Adults-only guesthouse
The Marquesa
Restored historic houses around pools and gardens in Old Town, with its own restaurant, Hot Tin Roof. Quiet, romantic and walkable.
Florida · Couples · Two nights
Key West
The end of the road. The start of Pan Am.
Palm-lined streets, Victorian guesthouses, sunsets over the Gulf and the town where Pan American Airways sold its first tickets. Key West is the longest flight in this collection, so it shines as a longer stay.
Island eveningsAviation historyOn the water
YOUR ROUTEKMYR to KEYW
STRAIGHT-LINE DISTANCE~567 NM
ILLUSTRATIVE FLIGHT TIME~4 hr 2 min
WEEKEND STYLETwo nights · On foot + bikes
Time illustration: direct distance at 150 KTAS plus 15 minutes for departure and arrival, matching the discovery page. At about four hours from KMYR, most piston aircraft will need a fuel stop. The route includes long stretches over water. Use ForeFlight for your actual flight plan.
01 / Aviation & getting around
Plan this one carefully.
KEYW, Key West International, is a towered airline airport at the end of the Keys, with restricted and military airspace nearby (Naval Air Station Key West).
One FBO
Signature Aviation
305-296-5422The only FBO at KEYW
Signature is the only FBO, and Key West is among the more expensive stops in this collection. Recent pilot reports describe 100LL above $11 a gallon, overnight parking around $125 a night for a single-engine aircraft and a hefty fee for departures after the FBO closes at 9 PM. Confirm every fee before you go; no live price is shown.
Review restricted and warning areas, NAS Key West traffic, overwater equipment (life vests, raft) and any special procedures for flights along the Keys. A fuel stop on the mainland is the norm.
02 / Where to stay
Choose your kind of weekend.
Adults-only guesthouses are Key West’s sweet spot for couples. Rates and availability need travel dates; winter is peak season.
Grand hotel · On the beach
Casa Marina
A historic 1920s grand hotel on its own beach, now part of Hilton’s Curio Collection. Choose it for beach time and a classic resort feel.
Small & adults-only
H2O Suites or Almond Tree Inn
Two other adults-only boutique options often recommended for couples. Compare rooms and location for your dates.
03 / Where to eat
Two dinners by the water.
Sunset tables book up. Reserve the special dinner first.
The romantic dinner
Latitudes, Sunset Key
Oceanfront dining on a small island a short boat ride from Old Town. Often called the most romantic table in Key West; the launch is part of the evening.
In Old Town
Hot Tin Roof
The Marquesa’s restaurant, a favorite for a polished, relaxed dinner within walking distance of Duval Street.
Aviation history · Casual
First Flight Island Restaurant & Brewery
At 301 Whitehead Street, in the building where Pan American Airways sold its first tickets in 1927. Lunch with a story.
04 / Things to do
Sunsets, seaplanes and stories.
Choose one big outing and let island time do the rest.
Seaplane to the Dry Tortugas
Fly about 70 miles west by floatplane to Fort Jefferson in Dry Tortugas National Park. Key West Seaplane Adventures is the only seaplane operator. Book well ahead; the ferry is the slower alternative.
Pan Am’s first office
Pan American Airways began Key West–Havana mail flights in October 1927. Stop at 301 Whitehead Street, now a restaurant, to see where it all began.
Sunset at Mallory Square
The nightly sunset celebration with street performers on the harbor. Arrive early, or watch from a quieter rooftop or a sunset sail.
Old Town on foot or by bike
Victorian houses, hidden lanes and the Hemingway Home and Museum. Rent bikes for an easy loop.
05 / 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.
December–April
Peak season
The best weather and the highest prices. Book lodging and the seaplane early.
June–November
Hurricane season
Lower rates, more heat and storm risk. Keep plans flexible and watch the tropics.
Year-round
Festivals
Key West hosts festivals through the year that fill hotels. Check the calendar before booking.
Concerts, festivals & local happenings
Check the destination calendar when choosing dates, and confirm details with the organizer.
06 / Suggested itinerary
Friday in. Sunday home.
A sample Friday–Sunday version. Given the flight, Key West works best as a longer stay; choose Longer stay on the homepage to see an extra day. No bookings or availability confirmed.
Day trip version
Just for the day
- Not a day trip
At about four hours each way from KMYR, Key West is not a day trip from most of the Southeast.
- If you are closer
From south Florida airports: lunch at First Flight, then a bike loop through Old Town.
- Afternoon
Hemingway Home, then back to the FBO well before it closes.
FRI
Arrive & unwind
- Midday arrival
Land at KEYW after a mainland fuel stop, subject to weather and your actual flight plan. Taxi to Old Town.
- Afternoon
Lunch at First Flight, then a bike loop through Old Town.
- Evening
Sunset at Mallory Square, then dinner at Hot Tin Roof.
SAT
Seaplane day
- Morning
Seaplane to the Dry Tortugas: Fort Jefferson, snorkeling and the flight itself.
- Afternoon
Back in town by mid-afternoon; pool time at your guesthouse.
- Evening
The launch to Sunset Key for dinner at Latitudes.
SUN
An easy departure
- Morning
Breakfast and the Hemingway Home.
- Before leaving
Get to the FBO with time to spare; late departures cost extra.
- Fly home
A long trip with a fuel stop. Plan for afternoon storms and daylight.
Longer stay · Add a day
With an extra day
- Morning
A snorkel or sail trip on the reef, or a lazy beach morning at Casa Marina.
- Afternoon
Bike to the Southernmost Point and Fort Zachary Taylor’s beach.
- Evening
A sunset sail, then a casual dinner in Old Town.
07 / Good to know
Keep the trip easy to change.
These details make the difference between an appealing list and a usable getaway.
Book in this order
FBO parking, lodging and the seaplane first, then Latitudes.
A serious cross-country
Four hours, a fuel stop and overwater flying. Build in a weather day.
Allow for the season
Winter is ideal and busy; summer and fall bring heat, storms and hurricane risk.
Dates come next
Rates, fees and tour availability are date-dependent. No availability or live price is implied here.
Testing / Destination 10
Draft for review.
Research-based selections, not personal-visit endorsements. Researched November 1, 2026. Several picks have no website link because official addresses could not be confirmed; 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.