St Augustine for 3 or 4 days

Question

I need some help planning a vacation to St Augustine. I am a solo traveler, mid 50’s, hoping to head there in a couple of weeks. I am planning a trip before I have some medical procedures, as I know that is going to limit my travel abilities. I want to be near restaurants and shops. I am not interested in sunbathing on the beach. I am looking for reasonably priced accommodations within walking or a short drive to restaurants. I am looking for relaxation and will likely spend a LOT of time doing that. I am not picky about accommodations but would like a pool if possible. Please let me know of hotel/motel or BNB recommendations you have. Thank you!

Answer

St. Augustine is a charming and historic city that is perfect for a relaxing solo trip, especially if you want to focus on walking around, exploring shops, enjoying restaurants, and soaking in the atmosphere rather than hitting the beach. Since you prefer reasonably priced accommodations with a pool, and want to be near restaurants and shops, focusing on the historic downtown and the Anastasia Island area is ideal.

Accommodations to consider:

St. George Inn – A small boutique inn located in the heart of historic downtown. It’s walking distance to restaurants, shops, and historic sites. Some rooms have a small pool or courtyard access.
Bayfront Marin House – Close to downtown and the waterfront, this inn offers a cozy experience with a pool and easy access to local eateries.
Casa Monica Resort & Spa – A historic hotel in the center of downtown with luxury touches and a pool. Rates can be reasonable if booked in advance or off-season.
Best Western Historical Inn – Located just a short drive from downtown, offering clean rooms, a pool, and convenient parking. Good mid-range option.
Anastasia State Park area motels/BnBs – A few boutique options here have pools and are close to nature trails, plus a short drive to downtown restaurants.

Activities and relaxation ideas:

Take a leisurely stroll along St. George Street for shopping, cafes, and historic sites.
Visit the Castillo de San Marcos and enjoy the grounds and historic architecture.
Consider a riverfront walk or a trolley tour for sightseeing without too much effort.
Check out local art galleries and boutique shops for a relaxing day indoors.
Enjoy casual dining or a coffee shop while people-watching and soaking in the historic charm.

Dining suggestions:

Columbia Restaurant – Classic Spanish cuisine in the heart of downtown.
Catch 27 – Seafood-focused local favorite with fresh options.
Blackfly – Upscale seafood and modern American dishes.
The Floridian – Farm-to-table southern-inspired menu, casual atmosphere.

For maximum relaxation, consider planning slow mornings with breakfast at a local café, gentle walks in the historic district, and afternoons by the hotel pool or exploring museums and shops. You’ll get a mix of historic charm, good food, and comfortable downtime without needing to focus on the beach.