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Orlando Pirate Adventure and Florida History

Experience the magic of Orlando through the lens of high-seas adventure and local history. This 7-day journey balances the excitement of the Pirate’s Dinner Adventure with historical town walks and Florida's unique heritage sites.

7days
17stops
610km

The route

Tap a day or a town

You sleep in Orlando · Winter Park · St. Augustine · Cocoa Beach · Mount Dora — start and end in Orlando.

DAY01

Orlando → Pirate's Dinner Adventure

28 km · 21m driving · Overnight in Pirate's Dinner Adventure
  1. 09:00
    Orlando International Airport· start
  2. 27 km · 18m
  3. 12:00
    International Drive
  4. 1.7 km · 3m
  5. 15:00
    ⭐ Pirate's Dinner Adventure· overnight
DAY02

Lake Eola Park → Church Street Station

19 km · 22m driving · Overnight in Church Street Station
  1. 09:00
    Lake Eola Park· start
  2. 19 km · 18m
  3. 12:00
    ⭐ Orange County Regional History Center
  4. 0.7 km · 4m
  5. 15:00
    Church Street Station· overnight
DAY03

Park Avenue Winter Park → Rollins College Campus

10 km · 19m driving · Overnight in Rollins College Campus
  1. 09:00
    Park Avenue Winter Park· start
  2. 9.4 km · 15m
  3. 12:00
    ⭐ Scenic Boat Tour Winter Park
  4. 0.7 km · 4m
  5. 15:00
    Rollins College Campus· overnight
DAY04

Castillo de San Marcos → St. Augustine

166 km · 1h 49m driving · Overnight in St. Augustine Pirate & Treasure Museum
  1. 09:00
    ⭐ Castillo de San Marcos· start
  2. 165 km · 1h 46m
  3. 12:00
    St. George Street
  4. 0.8 km · 3m
  5. 15:00
    St. Augustine Pirate & Treasure Museum· overnight
DAY05

Kennedy Space Center → Cocoa Beach

180 km · 1h 53m driving · Overnight in Cocoa Beach Pier
  1. 09:00
    ⭐ Kennedy Space Center· start
  2. 180 km · 1h 53m
  3. 12:00
    Cocoa Beach Pier· overnight
DAY06

Blue Spring → Mount Dora

137 km · 1h 29m driving · Overnight in Mount Dora Historic District
  1. 09:00
    ⭐ Blue Spring· start
  2. 137 km · 1h 29m
  3. 12:00
    Mount Dora Historic District· overnight
DAY07

Disney Springs → Orlando

70 km · 48m driving
  1. 09:00
    Disney Springs· start
  2. 70 km · 48m
  3. 12:00
    ⭐ Orlando International Airport
Booking timeline
Book these before you go
  1. Days 1–2Stay in Orlando · Nights 1-2
  2. Day 3Stay in Winter Park · Night 3
  3. Day 4Stay in St. Augustine · Night 4
  4. Day 5Stay in Cocoa Beach · Night 5
  5. Day 6Stay in Mount Dora · Night 6
Heads Up
  • Book Pirate's Dinner Adventure tickets at least 2 weeks in advance to secure preferred seating near the stage.
  • St. Augustine is a 2-hour drive from Orlando; start early to enjoy the historic walking district before crowds arrive.
  • Check the Kennedy Space Center launch schedule as some areas may close during active rocket launches.
  • Florida weather in June is humid with frequent afternoon thunderstorms; keep a flexible indoor backup plan.