St. Augustine Day Trip from Orlando: Historic Town & Optional Trolley

America's oldest city is 45 minutes from Orlando, and it's smaller than you'd expect

You get picked up at your Orlando hotel, driven to St. Augustine's 1700s-era Historic District, and left with free time to explore cobblestone streets, colonial buildings, and bayfront cafes. Add a trolley tour for guided stops and the ability to hop off as you please, or a boat cruise through Matanzas Bay for a water-based view of the landmarks. You handle your own lunch and pacing, but entry to the district and any add-on attractions are included. Return transport to Orlando is part of the package.

Step-by-step itinerary

Stops and time spent at each2 stops

1. Oldest Wooden School Housepassing by
2. Fort Matanzas National Monument1h 15m

Explore Historic St. Augustine

• Travel from Orlando to St. Augustine
• Visit the Historic District
• See Spanish Colonial architecture
• Walk past Oldest Wooden School House
• Shop and dine on St. George Street
• Optional: Take hop-on hop-off trolley tour
• Optional: Enjoy Victory III boat cruise

The experience

St. Augustine surprises you the moment you step onto the cobblestone streets of the Historic District. The buildings really are from the 1700s, not recreations, not restorations that look new. The Castillo de San Marco sits right there, and if you time it right, you'll hear actual cannon fire from a weapons demonstration echoing off the colonial facades. The day trip from Orlando picks you up at your hotel (or a central meeting point in Kissimmee, Disney area, or Universal), then drives you northeast about 45 minutes to what the US officially recognizes as the oldest continuously occupied European settlement in the country, established in 1565.

Once you arrive, the structure depends on what you book. The base option gives you free time to wander, and that's genuinely enough. St. George Street has the Oldest Wooden School House at its entrance, then opens into a stretch of souvenir shops and restaurants where you can grab lunch at your own pace. The Historic District is walkable in a way most American towns aren't. The streets are laid out exactly as they were centuries ago, so you're not fighting modern grid logic. If you add the hop-on hop-off trolley (90 minutes, local conductors included), you get a guided loop that lets you jump off whenever something catches your eye: the Colonial Quarter with its costumed reenactors, the Fountain of Youth, Fort Matanzas. The narration mixes actual history with humor, which keeps it from feeling like a school trip.

The optional boat cruise is a 75-minute ride on the Victory III through Matanzas Bay, narrated by the captain. You see the fort and the waterfront landmarks from the water, which is a different angle than walking gives you. There's also the Medieval Torture Museum if you're into that kind of thing. It's straightforward and a bit grim, but it's there if you want it. The day wraps around mid-afternoon or early evening depending on traffic back to Orlando, so you're not losing your whole day to driving.

What’s included

• Hotel pickup and drop-off (or meeting point pickup in Kissimmee, Disney area, or Universal), round-trip transport to St.
• Augustine, and free time in the Historic District.
• If you select the trolley option, a 90-minute hop-on hop-off tour with a local conductor is included.
• If you choose the boat cruise, a 75-minute narrated ride through Matanzas Bay on the Victory III is included.
• The Medieval Torture Museum is available as a separate add-on.
• Lunch is on your own.

Options for this experience

5 options

Day trip to St AugustineGuide in English · 07:30Day trip to Saint Augustine from Orlando, with pickup included

Historic Colonial Quarter add-onGuide in English · 07:30Transportation to St. Augustine and admission tickets to the Historical Colonial Quarter Living Museum are included, with pickup included

Pirate & Treasure Museum add-onGuide in English · 07:30Pirate and Treasure Museum add-on: transportation to St. Augustine from Central Florida plus admission tickets to the Pirate and Treasure Museum, with pickup included

See 2 more options

St. Augustine and scenic cruiseGuide in English · 07:30Saint Augustine day trip from Orlando including a scenic cruise, with pickup included

Day trip including a trolley rideGuide in English · 07:30Day trip to Saint Augustine from Orlando with a trolley tour, with pickup included

You'll see the exact price of each option when you check availability.See dates and prices

Information

Lasts 10h, runs Monday and Friday at 07:30, from US$ 100 per person, with a live guide in English, in groups of up to 14 and with free cancellation up to 24 h before.

Days and timesMonday and FridayDeparts at 07:30Another day? ›

GroupUp to 14 · max 9 per booking

Live guideEnglish

Meeting point and pickupHotel pickup included.

Book up to17h before

AgesAdult (12 and older) · Child (3 to 11 years) · Infant (under 3): free

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated 2 days ago

Good to know

Low physical effortStroller-friendlyInfants must sit on laps

Operated by Gray Line of Orlando

Is this one for you?Pick this if you want to see America's oldest city without renting a car or arranging your own transport and timing: the pickup from your hotel and the fixed return schedule handle both, leaving you free to explore at your own pace or add a guided trolley or boat tour if you want structure.

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Top questions

Can children come?

Yes. Ticket types: Child (3 to 11 years); Infant (under 3): free.

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

How long is the drive from Orlando to St. Augustine?

About 45 minutes northeast from Orlando.

What's included in the base tour?

Hotel pickup, transport to St. Augustine, and free time in the Historic District. Trolley, boat cruise, and Medieval Torture Museum are paid add-ons.

Can you get lunch in St. Augustine?

Yes. There are restaurants and cafes throughout the Historic District and along the promenade. Lunch is not included in the base price.

Is the trolley tour guided?

Yes. The 90-minute hop-on hop-off trolley includes a local conductor who provides history and commentary. You can stay on for the full loop or get off and on as you wish.

How long is the boat cruise?

The Victory III cruise through Matanzas Bay is 75 minutes, narrated by the captain.

Where is the pickup point in Orlando?

Hotel pickup is available, or you can meet at a central point in Kissimmee, Disney area, or Universal.