How to Book Flights and Hotels Around a Cruise Using Points and Miles for 83% off
Total trip value: $4,488.29 | Out of pocket: $725.56 | Redeemed: 83.83%
If you’ve ever wondered how to book flights and hotels around a cruise, you already know it’s a different puzzle than a normal points and miles trip. You’re not just booking one destination — you’re booking a pre-cruise hotel, timing flights around an embarkation window that doesn’t move, and figuring out a post-cruise hotel before you fly home.
Here’s exactly how I did it for a Norwegian cruise out of Long Beach, California, redeemed for 83.83% off using points, miles, and free night certificates.
Why This Trip Was Different
My husband and I planned this trip around Long Beach because my middle son lives in the LA area — so on top of the cruise, we were hoping to catch him playing a game while we were in town, and we were able to make that happen the Sunday after we got back.
That meant this trip had three moving parts instead of one:
- A hotel near the cruise port before embarkation
- The cruise itself
- A hotel near the cruise port again after disembarkation, before flying home
The Cruise Itinerary
We took a 7-night Mexican Riviera cruise out of the LA cruise port, which is actually located in Long Beach — our first time cruising that side of Mexico. This was our sixth cruise overall and our third with Norwegian; we’ve also sailed Carnival, Holland America, and MSC.
Our Puerto Vallarta port stop ended up being cancelled. This was the last week of February 2026, when a military operation against a major cartel leader in Jalisco triggered violent unrest in the region, leading multiple cruise lines to cancel their Puerto Vallarta calls for passenger safety. It was only the second port cancellation we’ve experienced across six cruises.
If you’ve never had a port cancelled, it’s worth knowing this is a real risk of cruising — itineraries can change with little notice for safety reasons, and it’s completely outside your control.
How to Book Flights Around a Cruise: Timing the Saturday Embarkation
We flew PIT → LAX on United, arriving Saturday to give ourselves a buffer before boarding Sunday.
- PIT → LAX (outbound): $714.36, paid in cash.
- LAX → PIT (return): $764.98 retail value, redeemed for 17,000 points (8,500 per person) — just $11.20 out of pocket in taxes. That’s a 4.434 cents per point redemption. found this award space using Seats.aero — it’s one of the tools I use for every award search, and it’s on my full tools and resources page if you want to see everything else I use.
Question this answers for readers: Should you pay cash or redeem points for cruise-adjacent flights? We could have booked the outbound flight with points, but the award flight times that were available didn’t work for our schedule — a good reminder that even when award space exists, limited timing options can push you toward paying cash instead, especially around a fixed embarkation date. The return flight, on the other hand, was a strong points redemption once we had flexibility on timing.
Getting from LAX to Long Beach: The Credit Most People Let Go Unused
Before we even got to the hotel, we used a Citi Strata Elite Blacklane credit to get from LAX to Long Beach instead of booking a rideshare. The total cost of the Blacklane ride was $139. Lyft would’ve been $47. We paid $8 for Blacklane — $39 ahead thanks to a $100 Citi Blacklane credit plus a $30 promo.
It’s a small piece of the trip, but it’s a good example of how these smaller card credits can quietly do as much work as points and free night certificates — you just have to actually use them.
Pre-Cruise Hotel: Crowne Plaza Near the Port
We stayed at a Crowne Plaza Los Angeles Harbor Hotel by IHG — walkable to the cruise port — the night before boarding.
- Retail value: $260.52
- Redeemed for: an IHG free night certificate — earned through the IHG business card, one of the cards I cover on my best credit cards page if you’re weighing which cards actually earn you free night certificates like this one
- Out of pocket: $0
Post-Cruise Hotel: The Oceana, Two Nights
After disembarking Sunday, we stayed two more nights at the Oceana, a Hilton property a street away from the beach, a few blocks north of Santa Monica but still walkable distance. I’ve written about this stay in more detail before — how two Hilton free night certificates turned into a $3,400 oceanfront stay and my full Oceana Santa Monica review.
The Oceana in Santa Monica was hands down the most beautiful hotel room we have ever stayed in. Absolutely gorgeous. And for the history buffs, Stan Laurel stayed there and entertained many Hollywood Icons in that very hotel.
- Retail value: $3,462.79 (upgraded value)
- Redeemed for: two Hilton free night certificates
- Out of pocket: $0
The Cruise Discount Most People Don’t Know About
This is the part of the trip that’s worth calling out on its own: our Norwegian Cruise Line cabin came with a built-in discount thanks to a status match most people don’t realize exists.
Here’s the chain: the Wyndham Business Earner card grants Wyndham Diamond Elite status, which status-matches to Caesars Diamond status (not Diamond Plus — that tier requires a separate match that has since changed). This discount however requires a bit of gambling and 15,000 tier credits even after the match. Something to be aware of before calling.
Caesars Diamond (with tier credits) status gets you:
- 20% off inside-to-suite cabins (categories SE–SJ and HI) on Norwegian Cruise Line
- 10% off suites and above (categories SD–S1 and HF–H1)
The discount applied to my cruise cabin portion. This is confirmed still accurate today, per Caesars Rewards’ official Norwegian Cruise Line partner page: Diamond status gets 20% off inside-to-suite cabins and 10% off suites and above. Other Caesars tiers (Platinum, Diamond Elite, Seven Stars) get different discount percentages on the same cabin tiers. You’ll need to call Norwegian Cruise Line’s Casino Reservation Center directly at 877-742-9521 and provide your Caesars Rewards number to receive the discount — it isn’t applied automatically through NCL’s website.
The Full Trip Breakdown
| Item | Retail Value | Redeemed For | Out of Pocket |
|---|---|---|---|
| PIT → LAX flight (cash, not counted toward redeemed value below) | $714.36 | Cash | $714.36 |
| LAX → PIT flight | $764.98 | 17,000 points (4.434 CPP) | $11.20 |
| Crowne Plaza (pre-cruise) | $260.52 | IHG free night cert | $0 |
| The Oceana (post-cruise, 2 nights) | $3,462.79 | 2 Hilton free night certs | $0 |
| Total redeemed value | $4,488.29 | — | $725.56 |
Note: the $4,488.29 total reflects the value of items booked with points, miles, and free night certificates — the outbound flight was paid in cash, so its retail value isn’t counted toward that figure, but its cost is included in your total out-of-pocket spend of $725.56. The cruise fare itself isn’t included in this breakdown at all — this post is focused specifically on how to book the flights and hotels around a cruise, not the cruise cost itself.
Redeemed: 83.83% off — $3,762.73 in travel value redeemed for $725.56 out of pocket.
The Takeaway
Booking around a cruise doesn’t have to mean paying full retail for every piece around it. The cruise itself was paid in cash, but every flight and hotel wrapped around it was either redeemed or discounted — and the free night certificates did the heaviest lifting, covering both hotel stays completely.
If you’re planning a cruise and wondering how to book flights and hotels around a cruise like this one, the strategy is the same one I use for any trip: look at each piece separately. What can be redeemed with points or certificates, and where does cash still make the most sense — like our Saturday outbound flight, where availability mattered more than redemption value.
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