8 ChatGPT Prompts to Help You Plan Your Perfect Vacation

Aug 17, 2025

By Richard D. Harroch and Dominique A. Harroch

Planning a vacation can feel like a full-time job. It can feel daunting or overwhelming to coordinate schedules, research destinations, and ensure everything aligns with your vision of the perfect trip. With so many destinations, accommodations, and activities to choose from, it’s easy to feel overwhelmed. But what if you had a personal assistant who could help you sort through the options and create an itinerary tailored just for you? That’s where ChatGPT comes in. With a little guidance, this AI tool can help you streamline your vacation planning process and ensure that your trip is as enjoyable as possible.

Whether you’re planning a romantic getaway, a solo adventure, or a family vacation, ChatGPT can help with everything from picking the perfect destination to finding the best deals on flights and hotels. Using research assistance and insight from Chat GPT, we put together eight tips on crafting ChatGPT prompts to plan your ideal vacation, complete with examples for couples, singles, and families. We’ll also explore how apps and other tools can complement ChatGPT to make your travel experience seamless.

1. Prompt ChatGPT to Suggest Destinations Based on Your Interests

Finding the perfect destination starts with understanding what you’re looking for. Craft a prompt that includes details about your preferences, travel goals, and budget.

Prompt Examples: "Suggest romantic destinations for a couple in their 30s traveling from San Francisco. We want a mix of relaxation and adventure, traveling from September 10-17, enjoying sunny weather around 75-85°F, and staying within a $5,000 budget for a week. We enjoy outdoor activities like hiking and water sports, and we’d like recommendations for both city and nature experiences."

Pro Tip: Once you’ve narrowed down a destination, ask ChatGPT for specific activities, local attractions, or seasonal events.

2. Use Prompts to Plan Flights and Transportation

Finding affordable and convenient flights is one of the most time-consuming aspects of vacation planning. Let ChatGPT help you narrow down your options.

Prompt Examples: "Find direct flights under $500 from Los Angeles to Europe for a solo traveler. The trip is from June 10-15, and I prefer destinations with temperatures around 70-80°F and opportunities for cultural activities. Provide options for flights that depart in the evening and arrive in the morning to maximize time spent at the destination."

Pro Tip: Combine ChatGPT’s suggestions with flight search apps like Skyscanner or Hopper for real-time price tracking.

3. Ask for Hotel Recommendations Based on Your Preferences

Accommodations can make or break your vacation. Use ChatGPT to find hotels or vacation rentals that align with your needs.

Prompt Example: "Recommend family-friendly resorts in Florida with kids’ activities and pool access. We’re traveling from Chicago from March 20-27, prefer temperatures around 75-85°F, and want nearby attractions like theme parks and nature trails. Focus on resorts with all-inclusive packages and options for childcare services."

Pro Tip: After narrowing down options, use apps like Booking.com or Airbnb to read reviews and book your stay.

4. Plan an Itinerary With ChatGPT

Having a daily plan helps you make the most of your vacation. ChatGPT can generate itineraries tailored to your pace and interests.

Prompt Example: "Create a 10-day itinerary for a trip to Florence, Milan, and Rome starting on May 10 for travelers flying from New York. Focus on art, food, and culture. Include guided tours of historical landmarks, cooking classes, and museum visits that are well-suited for spring weather (60-70°F). Allocate budget-friendly dining options along with recommendations for must-try Italian dishes."

Pro Tip: Enhance your itinerary with travel apps like Google Maps for navigation and GetYourGuide for activity bookings.

5. Use Prompts for Packing Lists

A well-organized packing list ensures you don’t forget essentials. Let ChatGPT help you create one tailored to your destination and activities.

Prompt Examples: "Make a packing list for a family of four traveling to a beach resort in Mexico from July 15-22. Include items for hot weather (85-95°F), water activities, and potential evening excursions. Suggest specific items like sunscreen with SPF 50, waterproof shoes, and lightweight evening wear for dining out."

Pro Tip: Use apps like PackPoint to cross-check your packing list and stay organized.

6. Find Local Restaurants and Activities

Discovering local gems can elevate your travel experience. ChatGPT can recommend restaurants, cafes, and activities tailored to your tastes.

Prompt Examples: "Suggest unique restaurants and nightlife options in Bangkok for a solo traveler visiting from August 1-5. Focus on places known for authentic Thai cuisine, rooftop bars, and live music venues that are popular among locals."

Pro Tip: Use Google Reviews or TripAdvisor to confirm ChatGPT’s recommendations and make reservations where necessary.

7. Ask for Travel Tips and Safety Information

Traveling comes with its challenges, and staying informed about safety and etiquette can make your trip smoother.

Prompt Examples: "What are some safety tips for traveling with kids to a crowded theme park on June 19? Include strategies for managing long wait times and tips for staying hydrated and avoiding fatigue." "What safety tips should I follow as a solo female traveler in South America for a trip starting July 5? Highlight advice on secure transportation, staying in safe neighborhoods, and handling emergencies." "What are the safety precautions for traveling to Tokyo during typhoon season in mid-September? Include tips for monitoring weather updates and preparing an emergency kit." "What are essential safety tips for a cross-country road trip in the U.S. starting October 10? Focus on car maintenance, planning rest stops, and staying connected with family or friends."

Pro Tip: Supplement ChatGPT’s advice with travel apps like TripIt for itinerary management and MyRadar for weather updates.

8. Consider Accessibility for All Travelers

Planning for travelers with disabilities or mobility challenges requires thoughtful preparation. ChatGPT can help you identify destinations, accommodations, and activities tailored to specific needs.

Prompt Example: "Suggest wheelchair-accessible destinations in the U.S. for a summer trip from June 20-27 for a family of five, with three kids (two using wheelchairs). Include recommendations for accessible hotels with pool lifts, activities like accessible nature trails, and dining options with accessible seating. Focus on attractions such as zoos, museums, or aquariums that accommodate families."

Pro Tip: Use apps like Wheelmap to find accessible venues. Contact hotels and attractions directly to confirm accessibility features, such as wheelchair ramps, elevators, and accessible bathrooms. Additionally, prioritize locations with family-friendly attractions that offer inclusive activities, such as theme parks with accessible rides or museums with sensory-friendly exhibits.

Conclusion on ChatGPT Prompts to Help You Plan Your Vacation

Planning the perfect vacation doesn’t have to be stressful. By using ChatGPT effectively, you can generate ideas, streamline logistics, and ensure every detail is covered. Whether you’re exploring Florence, Milan, and Rome as a couple, embarking on a solo adventure, or creating memories with your family, ChatGPT can act as your trusted travel assistant.

Complement AI-generated plans with travel apps for real-time updates, bookings, and organizational tools. With the right prompts and resources, you’ll be well on your way to enjoying a trip that’s unforgettable, stress-free, and perfectly tailored to your needs.

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About the Authors

Richard D. Harroch is a Senior Advisor to CEOs, management teams, and Boards of Directors. He is an expert on M&A, venture capital, startups, and business contracts. He was the Managing Director and Global Head of M&A at VantagePoint Capital Partners, a venture capital fund in the San Francisco area. His focus is on internet, digital media, AI and technology companies. He was the founder of several Internet companies. His articles have appeared online in Forbes, Fortune, MSN, Yahoo, Fox Business and AllBusiness.com. Richard is the author of several books on startups and entrepreneurship as well as the co-author of Poker for Dummies and a Wall Street Journal-bestselling book on small business. He is the co-author of a 1,500-page book published by Bloomberg on mergers and acquisitions of privately held companies. He was also a corporate and M&A partner at the international law firm of Orrick, Herrington & Sutcliffe. He has been involved in over 200 M&A transactions and 250 startup financings. He can be reached through LinkedIn.

Dominique Harroch is the Chief of Staff at AllBusiness.com. She has acted as a Chief of Staff or Operations Leader for multiple companies where she leveraged her extensive experience in operations management, strategic planning, and team leadership to drive organizational success. With a background that spans over two decades in operations leadership, event planning at her own start-up and marketing at various financial and retail companies. Dominique is known for her ability to optimize processes, manage complex projects and lead high-performing teams. She holds a BA in English and Psychology from U.C. Berkeley and an MBA from the University of San Francisco. She can be reached via LinkedIn.