AI Trip Planner
Plan a trip with
credit card points
Pick origin + destination + month → see best award flights, top hotels bookable on points, attractions, signature events, and the cards whose welcome bonus would cover the trip. 41 US origin airports, no bank link required.
US
Key West, FL
Hemingway's island, sunsets at Mallory Square, Caribbean vibes without a passport
Pay in cash
$2,850
$350 flight + $2,500 hotel
Pay with points
170,000 pts
+ $30 taxes & fees
Best card for this trip
Amex Hilton Aspire
150K Hilton bonus + free weekend night = ~3 nights at Casa Marina
Weather in June
⚠️ Off-season — weather can be challenging
Air temp
79°–88°F
26°–31°C
Water temp
84°F
29°C
Rainfall
high
Crowds
Low
Hot, humid, storms
Flights — JFK → EYW
EconomyChase Ultimate Rewards
via Southwest Rapid Rewards
JFK → EYW — check direct flights from JFK. Chase UR → Southwest to MIA/FLL, then drive 4h (Overseas Hwy)
14K/20K/28K
roundtrip · Wanna Get Away (dynamic)
+ $30 taxes
American AAdvantage
JFK → EYW — check direct flights from JFK. AA economy JFK-EYW via MIA (regional jet last leg)
30,000
roundtrip
+ $20 taxes
Open to cover:Sapphire Preferred
Top hotels for your points
Picked for best points value — Hyatt has the only fixed award chart left in major US hotels, so your points stretch the furthest here. Tap each option below for why it stands out.
Hyatt Centric Key West Resort & Spa
Hyatt·Best Hyatt in Key WestCat 6 — Old Town location, walk to Duval Street.
25K/30K/35K
off / std / peak · Hyatt Cat 7
$500/night cash
5 nights = 150,000 pts (~$2,500 value)
More hotels on points
Casa Marina, A Waldorf Astoria Resort
Hilton Honors·Historic luxury, beachDynamic 70-120K. Historic 1920s beachfront.
90,000/night
$750/night cash
5 nights = 450,000 pts (~$3,750 value)
The Reach Key West, Curio Collection
Hilton Honors·Beach + modernDynamic — sister to Casa Marina, more contemporary.
75,000/night
$600/night cash
5 nights = 375,000 pts (~$3,000 value)
Trip Strategy — open these cards and the trip is mostly free
Open Hilton Aspire (150K Hilton bonus) + Sapphire Preferred. Aspire covers Casa Marina Resort (Waldorf Astoria) 2 weekend nights free + bonus = 5+ nights.
150K Hilton bonus + free weekend night = ~3 nights at Casa Marina
$550/yr annual fee
Your out-of-pocket budget for this trip
🚗 Car rental needed · vs. $2,850 full cash trip
What to see & do in Key West, FL
Mallory Square Sunset Celebration
Only hereNightly street performers + sunset over the Gulf — Key West tradition since the 1960s.
Hemingway Home
SightAuthor's 1851 home with 60 six-toed cats. Tours daily.
Southernmost Point Buoy
SightIconic colorful concrete buoy, 90 miles from Cuba. Photo op (with queue).
Duval Street
Nightlife24-hour party street with bars, drag shows, live music.
Dry Tortugas National Park
Day trip70 miles west by ferry/seaplane — Fort Jefferson + pristine snorkeling.
Cuban Coffee Queen
FoodLocal cafecito + cubano sandwich shop. Bustling local favorite.
Events to know about
- Oct
Fantasy Fest
Late October week-long costume + parade festival — Key West's biggest party.
- Jul
Hemingway Days
July festival with lookalike contest + literary events.
- May
Key West Songwriters Festival
May — top Nashville songwriters playing intimate venues.