Itinerary Recommendations & GF Eating

Question

Hi Keys experts,

I've been reading a bunch of posts on here and some fantastic ideas, we will be a 50yo couple travelling with our adult (23) yo son. We were thinking of a RV trip, but reading some posts about parking difficulty are rethinking this and likely to just go a car and accommodation.

Time of year is mid-May, Mon-Fri in the Keys (with a Sun-night arrival and Fri night pre-departure night likely at MIA) as we are flying internationally from LAX on the Saturday night, so we'll fly MIA>LAX Saturday and don't want to miss flights, etc. Slight possibility of arriving into MIA on the Sunday morning so we'd get an extra day, but unsure at the moment.

Few questions for the experts:

> Is anything of note closed on specific days across the keys?

> Conch Fritters, Key Lime Pie and Sandwiches all sound amazing - but does anywhere offer any or all of these Gluten Free?

> What are your "must sees" in the Keys?

> If we've been on alligator airboats a few times near Orlando, is it worth doing the same in the "true" Everglades? on the way down to or way back from the keys.

Based on things we've seen to do in other posts I'm thinking maybe overnight stops in Key Largo, Key West, Islamorada across the week with KW having the 2 nights so we don't rush through any stops or activities. Things we like to do include snorkelling/boating/fishing, eating great food, drinking cocktails and watching scenery and the sunset and stargazing. Like sharks, so seeing them would be cool (either fishing or just seeing) - also enjoyed the movie True Lies, so seeing the famous location on the old bridge would also be a nice add.

If anyone wants to take a few minutes to either answer some of the Qs, or provide their thoughts on how we should best organise our time to get the most out of the visit and have some down time in between, I'd appreciate it. Thanks in Advance.

Answer

Mid-May is a great time to visit the Florida Keys—warm water, quieter crowds than peak winter, and still before the heavy summer heat. Planning a Mon–Fri itinerary with a Sun arrival works very well, and choosing a car over an RV is wise for most visitors. Parking is extremely limited, especially in Key West, and navigating an RV along US-1 can be stressful rather than relaxing.

Your interests—snorkeling, boating, fishing, amazing sunsets, cocktails, and food—fit perfectly with the Keys. Below is a detailed breakdown addressing all of your questions, along with itinerary recommendations to maximize your time.

Are attractions or restaurants closed on specific days?

Most major attractions (parks, museums, tours, boat operators) are open 7 days a week.
Some smaller shops and restaurants in the Upper and Middle Keys may close 1 day a week—often Tuesday or Wednesday—but this varies by business.
Key West generally stays open every day; it’s the least likely place to encounter closures.
Boat tours and snorkel trips run daily but may cancel due to wind or weather, so flexibility is helpful.

Gluten-free options (Conch Fritters, Key Lime Pie, Sandwiches)

The Keys have become increasingly GF-friendly, but traditional conch fritters are usually not gluten-free. That said, some places offer alternatives, and many offer GF sandwiches and GF key lime pie.

Gluten-Free Conch Fritters: Rare, but occasionally found as baked or alternative-flour versions at specialty seafood spots. Always call ahead to confirm.
Gluten-Free Key Lime Pie: Some restaurants offer GF crusts or crustless pies—not universal, but becoming more common.
Gluten-Free Sandwiches: Many popular cafés in Key Largo, Islamorada, and Key West offer GF bread.
Seafood and grilled protein: Very easy to find GF as long as you avoid fried items and ask about marinades.

Must-sees in the Florida Keys

There is a lot to choose from, but these highlights fit your interests very well:

Key Largo: John Pennekamp Coral Reef State Park—glass-bottom boat, snorkel trips, mangrove kayaking.
Islamorada: Robbie’s (tarpon feeding), Theater of the Sea (animal encounters), great fishing charters.
Seven Mile Bridge / Old Seven Mile Bridge: Includes the famous “True Lies” chase scene location.

Bahia Honda State Park:

Key West: Mallory Square sunset, Duval Street, Hemingway House, Southernmost Point, Fort Zachary Taylor State Park.
Night activities: Live music, star-gazing (especially in Lower Keys), and sunset cruises.

Is an Everglades airboat tour worth it if you’ve done the Orlando ones?

If you’ve done the Orlando-area airboat rides, the Everglades proper will feel similar, but the ecosystem is different and more wild. Whether it’s worth the stop depends on your interest level:

Reasons to do it: More authentic sawgrass prairie, more wildlife variety, deeper Everglades scenery.
Reasons to skip: The experience (airboat + alligators) is similar enough to central Florida that some find it repetitive.
Best compromise: Make a brief Everglades stop at a boardwalk trail or visitor center on your drive instead of a full airboat tour.

Recommended itinerary (Sun–Fri)

With your interests and desire for a relaxed pace, the following layout works extremely well:

Sun: Arrive in Miami → Drive to Key Largo → Settle in and enjoy a waterfront dinner.
Mon (Key Largo): Snorkeling at John Pennekamp or reef trip; cocktails at sunset.
Tue (Islamorada): Drive to Islamorada → Fishing charter or boating → Explore shops, breweries, or galleries.
Wed (Middle Keys → Key West): Visit Robbie’s, then stop at the Old Seven Mile Bridge “True Lies” filming location → Continue to Key West.
Thu (Key West): Explore Duval Street, Hemingway House, sunset cruise, or night-life.
Fri morning (Key West): Relaxed morning → slow drive back toward Miami → Overnight at airport hotel.
Sat: Fly MIA → LAX → International flight.

Notes on sharks: The Keys are excellent for shark sightings—especially during fishing charters or while snorkeling reefs and wrecks. Many charters specifically offer shark-viewing or catch-and-release shark trips.

Why this itinerary works well:

Minimizes rushed driving days.
Gives you 2 nights in Key West without feeling hurried.
Spreads out snorkeling, boating, beach time, and sightseeing.
Ensures you’re close to Miami the night before your long-haul flights.

Overall, you’ve chosen the perfect pace and destinations for a first visit to the Keys. With a mix of snorkeling, great food, sunset watching, the iconic bridges, and time in Key West, your mid-May trip will feel both adventurous and relaxing. It’s a fantastic plan for a family group with adults who enjoy both activities and down time.

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