3-Day Key West Itinerary: Historic Old Town, Beaches, Sunset Sails & Dry Tortugas Day Trip (2025-11-24 to 2025-11-26)

Day 1: Old Town & Sunset

Key West, USA on November 24, 2025

8:00am

Breakfast — Blue Heaven

Iconic Old Town breakfast spot in a tropical courtyard known for eggs Benedict and Key lime pie — arrive early to avoid the wait. Blue Heaven typically opens around 8:00am daily.
USD20.00, 1h0m

9:30am

Ernest Hemingway Home & Museum

Tour Ernest Hemingway’s house, meet the famous six-toed cats, and learn about his Key West years; the museum helps explain local literary history. Open daily roughly 9:00am–5:00pm (confirm same-day hours online).
USD18.00, 1h15m

11:00am

Southernmost Point landmark

Quick photo stop at the famous buoy marking one of the southernmost points in the continental U.S.; it's outdoors and always accessible (can be busy).
USD0.00, 20m

12:00pm

Lunch — El Siboney or Cuban Coffee Queen (full lunch option)

Hearty, authentic Cuban food at El Siboney (open from about 11:00am) — great for ropa vieja or fried plantains; Cuban Coffee Queen is a faster coffee-and-sandwich option if you're on the move.
USD20.00, 1h0m

1:30pm

Key West Lighthouse & Keeper's Quarters Museum

Climb the restored lighthouse for sweeping views of Old Town and visit the keeper’s quarters museum to learn maritime history. Typical hours are 9:00am–5:00pm.
USD14.00, 1h0m

3:00pm

Stroll Duval Street & shopping

Walk Duval Street for galleries, shops, and the lively bar scene — a good time to pick up souvenirs and see street performers; businesses vary but many are open mid-morning through late evening.
USD0.00, 1h30m

4:30pm

Mallory Square Sunset Celebration

Arrive about 45–60 minutes before sunset to enjoy performers, artisans, and the famous nightly sunset gathering at Mallory Square; the event is outdoors and free (sunset time varies — check local schedule).
USD0.00, 1h30m

6:15pm

Dinner — Louie's Backyard

Classic oceanfront fine dining with creative seafood and sunset views — reservations recommended (opens for dinner nightly; verify hours).
USD60.00, 1h30m

8:30pm

Optional evening — Duval nightlife

If you have energy, stroll Duval for live music at pubs like Sloppy Joe’s or smaller live-music venues; bars typically stay open late.
USD0.00, 2h0m

Day 2: Dry Tortugas Day Trip

Key West, USA (Dry Tortugas National Park day trip) on November 25, 2025

6:00am

Quick breakfast & coffee — Cuban Coffee Queen or grab-and-go

Grab a strong Cuban coffee and a pastry or sandwich to take aboard; Cuban Coffee Queen opens very early (check same-day hours) and is ideal before departures.
USD8.00, 30m

7:00am

Dry Tortugas National Park — Yankee Freedom Ferry (full-day)

Full-day ferry trip to Dry Tortugas (Garden Key) with Fort Jefferson visits, snorkeling, and island time; this is a long day but the highlight of Key West for many. Ferries typically depart early (around 7:00am) and return late afternoon — book in advance and confirm current schedule and boarding time.
USD190.00, 10h0m

6:30pm

Return & Dinner — Santiago's Bodega (tapas)

After the ferry returns to Key West, head to Santiago’s Bodega for casual tapas and shareable plates — open evenings (hours vary, reservations recommended).
USD35.00, 1h30m

8:30pm

Relaxed evening walk — Historic Seaport

Take a waterfront stroll around the Historic Seaport; many bars and small shops stay open late and the harbor looks lovely at night.
USD0.00, 1h0m

Day 3: Beaches, Nature & Departure

Key West, USA on November 26, 2025

8:00am

Breakfast — Banana Café

Relaxed French-style bistro breakfast in Old Town with omelettes and fresh pastries; Banana Café generally opens around 7:00–8:00am.
USD18.00, 1h0m

9:30am

Key West Butterfly & Nature Conservatory

A calm conservatory with hundreds of butterflies and small exotic birds — open roughly 9:00am–5:00pm, great for photos and a peaceful morning visit.
USD16.00, 1h0m

11:00am

Fort Zachary Taylor State Park — beach & snorkeling

Swim, snorkel at the rocky-coral shoreline, and relax on one of Key West’s best beaches; the park is typically open 8:00am–sunset (small entrance fee applies).
USD8.00, 2h30m

1:30pm

Lunch — Conch Republic Seafood Company

Casual waterfront lunch with local seafood specialties and harbor views — open midday and popular for conch fritters and seafood sandwiches.
USD25.00, 1h0m

3:00pm

Afternoon — Last-minute shopping on Duval / Museum stop

Spend a final hour shopping, or visit any small museum you missed (e.g., Mel Fisher Maritime Museum); many shops open through late afternoon.
USD0.00, 1h0m

4:30pm

Optional Sunset Sail (if not departing early)

A two-hour sunset sail offers a different perspective of Key West and a relaxed end to your trip; departure times shift seasonally — book in advance.
USD55.00, 2h0m

7:00pm

Dinner — Half Shell Raw Bar (if staying late) or airport transfer

Casual fresh-shellfish spot loved by locals; if you have an evening flight, instead plan on an earlier light meal and allow time for airport transfer (Key West International Airport).
USD35.00, 1h0m
0