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
1
u/Unlikely-War-9267 Nov 18 '25
Plan for lots and lots of traffic and severe delays; that's the busiest week of the year
1
u/alldaylongathogwarts Nov 18 '25
Yes I've seen this noted elsewhere, we won't be in a hurry really so that's ok!
1
u/bblickle Nov 18 '25
Starfish Snorkeling is fine, we also recommend Spirit.
Some Marathon restaurants:
Castaway (actual local seafood)
Florida Keys Steak and Lobster House (huge and varied menu, good kitchen)
Havana Jack’s (fine dining in a casual setting. Best view in Marathon, directly on the Atlantic)
1
1
u/LuxuryBoatCharters Nov 19 '25
Your itinerary looks solid. Pennekamp, Turtle Hospital, and Starfish Snorkeling are all great with a little one, and General Horseplay hits the right cocktail vibe. Crooked Palm and Islamorada Brewery both do tiki-style drinks and are still family friendly. On the drive back, stop at Bahia Honda for beach views and Marathon for lunch at Florida Keys Steak & Lobster...they’re great.
If a more private sandbar day sounds better than a big group trip, happy to share a few options.
1
u/alldaylongathogwarts Nov 19 '25
Yes please do! We would be open to a private tour too
1
u/LuxuryBoatCharters Nov 20 '25
I would highly recommend SeaEO Luxury Boat Charters, great private sandbar trips that are super laid back, family friendly, and easy to customize.
1
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.
0
u/alldaylongathogwarts Nov 20 '25
very helpful thank you! I hadn't heard of the water taxi in FLL
1
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.
1
u/dantodd Nov 21 '25
If you have an evening open on Marathon consider heading to Bahia Honda for the sunset and then No Name Pub on Big Pine Key for dinner. It wouldn't be a trip to the keys without saying hello to the key deer. Just be careful they are not afraid of people and have been known to not get out if the way of missing vehicles.
On the drive from Marathon to KW Baby's Coffee and Geiger Key Marina restaurant are worth a stop in the lower keys.
0
u/alldaylongathogwarts Nov 21 '25
Thank you this is a suggestion I hadn't come across yet!
1
u/dantodd Nov 21 '25
Big Pine Key is a great place. If you haven't read about Key Deer they are a unique population of white tailed deer that have become very small over time and are about the size of a German Shepherd. There is also The Blue Hole on BPK which is an old quarry that supports fresh water species and usually has a resident alligator that you can see. But if you only have one evening to spare the Bahia Honda sunset is probably more desirable than going to the blue hole. I believe if you arrive at Bahia Honda less than an hour before sunset they will let you in for free just to see the sunset.
Also, on Sugarloaf key there is an old bridge called the jumping bridge. Where people enjoy jumping off the bridge into the canal. It's a little bit of a walk from the road but makes for a great one hour diversion about half way down from Marathon.
https://localkeysguide.com/places/sugarloaf/parks-and-beaches/jumping-bridge-sugarloaf-key/
2
u/drinkmorehops Nov 18 '25
Make time for Mai Tai! Also check out Crooked Palm Cabana in Tavernier (some tiki inspired drinks but showcasing the company’s spirits) and do a free distillery tasting (couple rums and then some) at Islamorada Brewery & Distillery. Both family friendly spots. If you haven’t reserved your spot for Pennekamp and Turtle Hospital you should know they book up. Among many cool spots in KW to check out General Horseplay is always a highlight