The Dare Guides Membership
Your guide to off-the-beaten-path travel.
Discover hidden gems, vetted itineraries, product recommendations, and more. Join our community of Darlings for the price of a latte.
Why Join?
For the price of a latte, you’ll get access to thoughtfully vetted, “like a local” travel itineraries for new towns and cities each month. You’ll also have the chance to hop on and chat with Sheryl live each month, ask your travel questions, and get connected to other travel experts and fellow Daring Darlings.
Join Our Community of Darlings
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Join Our Community of Darlings ☕️
What’s Included…
✓ Off-the-beaten path itineraries for locations around the world.
✓ New itineraries added every month.
✓ Monthly "Coffee Chats” with Sheryl to go over travel questions and other hot topics.
✓ Guest chats with local experts.
✓ Budgeting tools for travel.
✓ Product recommendations specifically for women.
✓Exclusive deals and discounts to Dare and our brand partners.
✓Annual Members get a bonus 1:1 Consultation Call with Sheryl
Monthly Travel Itineraries & Resources
Every month, get access to expertly designed itineraries created specifically for female travelers for beautiful destinations around the globe. New guides are released each month and include a Google Maps list of places to see, packing lists, book recommendations, playlists, and more.
A Monthly Coffee Chat
Hop on a live call for 30 minutes each month, and enjoy an intimate conversation with Sheryl, guest experts and our Dare community. Get insider tips about the destinations, and participate in Q&A sessions. Can't make it live? Don't worry – recordings will be available for you to view at your convenience.
Budgeting Tools for Travel
Traveling doesn't have to be a financial stressor, rather it can be framed and planned for as an investment in yourself. Use tools like our "Budgeting for a Trip" resource and receive friendly reminders from Sheryl and her personal Financial Planner (Harriet Chase, Founder of Aspen Grove Wealth Management) to save for your trips. Turn your daily $7 coffee spend into a high-yield savings account and watch your travel funds grow - you’re worth it Darling!
Exclusive Content and Product Recommendations
Our "Weekly Loves" will transition into a comprehensive "Monthly Love" recommendation by category and season. Discover the best books, gear, beauty, and wellness products, and tips for travel with full transparency. You’ll also gain exclusive access to discounts and special promotions from some of our favorite brand partners.
Exclusive Perks for Dare to Detour®
$500 Savings: Your membership includes a $500 savings when you book any Dare to Detour® trip, a savings that will cover the cost of most domestic round trip flights to Bozeman, Montana.
Early Access: Be the first to know about new Detour announcements. Our Montana Detour sold out in just 2 hours - you'll be the first to know about retreats!
What you can expect
The Perfect Travel Companion
The Dare Guides Membership is your travel toolkit designed by the OG Daring Darling Sheryl Wright and our network of local experts. With your Dare Guides Membership, you’ll have access to travel itineraries that are anything but the “top 5 places to visit” and instead, are vetted, curated guides created by women who have been there and done it. Imagine having a monthly coffee date with Sheryl and her travel buddies, gaining exclusive insights into incredible destinations, and in the end, saving a ton of time planning trips that you know will be incredible. Whether you're plotting your next adventure or looking for inspiration, this is the perfect place to start.
Other Destinations Like:
North Coast 500, Scotland
London, United Kingdom
Dolomites, Italy
Marrakech, Morocco
Lisbon, Portugal
Oregon Wine Country
Bay Area, California
Bozeman, Montana
Camper Van Road Trips, North America
*New guides and fresh content being released every month.
FAQ’s
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Not at all! Even if you’re not planning a trip right now, you’ll love the budgeting tools, product recommendations, and inspiration from the "Coffee Chats" and expert chats. The membership is perfect for dreaming, planning, and staying ready for your next adventure.
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This membership is perfect for those who love to explore, dream about travel, or just want to simplify trip planning. Whether you’re a seasoned traveler or just starting to venture out, the Dare Guides are here to inspire and support your journey.
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Once you join, you’ll receive access to our member portal, where you can view travel guides, budgeting tools, product recommendations, and "Coffee Chats" recordings. The member portal is simple to navigate, and we’re always here to help if you have questions about accessing content. You’ll also get email updates with new content each month.
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Our guides are off-the-beaten-path itineraries curated by Sheryl and local experts. Each guide includes must-visit locations, Google Maps links, packing lists, playlists, and more. They’re designed specifically for women who want unique and thoughtful travel experiences.
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Absolutely! We’d love to hear where you’re dreaming of going. Members can share suggestions and ideas, and we’ll consider them for future guides.
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Yes! The membership is month-to-month, and you can cancel anytime if you feel it’s not the right fit for you. No long-term commitments.
