Portugal Trip Plan — May 6

Total Points

~300K

Total Cash

~$230

Trip Length

6 Days

Day

Wednesday, May 7 — Lisbon → Porto

Arrival + Train to Porto

Dom Luís I Bridge & Ribeira

Vila Nova de Gaia

Francesinha — Porto's iconic sandwich

Land at LIS early morning (red-eye from May 6)
Alfa Pendular train to Porto (~2h 40m)
Check into hotel, freshen up
Afternoon: Explore Ribeira district + Dom Luís I Bridge
Dinner: Francesinha (Porto's signature sandwich)

🚆 Train — Alfa Pendular ~2h 40m

Day

Thursday, May 8 — Porto

Full Day in Porto

Livraria Lello

São Bento Station — Azulejo tiles

Port Wine Cellars — Vila Nova de Gaia

Morning: Livraria Lello — one of the world's most beautiful bookstores
Clérigos Tower — climb for panoramic views of Porto
São Bento station — stunning azulejo tile murals
Afternoon: Port wine cellars in Vila Nova de Gaia (Taylor's, Graham's, or Sandeman)
Evening: Walk to Foz do Douro (beach district), sunset drinks

Day

Friday, May 9 — Porto → Lisbon

Train to Lisbon + Belém

Tower of Belém — UNESCO Heritage

Jerónimos Monastery

Pastéis de Belém territory

Morning train to Lisbon (~2h 40m)
Check into Hyatt Regency Lisbon
Afternoon: Belém district — Tower of Belém, Jerónimos Monastery
Pastéis de Belém — the original Portuguese custard tarts (get there)
Evening: Walk along the waterfront, dinner in Belém

🚆 Train — Alfa Pendular ~2h 40m

Day

Saturday, May 10 — Lisbon

Heart of Lisbon

Alfama — Lisbon's oldest neighborhood

São Jorge Castle — best views of Lisbon

Tram 28 — iconic Lisbon ride

Morning: Alfama district — oldest neighborhood, winding streets
São Jorge Castle — best views of the city
Ride Tram 28 through the historic neighborhoods
Afternoon: Time Out Market — food hall with Lisbon's best chefs
Evening: Bairro Alto — bars and nightlife district

Day

Sunday, May 11 — Sintra Day Trip

Fairytale Palaces

Pena Palace — colorful hilltop castle, UNESCO Heritage

Sintra — magical forest setting

Train from Lisbon Rossio station (~40 min)
Pena Palace — colorful hilltop castle, UNESCO World Heritage
Moorish Castle — 8th century ruins with stunning views
Optional: Quinta da Regaleira — underground tunnels + gardens
Evening: Back in Lisbon, farewell dinner

🚆 Train — Rossio → Sintra ~40 min

Day

Monday, May 12 — Fly Home

LIS → EWR (Premium Economy)

Sleep in, leisurely morning
Last pastéis de nata + bica (espresso)
Head to Lisbon airport
Premium Economy home — recline, sleep, arrive refreshed

✈️ Flight — Premium Economy ~7h

Booking Checklist

1

Check United Award Availability — Aldo
united.com → Book with miles. EWR→LIS May 6 (Economy) + LIS→EWR May 12 (Premium Economy).
Do NOT transfer points until you see saver availability.
2

Transfer Chase UR → United + Book Flights — Aldo
Transfer ~253K UR → United MileagePlus (instant, 1:1). Book both tickets. Pay ~$139 taxes.
Make sure Thu has a United MileagePlus number.
3

Book Porto Hotel on Capital One — Thu — Before April 2!
travel.capitalone.com → Porto, May 7–9 (2 nights). $250 credit auto-applies. $0 out of pocket.
4

Transfer Chase UR → Hyatt + Book Lisbon Hotel — Aldo
Transfer ~36–54K UR → World of Hyatt. Book Hyatt Regency Lisbon, May 9–12 (3 nights).
5

Book Trains — either person
cp.pt or Omio. Lisbon→Porto (May 7 AM) + Porto→Lisbon (May 9 AM). ~€25/person each way.
6

Book Sintra Tickets — either person
parquesdesintra.pt — Pena Palace + Moorish Castle combo. ~€20/person.

Hotel Strategy — $0 Total

Both hotels fully covered by points + credit. Zero cash on lodging.

Porto — Thu Books on Capital One (before April 2!)

Nations Porto — Best Value Pick

4 stars — Good location, clean, modern

$189 for 2 nights — fully covered by $250 credit ($61 leftover!)

Bom Sucesso Hotel — Upgrade Pick

4 stars — Free Wi-Fi, Parking Available

$247 for 2 nights — covered by $250 credit ($3 leftover)

Fontinha Porto — Trademark Collection by Wyndham

4 stars — Free Wi-Fi, Restaurant, Free Cancellation

$260 for 2 nights — $10 over credit (worth it for free cancellation)

Lisbon — Aldo Books with Hyatt Points

Hyatt Regency Lisbon

4 stars — Modern, waterfront area, reliable Hyatt quality

36–54K Hyatt points for 3 nights — $0 cash

Porto Hotel Comparison

Hotel	Stars	2 Nights	After $250 Credit	Key Perks
Nations Porto	4-star	$189	$0 ($61 left)	Best value, 4-star quality
Moov Hotel Porto Norte	2-star	$218	$0 ($32 left)	Modern budget, free Wi-Fi
Bom Sucesso Hotel	4-star	$247	$0 ($3 left)	Wi-Fi, parking
Fontinha Porto (Wyndham)	4-star	$260	$10 over	Restaurant, free cancel
Arts Hotel Porto (Hilton)	4-star	$410	$160 over	Premium, Hilton brand
Timbre Heroismo	4-star	$385	$135 over	Airport transport, parking

Full Cost Breakdown

Item	Who Pays	Points	Cash
Flights — EWR→LIS (Econ) + LIS→EWR (PE)	Aldo	~253K United	~$139
Porto Hotel — 2 nights (May 7–9)	Thu	—	$0 (C1 credit)
Lisbon Hyatt — 3 nights (May 9–12)	Aldo	~36–54K Hyatt	$0
Trains — LIS↔Porto round trip (2 pax)	Either	—	~$110
Sintra Tickets (2 pax)	Either	—	~$44
TOTAL		~289–307K	~$230

Portugal May 6–12