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ILUXURYTRAVELS

North America destination guide

The North America destination guide.

North America in our collection means three distinct trips: Caribbean islands in winter, Rocky Mountain lodges in ski season, and East Coast beach villas in summer. Hurricane season and the festive weeks shape almost every decision, so this guide starts with timing and works outwards.

Travel tips

Plan the connection, not just the flight

St Barths is reached by a connection from St Maarten, and Mustique and Canouan by connection from Barbados or St Lucia. Check the current last-departure time for that onward leg and plan to land in the gateway well before it.

Understand hurricane season before you book

The Atlantic hurricane season runs June to November. Check the current forecast outlook and ask the property about its cancellation policy, and take insurance that covers weather cancellation if you travel in this window.

Confirm services for the exact villa

Ask each St Barths, Mustique or Barbados villa directly what staffing is included. In Aspen, the Hamptons and Nantucket, confirm whether a chef, driver or ski valet needs to be arranged separately.

Hire a car in the US, take a driver on the islands

Aspen, Napa and Jackson Hole assume a car (four-wheel drive in winter). On St Barths a small jeep is the norm; on Mustique it is a Mule and nothing faster.

Check entry authorisations early

Confirm current processing times for the US ESTA, Canada's eTA and any Caribbean arrival form with the official government site, and check passport validity for onward island legs.

The best months to go

December – April
Ask the property directly about current weather expectations and its Christmas and New Year rate before booking — enquire as early as possible for those two weeks.
December – early April
Check current snow reports for Aspen and Jackson Hole, and ask the property directly about availability for the festive fortnight and Presidents' Week.
May – June
Ask Caribbean and Rocky Mountain properties directly for their current shoulder-season rate and conditions before booking this window.
June – September
Check current trail and river conditions with the property for Rocky Mountain hiking or rafting trips in this window.
August – October
Check the current hurricane forecast outlook and confirm with each island restaurant or property directly whether it's open before planning around this window.
September – October
Confirm current harvest timing directly with Napa properties, and check traffic advisories for East Coast beach routes before booking this window.

Local culture and etiquette

Tipping is part of the price in the US

Check whether a service charge is included and ask the establishment or accommodation for its current tipping guidance. We do not publish a verified universal percentage.

Island time is real, and it is not rudeness

On Mustique, Harbour Island and much of Barbados things move at their own pace. Greet before you ask — a good morning first is expected across the Caribbean.

Dress shifts by island

Mustique and Harbour Island are barefoot-relaxed; St Barths dresses for dinner in Gustavia; Barbados's west coast sits between the two. Swimwear stays at the beach everywhere.

Mountain towns run on early starts

Aspen and Jackson Hole eat early and ski earlier; book restaurant tables well ahead in season, and confirm your guide's preferred start time directly before the trip.

Must-visit places

  • St Barths

    The most concentrated villa market in the Caribbean — Pointe Milou for sunsets, Flamands for beachfront.

  • Mustique

    A private-island community of staffed estates; almost nothing is bookable any other way.

  • Aspen

    West End townhouses near the gondola, Red Mountain homes on the hillside above town.

  • Jackson Hole

    Serious terrain in winter, the Tetons and Yellowstone in summer.

  • The Hamptons

    Summer beach villas within reach of New York; book by February for August.

  • Punta Mita

    Staffed beach villas on the Pacific with golf, surf and whale season from December.

  • Napa Valley

    Vineyard estates and harvest from late August into October.

Collections in North America

Themed pages built on the houses we hold — each with published nightly rates, planning notes and the questions we're asked most.

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