From Orlando: Day Trip to St. Augustine with Hotel Pickup

About This Experience

A driver-guide picks you up at your Orlando hotel and drives about two hours north to St. Augustine, the old Spanish colonial town founded in 1565, with commentary on the way and sometimes a rest stop. Reviewers describe around seven hours of free time once you arrive, which you spend however suits your crew.

The option you book shapes the day. The hop-on hop-off trolley loops 22 stops around town and saves little legs a lot of walking; the Pirate and Treasure Museum is indoors and hands-on, a good bet for kids who love treasure chests; the Colonial Quarter has costumed guides, musket firing and a blacksmith; and the Matanzas Bay cruise shows the fort and waterfront from the water. Across from the pirate museum, the stone Castillo de San Marcos lets children under 16 in free with an adult.

Expect a long day with around four hours in a vehicle. Reviewers say the drop-off point sits a little outside the historic center, so the trolley option is worth having if your kids tire quickly, and one noted that the trolley to the beach and lighthouse runs on the hour, so do those early. Cobbled streets are bumpy for strollers, summer afternoons are hot and humid, and meals are not included.

This suits families with school-age kids who enjoy history, pirates and wandering, and parents who would rather not drive I-95 themselves. Toddlers who need a proper nap and kids who are only happy on rides will find it a slog. The trip must be booked at least two days ahead.

Highlights

• Wander the narrow lanes of the Spanish colonial historic district
• See Castillo de San Marcos, the coquina-stone fort on the bay
• Pick an add-on such as the pirate museum, bay cruise or hop-on trolley
• Look out for the oldest wooden schoolhouse and Flagler College
• Spend around seven hours in town at your own pace

What's Included

• ✓ Round-trip transport from your Orlando hotel
• ✓ Driver-guide assistance for the day
• ✓ Free time to explore St. Augustine
• ✓ Tickets for your chosen option: bay cruise, Colonial Quarter, trolley or pirate museum
• ✓ Digital Eat and Play Card with Orlando-area discounts
• ✓ Group limited to 10 participants

Not Included

• Food and drinks
• Gratuities for the driver-guide
• Entry to attractions not covered by the option you book
• Castillo de San Marcos entry for adults 16 and over

What to Bring

• Comfortable walking shoes for cobblestones
• Sun hats, sunscreen and refillable water bottles
• A light stroller or carrier, since cobbles are bumpy
• A payment card for the Castillo, which does not take cash
• Snacks for the drive and a small toy or tablet for the ride

Good to Know & Caveats

• Book at least two days before your trip; later bookings are not accepted.
• Reviewers report the drop-off is a little outside the historic center, so the trolley option helps with young children.
• A midway rest stop is not always possible, so pack snacks and plan restroom breaks.
• At Castillo de San Marcos, children 15 and under enter free with an adult; adults pay by card only.
• On the hop-on trolley, children 3 and under ride free.
• The Pirate and Treasure Museum is fully indoors and air-conditioned, a useful escape on a hot or rainy afternoon.
• Nights of Lights runs November 21, 2026 to January 18, 2027. Check if your return time lets you see it after dark.

Meeting Point

Pickup is from your Orlando hotel. The listing gives no single meeting point, so check your booking confirmation for the exact pickup place and time.