St. Augustine is one of my favorite day trips from Jacksonville. It’s only about an hour south, the downtown is incredibly walkable, and — this is the important part — almost everything is dog-friendly.

I’ve walked Ansel down St. George Street more times than I can count. We’ve done the bayfront, the fort, the cobblestone alleys. Most of the shops let dogs in. Most of the restaurants have patios. It’s one of those rare places where having your dog with you actually makes the trip better, not harder.

But here’s the thing: as a day trip, you’re always rushing. You get there mid-morning, you’re watching the clock by 3pm, and you’re back on I-95 before sunset.

So I started looking into overnight options — specifically, where can you stay with your dog and book it on points?

My Pick: Hilton Garden Inn St. Augustine Historic District

If you want to use hotel points, this is the move.

It’s about a mile from the heart of St. George Street — close enough that you could walk if you wanted, but most people drive and park downtown. The hotel has an outdoor pool, on-site restaurant, and a grassy area for pet relief.

Why this one over the Hilton Bayfront?

The Hilton St. Augustine Historic Bayfront has the better location (literally on the water), but it doesn’t allow pets. So if you’re traveling with your dog, the Garden Inn is your Hilton option in St. Augustine.

The Boutique Alternative: St. George Inn

If you don’t care about points and want to be right in the middle of everything, the St. George Inn is hard to beat.

This is a boutique inn at the start of St. George Street, across from Castillo de San Marcos. You literally walk out the door and you’re in the middle of downtown. They have a wine bar on-site called Bin 39 that’s dog-friendly too — they even have a “Sampson’s Cellar” dog treat menu.

The catch: 40 lb weight limit. Ansel wouldn’t make the cut at 70 lbs, and your dog might not either. But if you have a smaller dog, this is the most dog-friendly boutique option in the historic district.

How to Book the Hilton Free

The Hilton Garden Inn runs around 30,000-50,000 Hilton Honors points per night depending on dates.

The math:

• The Hilton Surpass card has a 155,000 point sign-up bonus
• That’s 3-5 free nights at this property
• You’d only pay the $50-75 pet fee out of pocket

Book 5 nights and the 5th night is free — so you’re really only spending 4 nights worth of points.

👉 Full breakdown of Hilton cards

What Makes St. Augustine So Dog-Friendly

This is what I love about this town: you don’t have to work to find dog-friendly spots. They’re everywhere.

Dog-Friendly Shops

St. George Street is a pedestrian-only street with dozens of shops, and a surprising number of them let dogs inside:

• Faux Paws Dog Shop — A pet boutique right on St. George Street. Obviously dog-friendly.
• Mod Mari — A funky clothing boutique that welcomes dogs
• The Irish Gift Shop — Celtic gifts and jewelry, dogs welcome
• Artsy Abode — Art and accessories, dog-friendly
• Perky Pelican Christmas Shoppe — Holiday decor year-round, pets allowed

Not every shop allows dogs (some are small with fragile merchandise), but enough do that you can browse for an hour without leaving your dog outside.

Dog-Friendly Bars & Restaurants

Almost every restaurant with outdoor seating in St. Augustine is dog-friendly. Here are some favorites:

Downtown:

• Bin 39 — Wine bar attached to St. George Inn, dog-friendly patio, dog treat menu
• Harry’s Seafood Bar & Grille — Courtyard seating, Creole food, very dog-friendly
• Barley Republic — Irish pub with a patio and a dog menu
• The Floridian — Southern comfort food, covered patio welcomes dogs
• Bull & Crown Publick House — British pub with a spacious deck on St. George Street
• Odd Birds — Trendy cocktail bar with a covered dog-friendly patio

At the Beach:

• Salt Life Food Shack — Same vibe as the Jax Beach location, dog-friendly patio
• Beachcomber — Laid-back spot steps from St. Augustine Beach

Dog-Friendly Attractions

• St. George Street — The whole pedestrian street is dog-friendly for walking
• Castillo de San Marcos — Dogs aren’t allowed inside the fort, but you can walk the grounds and enjoy the lawn outside (great spot for photos)
• St. Augustine Lighthouse — Dogs can’t climb the lighthouse, but they’re welcome on the grounds and gardens
• Fountain of Youth Archaeological Park — Dogs allowed on the grounds (watch out for the peacocks)
• San Sebastian Winery — Free tastings, dogs allowed on small leashes
• St. Augustine Distillery — Dogs welcome on the tour

The Beach Situation

St. Augustine Beach allows dogs on-leash, which is more than a lot of Florida beaches can say. There are dog bag stations at the beach entrances, but bring your own just in case.

The beach is about 15-20 minutes from downtown, so if you’re staying at the Hilton Garden Inn, you’re actually closer to the beach than you would be at the St. George Inn.

Quick Reference

The Bottom Line

St. Augustine is one of the most dog-friendly towns in Florida — maybe the most dog-friendly. You can walk the historic streets, pop into shops, grab drinks at multiple patios, and your dog is welcome almost everywhere.

If you’ve only done it as a day trip, try an overnight. Stay at the Hilton Garden Inn on points, walk downtown in the evening when the day-trippers have left, and actually enjoy the town without watching the clock.

And if you have a smaller dog and want the full boutique experience, the St. George Inn puts you right in the middle of everything.

Have a favorite dog-friendly spot in St. Augustine I missed? Email me — I’m always looking for new places to try with Ansel.

This is part of my Destinations series — one hotel pick per city, plus how to book it free with points.

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