How to Choose Your First Say Yes Trip
The hardest part is saying yes
Choosing your first Say Yes trip can feel like a mix of excitement and nerves. You’re ready for a new adventure, but maybe you’re not sure which destination fits you best or what kind of experience to start with. The good news? There’s no wrong choice. Each Say Yes trip is designed with connection, culture, and community in mind.
Whether you’re craving sun and sand, old-world charm, or a cozy stateside escape, your first Say Yes trip should reflect what you need most right now: rest, adventure, friendship, or maybe a little of all three.
Start with how you want to feel
Before picking a destination, think about what you want this experience to give you. Do you want to feel grounded and refreshed, or curious and inspired?
If you’re craving calm: Look for our slower-paced trips like Kauai, where mornings start with coffee on the lanai and afternoons unfold on island time.
If you’re craving connection: Our Gilmore Girls-inspired Connecticut getaway blends cozy nostalgia with conversation and laughter that lasts long after you’re home.
If you’re craving adventure: Trips like Santorini balance exploration with downtime, letting you discover new places and sides of yourself.
When you travel with intention, your “yes” becomes more than just a vacation. It’s an investment in how you want to feel when you return home.
Consider your comfort zone (and how far you want to stretch it)
Every Say Yes trip is created to be welcoming, even if you’ve never traveled solo before. Some guests prefer starting close to home with a domestic trip, while others are ready to hop across the ocean.
If you’re nervous about sharing a room or meeting new people, remember: every woman who joins a Say Yes trip once felt that same uncertainty. What they discover is that connection often starts the moment you decide to show up. These are safe, supportive spaces where you can ease into travel, laugh at the awkward moments, and find comfort in community.
Think about your season of life
Your perfect first trip might depend on what you need most right now.
Feeling burned out? Choose a slower itinerary that lets you breathe.
Needing a spark? Pick a destination that reignites curiosity.
Looking to connect? Join a trip known for its shared meals, group chats, and spontaneous laughter.
Travel can meet you exactly where you are. And sometimes, it shows you where you’re headed next.
Trust your “yes”
When something catches your eye, whether it’s a destination, a photo, a feeling, that’s your intuition nudging you toward what’s right. Trust your gut. Every Say Yes traveler has their own reason for booking that first trip. Some come solo, some come nervous, and all leave changed.
So take a look through the upcoming trips, see what resonates, and say yes to the one that feels right. Because sometimes, that single decision is where everything begins.
Ready to find your perfect first adventure? Explore upcoming Say Yes trips and see where your next “yes” might take you.
