How We Plan a Trip

Ashleigh and Christopher walk through their process for planning vacations, from deciding on destinations to booking flights and hotels.

Choosing Destinations

They keep a running list of places they'd like to visit and remain flexible, considering multiple options based on deals, weather, and what's going on in different locations at different times of year.

Searching Flights and Lodging

They start searching early to get a sense of prices and routes but don't book right away. For lodging, they look for something convenient and comfortable without overspending.

Evaluating Cost and Value

They consider the full cost of flights, lodging, activities, and food to determine if a trip makes sense for that time period compared to other options.

Booking Flights First

They typically book flights first since prices fluctuate. For lodging, they may book refundable reservations early to lock in options.

Buy Travel Insurance

They recommend once you make your first non-refundable booking, be sure to buy travel insurance in case anything comes up. If you travel more than twice a year, an annual policy could save you money.

Staying Flexible

They aim to stay flexible as long as possible before committing to nonrefundable plans to take advantage of price drops or new opportunities.

Wine Break

They sample an Oak-aged Marsanne white wine from Domain Berrien winery in Michigan, impressed by the light, fruity flavor combined with oaky vanilla notes.

Visiting Michigan Central Station

They share their awe at seeing the restored Michigan Central Station in Detroit after 30 years of abandonment. Ford took great care to accurately recreate original details. They recommend visiting this impressive revival of an iconic building if traveling through Detroit.