Toronto, Canada · Fora-certified travel advisor
Destinations
Some of these I have walked myself and can tell you which street to eat on. Others are ones I have researched hard for clients — comparing resorts, seasons and prices until the good option is obvious. Both are marked honestly below.
Not seeing yours? That is genuinely not a problem — tell me where you are thinking.
The one I keep going back to. Table Mountain and the wine country get the photographs, but it is the everyday texture that makes the trip — Camps Bay at dusk, the walk up Lion’s Head, a long lunch somewhere in Constantia. It rewards a slower itinerary than most people plan.
Usually treated as the airport you pass through on the way to safari. Give it two days and it is far more interesting than that — Maboneng, the Apartheid Museum, and some of the best food in the country. It also pairs naturally with a Kruger extension.
Where ancient traditions meet modern adventure, and where your money goes further than almost anywhere else I book. Hanoi for the chaos and the coffee, Ha Long Bay for the overnight boat, Hoi An for the tailors and the lanterns, Da Nang when you want the beach.
Ancient temples and modern city life in the same afternoon. Bangkok is the arrival shock everyone should have once — street food, rooftop bars, markets — and then the islands do the recovering. The two-week Bangkok-plus-islands split is the version I book most.
Three and a half hours from Toronto for water that colour is an unreasonably good trade. Nassau if you want everything on tap; the Exumas if you want sandbars, still water and yes, the swimming pigs — which are exactly as ridiculous and delightful as they look.
Everyone books Cinque Terre and then queues. One bay along, Camogli and the Portofino coast give you the same pastel houses and better dinners with a fraction of the crowd. This is the kind of swap that makes a trip, and it costs less.
The one nobody expects me to recommend, and the one I am most enthusiastic about. Surf towns, volcanoes, coffee country and a coastline that has not been priced for tourists yet. Go before that changes.
Proof that a very good trip does not need a passport or a long flight. A weekend of bagels, terrasses and the walk up Mount Royal — take the stairs, whatever your rideshare app implies. The easiest win in my whole list.
The most-booked corner of my business and the one where advice matters most: the resorts vary enormously at the same headline price. This is where I earn my keep — matching the property to the people, and arranging the small surprises that turn a good week into a memorable one.
Big-city Europe at South American prices, with the steak and the tango to match. A day trip across the river to Colonia del Sacramento in Uruguay is the addition my clients tell me was the highlight — so I now suggest it every time.
Where ancient wonders meet wild landscapes. Machu Picchu is the headline, but Cusco deserves its own days for altitude alone, and Rainbow Mountain, Huacachina and the Amazon turn one sight into a genuine journey. Needs real planning — permits and altitude both bite.
Whitewashed villages and endless blue water. Santorini and Mykonos for the postcard, then Paros and Antiparos for the version where you can actually get a table. Island hopping needs the ferry timetable built into the plan from day one — that is the part I do.
More than beaches — pure island soul. Waterfalls, the Blue Mountains and a music culture you can actually go and stand inside. The all-inclusives here range from excellent to tired at nearly identical rates, which is precisely why you want someone who tracks them.
Pura vida, and the easiest sell I have for anyone who wants nature without roughing it. Rainforest, volcanoes, wildlife and two coastlines in one manageable country. Works as well for a honeymoon as it does for a family with restless teenagers.
This list is where I have spent my own time and my clients’ money — it is not the limit. Tell me where you are dreaming of.
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