Santorini is well known for its iconic white and blue domed buildings crowding cliff edges with the Agean sea and sunset background. It is iconic for a reason! The views on essentially the entire island are incredible. This is a destination that I found is truly worth the hype – BUT I will say that there are ways that people typically experience Santorini that I would definitely NOT recommend. Listen for a curated list of experiences not to be missed, and what to skip. I promise my recommendations are going to differ from the crowded summer sunset views from Oia that you see again and again on social media. And best of all, I’m going to talk about how to do it on points and miles!

Panoramic Villa - Santorini Sky | Hotel in Greece - Elias- This was our specific villa at Santorini Sky. They all look amazing!

Ancient Thera - Museums and Archaeological Sites - Santorini

Akrotiri Village Guide: What to Do, Best Places to Eat & Stay

.Booking hotels on points is a great way to get started with using your points! It is generally simpler than booking flights (because there are fewer variables), so makes a great way to get started. Once you book your first trip, you’ll feel more confident and ready to take on more points bookings.

Many trips start with a specific destination in mind, flights are planned first, and hotels come next. There are some trips where the resort itself is the destination, and with those I typically book the hotel and then plan flights.

Ways to book hotels with points

• Transfer points to hotel partners (ex transfer Citi Thank you Points to Choice or Bilt Points to Hyatt)
• Use points earned with hotel brand from spend on a credit card or staying nights with that brand
• Free night certificates
• Portal bookings- brands not available to transfer to, using card-specific credits (like $300 Venture X, $50 CSP), Rove
• Booking with cash and using cash “credits” from specific credit cards (The Edit, FHR, Bilt hotel credit...)

Order of operations:

• Any free night certificates
• For shorter stays- Any credits that need to be used – FHR, The Edit, Bilt hotel credit. Skip these for longer stays in general unless piecing a few together
• What transferrable points chain hotels are available- Rooms.aero- Hyatt, Hilton, Marriot, IHG, Choice hotels, NO Wyndham
• Consider what points I have available and which I’m willing to part with
• Consider Portal bookings- brands not available to transfer to, using card-specific credits (like $300 Venture X, $50 CSP), Rove
  • Sign up here to earn 500 bonus Rove miles!
• If all else fails, Expedia through Rakuten or hotel site through Rakuten

Rooms.aero map view- Hyatt, Hilton, Marriot, IHG, Choice hotels

European Hotels that sleep a family of 4 -Click Here!

Booking a hotel is a great way to get started on turning your points into free travel! There are many ways to do this, but booking directly through a partner is my favorite way to get the best value. Cancellation fees are typically none (but check fine print), so it’s easy to book speculatively and then cancel or adjust plans after the fact if needed. Let me know how you have used your points to book hotel stays! Happy booking!

Booking flights on points can feel challenging at first- that’s ok! A common phenomenon in points and miles is finding it really easy to earn points, and then feel panicked when its time to use them. It IS true that earning points is harder than using them! Don’t get me wrong, there are tons of tips and tricks that can be used to maximize points earning, but it’s learning to SPEND your points wisely that makes it possible to unlock amazing free and almost free travel. There are more pitfalls when it comes to spending points, which often leads to “analysis paralysis” and people perpetually earning and never using them. Booking flights on points in particular is generally more complex than booking hotels, so overall booking flights on points is a HUGE topic that we could devote endless episodes to. This episode is starting with the basics of the process of how I think about planning flights for a points trip, and breaking down HOW I actually make it happen.