enjoy.
- Cherry blossom and autumn color book far in advance
- Rail passes and luggage forwarding arranged ahead of time
- Ryokan stays worth building the itinerary around
Tanzania & East Africa
The Serengeti, the Ngorongoro Crater and the camps in between. Timing is everything — the migration moves, and where you stay determines whether you’re driving two hours to the action or waking up in it. Zanzibar on the end turns a safari into a proper trip.
- Around ten nights in destination is the realistic minimum
- Camp location matters far more than camp thread count
- Vaccination and visa requirements handled well in advance
Hawaii
Each island rewards a different traveler. Kauai is green, quiet and dramatic. Maui is the classic resort week. Oahu suits first-timers who want history and a city. The Big Island is the one that feels like several countries stitched together.
- One island per week — island-hopping eats your holiday
- Resort fees and parking are worth pricing in up front
- Sunrise and helicopter tours book out months ahead
The Greek Islands
Santorini for the view everyone came for, Milos and Naxos for the version without the crowds, Crete when you want a whole island rather than a postcard. Ferries and flights need sequencing carefully — it’s the part most self-planned trips get wrong.
- Shoulder season is warmer and calmer than you’d think
- Caldera-view rooms justify the premium, most of the time
- Pairs naturally with an Aegean sailing
Northern Europe & the Fjords
Amsterdam, the Norwegian fjords, the Arctic Circle and the Baltic capitals — reachable by ocean cruise, or by river if you’d rather trade the sea for vineyards and castles. Summer sailings are long on daylight and short on availability.
- Adults-only sailings available on several lines
- Book eighteen months out for the best cabins
- Easy to extend with a few nights on land either end
Italy
Rome, Florence and the coast — or Puglia and Sicily if you’ve done the first list already. The trick is pacing: three cities in ten days is a holiday, five is a logistics exercise. Trains do most of the heavy lifting.
- Skip-the-line entries reserved well ahead
- Coastal towns are best either side of high summer
- Agriturismo stays for the parts that aren’t cities
Somewhere else in mind?
This page is a sample, not a limit. Tell me where you’re thinking — or describe the trip and let me suggest the where.
