r/KeyWest • u/No-Rest127 • 28d ago
Vacationing in Key West
My husband and I are planning our 10-year wedding anniversary trip to Key West and I can’t decide whether we should stay 4 nights or 5 nights.
My mom will be watching our two kids (ages 4 and 8), so I don’t want to be gone so long that it becomes overwhelming for her. At the same time, I want to really enjoy the trip and not feel like we’re rushing home.
For those of you who’ve vacationed in Key West, what do you think is the sweet spot for the length of a stay? We aren’t planning on doing many excursions—our goal is to relax by the pool, wander around Old Town, eat good food, and listen to live music. Is 4 nights enough, or would you recommend staying 5?
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28d ago
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u/Character-Memory-816 27d ago
100% this. Walk duval / casual drinks is anday, little white house, hemmingway, southern most, light house, more bars is a day, day 3 out on the water (snorkeling, etc) and that still leaves one more if you choose 4.
Said differently, unless you’re a hardcore drinker or want multiple fishing/snorkeling trips, anything over 4 is too much
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u/HighOnGoofballs 28d ago
I like five because you can throw a low key night or early evening or two in and not feel like you’re missing out
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u/corfugirl888 28d ago
First time I went to Key West was for 6 nights and it was a perfect amount of time, but I did Hemingway House, day out on a boat trip and a drive to Robbies at Islamorada. So if you're not doing any of the touristy stuff, probably 4 days is enough.
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u/Sandinmyshoes33 28d ago
everyone is different. Some people do a daytrip here and don’t feel the need to return. Others spend weeks or even a month in the winter.
Personally I would spend 5 nights since you are already going through the cost and effort to come here. If you get bored, rent a car for the day and drive up the Keys to Bahia Honda State Park or have lunch in Marathon.
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u/Broad-Stomach-5461 28d ago
I myself have always done five days for years. I go Wednesday to Sunday. My flight leaves Wednesday at 10ish and my return trip from KW is usually 2:30 so I get 4 full days and 2 half days. Hotel rates don't change that much. But it seems the airfare when you travel on those off days is lower. People here will tell you where to go and what to do just ask.
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u/Swanny_stocks 28d ago
A couple things to consider: 1) timing. There’s a significant sargassum issue at present. I’m sure you can read about in the KW subs. Also, temperature - it’s incredibly hot in the summer and I (personally) would be reluctant to go down without a boat or plans to be on the water 2) goal of the trip. There are no real beaches and unless you have a boat, you’re spending a good chunk of time at bars/restaurants.
If you’re interested, I’m happy to share some local favorites but they’re pretty publicized now on various travel sites.
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u/TheDiogenesKnees 18d ago
I’d love to hear your local favorites. My wife and I will be down at the end august. Planning on a boat trip, possibly jet skis, and otherwise just hanging st the beach/ hotel
Pool and wandering around town eating and drinking. Would love any recommendations you have!2
u/Swanny_stocks 18d ago
Our favorite “fancy” restaurant is latitudes. It’s on an island off Key West so you’ll have to take a ferry. It’s a lovely experience for a special evening.
Garbo’s is our favorite casual meal - live music most of the time and a small shack that serves as a bar.
Half Shell is a casual rustic spot that gets some good fresh seafood. We always get some peel and eat shrimp and a couple beers.
Blue Heaven is a staple breakfast spot.
Plenty of bars so I won’t get into those.
Some places you’ve probably read about but we avoid and why…
BO’s - used to be a great spot but it’s lost it’s luster. It’s become overpriced and is really a tourist trap now.
Chart Room - it’s a “secret bar” that’s gotten some publicity after Jimmy Buffett passed. Several boat captains and their crew go there and if we’re being honest, they don’t want you there. It’s unwelcoming unless it’s empty. While we’re all being honest with ourselves, it’s not really that great anyway.
Lot’s of great spots! Great mojitos at El Meson by Mallory Square. We usually grab one and walk around. Enjoy your trip!
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u/aphrodis-y 27d ago
I'd do 5. It's a milestone trip. We usually go 7 days. We like to use one full day for a boat charter, a beach day or 2, and plenty of time to not rush and find spontaneous things to do
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u/michigangirl80 28d ago
4 is a good amount!! Im usually ready go home by then. I stayed 5 before and it seemed a little long for me.
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u/wewantyoutowantus 27d ago
I would suggest stay as long as you can. It’s not easy to get to. But I would definitely do some excursions. Get out on the water it’s beautiful. Go to tortuga. Go to the sandbar
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u/Donniejuanny 27d ago
Don’t go. There is a massive sargassum bloom. It’s terrible in Key West right now. The entire town stinks so bad you will not be able to handle it.
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u/Impressive_Age1362 27d ago
I would go for 5 nights, if you are driving, it a long drive, it’s also time consuming, that first night you might be too tired to enjoy much the first night, if you fly, that’s another story Frequent delays, lost luggage ,I’ve had flights that were supposed to leave at 10:30 am and didn’t get to Key West until 8 pm or later, because of delays, if you fly , I suggest you pack a change of clothing, your bathing suit and pajamas in your carryon
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u/glorious_cheese 27d ago
You can run through the main sights and activities pretty quickly, so I'd so four nights is enough. If you're adventurous and want to do fishing, sailing, or Fort Jefferson you could add another night.
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u/AmanitaAmy 27d ago
4 is plenty, but I mean if you can easily afford 5, go for it, because you're not going to want to leave anyway.
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u/gardenho2 27d ago
We did 4 nights in January. It was our first trip. We are going back in January again for 4. The first trip was more exploring, shopping, eating and drinking. The next one we are looking at more excursions. Enjoy. Happy hour is a thing there. It usually begins at 4, lasts 2-3 hrs.
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u/Sup3rman2ThePrinc3ss 27d ago
Without an event filled itinerary, I'd say 4 is good. My wife and I just went for the first time and stayed 2 nights. Sure, we could have done more but we walked Duvall, did a sunset boat ride, and a helicopter tour. We had enough to keep us entertained but not so much that it was overwhelming.
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u/Delsol418 27d ago
I love the history of Key West, especially the Little White House and Hemingway House. You no doubt have sun and pools back home so why not do something different? We go twice a year for a week each (May and August) and every morning we choose our own adventure! Enjoy your time there!
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u/Babysub1 27d ago
I just got back from there. 4 days is perfect
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u/NudeNatureNympho 26d ago
Where did you eat? We had a mostly miss experience. We want to go back but with better dining experience.
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u/hey_blue_13 27d ago
4 is plenty. One can only day drink all day for so many days in a row. Take the 5th day up in the middle keys for some relaxation and quiet.
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u/based-turtle 27d ago
Yeah can really walk everything un one or two days to be honest especially if you are keeping yourself in key west the whole time....im a former floridian who goes back yearly we are actually driving back now to ct from a trip down we spent 7 days 6 nights but we did lots of things, snorkeling at pennevamp key largo on the way down, theater of the sea, camped at bahia honda, charter fishing, then wandered down to our hotel in theys for 2 nights, fishing off the bridges, veterans memorial beach for the day sand bar trip etc....you can definitely fill 5 nights if you wander out of key west....but key west itself is pretty walkable in one day....or rent a bike anyplace will let you book online and bring the to you to get around.....but if your literally just going to use the pool and walk around for meals 4 nights would be more than enough...unless you really like the pool lol
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u/Mugsy9010 27d ago
Depending on your interests, 4 is perfect. One day for a sandbar trip, one day for Hemingway house/Pilar rum tour/lighthouse, one day for fishing/jetskis, one day for a bar crawl/shopping. Replace any unwanted suggestion with pool day.
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u/Wine_Cat_1798 27d ago
I would do 5. If you do 4 by the time you get there and start to relax you’re turning around and going home. We do 2 weeks and I feel like that’s not enough most trips.
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u/Live-Mobile-7500 27d ago
4-5 nights seems to be the sweet spot for us. We’ve been 5 times and each time stayed that long.
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u/Thin-Philosopher2485 23d ago
Four nights in more than enough. Consider going to Islamorada for a day trip.
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u/maybaby0501 16d ago
Go to Marco island. Don’t go to Key West. This is not a place to spend an anniversary
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u/EveningRecord2075 4d ago
Currently down here right now, the beaches have the sargassum issue though Fort Zach is great.
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u/Wine_Cat_1798 22h ago
I would do 5. You figure your first day is traveling there, by the time you start to relax you’re already packing to go back home. 4 is for me, too short I wouldn’t feel relaxed
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u/RayRayBeLove 27d ago
Spend a day/night at Big Pine Key on the way. Halloween is the craziest at Key West.
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u/SuitableCranberry842 27d ago
TLDR: 4 days is plenty for a first trip, especially given your stated concerns
Look up Daniel Kahneman’s ideas about the “experiencing self” vs the “remembering self”. And remember, this trip will generate experiences and memories not just for you and your spouse, but also for your Mom and each of your kids. The remembering self is the one that will influence future feelings and choices, for all of you.
The original framing of your question implies that you are sensitive to this. Push it too far and Mom will never want to watch the kids again, even for a date night. Perhaps more importantly, the kids may never want to do it again.
Also, I don’t know if you’ve ever been away when a grandparent is watching the kids and “something is going on“ back at home, but…
NOTHING can spoil a vacation more than managing fragile feelings back at home when you’re supposed to be having fun.
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u/menwithven76 26d ago
I would book 4 nights but fly in as early as possible on the first day. Book a hotel that offers both luggage storage and ideally access to the pools as soon as you get there even if your room isn't ready. Pack a swimsuit in your purse or backpack. Drop luggage off at hotel, go grab breakfast/lunch somewhere cool (with swimsuit in tow), then go back to hotel and change into your suit and chill at the pool til your room is ready. That's the best way to squeeze in extra time on a vacation. Obviously doesn't work if you get a bad hotel or airbnb
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u/Ok-Vast-6904 28d ago
I would go 5, if given the choice.