Spring Break, Smarter ✈
Plus, what’s happening with the Pentagon, Airbnb, and AI in schools.
Hello M(AI)VENS,
As the calendar turns to March, can we start talking about spring? After multiple snowmageddons, I am ready. Ready for sun, sand, a good book, and a cocktail with a pretty tiny umbrella. Spring break cannot come fast enough.
And speaking of good books, our March 27 Book Club is coming up — and I would love to see you there. We’re reading Klara and the Sun, one of the most thoughtful AI novels of the past decade. If you’ve never joined us live, this is a great one to start with.
Register here for our March 27 Book Club Meetup (once you register, you’ll get a confirmation email with the Zoom link)
If you’re planning a trip while you’re still emotionally recovering from being snowed in, the last thing you want is to spend three evenings down a TripAdvisor rabbit hole with 17 browser tabs open and nothing booked. Sound familiar?
Before we map out spring break, here are three AI stories worth your attention this week.
Pentagon AI Shake-Up: Anthropic Out, OpenAI In
Anthropic and the U.S. Department of Defense fell out over contract terms after Anthropic (the maker of Claude) refused to drop strong safeguards that bar its Claude AI from supporting mass domestic surveillance and fully autonomous weapons, citing ethical concerns. When negotiations broke down, the Pentagon designated Anthropic a “supply-chain risk” and the White House directed federal agencies to phase out its products. Hours later, OpenAI (the maker of ChatGPT) struck its own classified AI deal with the Pentagon. After criticism that the agreement was rushed, OpenAI amended their contract to prohibit intentional domestic surveillance and restrict use by intelligence agencies without separate approval. If the whole situation has you scratching your head, you’re not alone.
One Million Students, One Big AI Decision
Across the country, school systems are making decisions on AI. Broward County, FL is deploying Microsoft Copilot districtwide. Miami introduced Google Gemini to more than 100,000 students. Universities such as Duke and Cal State now offer broad ChatGPT access. Meanwhile, New York City, the nation’s largest district, is considering its options. After briefly banning ChatGPT, leaders are now weighing next steps amid growing parent skepticism and calls for a moratorium. Chancellor Kamar Samuels is expected to release an AI road map soon. Whatever NYC decides will directly affect one million students. It may be the largest real-time AI education experiment in the country.
Airbnb Goes All In on AI
Airbnb is leaning confidently into AI, and CEO Brian Chesky believes it’s been a major advantage for the company. After a strong Q4 with revenue up 12% and bookings up 16%, he pointed to intentional product upgrades powered by AI. A custom AI agent, built by fine-tuning leading third-party large language models on Airbnb’s own customer data, now resolves about one-third of support issues, speeding response times while keeping costs steady. If you run a business, ask yourself where one-third of repetitive work could realistically be automated.
Now let’s get into today’s main topic.
Spring Break, Smarter ✈
Good news: AI trip planning has genuinely leveled up over the past year. Use AI as a structured thinking partner that understands your budget, your group dynamics, and your travel energy. If you use it well, it can function like a private travel agent. Here’s how.
Step 1: Start With a “Dream Dump”
Before you open a single booking site, open an AI chatbot — Claude, ChatGPT, or Gemini all work. Start with a conversation. Explain your vibe, your budget, who’s coming, what you hate, what you love.
Try this prompt:
“I need spring break ideas for [# of people with # adults and # children, ages x and y]. We want [beach/city/mountains], good food, and don’t want to feel like we’re in a tourist mob. Our total budget is around $[X]. Give me 5 destination options with pros, cons for each.”
Then keep talking. Tell it which option feels right, or what’s missing. This back-and-forth is where the magic is. Think of it as texting a very well-traveled friend who never gets tired of your questions.
Step 2: Build Your Itinerary
Once you’ve landed on a destination, ask AI to build a day-by-day plan. Be specific, then refine conversationally.
Try this prompt:
“We’re going to [destination] for [X] days, arriving around 3pm on Day 1. Build a day-by-day itinerary with morning, afternoon, and evening suggestions. We love [food/outdoors/spa days/nightlife]. Add restaurant recommendations near each activity with price ranges.”
Then iterate: “Make day 3 more low-key.” “We have a kid so swap the cocktail bar.” “Add a rainy day backup plan.” Within minutes you have something that would have taken hours manually.
Step 3: Save Real Money
AI is surprisingly excellent at trip budgeting, if you ask the right questions.
For a reality-check on your budget:
“We’re a group of [#] going to [destination] for [X] nights. Total budget is $[amount]. Break down what a realistic daily spend looks like for accommodation, food, activities, and transport. Tell me where we can cut costs without sacrificing the experience.”
For hidden gems:
“What are the best free or under-$20 experiences in [destination]? Think beyond obvious tourist stuff, like local markets, scenic walks, free museum days, local festivals.”
On the flights side, Google Flights now lets you describe your trip in plain language — “beach trip, flexible dates, under $400 round trip from DC” — and surfaces deals accordingly. Especially powerful if your travel dates have any wiggle room.
If you’re flexible, ask AI to analyze shoulder season pricing patterns for your destination. You’ll often uncover a 20–30% swing just by shifting dates by a few days.
And if you have hotel loyalty points or credit card travel rewards sitting unused, ask AI to help you strategize. Prompt it with your points balance and destination and ask what redemption options make the most sense. A free night might be closer than you think.
Step 4: Solve the Group Chat Nightmare
Planning with other people is often where a trip goes to die. The group chat becomes a graveyard of unanswered polls. AI can be helpful with this.
The conflict-resolver prompt:
“I’m planning a trip with [# people]. Person A wants beach and relaxing. Person B wants food and nightlife. Person C has a tight budget. Person D is bringing a kid. Suggest a destination and itinerary that works for all of them.”
A fun feature worth trying: share the AI chat directly with your travel crew.
ChatGPT: Use the Share button to generate a shareable link to your conversation. Send it to the group so everyone can read the full itinerary.
Claude: Create a Project and share it with your travel companions. Everyone sees the same running conversation and can add input in real time, like a shared planning doc that also thinks.
Start a new AI chat just for the trip, name it something like “Cabo April 2026,” and use it as your living planning document throughout the whole process.
🎁 Bonus Travel Prompts to Try:
These are worth bookmarking. Each prompt is written specifically for parents traveling with kids, so you can copy, fill in your details, and skip the back-and-forth of getting AI to understand your actual situation.
For your itinerary:
“I’m planning a [X]-day family trip to [destination] in late March. I’m traveling with kids ages [X, Y, Z]. One loves [interest], one loves [interest] and has a short attention span for museums but loves being outdoors. My priorities are [mix of downtime and activities / mostly active / cultural with kid-friendly options]. Our daily budget for food and activities is roughly [$X]. Build me a day-by-day itinerary that works for all of us and how to build in recovery time.”
For the reality check:
“Here is our family’s draft itinerary. We have kids ages [X] and [Y]. I want you to tell me where this plan falls apart. Is the pacing realistic with kids? Are there hidden logistics or travel time I have not accounted for? What would a parent who has done this trip tell me to change before I book anything?”
For finding the right activities:
“We’re going to [destination] with kids ages [X] and [Y]. I need activity recommendations that genuinely appeal to both age groups, not just activities that adults think kids like. I also want one experience per day that I as the parent will actually enjoy. Give me specific names, why each one works for this age mix, and whether we need to book ahead.”
For dining with kids:
“I’m traveling to [destination] with [X] kids ages [X] and [Y]. I need restaurant recommendations that have good food for adults but are genuinely kid-welcoming, meaning noise-tolerant, flexible with timing, and ideally have a kids menu or share-friendly dishes. Give me 5-7 specific picks with a note on vibe, price range, and whether a reservation is necessary.”
For packing:
“I’m packing for a [X]-day family trip to [destination] in April with kids ages [X] and [Y]. I want to keep it to one checked bag per adult and a backpack per kid. Build me a complete family packing list organized by person, flag the things parents always forget when traveling with kids, and tell me what I can buy there instead of hauling from home.”
For travel day:
“We have a family flight on [date] departing at [time] from [airport]. We have [X] kids ages [X] and [Y], [checked bags / carry-ons]. To help manage airport and travel time with kids, give me suggestions for age-appropriate books, podcasts, or shows to get the family excited about the trip.”
A Word of Caution
AI tools can now do more than suggest destinations. Some can pull live pricing, connect directly to travel platforms, and in certain cases even move you directly into the booking flow. For example, ChatGPT and Perplexity now offer connectors and embedded booking flows. The convenience is real.
Even so, it’s wise to stay attentive at the point of payment.
Before entering credit card details, confirm that you’re on the official airline, hotel, or rental site and that the URL is correct. AI systems surface links and partners based on available web data, but they don’t independently verify every transaction page. Look-alike domains and polished third-party booking sites are increasingly common.
Use AI to research, compare, and clarify your choices. When it’s time to pay, take a moment to confirm you’re completing the transaction on a verified, recognizable platform.
📚 Book: Klara and the Sun by Kazuo Ishiguro
Join us on Friday, March 27, 2026 | 12:00 PM Eastern | 9:00 AM Pacific
Register here (once you register, you’ll get a confirmation email with the Zoom link)
Klara is an Artificial Friend. When she joins a family with a fragile teenage daughter, she studies love, loyalty, illness, and social hierarchy from the outside looking in. The story unfolds through Klara’s perspective where the humans are the mystery.
By the way, a film adaptation is coming, with Taika Waititi directing and Jenna Ortega as Klara. Read it before Hollywood gets hold of it. 🎬
📖 Also, A Personal Note
I’m honored to be a contributing author to AI Everywhere: How Women Are Changing the World with Artificial Intelligence, a collaborative book that brings together 26 women from around the world to discuss how AI is transforming how we work, live, and lead.
My chapter is #13 — the lucky one. The title says it all: "Why Women Must Get AI Savvy Now." Influence, competitiveness, ownership of your future. If you've been reading this newsletter, you already know why. Now it's in print.
Pre-order for only $0.99 and help us climb the charts. 🥳
🏀 Basketball season came to an end in our house this week.
Our youngest played his final middle school game, and my husband coached his last season with an incredible group of boys.
They made it all the way to the championship game and came up just short, but I couldn’t be more proud. I’m proud of our son for the way he showed up this season, worked hard, and kept improving. And I’m so proud of my husband, who has coached both of our boys for more than a decade. From early youth leagues through middle school, he’s spent years on the sidelines, not only teaching teamwork, but teaching kids to truly believe in themselves.
There was something about that last buzzer in the middle school gym that has me feeling all the feels.
Spring is one of my favorite reset points of the year. A new season, new energy, and often a few new ideas worth exploring. Whether you're planning a trip, experimenting with AI for the first time, or simply carving out a little time for yourself, I hope something in today’s edition sparks an idea.
If you’ve been meaning to join one of our live conversations, I’d love to see you at book club on March 27. It’s free and you can even bring a friend.
Warmly,
Cheyenne 💜
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Love the planning tips!