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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 houses 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 short hop from St Maarten, Mustique and Canouan by connection from Barbados or St Lucia, and those legs stop at dusk. Land in the gateway by early afternoon.

Understand hurricane season before you book

The Atlantic season runs June to November, with the real risk concentrated mid-August to mid-October. Rates fall accordingly; if you travel then, take insurance that covers weather cancellation.

Caribbean villas are staffed; US houses are serviced

St Barths, Mustique and Barbados houses come with a cook and housekeeper. Aspen, the Hamptons and Nantucket rent unstaffed, with chefs, drivers and ski valets contracted alongside the booking.

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

The US ESTA, Canada's eTA and several Caribbean arrival forms are online but not instant. Apply a couple of weeks out, and check passport validity for onward island legs.

The best months to go

December – April
Caribbean high season — driest, calmest water; Christmas and New Year book a year ahead at double rates.
December – early April
Aspen and Jackson Hole ski season, with the festive fortnight and Presidents' Week busiest.
May – June
Best value shoulder: warm Caribbean water, quiet islands, and spring in the Rockies before the crowds.
June – September
Hamptons and Nantucket summer, Rocky Mountain hiking and rafting, Hawaii steady all year.
August – October
Peak Atlantic hurricane risk; lowest island rates and many restaurants closed for the season.
September – October
Napa harvest and the best East Coast beach weather without the August traffic.

Local culture and etiquette

Tipping is part of the price in the US

Restaurants, drivers and house staff expect 18–20%. It is not optional in practice, and it is worth budgeting as a line of the trip rather than a surprise.

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; the best tables fill by 19:00 in season, and guides want you on the mountain at first light.

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 estates for the long valley view.

  • Jackson Hole

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

  • The Hamptons

    Summer beach houses 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.

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