Grand historic hotel · Spa
Casa Monica Resort & Spa
An 1888 Moorish Revival landmark across from the Flagler buildings, now part of Marriott’s Autograph Collection, with a full-service spa. The splurge choice.
Florida · Couples · Two nights
St. Augustine
The oldest city. A long weekend’s worth of stories.
Coquina walls, narrow Spanish streets, Henry Flagler’s grand hotels and sunsets over Matanzas Bay. St. Augustine is the longest flight in this collection from KMYR and one of the most rewarding.
HistoryBayfrontDining
YOUR ROUTEKMYR to KSGJ
STRAIGHT-LINE DISTANCE~255 NM
ILLUSTRATIVE FLIGHT TIME~1 hr 57 min
WEEKEND STYLETwo nights · Rideshare + walks
Time illustration: direct distance at 150 KTAS plus 15 minutes for departure and arrival, matching the discovery page. Coastal Florida afternoon storms can build quickly in summer. Use ForeFlight for your actual flight plan.
01 / Aviation & getting around
Land, then head for the old city.
KSGJ, Northeast Florida Regional Airport, is a towered field about 15–20 minutes north of the historic district.
Full service or self-serve
Atlantic Aviation is the FBO. Directory listings also show self-serve 100LL on the field. Ask Atlantic about facility fees, two-night parking, waivers with fuel and after-hours fees. Prices vary widely between listings, so call ahead; no live price is shown.
The airport authority can be reached at 904-209-0090.
02 / Where to stay
Choose your kind of weekend.
Three different stays in the historic district. Rates and availability need travel dates.
Adults-only · Historic houses
The Collector Luxury Inn & Gardens
A collection of restored historic houses around courtyard gardens, adults-only and quiet, a few minutes’ walk from the plaza.
Classic inn · Oldest in town
St. Francis Inn
A long-running bed and breakfast in one of the city’s oldest buildings, on a quiet street in the historic district. Classic B&B charm.
Official details for St. Francis Inn03 / Where to eat
Two dinners. One long lunch.
The historic district is busy on weekends, so reserve your anchor dinner early.
Friday dinner · Intimate
Collage
A small, romantic restaurant known for globally inspired cooking and live piano. The classic St. Augustine date night. Reserve well ahead.
Saturday dinner · Lively
The Ice Plant Bar
A restored 1920s ice plant with craft cocktails and a farm-to-table menu, in the same building as the St. Augustine Distillery. Fun and buzzy rather than quiet.
Lunch · Spanish-Cuban
The Columbia
A long-running Spanish and Cuban restaurant on St. George Street. A leisurely lunch between sights; try the 1905 salad.
04 / Things to do
Walk five centuries.
Choose a few memorable experiences; the old city is compact enough to wander between them.
Castillo de San Marcos
The 17th-century Spanish stone fort on the bay, a National Park Service site. Go early or late in the day to avoid the heat and crowds.
Park informationSt. Augustine Lighthouse & Maritime Museum
Climb the striped lighthouse for the view in this guide’s photo, then explore the maritime museum. Across the bridge on Anastasia Island.
Flagler College & the Gilded Age
Henry Flagler’s 1888 Hotel Ponce de Leon is now Flagler College. Ask about guided historic tours of its Tiffany-glass dining hall and grand rotunda.
St. George Street & Lincolnville
The pedestrian heart of the old city, busy by day. For a quieter walk, wander Lincolnville’s historic streets or the bayfront at sunset.
Sunset on Matanzas Bay
Several operators run sunset sails and cruises from the downtown marina. Choose one water outing and book a day or two ahead.
Optional / Spa & relaxation
The spa at Casa Monica · Time for two
Casa Monica Resort & Spa has a full-service spa in the heart of the historic district, a good fit for a couples treatment after a morning of walking.
Booking: Ask about couples treatments, access for non-hotel guests, current pricing, gratuity and cancellation policy. No prices are shown here because they change, and no appointment has been booked.
Optional Saturday afternoon, before dinner.
05 / Wine & spirits
A glass, and no hurry.
Two downtown tasting stops, both walkable from the historic district.
King Street · Winery
San Sebastian Winery
A working winery at 157 King Street with tours and tastings of Florida wines, plus a rooftop bar. Check tour times and the rooftop’s hours.
Distillery · Tours
St. Augustine Distillery
Craft spirits made in the restored ice plant, with distillery tours and tastings. Pair it with dinner upstairs at the Ice Plant Bar.
06 / What’s happening
Sometimes the event is the reason to fly.
This prototype links to the destination calendar. It does not yet match events to your travel dates.
Mid-November to January
Nights of Lights
Millions of white lights across the historic district, a much-loved holiday tradition. Beautiful and crowded; book lodging early.
Spring & fall
Best seasons
Comfortable walking weather. Summer is hot and humid, with afternoon thunderstorms that can affect flights.
Year-round
Concerts & festivals
Music at the St. Augustine Amphitheatre and festivals through the year. Check the calendar for your dates.
Concerts, festivals & local happenings
Check the destination calendar when choosing a weekend, and confirm dates and tickets with the organizer.
07 / Suggested itinerary
Friday in. Sunday home.
A sample Friday–Sunday weekend: the fort, the Flagler buildings, a sunset on the bay and two very different dinners. No bookings or availability confirmed.
Day trip version
Just for the day
- Arrive
Land at KSGJ early and ride into the old city.
- Midday
Castillo de San Marcos, then lunch at The Columbia on St. George Street.
- Afternoon
A San Sebastian Winery tasting or a Flagler College tour, then fly home ahead of afternoon storms.
FRI
Arrive & unwind
- Midday arrival
Land at KSGJ, subject to weather and your actual flight plan, and ride into the old city.
- Afternoon
Lunch at The Columbia, then a slow walk down St. George Street. Check in when your room is ready.
- Evening
Dinner at Collage if reserved.
SAT
Fort, hotels & bay
- Morning
Castillo de San Marcos when it opens, then a Flagler College tour.
- Afternoon
San Sebastian Winery tasting, or a couples treatment at Casa Monica. Late afternoon: the lighthouse climb.
- Evening
Sunset on Matanzas Bay, then dinner at the Ice Plant Bar.
SUN
An easy departure
- Morning
Breakfast and a quiet walk through Lincolnville or along the bayfront.
- Before leaving
Check out and allow ample time at the FBO.
- Fly home
Plan around afternoon storms in warm months; a morning departure is often smoother.
Longer stay · Add a day
With an extra day
- Morning
Beach time on Anastasia Island or a quiet walk at Crescent Beach.
- Afternoon
The St. Augustine Distillery tour and a wander through Lincolnville.
- Evening
A sunset cruise on Matanzas Bay, then dinner at the Casa Monica.
08 / Good to know
Keep the weekend easy to change.
These details make the difference between an appealing list and a usable getaway.
Book in this order
Lodging first, then the Friday dinner, a Flagler College tour and one water outing.
Allow for the season
Summer heat and daily storms; holiday lights season is crowded. Spring and fall are easiest.
Wear good shoes
Old streets are uneven, and the lighthouse has a lot of steps.
Dates come next
Hotel rates, tours and restaurant hours are date-dependent. No availability or live price is implied here.
Testing / Destination 06
Draft for review.
Research-based selections, not personal-visit endorsements. Researched November 1, 2026. Several official links could not be opened during research; check each one, and confirm hours, prices and availability directly before booking.
WingAway Weekends helps you discover the destination. Use ForeFlight and current official aviation information for route, performance, weather, NOTAMs and preflight decisions. Flight planning and PIC responsibility stay with the pilot.