Travel Cheaper Playbook

1. Use Credit Card Points (Even Basic Cards Work)

You don’t need premium travel cards to save money. Start simple:

  • Use one card for everything to build points faster.
  • Look for cards offering cashback, points, or travel portal discounts.
  • Redeem points for flights, hotels, or statement credits.
  • Pro tip: Many cards offer $200–$750 signup bonuses—that alone can pay for a flight.

Best beginner cards:

  • Chase Freedom Unlimited / Flex
  • Capital One Quicksilver
  • Discover It (cashback)

2. Book Off-Peak for Huge Savings

Traveling in “shoulder seasons” can save 30–60% off normal prices.
Examples:

  • Caribbean cruises: October–early December, January–February
  • Flights to Europe: February–April, September–early November
  • Theme parks/hotels: Any weekday, non-holiday weeks
  • Vegas: Monday–Thursday

Rule of thumb: If kids are in school → travel is cheaper.

3. Stack Rewards

Stacking = using multiple savings at once.
Examples:

  • Cashback portal (Rakuten, TopCashback)
  • Credit card points
  • Airline/hotel loyalty points
  • Promo code or sale
  • Gift card discounts (Target RedCard, Kroger Fuel Points, etc.)

A $500 hotel can drop to $250 or less using stacking.

4. Use Casino Offers

Casino programs send out free cruise offers, discounted rooms, and resort credits.

Ways to earn offers without big gambling:

  • Low-stakes slots for tier multipliers
  • Joining loyalty programs (free)
  • Taking advantage of promo days
  • Staying at properties during slow months

Cruise lines like Royal Caribbean, Carnival, MSC, and Norwegian all send casino mailers with free or discounted sailings.

5. Sign Up for Travel Deal Alerts

Most people overpay simply because they book randomly. Use alerts to only book when prices drop.

Best tools:

  • Google Flights Alerts
  • Cruise price drop trackers
  • Hopper
  • Shipmate
  • Scott’s Cheap Flights

You’ll be shocked how often flights drop by $100–300 overnight.

6. Travel Midweek Instead of Weekends

Flying Tuesday–Thursday is almost always cheaper.
Cruises, hotels, and resorts also drop prices midweek.

If you’re flexible, you can save hundreds on a trip simply by shifting your dates.

7. Watch for Flash Sales & Holiday Sales

The best travel deals happen around:

  • Black Friday / Cyber Monday
  • Wave Season (Jan–Mar)
  • Labor Day & Memorial Day
  • Random 24–48 hour flash sales

Combine these with reward stacking → major savings.

8. Use Travel Apps to Save Automatically

  • Hopper – predicts price drops
  • Skiplagged – hidden city fares
  • HotelTonight – last-minute hotel deals
  • Turo – cheaper car rentals
  • CruiseWatch – cruise price alerts

Use these apps before booking anything.

9. Book Early OR Last Minute

Book early: Cruises, international flights, family trips
Book last minute: Vegas, all-inclusive resorts, some cruises, weekend getaways

Plan ahead or be flexible—both strategies save big.

10. Always Compare the “Real” Total Cost

The cheapest fare isn’t always the best deal. Check:

  • Taxes & fees
  • Baggage charges
  • Resort fees
  • Gratuities
  • Port fees (cruises)

A “$299 cruise” can become $650 after fees. Always compare full totals.

What’s Next?

If you found this helpful, there’s a lot more where that comes from! You can get access to all of my cruising playbooks to reference anytime you want!

  • How to Find Cruise Deals
  • Best Times to Book
  • How to Get Upgrades
  • How to Get Comps
  • How to Get Repeat Offers
  • The Cruise Packing System
  • Cost Templates & Budget System
  • Full Ship Cheat Sheets
  • Quick Reference Tools, Checklists, & Planner Pages