Expertly Crafted, Unhurried Adventures

Travel support, a real human, and local immersion you can’t get from an app.

Whether you’re craving a soul-stirring solo adventure, a memorable family trip, or a girlfriend getaway, Dare to Detour brings expertise, care, and, most importantly, takes the stress out of every voyage.

Start Planning

Travel Specialties

& Philosophy

To me, travel is less about checking boxes and more about savoring the journey. It’s about allowing for Detours, immersion, and genuine connection. I believe in thoughtfully-paced adventures that balance well-planned details with space for spontaneity and discovery, so you return home refreshed and with a new perspective. Every trip I plan is rooted in purpose, sustainability, and the joy of being truly present.

Types of Travel

Solo Travel

I believe women can travel at any age and should feel supported. Whether it’s your first solo trip or your fifteenth, let’s plan an itinerary that makes you feel bold and confident in your travels.

Inquire about Solo Travel

Road Trips & Adventure Travel

Scenic mountain passes and spontaneous Detours—this is where travel magic happens! I’ll design your ultimate road trip or adventure, from route planning and unique stays to outdoor experiences.

Inquire about Adventures

Multigenerational & Family Travel

Multigenerational travel is one of my favorites because of the different perspectives everyone brings to the trip. Whether it’s a big family milestone, reunion, or a gentle introduction to international adventure, I’ll balance everyone’s needs so you can just enjoy each other.

Inquire about Family Travel

Honeymoons & Babymoons

I’m a huge fan of celebrating new chapters with a special excursion! Let’s find you the best romantic corners, unforgettable stays, and local gems, adapting them for your needs and wishes at whatever stage you’re in.

Inquire about Honeymoons & Babymoons

Group Travel

Being a women’s retreat planner for 8 years, I bring a specialty to this type of travel and know a few tricks for keeping the coordination smooth and your gathering meaningful. From girls’ getaways to purpose-driven retreats, my goal is to create just the right balance of structure and spontaneity.

Inquire about Group Travel

Sustainable Cruises

Discover the world’s waterways with an intentional footprint that isn’t packed with thousands of people on deck. From National Geographic expeditions to intimate riverboat journeys, I specialize in booking only cruises that emphasize a commitment to conservation and responsible travel.

Inquire about Cruises

Find Your Travel Fit

Whether you just need a hand booking the perfect hotel or desire a full-service, multi-stop itinerary, my passion is to help ease the planning so you can fully immerse yourself when you get there. Every offering includes access to my real-time support before and during your trip.

→ Hotel Reservations

Find the best rates and VIP perks for your stay.

→ Itinerary & Logistics Support

Flights, transfers, train tickets, and more.

→ Restaurant Reservations

I’ll handle the research and bookings.

→ Unique Activities & Immersive Experiences

Vetted recommendations so you can skip the overwhelm.

→ Exclusive, Custom Travel Design

Luxury itineraries for single or multi-destination trips.

Learn More

Italy

•

Scotland

•

Greece

•

United States

•

Portugal

•

France

•

Italy • Scotland • Greece • United States • Portugal • France •

Destinations I Know and Love:

Perks & Benefits

VIP room upgrades, complimentary breakfast, and credits at select hotels

Early check-in and late check-out whenever possible
Packing lists, travel resources, and personal recommendations (right down to the best café for sunset)
Access to my supportive guidance via WhatsApp/text while you travel
Sustainable and local-first options every step of your trip

How it Works

“Sheryl left no stone unturned with all of her personal touches; from the ride ordered at the airport to the microbrew waiting for us in the room bar. What truly stood out was her kindness and deep knowledge—she went above and beyond to ensure a seamless experience and made us feel well taken care of throughout our stay. This level of service greatly enhanced our overall experience.”
“As always our booking experience with Sheryl was seamless. Surprising my Harry Potter loving daughter with a stay on Victoria Street was a thoughtful recommendation and such a fun memory. We were welcomed with a note, sweet treats and a bottle of wine all curated by Sheryl. Sheryl surprises and delights her clients at every turn.”
“When we were notified our flight home from the U.K. was canceled and we were being rerouted through Paris, I immediately texted Sheryl. Even with an 8 hour time difference, Sheryk quickly curated three hotels for us to preview and "auto book". I would have spent hours researching our options but instead I was able to review Sheryl's hotel recommendations -with in depth descriptions of the neighborhood and website links for me to preview. The booking was a quick and smooth process and even though it was a last minute booking, we were met with a warm greeting and a FORA perk welcome drink from the bar and room upgrade. We loved the property!”