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Kyla By Luxury
The Seasonal Guide
Where to go, and when. Conditions vary year to year; we confirm the specifics for your dates before anything is booked.
| Destination | J | F | M | A | M | J | J | A | S | O | N | D |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Miami | ○ | ● | ○ | ○ | △ | ○ | ||||||
| Los Angeles | ○ | ○ | ○ | ○ | ○ | ● | ○ | |||||
| Las Vegas | ○ | ● | ○ | ○ | ○ | ○ | ||||||
| St. Barthélemy | ● | ○ | ○ | ○ | △ | ○ | ||||||
| St. Thomas & St. John | ● | ○ | ○ | ○ | ○ | |||||||
| Turks & Caicos | ● | ○ | ○ | △ | ○ | |||||||
| Cap Cana & Punta Cana | ○ | ○ | ○ | ● | ○ | |||||||
| St. Maarten & St. Martin | ○ | ○ | ○ | ○ | ● | ○ | ||||||
| The Bahamas | ○ | ○ | ○ | ○ | ○ | △ | △ | ○ | ||||
| Puerto Rico | ○ | ○ | ○ | ○ | ○ | △ | △ | ○ | ||||
| Jamaica | ○ | ○ | ○ | ○ | △ | △ | ○ | |||||
| St. Kitts & Nevis | ○ | ○ | ○ | ○ | ○ | △ | ○ | |||||
| Los Cabos | ○ | ○ | ○ | ○ | △ | △ | ○ | |||||
| Dubai | ○ | ○ | ○ | ● | ○ | |||||||
| The Maldives | ○ | ○ | ○ | ○ | ○ | ● | ||||||
| Thailand | ○ | ○ | ○ | ● |
● featured month · ○ suggested window · △ higher weather risk, not strongest weather
Florida · United States · Suggested in Jan, Feb, Mar, Apr, Nov, Dec
Miami
City evenings, ocean mornings
Winter and early spring are a useful starting point for a beach-and-city stay. Miami Beach, the Design District and nearby coastal stops offer different rhythms; choose a base around the days you want rather than treating the whole area as one neighborhood.
Plainly: Summer is hot and humid, with thunderstorms and hurricane-season considerations. Major events can change prices and traffic; check the exact dates and neighborhood before choosing a stay.
California · United States · Suggested in Mar, Apr, May, Jun, Sep, Oct, Nov
Los Angeles
A city best explored one neighborhood at a time
Spring and autumn are useful starting points for a stay combining the coast, museums and dining. Los Angeles can form one part of a California route or pair with Las Vegas, with travel time considered before adding stops.
Plainly: Distances and traffic shape the day. Coastal weather can differ from inland neighborhoods, and heat, wildfire conditions or closures may require changes; avoid scheduling cross-city stops back to back.
Nevada · United States · Suggested in Mar, Apr, May, Sep, Oct, Nov
Las Vegas
A short stay with room for a different kind of day
Spring and autumn are useful starting points when outdoor time matters. A short city stay can combine shows and dining with a separately planned desert day, or become one stop in a wider western U.S. trip.
Plainly: Summer desert heat can limit outdoor plans, and winter evenings can be cold. Convention and event dates affect rates; desert excursions need realistic transfer times and operator confirmation.
French West Indies · Suggested in Jan, Feb, Mar, Apr, Nov, Dec
St. Barthélemy
The quiet end of a loud season
January holds the island at its best — dry trades, calm anchorages, and the kitchens fully staffed after the holidays. We design around villa placement first, because the difference between Colombier and Gouverneur is the difference between two entirely different weeks.
Plainly: Christmas and New Year sell out roughly a year ahead and price accordingly. Mid-January onward is the same island for materially less.
U.S. Virgin Islands · Suggested in Feb, Mar, Apr, May, Dec
St. Thomas & St. John
No passport, full Caribbean
February gives you the driest stretch of the year with water clear enough to make the day boat the centre of the trip. We place clients on St. John for quiet and use St. Thomas for arrival, provisioning and dinner.
Plainly: St. Thomas cruise days change the character of Charlotte Amalie entirely. We plan dinners and shopping around the ship schedule, not against it.
Turks & Caicos Islands · Suggested in Mar, Apr, May, Nov, Dec
Turks & Caicos
The beach the others are measured against
March is the balance point: reliable sun, water at its clearest, and the season's edge already softening rates. Grace Bay for service, the north shore villas for privacy, Parrot Cay when a client wants to disappear.
Plainly: There is very little to do beyond water, food and rest. That is the appeal — but it is the wrong island for a client who wants a city at the edge of the trip.
Dominican Republic · Suggested in Jan, Feb, Mar, Apr, Dec
Cap Cana & Punta Cana
Scale, staffing and short flights
April holds dry weather while the crowds thin after Easter. Cap Cana is where we place large private villas with full staff — the practical answer for a group of twelve who want one house, one chef and one plan.
Plainly: Quality varies enormously here. We work with a short list of properties and selected local specialists, and decline the rest.
Dutch & French Antilles · Suggested in Jan, Feb, Mar, Apr, May, Dec
St. Maarten & St. Martin
Two countries, one island, one dinner reservation away
May keeps the dry season while the island quiets down. We use the French side for the table and the Dutch side for the arrival, and treat the neighbouring islands as day trips by boat rather than second hotels.
Plainly: Beaches here are good, not exceptional by Caribbean standards. Come for the food, the sailing and the access.
The Bahamas · Suggested in Jan, Feb, Mar, Apr, May, Jun, Nov, Dec
The Bahamas
Close enough to leave on Friday
June is warm, still largely settled, and quiet in the Exumas before the season turns. Fifty minutes from Florida makes a genuine long weekend possible — which is why we design more three-night trips here than anywhere else.
Plainly: Atlantic hurricane season runs June through November, with higher activity often August through October. Review weather risk and the actual supplier cancellation terms before committing.
United States · Suggested in Jan, Feb, Mar, Apr, May, Jun, Jul, Dec
Puerto Rico
A city, a rainforest and a coast in one week
July works because the trip does not depend on the beach. Old San Juan carries the evenings, El Yunque and Vieques carry the days, and Dorado carries the rest. No passport, no currency, no roaming.
Plainly: Afternoon rain in July is ordinary, not exceptional. We build the day around mornings on the water and evenings in the city.
Jamaica · Suggested in Jan, Feb, Mar, Apr, Jul, Aug, Dec
Jamaica
Staffed villas, the way the island does them best
August is the island's own high season and the staffed villa tradition is at full strength — Round Hill and the Tryall side of Montego Bay, chef and housekeeping included, priced against a suite rather than a house.
Plainly: August is within Atlantic hurricane season, often a higher-activity period. Storms, heavy rain and changes are possible. Review supplier change and cancellation terms. Ground transfers are long; one coast is generally more practical.
St. Kitts & Nevis · Suggested in Jan, Feb, Mar, Apr, May, Sep, Dec
St. Kitts & Nevis
The Caribbean before it was styled
September is the island at its emptiest, which for Nevis is the point: plantation inns, no crowd, and staff who have time. It suits a client who wants quiet and reading rather than a scene.
Plainly: September is often a higher-activity part of Atlantic hurricane season, and some properties close. Quiet-season appeal is not a strongest-weather recommendation. Review property opening dates and supplier cancellation terms.
Mexico · Suggested in Jan, Feb, Mar, Apr, Oct, Nov, Dec
Los Cabos
Desert, ocean and a full kitchen
October is the year's turn: the humidity breaks, the water is still warm, and the corridor between San José and Cabo San Lucas is open again. We plan around the house and the chef, then the boat, then the two tables worth crossing town for.
Plainly: The Pacific side is often not swimmable. We check the specific beach a villa sits on before we recommend it, and tell you when it is a view rather than a swim.
United Arab Emirates · Suggested in Jan, Feb, Mar, Nov, Dec
Dubai
The season opens in November
November is when Dubai becomes comfortable outdoors — desert nights, the harbour, and the level of service that makes it a natural first or last stop on a longer route east. It pairs cleanly with the Maldives.
Plainly: From May to September the heat makes outdoor plans unworkable. We do not sell Dubai as a summer destination.
Republic of Maldives · Suggested in Jan, Feb, Mar, Apr, Nov, Dec
The Maldives
The dry season, and the reason to go far
December opens the dry northeast monsoon: flat water, clear visibility and the atolls at their best. One island, one villa, no transfers once you land — the simplest week we design, and the one clients repeat.
Plainly: Seaplanes fly in daylight only, so a late arrival can cost you a night on Malé. We route the long-haul flight around the transfer, not the reverse.
Kingdom of Thailand · Suggested in Jan, Feb, Nov, Dec
Thailand
Bangkok, the Andaman coast and the north in one route
December is the country's best month across all three: cool, dry mornings in Chiang Mai, settled seas off Phuket, and Bangkok at its most workable. We build it as one route with two internal flights, never as three separate holidays.
Plainly: Koh Samui runs on a different weather pattern and is wettest in November and December. If Samui is the priority, we move the trip to February.