Hopping on a plane, getting whisked off to a place other than home and enjoying a weeks-long stay somewhere nice & sunny is my ideal vacation. You’ll never convince me to pack my warmest coat for a trip to Antarctica—shivering to just death isn’t my idea of fun.
Now that the summer is starting to wind down, I’ve made a few attempts at preparing myself for an ideal getaway. ChatGPT, Gemini and Claude have played a huge role in setting up my summer vacation and even a staycation that will take me to the hidden corners and underrated hangouts I never knew about in New York City. Thanks to the combined efforts of those chatbots, I’ve created the best itineraries and mapped out the top hotspots for my future trips.
Now that August is approaching (a little too fast for my taste, I might add), I’ve been having dreams of screaming my head off while sitting in the front of a roller coaster and proceeding to stuff my face with overpriced cotton candy. I’m a simple man, which is why theme park thrills please me greatly.
Not only did I discover five ChatGPT prompts that helped me schedule the perfect vacation with those activities in mind, but I also found four other prompts that work equally well in planning my vacays.
The prompt that built a theme park excursion for me
With my sights set on setting foot in a warm state for a five-day escape from NYC, I used this ChatGPT prompt to set me up for the best trip possible:
Act as a professional travel advisor, airline pricing analyst, and local guide.
Help me plan the best possible summer trip in Orlando, Florida, based on my budget, interests, available vacation days, and departure airport. Recommend destinations, the best time to visit, how to avoid crowds, estimated costs, hidden gems, common tourist mistakes, and a realistic day-by-day itinerary.
Prioritize value over luxury and explain why each recommendation is worth considering.
Here's my budget, interests, available vacation days, and departure airport:
Budget: $2000
Interests: Theme parks, arcades, and museums
Available vacation days: August 17 to August 21
Departure airport: John F. Kennedy International Airport
ChatGPT then went into full “fun summer getaway planner” mode and laid out everything for me to follow with ease. First, it generated a budget breakdown that came out to a total of $1660 to $1950 and mentioned how my budget leaves a small amount for a few souvenir pickups or unexpected expenses.
Then the chatbot went on to detail the best departure days from both NY and Florida, plus the airlines I should consider when planning my flight in and out of Orlando. As for where I should stay, ChatGPT landed on International Drive (I-Drive) as the perfect sweet spot since it’s close to Universal Studios, has plenty of restaurants in the area, is close to a few arcades, has plenty of transportation options to consider and has lower hotel prices than the ones featured on Disney resorts.
Since I mentioned theme parks being a love of mine, my digital vacay planner set aside whole days for visits to Universal Studios, Islands of Adventure and Epic Universe. With ChatGPT’s recommendation of getting a 3-day ticket for all three parks and a few mentions of each park’s best attractions, I had the right idea for how to bask in my theme park hobby in Orlando.
From that point forward, the chatbot gave me the heads up about nearby arcades (Arcade Monsters and the Player 1 Video Game Bar piqued my interest), museums (looks like I have to spend the day at the Orlando Science Center) and hidden gems (Lake Eola Park sounds like a cool destination for me to check out).
With ChatGPT’s added counsel, such as common Orlando tourist mistakes I should avoid, the best times to beat large crowds at the theme parks, a working itinerary, money-saving tips and an overall recommendation for what I should do, I left my latest ChatGPT session with a solid plan in mind for my stay in Orlando.
Four other prompts that are perfect for setting up summer getaways
With these four other ChatGPT-generated prompts, I’ll have no issue planning future trips for my domestic and international stays. I’m sure that’ll apply to you if you end up testing them out for yourself:
- The "Travel Like a Local" Prompt: Act as a resident who's lived in my destination for 20 years. Ignore the obvious tourist attractions unless they're genuinely worth it. Instead, recommend restaurants, neighborhoods, beaches, parks, viewpoints, coffee shops, events, and experiences locals actually enjoy during the summer. Tell me what tourists usually waste time on and what they should do instead.
- The Money-Saving Expert Prompt: Become my travel budget coach. Find every realistic way I can save money on a summer vacation without making the trip less enjoyable. Cover flights, hotels, vacation rentals, transportation, food, attractions, travel insurance, packing, airport tricks, loyalty programs, credit card rewards, and timing strategies. Rank each tip by how much money it could realistically save.
- The Summer Vacation Optimizer Prompt: Help me maximize every day of my summer vacation. Build the ideal itinerary that balances sightseeing, relaxation, food, nightlife, outdoor activities, and downtime. Schedule activities around weather, crowds, opening hours, and local events. Include backup plans for rain, extreme heat, or unexpected closures.
- The Family & Group Trip Planner Prompt: Help me plan a summer trip for multiple people with different interests, budgets, and energy levels. Create an itinerary everyone will enjoy, recommend activities for different age groups, identify potential conflicts before they happen, suggest ways to split costs fairly, and include contingency plans if the weather changes or someone wants to do something different.
Final thoughts
With ChatGPT’s roleplaying assistance and additional travel-planning plugins (Expedia, Road Trip Planner and Travel 101: Trip Itineraries are just a few of the many from that massive library), it’s so easy to get all the info you need for your next getaway.
Of course, doing some proper research outside of the chatbot to make sure your vacation plans come together nicely is key — some digital assistance and your own desired destination study sessions will set you on your way to someplace delightful before the summer season ends.
Follow Tom's Guide on Google News and add us as a preferred source to get our up-to-date news, analysis, and reviews in your feeds. Subscribe to Tom's Guide on YouTube and follow us on TikTok.
More from Tom’s Guide
- Someone created a 'Ghost Font' that humans can read but AI can't — I had to try it for myself
- Waze is adding a bunch of AI-powered features including Motorcycle Mode, Personalized Navigation and more
- The Apple Car development may not have been as big a waste of time and money as everyone thought — in fact, it may be the thing that enabled Apple's new AI boom
