3-Day Key West Weekend: Old Town Sights, Dry Tortugas Day Trip, Beaches & Sunsets
Viewed by 278 travelers
Day 1: Arrival & Old Town
Key West, USA on October 29, 2025
2:30pm
Hotel check-in / drop bags
Settle into your Old Town accommodation (many hotels/guesthouses are within walking distance of Duval Street and the historic seaport). This gives you time to freshen up before exploring — Key West is highly walkable.
USD0, 0h30m
3:15pm
Ernest Hemingway Home & Museum
A guided/self-guided visit to the famous writer's residence to see the house, gardens and famously polydactyl cats; great to learn Key West literary history. (Open daily, typically 9:00am–5:00pm; last entry often 4:30pm—check exact seasonal hours.)
USD20, 1h15m
4:45pm
Stroll Duval Street & shops
Walk Duval Street for galleries, cigar shops and snacks — good spot for a coffee or a light local bite while watching the town’s lively afternoon vibe.
USD0, 0h45m
6:00pm
Mallory Square Sunset Celebration
Join the nightly sunset celebration with street performers and vendors; arrive 30–60 minutes before sunset for the best viewing (sunset around 6:15pm–6:30pm in late October). Mallory Square is open year-round at sunset.
USD0, 1h00m
7:30pm
Dinner — Conch Republic Seafood Company
Classic Key West seafood in a lively waterfront setting; good for conch fritters, fresh fish and waterfront views. Open evenings (typically 11:00am–10:00pm). Reservations recommended at peak times.
USD35, 1h15m
9:00pm
Evening: Duval nightlife or quiet walk
Choose a bar with live music (many venues run late) or take a quieter post-dinner stroll through lamp-lit streets in Old Town.
USD0, 1h30m
Day 2: Offshore Adventure
Key West, USA on October 30, 2025
6:00am
Breakfast — Cuban Coffee Queen (grab-and-go)
Quick Cuban coffee and a breakfast sandwich or pastry to take on your day-trip; opens early for guests catching morning departures. Ideal before long boat or plane trips.
USD8, 0h20m
7:00am
Dry Tortugas National Park (Yankee Freedom ferry) — recommended
Full-day ferry to Dry Tortugas and Fort Jefferson for snorkeling, history and turquoise water; ferry usually departs early (~7:00am) and returns late afternoon/early evening. Check Yankee Freedom schedule and book ahead (seasonal changes apply).
USD190, 11h00m
Alternative 8:00am
Alternative: Half-day reef/snorkel trip (Molasses/Flat Keys)
If you prefer a shorter option, morning snorkel trips depart around 8:00–9:00am for the patch reefs — great coral, tropical fish and easier half-day timing (returns midday).
USD75, 4h00m
7:00pm
Dinner — Louie's Backyard
Elegant seaside dining with Caribbean-influenced cuisine; perfect to unwind after a long day on the water. Louie's typically serves dinner from early evening (reservations recommended).
USD50, 1h30m
9:00pm
Relaxation or live music
After dinner, enjoy live music at a nearby venue or relax on your hotel porch — Key West nights are warm and lively.
USD0, 1h30m
Day 3: Beaches & Historic Sights
Key West, USA on October 31, 2025
8:00am
Breakfast — Blue Heaven
Iconic Key West spot with outdoor courtyard dining, great for eggs Benedict, Caribbean-inspired breakfasts and a laid-back vibe; opens mornings (commonly ~8:00am).
USD20, 1h00m
9:30am
Fort Zachary Taylor State Park (beach & short walk)
Historic Civil War-era fort and one of Key West’s best beaches for snorkeling and swimming; park typically open 8:00am to sunset — go early to secure shade and good reef visibility.
USD8, 2h00m
11:45am
Key West Butterfly & Nature Conservatory
A climate-controlled conservatory with hundreds of butterflies, tropical plants and birds — great for families and a cool contrast to beach time. Generally open around 9:00am–5:00pm.
USD16, 1h00m
1:00pm
Lunch — Santiago's Bodega
Spanish tapas-style plates perfect for sharing and sampling local flavors in a relaxed setting; open midday through evening.
USD25, 1h00m
2:30pm
Key West Lighthouse & Keeper's Quarters
Climb the historic lighthouse for panoramic views of Old Town and visit the small keeper’s museum to learn maritime history; typically open 9:00am–5:00pm.
USD11, 0h45m
3:30pm
The Truman Little White House
Tour the former presidential retreat with guided tours explaining its role in 20th-century history; most days have tours from mid-morning to late afternoon — check exact tour times and book ahead when possible.
USD18, 1h00m
5:00pm
Early dinner / Farewell cocktail — Sunset Pier (Ocean Key Resort)
End your visit with waterfront views and a casual meal or cocktail on the pier as the sun lowers; menu and hours vary but many pier restaurants open until sunset and later.
USD30, 1h15m
6:30pm
Departure or last stroll
Head back to your hotel to collect bags or take a last walk along the harbor — if you have a late ferry/flight, enjoy one more Mallory Square sunset or Duval stroll.
USD0, 0h30m
No packing list attached yet.
When are you going?
Add your start date and we'll check in at two weeks out, one week out, and the day before — bookings, packing, and a day-one brief. Reply to any of them if plans change.
Things to do in Key West
Bookable experiences via our partner Fever — we may earn a commission.
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version