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 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 — what does that mean for a trip to North America?
- 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 — what does that mean for a trip to North America?
- 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 — 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?
- 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 time to visit North America
- When is the best time to visit North America?
- 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. Rates on every villa 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?
- 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.
- What is North America like in 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.
- What is North America like in May – June?
- Ask Caribbean and Rocky Mountain properties directly for their current shoulder-season rate and conditions before booking this window.
- What is North America like in June – September?
- Check current trail and river conditions with the property for Rocky Mountain hiking or rafting trips in this window.
- What is North America like in 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.
- What is North America like in 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 in North America
- Tipping is part of the price in the US — what is expected of visitors?
- 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 — 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; book restaurant tables well ahead in season, and confirm your guide's preferred start time directly before the trip.
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 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.
- How do I book a villa in North America?
- Browse recorded listings in North America estates, then check Stay22 partner searches for your dates and party. Editorial listing identity and exact partner availability are not guaranteed matches; confirm the exact accommodation and terms on the partner site.