Skip to content
ILUXURYTRAVELS

North America, answered

Luxury travel in North America: your questions answered.

Season timing from the Rockies to the Caribbean, which island suits which trip, what staff come with the house, flights and entry rules, and how booking a stay in the collection actually works.

When to go

When is the best time to visit North America and the Caribbean?
It splits by climate rather than by country. The Caribbean and Mexico's Pacific coast are at their most reliable from December to April, before the summer heat and the June to November hurricane season. Colorado and Wyoming ski from roughly December to early April, then reopen for hiking and rivers from June to September. The Hamptons, Nantucket and Napa Valley run late May to early October, with September often the best of it — warm water, thinner crowds, the harvest under way in Napa.
When is hurricane season in the Caribbean?
Officially 1 June to 30 November, with the highest risk concentrated between mid-August and mid-October. Most days in that window are simply hot and quiet, and rates fall sharply, but flights and boat transfers can be disrupted at short notice. If you travel then, take insurance that covers weather disruption and keep the itinerary loose.
When are rates highest?
Christmas and New Year across the Caribbean and Mexico, Presidents' Week and the Christmas fortnight in Aspen and Jackson Hole, July and August in the Hamptons and Nantucket, and the September harvest weeks in Napa. Those dates also carry the longest minimum stays — festive weeks in St Barts and Mustique are typically seven nights and sell out close to a year ahead.

Where to base yourself

Which Caribbean island should I choose?
St Barts for restaurants, shopping and a French-Caribbean crowd; Mustique and Canouan for privacy, staffed estates and almost no passing traffic; Barbados for the west-coast beaches, golf and the easiest direct flights from the UK; Harbour Island in the Bahamas for the pink-sand beach and a small, walkable settlement. All four suit a week rather than a weekend, because the flights are the hard part.
Where should I base myself in the United States?
Aspen and Jackson Hole for mountains in either season — skiing in winter, hiking, rivers and national parks in summer. The Hamptons and Nantucket for East Coast summer beach houses within reach of New York. Napa Valley for wine country, with the best houses set among the vineyards rather than in town. Hawaii for year-round warm water and ocean-front estates.
Where should I base myself in Mexico?
Punta Mita for a gated peninsula with beach clubs, golf and staffed villas near Puerto Vallarta's airport; Los Cabos for desert-meets-sea estates, sport fishing and a short flight from California; Careyes for the Costalegre's cliffside casitas and a deliberately remote, design-led scene. All three are villa-and-staff destinations rather than city stays.

Villas, staff and groups

Do these houses come with staff?
Most Caribbean and Mexican estates in the collection include a housekeeper and often a cook, with drivers, butlers and nannies arranged on request. US mountain and beach houses are more usually self-catering with housekeeping arranged around your stay. Each listing sets out exactly what is included, because it varies house by house rather than by country.
Can I book a whole island or estate for a group?
Yes. Mustique and Canouan hold multi-bedroom estates with their own staff and grounds, and several Mexican and Hawaiian properties take a full family or wedding party in one place. For anything above roughly twelve guests it is often two neighbouring houses rather than one, which the collection can pair in the same destination.
Is a villa or a hotel better here?
For a long weekend in a city or a first look at an island, a hotel is usually simpler. For a week with family or friends — Caribbean Christmas, an Aspen ski week, a Hamptons August — a staffed villa gives you the pool, the kitchen, the space and, once the party is more than four people, usually the better value per bed. This collection carries both, and each page shows live prices for the dates you enter.

Flights, entry and getting around

Do I need a visa or an ESTA?
Most UK and EU passport holders enter the United States on an approved ESTA under the Visa Waiver Program, and Mexico for tourism without a visa. The Caribbean islands set their own rules — St Barts follows French entry policy, Barbados and the Bahamas admit most Western passports visa-free for short stays. Rules change, so check your own government's current advice before booking flights, as that is the only version that binds.
How do I get to the smaller Caribbean islands?
Almost always by a connection. St Barts is reached by a short hop from St Maarten on a small aircraft that only lands in daylight; Mustique and Canouan connect through Barbados or St Lucia; Harbour Island is a flight to North Eleuthera then a short boat. Book the international leg to arrive early enough for the last connection of the day, or plan a night on the gateway island.
Do I need a car?
In Napa, the Hamptons and Jackson Hole, yes — distances are real and taxis are scarce. Aspen and Nantucket are walkable with shuttles and bikes. On St Barts a small car or a moke is normal; on Mustique it is a golf buggy, and on Canouan the resort moves you. Mexican estates generally come with, or arrange, a driver rather than expecting you to drive yourself.

Rates and booking

How much does a luxury stay in North America or the Caribbean cost per night?
It ranges enormously between a Napa vineyard house, an Aspen ski lodge, a Punta Mita beach villa and a staffed Mustique estate at Christmas, so rather than quote an average, each house shows its own nightly rate and every page carries a live partner panel returning real prices for your dates.
How do I book a house?
Each listing carries a booking link that opens live availability and rates for that stay with our booking partners, where you choose dates and confirm directly. The partner's checkout shows the final price, taxes and cancellation terms before any payment is taken.
How far ahead should I book?
Nine to twelve months for Christmas and New Year in the Caribbean and for the festive and Presidents' Week ski dates; four to six months for Hamptons and Nantucket summer, Napa harvest and Mexican winter sun; a few weeks is often enough in the shoulder months of May, early June and November. Staffed estates and ski-in houses are the first to go in every market.