Destinations
The destination question is almost always the wrong first question. The right one is: what do you want this trip to feel like? What follows is organized by how I think about it, with honest hotel comparisons and destination guides linked throughout. If you already know where, skip straight to the region below. If you don't, start with the filter or the planning link.
Caribbean
Europe
Latin America
The Caribbean
The water is good everywhere. The hotel quality, island character, and fit for different clients vary considerably. Anguilla, Grand Cayman, St. Barth, and the British Virgin Islands are the four I know well enough to recommend with confidence. Best months: December through April.
Anguilla
Seventeen miles, no cruise ships, and three hotels that tell genuinely different stories. Four Seasons for families who want everything working. Cap Juluca for couples who want to disappear. Malliouhana for the bluff view.
Best for: families, couples, repeat Caribbean travelers Anguilla Guide → Destination GuideGrand Cayman
Seven Mile Beach ends most debates. The Ritz-Carlton is the seamless family answer. Palm Heights is for people who find that slightly too polished and want something cooler.
Best for: families with young kids, easy East Coast flights Grand Cayman Guide → Destination GuideSt. Barth
Cheval Blanc arrived and the island rearranged itself accordingly. French glamour, a Guerlain spa, and the kind of effortlessness that feels studied but isn't.
Best for: couples, honeymoons, adults-only St. Barth Guide →
Cap Juluca
Maundays Bay. Whitewashed rooms opening onto sand. Service that knows when to appear and when to leave you alone.
The Ritz-Carlton Grand Cayman
The beach that ends every debate. A naturalist kids' program, a sushi bar that grates wasabi fresh at your table.
Cheval Blanc St. Barth
Flamands Beach. The chicest address in the Caribbean. For people who want glamour without sacrificing actual taste.
Europe
Paris, the South of France, Greece, Italy, Switzerland, and the Netherlands. I've been going to Paris since I was fifteen and spent a year in Aix-en-Provence. The hotel landscape here changed significantly in the last five years. The destination guides below hold the fuller comparisons. Best months: late April through June, September through October.
Paris
Three hotels with genuinely different personalities: Cheval Blanc for the modern palace experience, Le Grand Mazarin for the design-forward Marais client, and Pavillon de la Reine for quiet romance on the Place des Vosges.
Best for: first-timers, anniversaries, families, repeat visitors Paris Guide → Destination GuideSouth of France
Hotel du Cap is still the standard. The Maybourne Riviera above Monaco is the modern alternative. August is inadvisable. The south of France is entirely unconcerned with your opinion of it.
Best for: couples, summer celebrations, Paris add-on South of France Guide → Destination GuideGreece
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.
Best for: couples, milestone anniversaries, island-hopping Greece Guide →
Cheval Blanc Paris
The palace hotel that doesn't act like one. A Dior Spa, five Michelin stars in the building, and breakfast that will ruin you for home.
Hotel du Cap-Eden-Roc
The reason people believe in summer as a feeling. A private peninsula and that seawater pool carved into the rocks.
Amanzoe
A modern acropolis above the Aegean. The kind of silence that makes you realize how loud your life has been.
Ski
Zermatt, Courchevel, Megève, and St. Moritz. European ski trips require more logistics planning than any other trip I book. Hotel, village layout, ski school reputation, and transfer time all interact. I have specific opinions about which resort works for which family. Best months: December through March, book six or more months ahead for festive week.
Zermatt
Car-free, guaranteed snow, and the Matterhorn hovering above everything. The Omnia for design-forward couples. Riffelalp for ski-in/ski-out above the village. For a first European ski trip with kids, usually the right call.
Best for: families, first European ski trip, festive week Zermatt Guide → Destination GuideCourchevel and Megève
Courchevel for unapologetic glamour. Aman Le Mélézin on the Bellecôte slope, Rosewood for something more social. Megève for the romantic who also wants Michelin-starred dining and cobblestone streets.
Best for: glamour seekers, couples, terrain variety French Alps Guide → Destination GuideSt. Moritz
Where Alfred Hitchcock honeymooned and the Rolls-Royce transfer is not an upgrade but the standard. For clients whose idea of ski glamour involves an actual palace on the lake.
Best for: old-money elegance, lake views, special occasions St. Moritz Guide →
The Omnia
Built into a cliff, reached by private tunnel. The couples answer to Zermatt.
Aman Le Mélézin
Ski-in/ski-out on the Bellecôte slope. Aman's signature calm applied to Alpine life.
Badrutt's Palace
The crown jewel of St. Moritz. Where old-money ski glamour is entirely unselfconscious about itself.
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.
Not Sure Where? Start HereLatin America
Costa Rica and the Riviera Maya. My two most researched destinations. I've stayed at multiple properties in both corridors and written honest comparisons. In Costa Rica, the routing matters as much as the hotel. In the Riviera Maya, the right room matters more than most people realize when they book. Best months: December through April for Costa Rica, year-round for Riviera Maya.
Costa Rica
Not one trip. Three: jungle and hot springs in Arenal, barefoot surf and wellness in Nosara, polished beach luxury on Peninsula Papagayo. The routing is as important as the hotel.
Best for: families, wellness, milestone celebrations Costa Rica Guide → Destination GuideRiviera 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've stayed at all four.
Best for: quick getaways, families, design lovers Riviera Maya Guide → The EditCosta Rica Wellness
One of the world's five Blue Zones, under five hours from the East Coast, and no jet lag to negotiate. Silvestre Nosara, Hacienda AltaGracia, and Nekajui are three genuinely different versions of this trip.
Best for: solo resets, couples wellness, no jet lag Costa Rica Wellness →
Nekajui, a Ritz-Carlton Reserve
Architecture that changes your mood. A funicular to a cove with marbled volcanic sand. The sunset is visible year-round.
Silvestre Nosara
Nine residences. Steps from Playa Guiones. The anti-resort done correctly.
Etéreo, Auberge Resorts
The rooftop pool is the star. Quiet, edited, and genuinely restorative. The sushi is the best meal in the corridor.
Japan
Two completely different trips, both very good. Tokyo for city stays that redefine what a hotel lobby can be. Niseko for powder skiing and onsen culture in Hokkaido. I book both and have strong opinions about each.
Tokyo
Aman Tokyo is the hotel that made me rethink what a city stay could feel like. The lobby alone changes your breathing. For clients who want precision, beauty, and complete calm in the middle of one of the world's loudest cities.
Best for: design lovers, repeat travelers, city stays Tokyo Guide → Destination GuideNiseko
Higashiyama Niseko Village, a Ritz-Carlton Reserve. Powder skiing, onsen culture, and the kind of winter that makes the Alps feel slightly suburban by comparison.
Best for: advanced skiers, cultural immersion, winter trips Niseko Guide →
Aman Tokyo
The pool alone justifies the trip. Minimal rooms, telepathic service, and the kind of calm that makes you rethink what a city hotel can be.
Higashiyama Niseko Village, Ritz-Carlton Reserve
Powder skiing and onsen culture at one of only eight Ritz-Carlton Reserves in the world. The winter that makes the Alps feel suburban.
"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.
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. If you want a resort with programming, service, and easy logistics, Grand Cayman usually wins. The full Grand Cayman guide breaks this down further.
Where should I go instead of St. Barth with kids?
Anguilla. Same turquoise water, less traffic, and three hotels that genuinely welcome families. The Four Seasons has a kids' club, connecting rooms, and a beach that works for all ages. St. Barth is beautiful but the island is not built for children the way Anguilla is.
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. The Greece guide covers the full routing.
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. Courchevel has more terrain variety and a livelier feel. For a first European ski trip with kids, Zermatt is usually easier to land in.
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. The suites have separate living rooms and nobody side-eyes your toddler at breakfast. If the rate doesn't work, Pavillon de la Reine on the Place des Vosges is the next call. The full Paris guide compares every tier.
How far in advance should I book a luxury Caribbean trip?
For festive week and spring break, six to twelve months is not early. For February and March travel, booking in fall is right. The best rooms at the best properties fill early and do not discount.
What do I get when I book through Sebastian Luxe Travel?
At preferred partner properties: complimentary daily breakfast, room upgrade on arrival when available, a hotel credit (usually 100 to 150 USD equivalent), and early check-in or late checkout when possible. Plus pre-arrival coordination, restaurant reservations, and a direct line while you are traveling. The hotel rate is the same as booking direct. Full details on the services page.
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 detailed 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 and when a cheaper room is the smarter call.
Pre-arrival coordination, restaurant reservations, transfer logistics, and a direct line while you are traveling. Planning does not end when the booking confirms.
Send me your dates. We figure it out from there.
Tell me what the trip is for and I'll tell you where I'd send you and why.
Tell Me Your Dates