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Started By
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Key West for January or February trip
Posted on 11/3/25 at 8:29 pm
Posted on 11/3/25 at 8:29 pm
Would you fly into Miami and then rent a car and drive through the keys
OR just fly into KW?
Also how many days would be enough? 3? 4?
We know it’s expensive but it’d be an anniversary trip and don’t mind spending $$ if it’s worth it.
OR just fly into KW?
Also how many days would be enough? 3? 4?
We know it’s expensive but it’d be an anniversary trip and don’t mind spending $$ if it’s worth it.
10
Posted on 11/3/25 at 10:22 pm to tiger91
Key West is definitely worth it.
It is easy to fly directly in to Key West. I would do that unless you want to spend some time on another key.
We stayed at the Key West B&B. Nice little place on a quiet street just a short walk from Duval St.
We had an anniversary dinner at Latitudes. You take a boat to get there. The food was delicious, and the setting is beautiful. We sat at an outdoor table right next to the water.
Louie's Backyard was another favorite restaurant.
4 days would be fine.
It is easy to fly directly in to Key West. I would do that unless you want to spend some time on another key.
We stayed at the Key West B&B. Nice little place on a quiet street just a short walk from Duval St.
We had an anniversary dinner at Latitudes. You take a boat to get there. The food was delicious, and the setting is beautiful. We sat at an outdoor table right next to the water.
Louie's Backyard was another favorite restaurant.
4 days would be fine.
Posted on 11/4/25 at 5:24 am to tiger91
4 days is too much for me in KW. I personally would prefer to fly into FLL or MIA, drive down to a middle key like Islamorada or Marathon, spend two nights there, then maybe two nights in KW and fly home from there.
Rent your own boat in the middle keys and have the sunset dinner in privacy.
Rent your own boat in the middle keys and have the sunset dinner in privacy.
This post was edited on 11/4/25 at 5:26 am
Posted on 11/4/25 at 5:48 am to tiger91
We are going for Christmas. Flying into KW and home from Orlando
3 nights KW
3 night WPB
3 nights Orlando(kids sports tournament)
3 nights KW
3 night WPB
3 nights Orlando(kids sports tournament)
Posted on 11/4/25 at 8:10 am to tiger91
the drive from Miami is part of the reason to go to the keys. Do 2 nights in marathon and 2 nights in key west
Posted on 11/4/25 at 8:55 am to cgrand
Thanks all. We’ve never been and my husband doesn’t love to travel like I do .. when I mentioned the keys he got excited. He wants to go fishing lol.
Appreciate the comments.
Appreciate the comments.
Posted on 11/4/25 at 10:27 am to tiger91
Key West is awesome and the drive through the keys is beautiful.
I'm sure there's multiple threads on it here but a few of our favorites:
- Hanks hair of the dog (great live music)
- Irish Kevin's
- Green Parrot
- Thirsty Mermaid for dinner
- Blue Heaven for brunch
- Fury Island Adventure Eco Tour (or just their sunset tour if you don't want to do the other stuff)
- Happy hour bouncing around the harbor at Key West Bight
- Beach afternoon at Ft Zachary Taylor
- Sunset celebration at Mallory Square (though I think this has tailed off a bit in recent years)
Lots more. I'll keep thinking.
I'm sure there's multiple threads on it here but a few of our favorites:
- Hanks hair of the dog (great live music)
- Irish Kevin's
- Green Parrot
- Thirsty Mermaid for dinner
- Blue Heaven for brunch
- Fury Island Adventure Eco Tour (or just their sunset tour if you don't want to do the other stuff)
- Happy hour bouncing around the harbor at Key West Bight
- Beach afternoon at Ft Zachary Taylor
- Sunset celebration at Mallory Square (though I think this has tailed off a bit in recent years)
Lots more. I'll keep thinking.
Posted on 11/4/25 at 11:01 am to tiger91
quote:you’d be better off doing that in marathon or islamorada, definitely would be cheaper. If the weather is right and y’all are up for an adventure you can book a trip out to the dry tortugas from KW and get your minds blown. That will eat up a whole day though
He wants to go fishing lol.
Posted on 11/4/25 at 11:09 am to cgrand
The sea plane to the dry tortugas was alot of fun. I'd go down the day before and take the first flight out; you'll be done and basically wrapping up when he fist ferry arrives and you'll be back in KW before most of the area is busy. shite, alot of it won't even be open yet.
Key West Seaplane Charters
Key West Seaplane Charters
This post was edited on 11/4/25 at 12:05 pm
Posted on 11/4/25 at 11:15 am to LSUfan4444
yes that’s a great idea
Posted on 11/4/25 at 11:48 am to Chucktown_Badger
I agree with all of this except Fury. They will pack you on like sardines. Try Danger Charters for water excursions.
Posted on 11/4/25 at 11:59 am to cgrand
Idk that I’d go fishing .. sad to admit I get seasick even with meds. Thanks for the tip about where though!
This post was edited on 11/4/25 at 11:59 am
Posted on 11/4/25 at 3:18 pm to tiger91
Unless someone is going scuba diving or going out to the Dry Tortuga's, I think key West is a 2 or 3-day trip.
If you want to spend more time, you should definitely spend it on other Keys. That's especially true if you want to spend time on the beach, as Key West has extremely limited actual beach, and most of it is rocky and not very good.
If you want to spend more time, you should definitely spend it on other Keys. That's especially true if you want to spend time on the beach, as Key West has extremely limited actual beach, and most of it is rocky and not very good.
Posted on 11/4/25 at 5:59 pm to GOP_Tiger
Thanks for this.
Posted on 11/4/25 at 7:45 pm to tiger91
Fly into Key West directly if at all possible. I’d do 5 or 6 nights if possible. Lots to do. Biking around the city is fun and easy.
This post was edited on 11/4/25 at 7:47 pm
Posted on 11/8/25 at 6:13 pm to tiger91
1 day is plenty. Take a cruise that includes a port of call at Key West. You can walk from one side of the island and back and stop off at a few of places along the way.
Posted on 11/10/25 at 1:40 pm to Chucktown_Badger
- Fury Island Adventure Eco Tour (or just their sunset tour if you don't want to do the other stuff)
MUCH prefer Danger Tours to Fury (smaller groups, better crews)
We love the eco day tour, and the sunset wine cruise as well. Do one or other every trip.
For only a 3 night stay, fly into EYW, the drive from Miami can take 3 hours or all day depending on traffic, wrecks, etc.
If you're a somewhat experience boater, we love renting a boat from Spencer's Boatyard and heading out to Boca Grande which is about 14 miles west of KW. GREAT sandbar and scenery. Usually a handfull of other boats out there to hang with. More info on this if you want. They will rent you fishing gear for pretty cheap, just need some frozen bait.
We go once or twice a year. Let me know if you want any other info on food, nightlife, etc.
MUCH prefer Danger Tours to Fury (smaller groups, better crews)
We love the eco day tour, and the sunset wine cruise as well. Do one or other every trip.
For only a 3 night stay, fly into EYW, the drive from Miami can take 3 hours or all day depending on traffic, wrecks, etc.
If you're a somewhat experience boater, we love renting a boat from Spencer's Boatyard and heading out to Boca Grande which is about 14 miles west of KW. GREAT sandbar and scenery. Usually a handfull of other boats out there to hang with. More info on this if you want. They will rent you fishing gear for pretty cheap, just need some frozen bait.
We go once or twice a year. Let me know if you want any other info on food, nightlife, etc.
This post was edited on 11/10/25 at 1:46 pm
Posted on 11/10/25 at 1:46 pm to AeroFan
quote:
1 day is plenty.
bad take
KW isn't for everyone but theres plenty for 3-4 nights if you enjoy good food, great music, offshore excursions, and a few touristy type things.
Its far enough away you don't feel like you're anywhere near home, amazingly safe, and has great service industry folks wanting to make sure you have a good time.
This post was edited on 11/10/25 at 1:48 pm
Posted on 11/10/25 at 9:01 pm to YumYum Sauce
quote:
If you're a somewhat experience boater, we love renting a boat from Spencer's Boatyard and heading out to Boca Grande which is about 14 miles west of KW. GREAT sandbar and scenery. Usually a handfull of other boats out there to hang with. More info on this if you want. They will rent you fishing gear for pretty cheap, just need some frozen bait.
Do they have plenty of boats readily available for walk ins? I plan to get one but I don’t want to book/pay ahead of time then I get there and it’s too rough to do anything
Posted on 11/11/25 at 9:21 am to yellowfin
quote:
Do they have plenty of boats readily available for walk ins? I plan to get one but I don’t want to book/pay ahead of time then I get there and it’s too rough to do anything
I’ve never used them but I went to their website. Tons of availability the next month. Boats are $550-600/ day plus taxes which seems very reasonable for KW. Right now is one of the slowest times of year for them. They did NOT have a ton of boats, just 4-5 options as best I could tell. It’s possible they have multiple of some of the models.
That’s not a terrible price for a day of fun there. The water is going to be questionably warm to swim and as you said it’s very possible to get a breezy day and be cold with bad seas. The nice thing about the keys though is you can generally get out of the wind by hiding out on the downwind part of the islands.
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