Oceanfront · Resort
Cheeca Lodge & Spa
A classic Islamorada resort on the ocean, with a long pier, a spa and golf.
Official details for Cheeca Lodge & SpaFlorida · Couples · Two nights
Islamorada
Turquoise water, tarpon and sunsets in the sand.
Islamorada, in the upper Florida Keys, calls itself the sport-fishing capital of the world. Stay at a relaxed oceanfront resort, hand-feed giant tarpon at Robbie’s, snorkel the reef, and watch the sunset from a table in the sand on Florida Bay. It is quieter and greener than Key West.
Florida KeysFishing & snorkelingSunsets
YOUR ROUTEKMYR to KMTH
STRAIGHT-LINE DISTANCE~549 NM
ILLUSTRATIVE FLIGHT TIME~3 hr 55 min
WEEKEND STYLETwo nights · Rental car
Time illustration: direct distance at 150 KTAS plus 15 minutes for departure and arrival, matching the discovery page. Use ForeFlight for your actual flight plan.
01 / Aviation & getting around
Land in Marathon, 45 minutes south.
KMTH, Florida Keys Marathon International, is the closest public airport to Islamorada, about 45 minutes north up the Overseas Highway.
The FBO
Million Air Florida Keys
305-743-19959400 Overseas Highway, Marathon, FL 33050
Listed hours are 7 a.m. to 7 p.m., with an after-hours call-out fee; sources give slightly different street numbers, so confirm. Arrange a rental car ahead. No live fuel price is shown.
The route crosses open water and military airspace near Key West and Homestead. Summer brings afternoon storms; hurricane season runs June to November. Review the sectional, restricted areas and current NOTAMs.
02 / Where to stay
Oceanfront and laid-back.
Rates and availability need travel dates.
Bayside · Cottages
The Moorings Village
Romantic cottages under the palms on a private beach.
Official details for The Moorings VillageExplore more
Islamorada visitor guide
More resorts and inns from the Florida Keys visitor site.
Official details for Islamorada visitor guide03 / Where to eat
Two dinners. One in the sand.
Reserve sunset tables.
Friday dinner · Sunset in the sand
Morada Bay Beach Café
Tables in the sand on Florida Bay, best at sunset.
Official details for Morada Bay Beach CaféSaturday dinner · Oceanfront
Atlantic’s Edge
Cheeca Lodge’s oceanfront restaurant, the special-occasion dinner.
Official details for Atlantic’s EdgeLunch · Waterfront
Islamorada Fish Company
Casual waterfront seafood on Florida Bay.
Official details for Islamorada Fish Company04 / Things to do
Water, fish and history.
Plan one day on the water.
Robbie’s of Islamorada
Hand-feed giant tarpon from the dock, then rent a boat or kayak.
Visit informationSnorkel or dive the reef
Trips go out to Alligator Reef and other spots on the only living coral barrier reef in the continental U.S.
A fishing charter
Backcountry or offshore charters for tarpon, bonefish and sailfish.
Optional / Spa & relaxation
The spa at Cheeca Lodge · Time for two
Cheeca’s spa offers couples treatments steps from the ocean.
Booking: Ask about couples treatments, access for non-guests, current pricing and cancellation policy. No prices are shown here, and no appointment has been booked.
05 / What’s happening
Sometimes the season is the reason to fly.
This prototype links to the local visitor site. It does not yet match events to your travel dates.
Spring
Tarpon season
Prime months for tarpon fishing.
December–April
High season
Dry, warm and busy.
Summer & fall
Quiet season
Calm seas for snorkeling; afternoon storms and hurricane season.
Concerts, festivals & local happenings
Check the local calendar when choosing a weekend, and confirm dates and tickets with the organizer.
06 / Suggested itinerary
Friday in. Sunday home.
A sample Friday–Sunday weekend: tarpon, the reef and two sunset dinners. No bookings or availability confirmed.
Day trip version
Just for the day
- Arrive
Land at KMTH early and drive north.
- Midday
Tarpon at Robbie’s and lunch on the water.
- Afternoon
A swim, then back to Marathon.
FRI
Arrive & sunset
- Arrival
Land at KMTH, subject to weather and your actual flight plan, and drive north.
- Afternoon
Check in and feed the tarpon at Robbie’s.
- Evening
Sunset dinner at Morada Bay Beach Café.
SAT
On the water
- Morning
A reef snorkel trip or a fishing charter.
- Afternoon
Lunch at Islamorada Fish Company, then the spa.
- Evening
Dinner at Atlantic’s Edge.
SUN
An easy departure
- Morning
The History of Diving Museum.
- Before leaving
Allow time for the drive and the FBO.
- Fly home
Summer storms build in the afternoon; leave early.
Longer stay · Add a day
With an extra day
- Morning
A backcountry fishing charter.
- Afternoon
A boat to Indian Key Historic State Park.
- Evening
Sunset in the sand at Morada Bay.
07 / 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 and a car first, then charters and dinners.
Airport
Marathon is 45 minutes away. Plan the drive.
Military airspace
Brief restricted areas near Key West and Homestead.
Hurricane season
June through November. Keep plans flexible.
Reviewed · Destination 58
Reviewed November 3, 2026.
Picks and links reviewed by WingAway Weekends. Hours, prices, menus and availability change often, so confirm directly with each place before booking. Spotted something out of date, or have a favorite we missed? Email us at [email protected].
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.