8 days in Orlando, St. Augustine & Siesta Key Itinerary

8 days in Orlando, St. Augustine & Siesta Key Itinerary

Created using Inspirock Florida trip maker

Make it your trip
Fly
1
Orlando
— 3 nights
Drive
2
St. Augustine
— 2 nights
Drive
3
Siesta Key
— 2 nights
Fly

S M T W T F S
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Orlando

— 3 nights

Theme Park Capital of the World

For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Take a break from Orlando with a short trip to Boat Tours & Water Sports in Kissimmee, about 34 minutes away. Pack the 20th (Sun) with family-friendly diversions at Universal Orlando Resort. Pack the 22nd (Tue) with family-friendly diversions at Universal's Islands of Adventure. The adventure continues: get in on the family fun at SeaWorld and look for gifts at American Girl Orlando.

To find traveler tips, maps, reviews, and more tourist information, read Orlando attractions planner.

Baltimore to Orlando is an approximately 4-hour flight. You can also drive; or take a train. Traveling from Baltimore in June, you will find days in Orlando are a bit warmer (91°F), and nights are about the same (73°F). Finish up your sightseeing early on the 22nd (Tue) so you can go by car to St. Augustine.

Things to do in Orlando

Theme Parks · Shopping · Outdoors · Tours

Side Trip

St. Augustine

— 2 nights
St. Start off your visit on the 23rd (Wed): get engrossed in the history at St. Augustine Pirate & Treasure Museum, stop by Market to Market, take a tour by water with Boat Tours & Water Sports, then deepen your understanding at Flagler College, and finally brush up on your knowledge of spirits at St. Augustine Distillery. Get ready for a full day of sightseeing on the next day: tee off at TPC at Sawgrass Stadium Course, enjoy the sand and surf at St. Augustine Beach, and then enjoy the sea views from St. Augustine Lighthouse & Maritime Museum, Inc..

To see photos, reviews, more things to do, and other tourist information, read St. Augustine trip planning tool.

You can drive from Orlando to St. Augustine in 2 hours. Another option is to take a bus. In June, daytime highs in St. Augustine are 88°F, while nighttime lows are 73°F. Wrap up your sightseeing on the 24th (Thu) to allow time to drive to Siesta Key.

Things to do in St. Augustine

Outdoors · Museums · Parks · Beaches

Side Trip

Siesta Key

— 2 nights
Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
Kick off your visit on the 25th (Fri): kick back and relax at Siesta Beach, then stroll through Crescent Beach, then stop by Silver City Sarasota, and finally stroll through Turtle Beach. Get ready for a full day of sightseeing on the next day: relax and rejuvenate at some of the best spas, kick back and relax at St. Pete Beach, and then glide peacefully along the water with some of the best stand-up paddleboarding in the area.

For reviews, photos, maps, and more tourist information, refer to the Siesta Key tour builder.

You can drive from St. Augustine to Siesta Key in 4.5 hours. Alternatively, you can fly; or take a bus. Expect a daytime high around 89°F in June, and nighttime lows around 75°F. Wrap up your sightseeing on the 26th (Sat) to allow time to fly back home.

Things to do in Siesta Key

Outdoors · Parks · Beaches · Adventure

Side Trips