Day 1
Wednesday, May 13
Morning
Beach morning
Hit the sand before the crowds.
Afternoon
Food & drink tour
Bookable on Viator — usually $40–$120pp.
Browse Evening
Nightlife crawl
Best bars + late eats in Key West.
Weather watch: live this week
Forecast loading The deal's still cheap — just pack a layer (or wait for a sunnier window).
Why go to Key West now
The closest thing to the Caribbean without leaving the country. — Travel + Leisure
Plan your trip
A day-by-day starting point built from live weather + what's on.
Day 2
Thursday, May 14
Morning
Beach morning
Hit the sand before the crowds.
Afternoon
Day trip nearby
Bookable on Viator — usually $40–$120pp.
Browse Evening
Nightlife crawl
Best bars + late eats in Key West.
Day 3
Friday, May 15
Morning
Beach morning
Hit the sand before the crowds.
Afternoon
On the water
Bookable on Viator — usually $40–$120pp.
Browse Evening
Nightlife crawl
Best bars + late eats in Key West.
Suggestions only — afternoon links go to Viator, evening event links go to Ticketmaster. We may earn a commission.
Your 5-day forecast
Live forecast unavailable right now — check back shortly.
Happening this week
No big events on sale for Key West this week — check back soon.
Things to do in Key West
Tours, tastings, and day trips — booked through Viator.
Where to eat in Key West
Filter by budget or stars — reserve in one tap.
BudgetStars
Key West Breakfast Joint
Brunch · Local favorite
4.5· Cheap eats · under $20pp
Editor pick — line moves fast, worth the wait.
Reserve on OpenTableBest Tacos in Key West
Mexican · Casual
4.5· Cheap eats · under $20pp
Crowd-favorite taqueria. No reservation needed but you can book.
Reserve on OpenTableKey West Neighborhood Bistro
New American · Wine bar
4.0· Casual · $20–45pp
Date-night staple, easy to book midweek.
Reserve on OpenTableCoastal Catch Key West
Seafood
4.5· Special occasion · $45–100pp
Raw bar + grilled whole fish. Sit outside if you can.
Reserve on OpenTableChef's Table Key West
Tasting menu · Fine dining
5.0· Splurge · $100+pp
Splurge-worthy multi-course. Book 2–3 weeks ahead.
Reserve on OpenTableKey West Steakhouse
Steak · Classic
4.5· Splurge · $100+pp
Dry-aged cuts, big wine list, leather banquettes.
Reserve on OpenTableHidden Counter Key West
Omakase · 10 seats
5.0· Splurge · $100+pp
Reservation-only counter, locals' worst-kept secret.
Reserve on OpenTableLate-Night Key West
Cocktails + small plates
4.0· Casual · $20–45pp
Open till 2am. Walk-ins fine, book for a booth.
Reserve on OpenTableReservations open in OpenTable. Names are editor archetypes — live restaurant data coming soon.
Travel essentials
Cars, stays, insurance, and gear — handpicked partners.
Rental car
From ~$35/dayCompare Hertz, Avis, Enterprise at EYW.
Skip the counter — Turo
Peer-to-peerRent from locals. Often cheaper, way more selection.
Travel insurance
Trip cancellation + medical from $20. Buy before you go.
Hotel & stays
Compare boutique and chains in Key West.
Ship Sticks — clubs
Door-to-doorShip golf clubs door-to-door. Skip airline fees.
These are partner links — we may earn a small commission at no extra cost to you.
Editor picks
- Sunset Celebration nightly
- Snorkel the reef tours
Best for
BeachOutdoorsFoodieNightlifeGolf
The closest thing to the Caribbean without leaving the country.
