Honeymoon in St. Augustine
The oldest street in America is St. George Street — and on a Tuesday evening in October, after the last tour group has cleared out and the gas lamps have come on, it’s one of the most unexpectedly romantic places in Florida. No engineering required. Just 450 years of history, cobblestones worn smooth by centuries of foot traffic, and a pace that drops the moment you stop walking fast.
Most Florida honeymoon destinations are built around beaches or pools. St. Augustine is built around 1565 — the year Spanish settlers founded the first permanent European settlement in North America — and the city has never stopped looking the part. For honeymooners, that history is the amenity. The boutique B&Bs occupy genuine Victorian-era mansions. The candlelit restaurants are in buildings that predate the state of Florida itself. And the romance here isn’t something the tourism board manufactured — it’s been accumulating for four and a half centuries.
Source: Source: St. Johns County Visitor & Convention Bureau,
← Back to Honeymoon Destinations in Florida →📋 Honeymoon in St. Augustine at a Glance
Stay: 3–4 days
Budget: Typical spend: $900–$1,600 per couple
Sweet spot: March–May and September–November
Summer is hot and humid; December–February is mild but busier
Getting there: Jacksonville 45 min · Orlando 1.5 hrs · Miami 5 hrs
Atmosphere: Historic, intimate, and walkable — distinctly un-resort-like
Busiest on event weekends; quieter mid-week year-round
Romantic things to do in St. Augustine
Cobblestone street St. Augustine historic district Florida honeymoon
Evening walk through the historic district
The best thing to do in St. Augustine after dark costs nothing — walk St. George Street and the surrounding lanes after 8 PM, when the day-trippers have left and the city feels entirely different. The Castillo de San Marcos glows under floodlights against the water, the carriage horses are still running tours, and the cobblestones and gas-lit streetlamps create a setting that feels genuinely old rather than recreated. Most couples who rate their St. Augustine trip highest mention this specific experience: the night version of the historic district, unscheduled and unhurried.
→ Plan your visit at nps.gov/casaCastillo de San Marcos National Monument
The oldest masonry fort in the continental US, built by the Spanish in the late 1600s and remarkably intact. Walking the fort's ramparts with views across Matanzas Bay is a memorable experience, and the surrounding grounds are open and uncrowded in the early morning. Entry is $15 per person (National Park Service fee); worth building into a morning before the day-tour crowds arrive around 10 AM. → Plan your visit at nps.gov/casa
Horse-drawn carriage tour
St. Augustine's carriage tours are one of the few tourist-adjacent activities that work particularly well for couples — slow enough to absorb the historic district without walking fatigue, and atmospheric after dark in a way that the daytime version isn't. Ancient City Tours and St. Augustine Transfer Company run evening departures; booking a private carriage for two is worth the premium.
St. Augustine Lighthouse
The 1874 lighthouse — still active — sits on Anastasia Island, a short drive from the historic district. Climbing the 219 steps earns panoramic views of the city, the inlet, and the Atlantic coast. The lighthouse museum is well-curated and genuinely interesting; the keeper's house has been restored and is worth walking through. Best visited in the morning before the afternoon heat. → staugustinelighthouse.org
Anastasia State Park beach
Four miles of Atlantic beach just across the Bridge of Lions from the historic district — clean, uncrowded by Florida standards, and backed by dunes rather than development. A good half-day option for couples who want beach time without building an entire trip around it. Parking fills by mid-morning on summer weekends; arrive early or go on a weekday. → Check hours via floridastateparks.org
Wine and spirits tasting on the historic district
St. Augustine has a small but well-regarded collection of wine bars and distilleries within walking distance of the historic core — including the St. Augustine Distillery, which offers free tours and tastings. The San Sebastian Winery (a short walk from St. George Street) produces Florida wines and offers a rooftop bar overlooking the city. A good option for an afternoon activity that transitions naturally into evening. → sansebastianwinery.com
Flagler College and the Ponce de León Hotel
The Spanish Renaissance main building of Flagler College — originally built as the Ponce de León Hotel in 1888 — is one of the most architecturally striking buildings in Florida. Free guided tours run during summer months; the interior Tiffany stained glass windows are genuinely worth seeing. Located directly on the Plaza de la Constitución, it's an easy stop on any walking tour of the historic district.
Best restaurants for couples
The Floridian (Historic District, $$) — A local favorite for couples who want farm-to-table Florida cooking in a relaxed, unhurried atmosphere. The menu changes with seasonal ingredients; the porch seating on a warm evening is particularly good. No reservations — arrive early or expect a short wait on weekends, which is worth it.
(St. George Street, $$$) — The St. Augustine location of the Tampa institution, serving Cuban and Spanish cuisine in a historic setting with flamenco shows on select evenings. A more theatrical dining experience than most of the city’s options — good for couples who want dinner to feel like an event. Reservations strongly recommended.
Preserved Restaurant (Historic District, $$$) — One of the most consistently praised fine-dining options in the city, with a seasonal New American menu and an interior that manages to feel intimate despite being a full-service restaurant. The right choice for a splurge dinner — make reservations well in advance, especially on weekends.
Ice Plant Bar (Historic District, $$) — A craft cocktail bar in a beautifully restored 1920s ice plant, with an extensive spirits menu and small plates. Not a dinner restaurant, but an excellent option for a pre-dinner or late-evening drink in a space that has genuine architectural character. No reservations; the bar fills quickly on weekend evenings.
How to get there
Nearest airport: Jacksonville International Airport (JAX) — 45 minutes north of St. Augustine via I-95. Direct flights available from most major East Coast and Southeast hubs. Daytona Beach International Airport (DAB) is 60 miles south and offers another option for couples flying from limited markets.
By car: Jacksonville (~45 min via I-95), Orlando (~1.5 hrs via I-95 S), Miami (~5 hrs via I-95 N), Atlanta (~6 hrs via I-75/I-10). St. Augustine’s position on I-95 makes it one of the most accessible historic cities on the East Coast for road trips — a natural stopping point on any Florida drive.
Getting around once there: The historic district is fully walkable once you’re parked. The St. Augustine Sightseeing Trains and Old Town Trolley cover most major attractions for $35–$40 per person. Parking is available in several garages near the historic district ($2–5/hour); the Anastasia Boulevard garage is the most convenient for day visits. A car is useful for reaching Anastasia State Park beach, the lighthouse, and dinner options outside the historic core.
What to know before you visit
Cobblestones and walking surfaces. The historic district’s signature cobblestone streets and brick sidewalks are charming but uneven — genuinely uneven, not just slightly rough. Wear comfortable shoes, especially for evening walks. The most-photographed streets (including parts of St. George Street) have sections that are difficult in heels or thin-soled shoes.
Event weekends book out fast. St. Augustine hosts several major events that fill the historic district inns months in advance: the Nights of Lights (November through January), the Celtic Music and Heritage Festival (February), and Gamble Rogers Folk Festival (May) are the ones most likely to affect availability and rates. Check the city’s events calendar before booking if you’re visiting between November and March.
Parking and getting around. The historic district has limited street parking; the Castillo de San Marcos area and Anastasia Boulevard garages are the most reliable ($2–5/hour). Park once and walk — the historic core is compact enough that driving between sights is unnecessary and often slower than walking. The Sightseeing Train and Old Town Trolley are worth the price if you want a guided overview on arrival.
Summer heat and humidity. June through August temperatures regularly hit the low-to-mid 90s°F with high humidity. Afternoon thunderstorms are common and pass quickly. If you’re visiting in summer, plan outdoor sightseeing for the morning, take a break through the hottest part of the afternoon, and resume in the early evening when temperatures drop and the city empties out pleasantly.
Most couples spend $900–$1,600 for three to four days — making St. Augustine one of the better-value honeymoon options in Florida. The biggest cost is lodging — historic district B&Bs run $180–$280 a night on weekends, often including breakfast. Budget $70–$100 a day for food if you’re mixing one nice dinner (Preserved or Columbia, $80–$120 for two) with casual lunches on St. George Street. A carriage tour runs $55–$80 for two. Parking and trolley transport add $20–$40 per day if you’re not walking everywhere.
3-day St. Augustine honeymoon itinerary
Cobblestone streets evening St. Augustine historic district Florida honeymoon couple Photo: St. Johns County Visitor & Convention Bureau Day 1 Arrive, check in, and walk St. George Street while it's still mid-afternoon and the light is good. The street runs the full length of the pedestrian historic district — start at the City Gate at the north end and walk south to the Plaza de la Constitución. Stop at San Sebastian Winery for a tasting, then continue to the Bayfront and watch the light change over Matanzas Bay. Dinner at The Floridian or a reservation at Preserved for a first-night splurge.
Morning visit to the Castillo de San Marcos — arrive before 10 AM to beat the tour groups. Walk the ramparts with views across the bay, then explore the fort's interior at your own pace. Afternoon at the St. Augustine Lighthouse on Anastasia Island, followed by an hour at Anastasia State Park beach. Return to the historic district for dinner and an evening horse-drawn carriage tour after dark, when the city looks entirely different.
Slow morning — this is the day to linger over the B&B breakfast rather than rushing out. Late morning tour of Flagler College (free, runs through summer) to see the Tiffany stained glass interior. Lunch at a cafe on the historic district, then a walk through the quieter residential streets east of St. George Street that most day-trippers miss. Depart by early afternoon to avoid I-95 rush hour traffic building north toward Jacksonville. → Check hotels on Booking.com → Read reviews on TripAdvisor
Frequently asked questions
Official resources
For the most current information on reservations, events, and local conditionsHow we created this guide
This guide was researched and written by Arif Chow. Every destination in this list was evaluated against the same criteria — lodging availability and pricing verified on Booking.com, activity costs confirmed via operator websites, and crowd and timing data drawn from Florida tourism authority sources. Traveler sentiment was gathered from 50+ TripAdvisor reviews and Reddit discussions on r/florida and r/honeymoon from 2024–2025, and paraphrased without referencing any usernames or personal details. We don't visit every destination. We research them obsessively so you don't have to.
This guide was researched and written by Travel Budget Editorial Team using a multi-source verification process: official tourism data from the St. Johns County Visitor & Convention Bureau and Florida State Parks, hotel availability cross-checked on Booking.com, activity pricing confirmed via operator websites, and traveler sentiment drawn from public traveler reviews and discussions. Traveler insights are paraphrased from public reviews — no usernames or personal information are referenced. We don’t visit every destination. We research them obsessively so you don’t have to.