dare to detour
Dare to Detour is a Bozeman, Montana-based, founder-operated travel advisory that designs personalized itineraries and curated women's retreats across domestic and international destinations. The solo-operated business serves solo women travelers, multi-generational families, and small groups through consultation-led planning, free membership community content, and affiliated booking via Fora Travel.
- Company typePrivate
- Founded2017
- HeadquartersBozeman, United States
- Headcount—
- GTM typeB2C
- OfferingServices
What dare to detour does
Dare to Detour, LLC is a founder-operated women's travel advisory and retreat business headquartered in Bozeman, Montana. Founded in 2017 by Sheryl Wright, the company delivers personalized travel planning services, curated group retreats, and a free membership community (Dare Guides) targeted primarily at solo women travelers, multi-generational families, and small groups seeking transformational travel experiences. The core product is end-to-end itinerary design — covering accommodations, transportation, activities, and supplier liaison — delivered through an initial 30-minute consultation call and billed at $75 for the consultation plus $35 per day of booked travel. The flagship revenue driver has been an annual all-inclusive women's retreat at Nine Quarter Circle Ranch in Montana priced at $6,847 per participant, with supplemental retreats and custom journeys in destinations including Italy, Scotland, Morocco, Portugal, France, Greece, Peru, and the Dolomites.
The business has no proprietary technology platform. Operations run on Squarespace for bookings and content delivery, Substack for the Detour Diaries blog, email, Instagram, and a free Dare Guides member portal. Sheryl books travel as an independent advisor affiliated with Fora Travel, Inc., a host agency that provides supplier commissions and VIP perks such as room upgrades and spa credits. Additional revenue streams include affiliate commissions, speaking and facilitation engagements at conferences and corporate events, and a recently launched DIY Detour 8-week self-guided program. The company employs a solo operator with occasional contractors and retreat collaborators (yoga instructors, equine facilitators, photographers).
In September 2025, the founder announced the Montana ranch retreat as the final Dare-hosted retreat, and is pivoting toward international travel planning, facilitation for Cancer Support Community Montana, and a personal lifestyle of extended solo van travel and time abroad beginning in 2026/2027. The company remains founder-owned with no disclosed institutional investment.
dare to detour firmographics
Firmographics- Name
- dare to detour
- Legal name
- Dare to Detour, LLC
- Website
- https://daretodetour.com
- Company type
- Private
- Founded year
- 2017
- Operating status
- Operating
- Short description
- Dare to Detour is a Bozeman, Montana-based, founder-operated travel advisory that designs personalized itineraries and curated women's retreats across domestic and international destinations. The solo-operated business serves solo women travelers, multi-generational families, and small groups through consultation-led planning, free membership community content, and affiliated booking via Fora Travel.
- Ownership category
- akta.pro rank
dare to detour industry classification
Industry- Product category
- Travel Advisory & Wellness Retreats
- NAICS
- Tour Operators (561520), Recreational and Vacation Camps (except Campgrounds) (721214)
- SIC
- Services-Amusement & Recreation Services (7900)
- akta.pro primary industry
- Adventure & Outdoor Local Operators (Trekking/Safari/Diving) (THAKAEAF)
- akta.pro secondary industries
- Mountain & Adventure All-Inclusive Resorts (THAGAKAH), Recreation & Activity Services (Hiking, Boating, Climbing, Fishing—Guided/Authorized) (THAAAGAF)
Keywords
Where dare to detour is headquartered
LocationHeadquarters
- HQ city
- Bozeman
- HQ country
- United States
- HQ region
- North America
Offices1 record
Markets served
dare to detour business model
Business model- GTM type
- B2C
- Offering type
- Services
- Cost components
- Personnel, Operations, Marketing or Sales, Others, Technology or R&D
Revenue model
- Travel Planning Services: Travel advisor services charged at $35 per day for each day of booked travel, plus a $75 one-hour trip consultation fee. Sheryl handles booking accommodations, transportation, activities and tours as a liaison between clients and travel suppliers. All fees are non-refundable.
- Group Retreats: All-inclusive curated group retreats for women at premium destinations. Montana retreats at Nine Quarter Circle Ranch priced at $6,847 all-inclusive (excluding airfare and travel insurance). Includes $925 non-refundable deposit. Payment plans available over 3-6 months at 3% simple interest.
- Affiliate Commissions: Dare to Detour participates in affiliate programs including Fora Travel. Sheryl earns commissions on travel bookings made through the Fora platform and may agree on commissions for bookings outside the platform. Sheryl discloses she promotes products/services she has used or thoroughly researched.
- Dare Guides Membership: Free community membership providing off-the-beaten-path itineraries, monthly coffee chats with Sheryl, budgeting tools, and product recommendations. Serves as customer acquisition and retention channel rather than direct revenue source.
- Speaking & Facilitation: Keynote addresses, workshop facilitation, retreat leadership, and custom group experiences. Fee structure varies by format, length, and location with customized proposals provided after initial consultation.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| One time/ perpetual license | Pay-as-you-go | One-Hour Trip Consultation: $75.00 |
| Unit Pricing | Pay-as-you-go | Travel Advisor Services: $35.00 per day |
| One time/ perpetual license | Multi-year contract | Montana Women's Retreat: $6,847 all-inclusive |
| Subscription | Monthly | Payment Plan Option: 3-6 months at 3% interest |
| Freemium | Pay-as-you-go | Dare Guides Membership: FREE |
| Other | Pay-as-you-go | Speaking & Facilitation: Varies by engagement |
Go-to-market motion4 records
Distribution channels5 records
Marketing channels8 records
dare to detour product offering
Product offeringCore offering
Dare to Detour is a women-focused independent travel advisory that designs and books end-to-end customized itineraries (hotels, flights, transfers, immersive activities) charged at $35 per booked travel day plus a $75 one-hour consultation. Its flagship offering is the annual all-inclusive Montana women's ranch retreat at Nine Quarter Circle Ranch priced at $6,847, complemented by international retreats in Italy, Scotland, Morocco, and the Dolomites. A free Dare Guides membership community with curated itineraries, budgeting tools, and monthly coffee chats supports customer acquisition and retention.
Product overview
Dare to Detour is a women-focused travel advisory and wellness community. The core offering consists of personalized travel planning and advisory services (offered through consultation calls), supplemented by the free Dare Guides Membership (providing curated itineraries, budgeting tools, and community coffee chats). Additional offerings include DIY Detour (an 8-week self-guided program), speaking and facilitation services, and the Detour Diaries Blog content platform. The company operates as an independent travel advisor affiliated with Fora Travel, coordinating retreats, itinerary design, and travel logistics for solo travelers, families, and groups.
Differentiator
Problem solved
Functional benefit
Brands
- Dare Guides: Subscription membership providing off-the-beaten-path travel itineraries, coffee chats, budgeting tools, and product recommendations for women travelers
- DIY Detour
- Detour Diaries
Products and services
- Travel Planning & Advisory Services End-to-end custom travel advisory service for individual women, families, and groups, covering itinerary design, destination recommendations, lodging, flights, car transfers, and immersive activities. Engaged through a $75 one-hour consultation and charged at $35 per booked travel day as liaison between client and travel suppliers. Non-refundable.
- Montana Women's Ranch Retreat (Group Retreats) 5-day all-inclusive curated women's retreat at Nine Quarter Circle Ranch (working horse ranch in Lee Metcalf Wilderness). Priced at $6,847 all-inclusive (excluding airfare and travel insurance); includes accommodations, airport shuttle from Bozeman, all meals, guided trail rides, workshops, activities, gratuities, and a $925 non-refundable deposit. Payment plans available over 3-6 months at 3% simple interest. The September 2025 retreat is announced as the final Dare-hosted Montana retreat.
- DIY Detour An 8-week self-guided guide/program designed to help individuals get off the beaten path in their own hometown or anywhere, focused on wellness, exploration, and self-discovery as a lower-friction entry point to the Dare to Detour brand.
- Speaking & Facilitation Engagements Keynote addresses, conference talks, panel participation, workshop facilitation, retreat leadership, and custom-designed group experiences for corporate events and conferences. Topics include embracing detours, travel as catalyst for growth, women's empowerment, navigating cancer, self-reinvention, and aging joyfully. Fee structure varies by format, length, and location, with customized proposals after initial consultation.
- Dare Guides Membership Community Free (with paid annual tier) community membership offering curated off-the-beaten-path itineraries for destinations including Scotland, Italy, Morocco, Portugal, and the Dolomites, plus monthly coffee chats with Sheryl, budgeting tools, packing lists, Google Maps integrations, book/playlist recommendations, and guest expert appearances. Annual members receive a bonus 1:1 consultation call with Sheryl.
Quantifiable outcome
- 200+ women guided on Detours in Montana and beyond
- +2 more outcomes
Companies that use dare to detour
Customer profileNamed customers4 records
Segments5 records
Ideal customer profiles3 records
dare to detour technology and API
TechnologyTechnology focussed No
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
dare to detour partnerships and signals
Strategic signalPartnerships
Nine partnerships are on record, tiered core and minor.
- Fora TravelcoreDare to Detour operates as an independent travel advisor affiliated with Fora Travel, Inc. Sheryl is not an agent, representative, or employee of Fora. Fora is a technology provider and host agency, not a travel service provider. Sheryl books travel through the Fora platform and receives commissions. Clients have no claim against Fora for losses arising from Sheryl's services.
- Cancer Support Community MontanacoreSheryl facilitates retreats for this organization that supported her through her own breast cancer journey. This represents her strategic focus on giving back to organizations that supported her through health challenges. She facilitated her first Cancer Support Community retreat in fall 2025.
- Nine Quarter Circle RanchcoreAnnual venue partner for Montana women's retreats. A working horse ranch owned and operated by the Kelsey Family for over 75 years, providing access to Lee Metcalf Wilderness. Sheryl has led retreats there since 2017, with 2025 marking her final Dare retreat at this venue.
- Sky's the Limit ToursminorYellowstone add-on experience partner for Montana retreat participants. Offers 2-day private wildlife safari and hot springs tours with 16% discount for retreat guests. Includes pickup from ranch, Under Canvas glamping accommodation, and guided park exploration.
- Honor Equine (Sydney)minorHorse guidance partner leading both large-group sessions and intimate round pen work during Montana retreats. Sydney guides participants through transformative work with horses as 'mirrors' for personal growth.
- Soulstice Yoga (Nico)minorMovement and meditation facilitator leading morning grounding sessions at Montana retreats. Nico provides daily mindfulness practices to help participants 'come home to their bodies' before adventures under the Montana sky.
- Western Roots Country Dancing (Suzi)minorLine dancing instruction at Montana retreats. Suzi teaches line dancing with abandon, contributing to the 'vibes' and collective joy that participants experience during the week-long retreats.
- Fawn & CominorBozeman-based upcycled cowboy jeans and vintage wear retailer. Has showcased at Montana retreats for 5 consecutive years. Sheryl actively supports women-owned small Montana businesses as part of her retreat programming.
- Sara SaxtonminorPortrait photographer who created magical portraits of retreat participants during Montana retreats. Contributed to the creative and memorable experiences Sheryl weaves into each retreat week.
Scale indicators4 records
Recent moves5 records
Expansion highlights5 records
dare to detour competitors and assessment
Company assessmentDirect peers
- Wild Women Expeditions: Women-only adventure travel tour operator offering small-group hiking, trekking, and wildlife experiences worldwide. Directly comparable to Dare to Detour because both target women seeking outdoor, transformational, community-focused adventures with experienced local guides.
- AdventureWomen: Long-running women-only active travel company offering curated adventure trips globally (hiking, kayaking, cultural journeys). A near-direct peer to Dare to Detour's Montana retreat and abroad itineraries given the shared 'women-only, expert-guided, off-the-beaten-path' positioning.
- Black Tomato: Boutique luxury experiential travel agency offering custom itineraries and exclusive experiences for high-end travelers. Comparable as a personal-advisor-led, design-forward model targeting affluent clients seeking intentional, transformative journeys.
- WOLO Travel (Women Only Life of Adventure): Women-only tour and expedition company running group trips worldwide with hand-curated experiences. Directly comparable to Dare to Detour's retreat and group-trip model in both audience (women seeking meaningful travel) and structure (curated group departures).
Broad incumbents
- Backroads: Established active-travel operator running thousands of biking, hiking, and multi-adventure trips annually. Overlaps in 'curated adventure travel with full logistics support' but at much larger scale and broader, non-women-exclusive audience.
- REI Adventures: The adventure-trip arm of REI offering guided hiking, multisport, and cultural trips worldwide. Comparable in activity style to Dare to Detour retreats (horseback, hiking, wilderness), though at a much larger scale, with broader demographics.
- Miraval: Multi-property wellness resort brand offering all-inclusive wellness retreats with mind-body programming. Comparable in the 'wellness retreat' niche that Dare to Detour's Montana ranch occupies, though Miraval operates owned resort properties at far greater scale.
Emerging players
- Roaming the Americas: Boutique travel advisor specializing in women-over-50 trips across Latin America. Compares as a niche women-focused personal travel-advisor brand, though smaller and regionally focused versus Dare to Detour's global destination mix.
Others
- Fora Travel: Host travel-agency platform and network of independent travel advisors (the platform Sheryl is affiliated with). Comparable ecosystemically — independent advisors earning commissions on hosted bookings — rather than as a direct competitor.
- Brownell Travel: Long-established host travel agency representing high-touch independent travel advisors. Comparable as an organizational / host-agency peer that supports independent advisors in the same network-of-advisors model, useful for benchmarking commission and training economics.
Market position
Strengths5 records
Weaknesses5 records
Competitive moat3 records
Key risks6 records
Key highlights6 records
Customer concentration
dare to detour social profiles
Digital presencedare to detour financial estimates
Financial estimateRevenue estimate
Valuation estimate
dare to detour leadership team
Management profileNumber of profiles
Profiles1 record
dare to detour funding detail
Funding detailFunding overview
Funding rounds
Investors
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
dare to detour M&A and investment
M&A and investmentM&A
Investments
M&A and investment is available on the Subscription and Enterprise plan.Contact sales →
Frequently asked questions about dare to detour
What does dare to detour do?
Dare to Detour is a women-focused independent travel advisory that designs and books end-to-end customized itineraries (hotels, flights, transfers, immersive activities) charged at $35 per booked travel day plus a $75 one-hour consultation. Its flagship offering is the annual all-inclusive Montana women's ranch retreat at Nine Quarter Circle Ranch priced at $6,847, complemented by international retreats in Italy, Scotland, Morocco, and the Dolomites. A free Dare Guides membership community with curated itineraries, budgeting tools, and monthly coffee chats supports customer acquisition and retention.
Is dare to detour a public or private company?
dare to detour is a private company. It is classified as founder individual operated bootstrapped and is currently operating.
When was dare to detour founded?
dare to detour was founded in 2017.
Where is dare to detour based?
dare to detour is headquartered in Bozeman, United States, in the North America region.
How does dare to detour make money?
Five revenue lines are on record. Travel Planning Services are the primary driver. The others are group Retreats, affiliate Commissions, dare Guides Membership and speaking & Facilitation.
Who are dare to detour's main competitors?
Direct peers on record are Wild Women Expeditions, AdventureWomen, Black Tomato and WOLO Travel (Women Only Life of Adventure). Broad incumbents are Backroads, REI Adventures and Miraval. Roaming the Americas is listed as an emerging player. Others are Fora Travel and Brownell Travel.
Does dare to detour have an API?
No public API is recorded for dare to detour.
What industry is dare to detour in?
dare to detour's product category is Travel Advisory & Wellness Retreats. Its primary akta.pro industry code is THAKAEAF, Adventure & Outdoor Local Operators (Trekking/Safari/Diving), with a secondary code of THAGAKAH, Mountain & Adventure All-Inclusive Resorts. Its NAICS code is 561520 and its SIC code is 7900.