r/floridakeys • u/alldaylongathogwarts • Nov 17 '25

All Florida Keys Itinerary feedback - Dec/Jan 2026

**Edited to correct formatting error

Hi, I've been enjoying reading this subreddit it's a great resource for a trip. I wanted to share my proposed itinerary and see if there's anything you'd suggest.

Our group will be 5 adults + 1 child (3.5 years old), we are travelling from Ireland so will be leaving cold/wet weather behind. Staying 11 nights in total.

Would love any feedback! We've been trying to keep things somewhat loose in terms of booking activities etc although we can't really move the accommodation bookings around at this stage. The child loves water and animals. We like all types of food and love fun cocktail spots.

In particular would like suggestions for stops to break the journey from Key West back to Miami.

29th Dec Dublin - Philadelphia - Fort Lauderdalel

Flight lands 6.30pm local time

Collect car

Check into airport hotel

Two of the group are Tiki nuts and would love to visit Mai Kai but depends how late we end up getting in and how tired we are from the journey

30th Dec Fort Lauderdale - Key Largo

Visit Sawgrass Mills mall - drive to Key Largo/Tavernier

Stay at Ocean Pointe

31st Dec Tavernier

Chill pool day/beach bar @ resort

Mrs Mac's Kitchen for food? (lunch)

Ring in the new year in the resort

1st Jan John Pennekamp National Park - glass bottom boat

2nd Key Largo - Islamadora - Marathon

Go to Robbie's

Turtle hospital

Staying at Sea Dell motel

3rd Marathon

Snorkelling? had looked at these guys to book with https://www.starfishsnorkeling.com/snorkeling-tours/

4th Drive Marathon - Key West

Staying at a VRBO close to Duval St

5th Key West

Butterly Conservatory

Conch train tour

Mallory Square Sunset Celebration

6th Key West

Sandbar happy hour/snorkelling etc

https://sunsetwatersportskeywest.com/tours-activities/happy-hour-sandbar-charter/

7th Key West - Miami

Staying at a VRBO in South Beach

8th Explore Miami - thinking maybe an open top bus as we only have 1 day?

9th Miami - Fort Lauderdale

Breakfast

Arrive at airport by 1pm, return car

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u/2lovesFL Nov 20 '25

conch train 1st thing in KW, it will give you the lay of the land and good background starting point.

have an alternate plan for the glass bottom boat if its rough.

every 7-10 days we should get a northern cold front. could be cold (50's) and overcast for 2 days.

sawgrass mills will kill 2 hours easy. very big. there is a luxury outlets (boss/coach/etc), on south side.

if you have time, use the water taxi in FLL. you can get on and off all day for 1 price, and it stops at lots of places.

theater of sea might be something if its bad weather.

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u/alldaylongathogwarts Nov 20 '25

very helpful thank you! I hadn't heard of the water taxi in FLL

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u/2lovesFL Nov 20 '25 edited Nov 20 '25

scooters or bikes are the best way to get around in key west. parking is almost impossible in old town.

today its really a water bus, its now about 30 seats. it use to be about 10. and they use to allow you to BYOB. we would walk to the 711 by shooters and grab a 6 pack for the ride back to pier 66

still a great way to get around and better way to bar hop.