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January 31, 2025

How to plan a winter vacation with AI

Whether you’re heading to the mountains for a ski trip or escaping the cold to a balmy island, take advantage of AI tools to plan a winter vacation to remember.

Two individuals skiing in a snowy pine tree forest

Find a getaway

Torn between several countries or don’t know where you want to go at all? Consult search and generative AI for recommendations for winter vacation destinations based on your interests, preferences, travel companions, and desired experiences.

For example, if you’re a first-time solo female traveler abroad, ask for easy and safe destinations with a prompt like, “I am a first-time solo traveler going abroad to Europe. What are the easiest and safest countries to navigate alone as a woman?” Same if you’re curious about cultural activities. Try a prompt like, “What countries are known for having vibrant nightlife?” Also, if you’re on a budget, have AI recommend affordable destinations that fit the bill. Let’s say you want to go somewhere warm and tropical with white sand beaches. Ask AI, “What are tropical destinations with nice beaches that are relatively affordable?”

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Create an itinerary

Ask AI tools to conjure up ideas like local attractions to see, family-friendly activities, towns to visit, or whatever else interests you most. AI will place these vacation ideas in an itinerary that stays within your chosen timeframe. If you plan on going to multiple countries over two weeks, provide information about your whereabouts, and AI will formulate an itinerary that includes must-sees. Pro tip: Also tell AI to create a list of items to pack.

Manage a budget

Yes, traveling can be expensive, but with AI, managing a budget and finding a destination that won’t break the bank are more straightforward. Once you choose an itinerary, let AI do the guesswork by creating a comprehensive budget. It can consider factors like your planned number of nights abroad, hotel and flight preferences, and intended spending on meals, drinks, and attractions. Simply share your itinerary, destination, and budget with AI, and it will divide your expenses into manageable categories. Try this prompt: “Here’s my itinerary, destination, and the amount of money I set aside; help me budget for flights, hotels, entertainment, food, and other important categories.”

“Torn between several countries, or don’t know where you want to go at all? Consult AI for recommendations for winter vacation destinations based on your interests, preferences, travel companions, and desired experiences.”

Get booking assistance

Finding and booking hotels can be a hassle, especially abroad. Use AI to find hotel locations that fit your price range and align with your itinerary. If you’re going to do a tour of France for two weeks, hitting up a new town every other day, leverage AI to identify hotels in these locations by providing your itinerary and budget. It will suggest hotels along the way and even help with booking. Same with restaurants. If you plan on dining out somewhere fancy that requires booking, AI can redirect you to the site for easy booking.

Learn about culture and language

Different places have different customs. For example, in Japan, covering up tattoos is customary. You want to ensure you respect others’ cultures while abroad. Inform your AI tool of the area(s) you’re traveling within, and it’ll recommend what you should and shouldn’t do. Start with a prompt like, “What customs should I know about when traveling to Japan?”

Planning a winter vacation with AI is just another way that AI opens doors for adventures. From going on a camping trip to making commuting fun, read up on more tips to see how else AI can take you to new sights and sounds.

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