Your Free Itinerary

Romantic Weekend in St. Augustine, Florida
Suggested 3-Day Romantic Itinerary for Couples Visiting 

St. Augustine, Florida

Estimated 2-Night Total (per couple): $700–$1,800+
Flexible based on lodging, dining, and activity selections. Transportation not included.

Disclaimer: This itinerary is intended as a helpful guide and suggestion only, not a confirmation of bookings or reservations. Business details, including pricing, hours of operation, menu offerings, and contact information, are subject to change without notice and should be independently verified prior to your visit. We recommend calling ahead or checking Google Maps for current information, making reservations, and ensuring a seamless experience.

Note: All business names in this itinerary are clickable links that will open their location in Google Maps.
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Day 1 – Arrival & Evening Romance

Where to Stay (Choose Your Style & Budget)

Economy Option ($150–$220 per night)
→ Agustin Inn – Victorian B&B with whirlpool tubs and gourmet breakfast in the heart of the historic district
29 Cuna Street, St. Augustine, FL 32084
Phone: +19048239554

Mid-Range Option ($220–$320 per night)
→ Carriage Way Inn Bed & Breakfast – 1880s Victorian inn with canopy beds, fireplaces, and free sherry
70 Cuna Street, St. Augustine, FL 32084
Phone: +19048292646

Luxury Option ($350–$550+ per night)
→ Casablanca Inn on the Bay – Waterfront inn with a legendary tiki bar and stunning bay views
24 Avenida Menendez, St. Augustine, FL 32084
Phone: +19048290928

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Evening Activity (Choose Your Arrival Night Vibe)

Sunset & Sailing
→ Schooner Freedom Sunset Sail – Romantic evening sail on a classic schooner with golden-hour views
111 Avenida Menendez, St. Augustine, FL 32084
Phone: +19048101010

Rooftop Romance
→ River & Fort Restaurant & Rooftop Lounge – Panoramic sunset views with craft cocktails on a stunning rooftop
12 Avenida Menendez, St. Augustine, FL 32084
Phone: +19044818396

Historic Evening Stroll
→ Aviles Street – America's oldest street, lined with art galleries and live music venues
Aviles Street, St. Augustine, FL 32084
Phone: NA

Weather Backup (If Rain Interrupts)

Cozy & Crafty
→ Forgotten Tonic – Intimate cocktail bar with festive drinks and beautiful ambiance
6 Aviles Street, St. Augustine, FL 32084
Phone: +19048279055

Cultural & Warm
→ St. Augustine Distillery – Free craft spirits tour and tasting in a historic ice plant
112 Riberia Street, St. Augustine, FL 32084
Phone: +19048258680

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Day 2 – Full Day of Adventure & Romance

Breakfast (Choose Your Morning Mood)

Garden & Cozy
→ Sunday Gathering Table – Charming garden patio with exceptional coffee and brunch
108 King Street, St. Augustine, FL 32084
Phone: NA

Quick & Authentic
→ Fountain of Juice – Locally owned Cuban coffee shop with fresh-squeezed lemonade and smoothies
31 Williams Street, St. Augustine, FL 32084
Phone: NA

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Morning Activity (Choose Your Adventure Mood)

Iconic & Historic
→ Castillo de San Marcos National Monument – *17th-century fortress with breathtaking views of the bay*
11 South Castillo Drive, St. Augustine, FL 32084
Phone: +19048296500

Beach & Nature
→ Anastasia State Park – Pristine beaches, kayaking, and nature trails for a morning adventure
300 Anastasia Park Road, St. Augustine, FL 32080
Phone: +19044612033

Gilded Age Splendor
→ Lightner Museum – *Fascinating collection of 19th-century art and artifacts in the former Alcazar Hotel*
75 King Street, St. Augustine, FL 32084
Phone: +19048242877

Weather Backup (If Rain Interrupts)

Interactive & Fun
→ St. Augustine Pirate & Treasure Museum – Genuine pirate artifacts and interactive displays
12 South Castillo Drive, St. Augustine, FL 32084
Phone: +19044662530

Literary & Cozy
→ The Spanish Military Hospital Museum – Fascinating guided tour of colonial medical practices
3 Aviles Street, St. Augustine, FL 32084
Phone: +19048265168

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Lunch (Choose Your Midday Vibe)

Historic & Romantic
→ Columbia Restaurant – Stunning Spanish atrium setting with legendary 1905 salad and Cuban cuisine
98 St. George Street, St. Augustine, FL 32084
Phone: +19048243341

Waterfront Escape
→ St. Augustine Fish Camp – Local favorite for shrimp and grits and fried green tomatoes
142 Riberia Street, St. Augustine, FL 32084
Phone: NA

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Afternoon Activity (Choose Your Adventure Mood)

Climb & Propose
→ St. Augustine Lighthouse & Maritime Museum – 219 steps to panoramic views—a legendary proposal spot
100 Red Cox Drive, St. Augustine, FL 32080
Phone: +19048290745

Butterflies & Romance
→ St. Augustine Alligator Farm Zoological Park – Unique wildlife encounters and a stunning crocodile exhibit
999 Anastasia Blvd, St. Augustine, FL 32080
Phone: +19048243337

Quirky & Fun
→ Medieval Torture Museum – Interactive self-guided tour through dark history
100 St. George Street, St. Augustine, FL 32084
Phone: NA

Weather Backup (If Rain Interrupts)

Wine & Relax
→ San Sebastian Winery – Free wine tasting in a historic downtown building
157 King Street, St. Augustine, FL 32084
Phone: +19048265934

Escape Room Adventure
→ St. Augustine Mystery & Magic Experience – Engaging escape room adventure for two
Downtown St. Augustine (exact location provided upon booking)
Phone: NA

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Dinner (Choose Your Romance Level)

Intimate & Award-Winning
→ Collage Restaurant – *48-seat romantic gem with exceptional seafood and wine pairings*
60 Hypolita Street, St. Augustine, FL 32084
Phone: +19048295193

Waterfront Sunset
→ Cap's On the Water – Breathtaking sunset views over the Intracoastal with fresh seafood
4325 Myrtle Street, St. Augustine, FL 32084
Phone: +19048248794

Upscale & Historic
→ Sainte-George Restaurant – Charming outdoor seating with twinkling lights and sunset views
1 St. George Street, St. Augustine, FL 32084
Phone: +19044299345

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Night Activity (Choose Your Evening Vibe)

Live Music & Spirits
→ Prohibition Kitchen – *Live bands starting at 10pm in a high-energy historic setting*
119 St. George Street, St. Augustine, FL 32084
Phone: +19048232840

Ghostly Adventure
→ Ghosts & Gravestones Tour – Trolley tour of haunted spots with exclusive access
167 San Marco Avenue (departure point), St. Augustine, FL 32084
Phone: +19048425556

Hidden Dive Bar
→ No Name Bar – Ultimate dive bar where signing the wall is a rite of passage
Address shared upon arrival (locals' secret spot)
Phone: NA

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Day 3 – Leisurely Farewell

Breakfast (Choose Your Morning Mood)

Disco Balls & Coffee
→ Address Coffee – Disco ball-lit coffee shop that transforms into a wine bar by night
152 King Street, St. Augustine, FL 32084
Phone: NA

Garden Brunch
→ Sunday Gathering Table – Return for one last garden patio moment
108 King Street, St. Augustine, FL 32084
Phone: NA

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Farewell Activity (Before Departure)

Sunrise & Serenity
→ Bridge of Lions – Leisurely stroll with commanding views of the bayfront and harbor
Bridge of Lions, St. Augustine, FL 32084
Phone: NA

Sweet Souvenir
→ The Hyppo Gourmet Ice Pops – Handcrafted ice pops in unique flavors for the road
48 Charlotte Street, St. Augustine, FL 32084
Phone: +19046239005

Historic Finale
→ Colonial Quarter – Living history museum with blacksmith demonstrations and colonial life
33 St. George Street, St. Augustine, FL 32084
Phone: +19043425003

Weather Backup (If Rain Interrupts)

Art & Inspiration
→ St. Augustine Art Association – Contemporary works by local and regional artists
22 Marine Street, St. Augustine, FL 32084
Phone: +19048248526

Historic House Tour
→ The Oldest House Museum Complex – 1798 coquina house with beehive oven and period furnishings
14 St. Francis Street, St. Augustine, FL 32084
Phone: +19048243722