Destinations
The destination question is almost always the wrong first question. The right one is: what do you want this trip to feel like? The guides below are organized by how I actually think about it.
Caribbean
Europe
Ski
Places I Know Well Enough to Be Honest About
Each guide covers which hotel actually fits you, what to know before you go, and what most travel sites get wrong. These are the destinations I book regularly.
Anguilla
Seventeen miles, no cruise ships, three hotels that tell genuinely different stories. Cap Juluca for couples who want to disappear. Four Seasons for families. Malliouhana for the bluff view.
Anguilla Guide →
Grand Cayman
Seven Mile Beach ends most debates. Ritz-Carlton for seamless family luxury. Palm Heights for people who find that slightly too polished. Kimpton Seafire for social energy and toddlers.
Grand Cayman Guide →
St. Barth
In St. Barth, the hotel is the trip. Pick the right one and everything feels effortless. Pick the wrong one and you spend the week quietly spiraling every time you pass someone else's pool.
St. Barth Guide →
Amsterdam
Secretly one of Europe's best family destinations. The Pulitzer for the canal house experience. Rosewood for design and service. Waldorf for classic luxury. The city is flat, beautiful, and endlessly walkable.
Amsterdam Guide →
Greece
The Dolli in Athens for arrival. Amanzoe for couples who want silence above the Aegean. Cosme in Paros for people who found Mykonos exhausting. Three very different trips wearing the same country.
Greece Guide →
Switzerland
Zermatt for car-free skiing under the Matterhorn. Zurich for the city before or after the Alps. The Dolder Grand, the Baur au Lac, and the Widder Hotel are three very different answers to the same city.
Switzerland Guide →
Costa Rica
"I'm going to Costa Rica" is not a trip plan. The routing matters as much as the hotel: Papagayo for polished beach luxury, Nosara for wellness and surf, Arenal for jungle and hot springs.
Costa Rica Guide →
Riviera Maya
Etéreo for quiet and wellness. St. Regis Kanai for families who want everything working. The Edition for design and social energy. Nizuc is beautiful and requires specific room guidance. I have stayed at all four.
Full Comparison →
Ski
Zermatt, Courchevel, Megève, St. Moritz. Hotel, village layout, ski school reputation, and transfer time all interact. I have specific opinions about which resort works for which family.
Family Ski Guide →Every property I recommend firsthand. Click through to the hotel guide.
Grand Cayman
St. Barth
British Virgin Islands
Riviera Maya
Costa Rica
Amsterdam
South of France + French Alps
Switzerland
Italy
Austria
Filter by what the trip is actually for.
The conversation usually takes ten minutes and saves a lot of tabs.
Greece, Grand Cayman, Costa Rica, a ski week. Tell me the occasion and I'll tell you where I'd send you and why.
"Some hotels look extraordinary online and are exhausting in real life. My job is making sure you end up at the right one for you specifically."
Probably a fit if:
Less ideal if:
If the first column sounds like you, the conversation is usually short. See what clients say →
The real ones, answered honestly.
Is Grand Cayman worth it compared to Turks and Caicos?
They serve different clients. Grand Cayman has more hotel infrastructure, easier East Coast flights, and Seven Mile Beach is genuinely one of the best in the Caribbean. Turks is quieter and better if the beach is the entire trip. Full Grand Cayman guide →
Where should I go instead of St. Barth with kids?
Anguilla. Same turquoise water, less traffic, and three hotels that genuinely welcome families. St. Barth is beautiful but not built for children the way Anguilla is. Anguilla guide →
Which Greek hotel is best for couples versus families?
Amanzoe is the couples answer. Cosme in Paros works better for people who want more social energy. For families who want a proper city arrival first, The Dolli in Athens is the right opening stop. Greece guide →
Is Zermatt or Courchevel better for a luxury family ski trip?
Both work. Zermatt is car-free which makes it easier logistically with children, and the Matterhorn view impresses even bored teenagers. For a first European ski trip with kids, Zermatt is usually easier to land in. Zermatt guide →
What is the best Paris hotel for families?
Cheval Blanc Paris. The kids club is free, staffed, and has live axolotls in a fish tank. If the rate doesn't work, Pavillon de la Reine on the Place des Vosges is the next call. Paris guide →
What do I get when I book through Sebastian Luxe Travel?
At preferred partner properties: daily breakfast, room upgrade, hotel credit, early check-in and late checkout. The rate is the same as booking direct. Plus pre-arrival coordination and a direct line while you travel. How it works →
Virtuoso, Four Seasons Preferred, Hyatt Privé, Marriott Stars and Luminous, and Oetker Pearl. Your booking unlocks amenities you cannot get on your own.
I recommend from firsthand stays, site inspections, and hotel knowledge, not from a press kit. These are opinions formed in real rooms.
The right hotel for your trip, not the one with the highest commission. I will tell you when a property is not worth the rate.
Pre-arrival coordination, restaurant reservations, and a direct line while you travel. Read client stories →
Tell me what the trip is for. I'll tell you where I'd send you.
The occasion, the group, the vibe. That is usually enough to get to a real answer in one conversation.