If you want to fly in ultimate comfort without draining your bank account, you have to be willing to break the mold. As a St. Louis (STL) based traveler, I rarely book premium award flights directly out of my home airport. Instead I rely on positioning flights — a cheap cash ticket to a major hub to unlock jaw-dropping award availability.
For our recent family trip to France and Italy, this strategy paid off massively. We built a 10-night European adventure across the French Riviera and Southern Italy by anchoring the trip around two unbelievable flight redemptions. Here is exactly how we did it — and how you can replicate the math.
The Outbound Hook: The EWR → ARN Sweet Spot
Virgin Atlantic miles are fantastic but notorious for high surcharges. Since Scandinavian Airlines (SAS) joined SkyTeam, a new sweet spot opened up. I booked during a 40% transfer bonus to Virgin Atlantic, cutting the cost to roughly ~26,785 credit card points per person — for just $5.60 in taxes.
We enjoyed the transatlantic comfort to Sweden, then booked a short ARN→NCE repositioning flight the next morning to kick off the vacation on the French Riviera. The extra travel time is 100% worth the thousands saved.
The Ground Game: 10 Nights in Europe
Phase 1: The French Riviera
May 24 – May 28
From Nice we drove to Antibes and stayed in the old town — restaurants, a marina, and a sandy beach. We stopped in Villefranche-sur-Mer on our way to Menton, where we stayed two nights overlooking the city near the famous central steps.
We continued to Eze for a cheese board and wine at Château Eza, explored Nice’s old town and pebble beaches, then finished at Saint-Paul-de-Vence and Hotel Du Lac — straight out of a storybook, with a fantastic dinner on our property credit.
Phase 2: Puglia & The Trulli
May 28 – May 30
We flew Nice → Bari to reach Puglia, far from the main tourist hubs, and checked into Poseia Suites in Polignano a Mare — a balcony room overlooking the beach and the town’s famous bridge.
The next day we visited the cone-roofed trulli of Alberobello, then stayed at Borgo Canonica built into restored trulli houses. That evening we drove to Ostuni for a lively dinner.
Phase 3: Matera & The Amalfi Coast
May 30 – June 1
We stopped in Locorotondo for lunch, then reached Matera — the ancient cave city viewed from our Le Origini suite was beyond words. We explored it end to end into the night.
The next morning we discovered Castelmezzano perched atop a mountain, then continued to Ravello and Villa Cimbrone. On our final morning we explored Pompeii before flying Naples → Frankfurt to begin the journey home.
The Return Splurge: Singapore Airlines Business
After a night at the Hilton Frankfurt Airport we woke up to one of the best transatlantic redemptions in the game: Singapore Airlines SQ026 to JFK. Using a Air Canada Aeroplan's cash + miles strategy we cut the price from ~60K to just 36K points per passenger — lie-flat seats and “Book the Cook” made the trip home a vacation in itself.
The Final Math: Retail vs. Reality
Estimated Retail Cost
- EWR → ARN (Premium Econ ×3)~$3,000
- FRA → JFK (Business ×3)~$12,000
Actual Award Cost
- Virgin Pts (after 40% bonus)~80,355 pts
- Singapore Business (cash + miles ×3)108,000 pts
Key Takeaways for Your Next Booking
Don’t search from your home airport.If you live in a mid-size city, search award space out of major hubs (JFK, EWR, ORD, IAD) and bridge with cash flights later.
Follow the transfer bonuses.A 30–40% transfer bonus turns a good redemption into a spectacular one — it drastically cut our EWR–ARN cost.
Use cash + miles when it beats all-miles.On the Singapore return, a cash + miles rate cut the points from 60K to 36K per passenger — sometimes the hybrid price is the real sweet spot.
Embrace European repositioning.Flying into Stockholm or Frankfurt when your destination is Nice or Naples sounds crazy, but a cheap intra-Europe flight bridges the gap and secures long-haul comfort.