North America destination guide FAQ
Your North America questions, answered.
The same ground the North America destination guide covers — travel tips, the best months, local culture and where to go — set out as the questions people actually ask us before they book.
Planning a trip to North America
- Plan the connection, not just the flight — what does that mean for a trip to North America?
- 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 — what does that mean for a trip to North America?
- 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 — what does that mean for a trip to North America?
- 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 — what does that mean for a trip to North America?
- 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 — what does that mean for a trip to North America?
- 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 time to visit North America
- When is the best time to visit North America?
- 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. Rates on every house move with these seasons, and the live partner panels on each listing show what a given week actually costs.
- What is North America like in December – April?
- Caribbean high season — driest, calmest water; Christmas and New Year book a year ahead at double rates.
- What is North America like in December – early April?
- Aspen and Jackson Hole ski season, with the festive fortnight and Presidents' Week busiest.
- What is North America like in May – June?
- Best value shoulder: warm Caribbean water, quiet islands, and spring in the Rockies before the crowds.
- What is North America like in June – September?
- Hamptons and Nantucket summer, Rocky Mountain hiking and rafting, Hawaii steady all year.
- What is North America like in August – October?
- Peak Atlantic hurricane risk; lowest island rates and many restaurants closed for the season.
- What is North America like in September – October?
- Napa harvest and the best East Coast beach weather without the August traffic.
Local culture and etiquette in North America
- Tipping is part of the price in the US — what is expected of visitors?
- 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 — what is expected of visitors?
- 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 — what is expected of visitors?
- 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 — what is expected of visitors?
- 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.
Where to go in North America
- Which places in North America should I build a trip around?
- 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.
- How do I book a house in North America?
- Every house on North America estates shows live partner rates for your dates. Choose the dates and party size on the listing, and the booking completes with our partner — Booking.com, Expedia or Hotels.com — at the partner's own price. We never take a deposit ourselves.