Sarah Riley
Co-Founder & Luxury Travel Advisor
Based in Dade City, FL
Let's plan something worth remembering.
I'm Sarah Riley, co-founder of Travel Squad Vacations. I've been planning travel professionally since 2021, and I've been the family trip planner for as long as I can remember. I'm the advisor clients call when the trip simply has to be perfect.
I work with families, couples, multigenerational travelers, seasoned explorers, and destination wedding guests. My specialty is elevated travel that balances real luxury with smart value: all-inclusive Caribbean escapes, bucket-list European itineraries, and complex multi-cabin group cruises.
Both of my kids are dairy and gluten free, so traveling with food allergies isn't theoretical for me. It's every trip we take. I know which resort kitchens and cruise dining teams genuinely take it seriously, how to confirm safe options before you board, and how to pack for travel days so no one is stuck hungry at 30,000 feet. If you're planning around dietary needs, you're in the right hands.
Professional Network — I'm a cornerstone member of the Carrollwood BNI Chapter and a CLIA-credentialed advisor, which keeps me plugged into Tampa's strongest small-business community and the cruise industry's leading association.
If you're planning something that matters, I'd love to hear about it.
— Sarah
A Message From Sarah · 45 sec
By Invitation
An appointment held by few.
Sarah is a member of Opulence,
the luxury division of our host agency.
Opulence is a quiet circle of advisors entrusted with the industry's most discerning travelers, vetted by referral and bound by a standard of taste rather than volume. Through this affiliation, Sarah secures privileged access to ultra-luxury villas, hosted private yacht charters, suite-level cruise upgrades, and the kinds of doors that quietly close to the rest of the market.
Private Access
Suites, residences, and experiences released only to Opulence advisors.
Quiet Perks
Resort credits, complimentary upgrades, and early embarkation as standard.
Vetted Standard
A roster maintained by referral and reputation, never application.
Credentialed, networked, accountable.
Sarah is an active member of the industry and local-business organizations below — verifiable, vetted affiliations that hold every booking to a higher standard.
Carrollwood BNI Chapter
Cornerstone member · weekly Tampa referrals
Greater East Pasco Chamber of Commerce
Member · Dade City & East Pasco County business community
CLIA — Cruise Lines International Association
Credentialed cruise advisor
ASTA — American Society of Travel Advisors
Verified industry member
Where I'm most in my element.
Trips I've loved.
A small sample of the journeys I've designed — and the moments that still make me smile.
Alaska · With My Kids
Alaska with my kids. It felt like God's country — so much untouched wilderness, and the feeling of standing somewhere truly vast stayed with all of us.
Greece · The Islands
Greece stole a piece of my heart. The islands, the food, the culture — I came home changed.
Scotland · Regent Seven Seas
Scotland on Regent Seven Seas. Misty castles, windswept coastlines, and the kind of seamless luxury that spoiled me for other cruise lines.
Caribbean · Icon of the Seas
Spring break on Icon of the Seas with friends and family. Loud, joyful, chaotic in the best way — proof that big-ship cruising done right is still magic.
Riviera Maya · Secrets Moxché
Secrets Moxché with my husband. Quiet mornings, slow dinners, and the kind of adults-only escape every couple needs once a year.
UPCOMING
Mediterranean · Crystal · September 2026
Up next: Athens to Rome aboard Crystal in September 2026. Small-ship luxury through the Mediterranean I've been dreaming about for years.
What Sarah's clients actually say.
★★★★★ · 5.0 from 16+ reviews for Sarah
"Sarah Riley is simply amazing. We planned the perfect honeymoon."
"Planned an anniversary trip to Hawaii in less than 2 weeks. Turned a stressful situation into a perfect celebration."
"Sarah is my go-to girl for all my travel needs. I've got my friends hooked on using her too."
"I hadn't traveled internationally before and she made it very easy and reassuring."
"Sarah is the travel expert queen — better deals and experiences than booking directly."
"Incredibly knowledgeable and always willing to answer every question, no matter how small."
Let's plan together.
Tell me a little about the trip you're dreaming of, and I'll be in touch within two business days.
Prefer email? Reach Sarah directly at sarah@travelsquadvacations.com
Not quite the right fit?
Every advisor on our team has her own specialty. Meet the four others below.
Ready when you are — no pressure, no commitment.
Ready to travel better?
Tell us where you're dreaming of, and one of our advisors will be in touch within two business days.
Mon – Fri 9 AM – 6 PM · Sat 9 AM – 5 PM