01 · Together is better
Group getaways
Reunions, retreats, celebrations and shared adventures—with the group details kept in one place.
Plan a group trip
Start planning
Personal planning · Memorable getaways
Life is worth living.
Let's go somewhere.
Cruises, group trips, weekend escapes and custom vacations—planned with real care from the first idea to the final payment.
PersonalOne-on-one planning
FlexibleGroup and custom travel
SecureStripe-powered payments
Life worth living starts with something to look forward to. You bring the people and the dream; we'll help organize the details.
Real trips · real joyThe S&S Travel spirit
“Life worth living” means making room for the memories you'll talk about for years.
That spirit is behind every getaway we help plan.
Made for the way you travel
More joy. Less trip-planning stress.
Whether everyone is coming along or you need a getaway of your own, S&S Travel helps turn the idea into a clear plan.
02 · Sail, stay, relax
Cruises & resorts
Relaxing stays and sailings matched to your budget, timing and travel style.
Plan a cruise or resort
03 · Make it yours
Custom experiences
Tell us what would make the trip special. We'll help shape a getaway that feels like yours.
Plan a custom getawayOn the S&S calendar
Something wonderful is coming up.
See newly released group getaways, cruises and special experiences—then sign up online when deposits are open.
- Universal Studios & SeaLife GetawayOrlando, Florida
- Carnival Vista 2027 CruiseCaribbean from Port Canaveral
Custom Experience
Universal Studios & SeaLife Getaway
Orlando, Florida Mar 29–Apr 1, 2027
Round-trip transportation, a Hampton Inn stay with hot breakfast, one Universal Studios ticket, and one SeaLife Aquarium ticket. Pricing varies by room occupancy.
Deposit due Nov 1, 2026$50 per traveler
Couples can pay together; other group travelers can pay separately.
View the trip post ↗Cruise
Carnival Vista 2027 Cruise
Caribbean from Port Canaveral Oct 9–16, 2027
A seven-day Carnival Vista cruise with round-trip motorcoach transportation and an S&S Travel souvenir T-shirt. The itinerary includes Port Canaveral/Orlando, San Juan, St. Thomas, and Celebration Key.
View the trip post ↗See what's happening
Real trips. Real people. Life worth living.
Traveler love from Facebook
What travelers are saying
Selected from real S&S Travel trip posts. Comments are lightly shortened for layout; traveler names are omitted for privacy.
The story behind S&S
Two founders. One shared belief: life is worth living.
S&S Travel grew from Sheryl Davis and Sydney Calhoun's love of bringing people together, opening the door to new experiences and creating memories that last long after everyone returns home.
Founder · Carrying the vision forward
Sheryl Davis
A breast cancer survivor, Sheryl leads S&S Travel with resilience, warmth and personal care. Her journey deepened the belief at the heart of the agency: life is worth living, meaningful moments matter and travel can bring people closer.
Co-Founder · In loving memory
Sydney Calhoun
Sydney was the other “S” in S&S Travel. After her passing from cancer, her adventurous spirit, warmth and love of bringing people together continue to shape the agency's heart and purpose.
Simple from day one
A clear path from “where should we go?” to “we're booked.”
You'll always know the next step. Your S&S Travel agent handles the planning while the secure client system keeps payment links, receipts and reminders organized.
Life worth living starts with the next step.
Tell us what you're dreaming about—we'll help make the path clear.
- 1
Share the dream
Complete the short trip request with your destination, dates, group and budget.
- 2
Review your plan
A real agent follows up with options, details and the required deposit.
- 3
Pay securely
Use your private S&S Travel link and receive confirmation automatically.
- 4
Get ready to go
We keep the important dates and next steps clear as the trip gets closer.
Technology with a human touch
A real travel agent stays at the center of your trip.
Our secure tools make requests, payments, receipts and reminders easier. They do not replace personal planning or judgment.
- A real agent reviews your trip request and booking details.
- Sam, our AI phone assistant, can collect information and help with routine account steps.
- Changes, disputes, refunds and special circumstances go to a real S&S Travel agent.
New to S&S Travel?
Let's start with your trip idea.
Complete our short trip request so we can understand the destination, dates, group size and budget before an agent follows up.
Business hours: Monday–Friday, 9 AM–5 PM
Already traveling with us?
Your trips, balances and payments—all in one account.
Open your secure client account to review your trips, payment history and available payment options.
01
Verify your email and phone
02
Review trips, balances and payment history
03
Pay securely or save a card with Stripe
Have a private payment link?You can still use the exact link sent by S&S Travel.
It opens the correct trip and amount, then Stripe handles your card securely.
Need your link resent or have an account question? Call us or send an email.
Travel with confidence
Real people when you need help. Secure tools when you're ready to pay.
- ✓ Clear deposit and balance information
- ✓ Private, client-specific payment links
- ✓ Automatic receipts and friendly reminders
- ✓ A real S&S Travel agent for exceptions and questions
Good to know
Questions before you get started
Clear answers about planning, deposits, payments and Sam, our AI phone assistant.
How do I start planning a trip?
Complete the short trip request with your destination, dates, travelers and budget. A real S&S Travel agent will review it and follow up with you.
How do deposits and trip contributions work?
Your trip has a fixed required deposit and due date. The deposit must be paid in full before flexible trip contributions are available, unless a real S&S Travel agent has approved an exception or waiver.
Can couples pay together while other group members pay separately?
Yes. For each adult, the organizer chooses whether one account will cover that traveler or the traveler will use a separate private account. Everyone stays connected in the same Travel Party and rooming request, but only independent payers receive separate balances and payment links. A real agent confirms final room or cabin arrangements.
Are payment links secure?
Yes. Every private payment link connects to one exact payment or trip. Stripe securely collects and stores card information; full card numbers and security codes are not stored in Airtable or shown to S&S Travel.
Can I save a card or pay by phone?
Eligible clients can securely enroll a card with Stripe. After account verification, Sam may help use a saved card only after confirming the payment amount and the card's last four digits. Sam will never ask you to read a full card number or security code aloud.
Who is Sam?
Sam is S&S Travel's AI phone assistant. Sam can collect trip inquiries, help locate an account and assist with routine payment steps. A real agent handles booking promises, disputes, refunds, policy exceptions and special circumstances.
What if I need to cancel or request a refund?
Contact S&S Travel directly. Eligibility and timing depend on the written terms for your trip and its travel suppliers. Sam cannot approve a refund or make a binding exception.