How to best experience the Florida Keys?

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rocket354
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How to best experience the Florida Keys?

Post by rocket354 »

I've searched and read a lot of the old threads on this forum, and many seem to focus on Key West, in particular. Here's my situation:

We are trying to plan a multi-generational family trip for six (with a small chance of a few more) to the Keys, ages 8-80. Most everyone has never been there, so it is very much a bucket list excursion.

Trip would be either over the week of Thanksgiving, or Christmas-time. Trip length is variable, probably no shorter than 5 days just to not feel cramped, but no longer than 8-9 days if over Thanksgiving, and no more than two weeks if over Christmas. I assume, especially if it's over Christmas, that this is an expensive time to go. Budget is fairly open, but we are frugal by nature. General approach is 1) identify what we want to do, then, 2) find out how to do it as inexpensively as possible.

Current plan would be to fly into Miami and do the drive. Most of us have never been to the Everglades, either, so a stop there of some kind might be enticing, depending on time limitations.

There seems to be a lot of things to do all along the keys, so one consideration is trying to spend one to a few nights in a few different places. Tranquility Bay and Key West both seem likely spots. What are some other good places to consider? Might picking one place to stay for the duration and driving/travelling as needed seem better?

I'd definitely like to also see Dry Tortugas. Is one day sufficient, in general?

For interests, most of us love being in the water. Snorkeling, scuba diving, and boating are all welcome activities. A few of us would also really like to do "the beach" thing, even though it sounds like the Keys are not exactly ideal. Is there a "best" or at least an adequate beach somewhere?

I think most of us are less enticed by nightlife, or touristy places, so would be very happy in some out of the way spot (relatively speaking, of course). I suspect although we'd like to see what Key West has to offer, we'd probably prefer to not spend too much time there, maybe just a day or perhaps two, and then more time in other areas.

So, with all that said, what are people's thoughts on places to go/see, what's not to miss, what can be missed, and what are people's thoughts on the logistics of it all?

Thanks, in advance, for all advice!
Gill
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Re: How to best experience the Florida Keys?

Post by Gill »

I think the ideal place to stay is Marathon which is about half way through the Keys and enables you to take day trips in either direction. Also would not be too far from the Everglades if you wish to make that trip.
Gill
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Small Savanna
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Re: How to best experience the Florida Keys?

Post by Small Savanna »

We flew into Miami and drove - it's not that far, and you get to see the other Keys on the way to Key West. Thing we enjoyed in Key West: Truman's winter White House, the glass bottom boat tour, and a kayak tour through one of the lagoons / mangrove swamps. We ended up with some extra time in Miami and went to the art museum.
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Re: How to best experience the Florida Keys?

Post by Barefootgirl »

I used to travel there in the 80s, then recently again and found it to be an overcommercialized travesty, a mere shadow of its former self....ruined in my opinion.

What I'm getting at is that it used to have tons of organically grown human character and now, much like Times Square, it has been Disneyfied.

From now on, I'll just read books about KW and go elsewhere....sorry, my two cents. There are better places for island adventures.
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Matahari
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Re: How to best experience the Florida Keys?

Post by Matahari »

In case this interests you:

Along the drive towards the Key West, one of the most interesting things for me was seeing a big cross-section of the fossilized coral limestone that underlies Florida. You can see it here in the former quarry at Windley Key:

https://www.floridastateparks.org/WindleyKey
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Matahari
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Re: How to best experience the Florida Keys?

Post by Matahari »

Barefootgirl wrote: Sat Jun 19, 2021 3:25 pm I used to travel there in the 80s, then recently again and found it to be an overcommercialized travesty, a mere shadow of its former self....ruined in my opinion.

What I'm getting at is that it used to have tons of organically grown human character and now, much like Times Square, it has been Disneyfied.

From now on, I'll just read books about KW and go elsewhere....sorry, my two cents. There are better places for island adventures.
With regard to the commercialization, I absolutely agree.

If OP is planning on snorkeling, John Pennekamp Coral Reef State Park is one place to consider:

https://www.floridastateparks.org/parks ... state-park
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Re: How to best experience the Florida Keys?

Post by Gill »

Barefootgirl wrote: Sat Jun 19, 2021 3:25 pm I used to travel there in the 80s, then recently again and found it to be an overcommercialized travesty, a mere shadow of its former self....ruined in my opinion.

What I'm getting at is that it used to have tons of organically grown human character and now, much like Times Square, it has been Disneyfied.

From now on, I'll just read books about KW and go elsewhere....sorry, my two cents. There are better places for island adventures.
Totally agree. One of the worst things that happened to Key West is the cruise ships docking there. When they disgorge their 3,000 crew and passengers they completely take over that little island.
Gill
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SnowBog
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Re: How to best experience the Florida Keys?

Post by SnowBog »

Gill wrote: Sat Jun 19, 2021 3:12 pm I think the ideal place to stay is Marathon which is about half way through the Keys and enables you to take day trips in either direction. Also would not be too far from the Everglades if you wish to make that trip.
Gill
+1 This is our plan for our next trip.

We went to the keys last October. We flew into Miami spent one night there, drove to Key Largo, spent a few nights there, drove to Key West for the rest of the trip.

Driving through the "middle keys" area (around Marathon), the views were amazing. We saw nothing like it in the rest of the keys. So when we go back again, my goal is to spend most (if not all) of the time in the Marathon area. That said, Key West has its own vibe, amazing food, etc. We might end up back there for several days... Unsure if we'll relocate or day trip next time...
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Re: How to best experience the Florida Keys?

Post by THY4373 »

It has been decades since I drove from Miami to Key West so I won't comment on that though I remember enjoying the drive a lot. I went back to Key West (flew in) a couple of years ago and the highlight easily for me was a day trip out to Dry Tortugas National Park: https://www.nps.gov/drto/index.htm . One of the least visited National Parks but in my opinion totally worth the effort. I'd buy your tickets in advance if you are interested in this as there is one boat and I think one seaplane going out there and they sell out in advance.
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Re: How to best experience the Florida Keys?

Post by four7s »

Having lived in The Fabulous Florida Keys for 15 years I absolutely agree with the idea of using the middle keys around Marathon as your base. Hawks Cay on Duck Key would be perfect but can be a bit pricey around the holidays. YOLO. Please pay little or no attention to the naysayers on this thread. The Keys and its residents are funky and different. The favorite t-shirt of locals reads, “we’re all here ‘cause we’re not all there.” Commercialization has crept into the islands but it still remains a very unique slice of Americana and way off the beaten track. Life’s a breeze in the Florida Keys. Have a fabulous time. 8-)
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Re: How to best experience the Florida Keys?

Post by JonnyDVM »

If you want an easy Everglades experience on the way to the Keys, do Anahinga Trail. It’s teeming with alligators, fish, and birds.

As far as visiting the Florida Keys- don’t let the naysayers get you down. I love the Keys Experience. If this sounds like your cup of tea, my personal favorite way to experience the keys is to rent a house in the lower keys (Big Pine, Ramrod, or one of the Torch keys) with a dock and rent a boat as well. You can have a great time fishing, swimming, snorkeling Looe Key, and you can visit Bahia Honda by boat. You can also drive down and make an easy day trip to key west and a second day trip down to hit up the Dry Tortugas.
Last edited by JonnyDVM on Mon Jul 05, 2021 2:54 pm, edited 1 time in total.
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Watty
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Re: How to best experience the Florida Keys?

Post by Watty »

Getting hotel reservations may be a challenge. I've been planning some beach trips at other places and even in non-prime weeks in the fall many places are already fully booked up or real expensive. It seems like everyone wants a beach vacation this year for some reason. :D

Especially over Thanksgiving or Christmas it would be good to firm up your plans as soon as you can.

Rental cars are also in short supply so pay a lot of attention to those too.
rocket354 wrote: Sat Jun 19, 2021 3:03 pm ...ages 8-80....
It would be good to check the schedules to see what is going on when you are there since in Key West things can be a bit colorful at times.
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Ralph Furley
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Re: How to best experience the Florida Keys?

Post by Ralph Furley »

I've driven from Miami to Key West and back three times. Some people think I'm crazy (they fly), but I love that drive. It's part of the experience for me.
mike@jb
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Re: How to best experience the Florida Keys?

Post by mike@jb »

four7s wrote: Sat Jun 19, 2021 6:34 pm Having lived in The Fabulous Florida Keys for 15 years I absolutely agree with the idea of using the middle keys around Marathon as your base. Hawks Cay on Duck Key would be perfect but can be a bit pricey around the holidays. YOLO. Please pay little or no attention to the naysayers on this thread. The Keys and its residents are funky and different. The favorite t-shirt of locals reads, “we’re all here ‘cause we’re not all there.” Commercialization has crept into the islands but it still remains a very unique slice of Americana and way off the beaten track. Life’s a breeze in the Florida Keys. Have a fabulous time. 8-)
Hawk’s Cay is a great base for exploring the Keys. Great resort with great pools and access to fishing guides.
It’s not a bad drive to Key West from Duck Key.
However you can schedule it, you should spend at least one day at Everglades National Park.
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Re: How to best experience the Florida Keys?

Post by Vanguard Fan 1367 »

I love the Keys and to keep things within my budget I like to stay in the Homestead area. I checked my Hilton App quickly and came up with 2 November 2021 weekday nights in the Hampton Hotel South Homestead for 118 a night per room. If you would consider staying there then the Everglades are pretty close to that hotel. An option for a good beach would be Crandon Park, which is 34 miles from that Hotel. Crandon Park is on Key Biscayne and is the opposite direction of a Key West trip.

I agree with those who say that the drive to Key West is wonderful. I have done it a number of times. The view is fantastic. I still remember my dad who has gone onto his reward commenting on the great scenic drive as we did it.

Once you get to Key West your hotels could be a lot pricier in November and December than most places you have ever stayed. Key Largo might be a source for more budget friendly hotels than Key West.
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Re: How to best experience the Florida Keys?

Post by fishmonger »

You can definitely do Dry Tortugas in one day. It's a great spot for all ages as well - you can snorkel/be active, or also just walk around the fort and gift shop.

It would be pricey, but since you mentioned this is sort of a "bucket list" trip, I would highly recommend taking the seaplane out there. Our family of 4 did it (myself, DW and two kids 8 and 9 at the time), and it was a really cool experience. They still talk about it 2+ years later.

We found Key West a great place to spend 3-4 days. More than that and I think you would have to explore other parts of the Keys/Florida
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Re: How to best experience the Florida Keys?

Post by flyfishers83 »

My wife and I have rented a house on Marathon. We stayed on the water. We love it-have been back twice. Private pool so can swim/relax during the day. Snorkel right out back. I like to fish, and I’ve caught lots of snapper, small sharks, rays and barracuda. You could rent kayaks for the week. Makes for a very relaxing week for us, and you can explore the rest of the keys whenever you like.
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Re: How to best experience the Florida Keys?

Post by Goldwater85 »

The Keys are best experienced from a boat. If you can swing one with a large enough cabin.
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Re: How to best experience the Florida Keys?

Post by jcpct »

We did something like you are planning a few years ago. Flew into Miami and drove. We stayed in Marathon for a week renting a private home. Did one day trip to Key West but the rest of the time spent around Marathon. You mentioned you like boating...you will be in heaven because it seams everything is about boating and fishing in that area. One thing to check is if you are planning on renting a boat I believe you need a captains license or something like that to take a boat out on your own. Beaches are not the Florida style beaches I am used to. Mostly small and rocky but maybe there are some larger beaches we just didn't find. We did stop at Everglades Park on the way back to Miami and that was a nice and interesting stop.
I think if I ever went back to the Keys I would stay only in Key West. There is just more to do there. We found Marathon to be pretty limited.
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Re: How to best experience the Florida Keys?

Post by midareff »

Make reservations well in advance...... you are not the only one thinking Keys in the Northern US winter months.
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Re: How to best experience the Florida Keys?

Post by Shallowpockets »

Barefootgirl wrote: Sat Jun 19, 2021 3:25 pm I used to travel there in the 80s, then recently again and found it to be an overcommercialized travesty, a mere shadow of its former self....ruined in my opinion.

What I'm getting at is that it used to have tons of organically grown human character and now, much like Times Square, it has been Disneyfied.

From now on, I'll just read books about KW and go elsewhere....sorry, my two cents. There are better places for island adventures.
This is true for almost anywhere. You cannot go back now and expect it to be like the 80s. It is 40 years later. Most everything will have changed. More people, and all the trappings that they require. Don’t ever try and “go back”, to anywhere.
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Soul.in.Progress
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Re: How to best experience the Florida Keys?

Post by Soul.in.Progress »

Another recommendation for Hawks Cay, which is a resort on Duck Key near Marathon. Nice and central in the middle of the keys, away from party scenes (felt nice and residential), but also had a ton of resort activities: multiple pools on site, dolphin center on-site, restaurants onsite, free bikes, mini golf, soccer, basketball, volleyball all on site, ocean in our backyard which we used our own stand up paddle boards on. No beach per se, but there’s a small man made one for younger kids. We took a day trip to Key west since it’s a little over an hour to get to. We rented a unit with a kitchen.
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Re: How to best experience the Florida Keys?

Post by RickBoglehead »

We hit the Keys a few years back. Found it to be a low-end version of the Jersey shore. Snorkeling was massively unimpressive as compared to The Big Island. To each their own.
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Re: How to best experience the Florida Keys?

Post by galawdawg »

Goldwater85 wrote: Sun Jun 20, 2021 7:29 am The Keys are best experienced from a boat. If you can swing one with a large enough cabin.
Yes. To answer OP's question, "How to best experience the Florida Keys?", I'd say on, in or under the water. :beer
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Re: How to best experience the Florida Keys?

Post by RuralLivin »

I visited the Keys & Key West last year. I arranged my trip so I spent the night in Homestead (Hilton Garden Inn). I wanted to do the awesome drive early in the morning.

Fuel is slightly cheaper in Homestead than lower Keys. Having lived in a coastal environment, I always make sure I have enough fuel to leave the area in case there is a power outage due to an afternoon storm.

I did the ferry day trip to Dry Tortugas' Fort Jefferson and it seemed to be booked up a month in advance; it was nice trip, snorkeling is available, and the fort was amazing to see. The views from the ferry were great.

Fort Zachary Taylor State Park on Key West has a minimal parking fee, a much smaller fort to walk around, a beach (were shoes due to coral), picnic tables, shade, palm trees, PARKING, for a minimal fee. There is a snack bar as well.

PARKING can be painful in parking is not available at the hotel. Most parking spots on the street are re-reserved for residents, business, etc. I parked at the municipal garage ($32.00 per day, but it is covered!) and walked 1/4 mile to the hotel. It was a bit cumbersome with a suitcase; I'll plan better next time.
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Re: How to best experience the Florida Keys?

Post by Wilderness Librarian »

Shallowpockets wrote: Sun Jun 20, 2021 8:17 am
Barefootgirl wrote: Sat Jun 19, 2021 3:25 pm I used to travel there in the 80s, then recently again and found it to be an overcommercialized travesty, a mere shadow of its former self....ruined in my opinion.

What I'm getting at is that it used to have tons of organically grown human character and now, much like Times Square, it has been Disneyfied.

From now on, I'll just read books about KW and go elsewhere....sorry, my two cents. There are better places for island adventures.
This is true for almost anywhere. You cannot go back now and expect it to be like the 80s. It is 40 years later. Most everything will have changed. More people, and all the trappings that they require. Don’t ever try and “go back”, to anywhere.
Sadly this is case and frankly where I am having some uneasiness with retirement. Places I frequent in the west - backcountry wilderness, national parks, semi-rural areas, downtown Seattle - you name it everything is different and requires a somewhat different approach. As the saying goes you can never step into the same river twice.
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Re: How to best experience the Florida Keys?

Post by pennywise »

Vanguard Fan 1367 wrote: Sat Jun 19, 2021 11:13 pm I love the Keys and to keep things within my budget I like to stay in the Homestead area. I checked my Hilton App quickly and came up with 2 November 2021 weekday nights in the Hampton Hotel South Homestead for 118 a night per room. If you would consider staying there then the Everglades are pretty close to that hotel. An option for a good beach would be Crandon Park, which is 34 miles from that Hotel. Crandon Park is on Key Biscayne and is the opposite direction of a Key West trip.
I live in Key Largo and I would strongly caution against doing this. Don't know last time you used this strategy Vanguard Fan, but the single road to/from the Keys, US1 AKA the stretch (18 mile limited access road) is a nightmare to navigate pretty much any time during the weekend and during holidays. NOTE: there is actually a second route, Card Sound Road, but it's not as safe, is longer and has had some pretty scary situations including literal highway robbery.

Traffic into/out of Miami proper from Homestead is also a nightmare. OP's schedule puts them in South Florida during tourist season-especially an Xmas time frame-and going to Crandon Park from the very southern of the county will be a very long, VERY aggravating experience.

So trying to save some money by basing in Homestead you're committing yourself to extensive driving in unpleasantly crowded conditions to even get to where you want to go to enjoy your trip. Don't do it.

I'd definitely agree on booking a house on the water with a dock and if possible a boat. Ocean side will get you closer to reefs, gulf side will let you explore parts of Everglades by boat, as well as somewhat calmer water that is great for paddling a kayak, canoe or SUP. Sunsets on the gulf side will be spectacular, there's not much that is more pleasant than enjoying your favorite beverage on a patio watching that after a day of fun on the water.

Marathon/middle keys is also a nice sweet spot as a visitor. The upper keys (Key Largo/Tavernier/Islamorada) are more easily drivable from Miami for day trippers so there's more commercial-honky tonk development and, um, a lot more day trippers. Again, weekends and holidays are jam packed in this area for that reason. Most locals (me included) stick close to home because restaurants are jammed, roads are clogged, even grocery stores are obnoxious to deal with since you are shopping with everyone who needs their beer n subs for the day...and forget leaving the rock. You don't do that unless you're in an ambulance :annoyed

Key West is Key West. About a third of the entire population of the entire county is jammed on a VERY tiny island. It's definitely colorful, and definitely a mecca for colorful behavior LOL. Fun for a day trip but not sure a family vacation would be optimal. Again, you can easily hop down for that day visit from Marathon. In addition to the spots mentioned, Hemingway's house is a very cool tour including those famous six-toed cats. Lots of other interesting historical tidbits since for many years Key West was pretty much the only area of the Keys that was populated.

And for sure get out to see Ft. Jefferson and the Dry Tortugas. Also agree if you can swing the seaplane that's the way to go. It is quicker than the boat, you fly low enough to see some very cool wreckage and reef areas and hey, it's a seaplane and how often can you ride around in one of those?!

Be sure too to take advantage of some good dining options. There are some fabulous chefs doing amazing creative cuisine using (of course) fresh seafood, island/tropical fruits and spices and Latin influenced techniques and menus.
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rocket354
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Re: How to best experience the Florida Keys?

Post by rocket354 »

OP here. First, thanks to everyone for the wealth of responses. This forum is great!

One item of concern is the boating. The max boating experience in our group is piloting pontoon boats on medium-sized lakes. Am I right in assuming that more experience/licensure might be required to fully take advantage of any boating around the Keys?

A few people have mentioned restaurants. Are there specific recommendations?

I'm starting to formulate the beginnings of a plan. I'm thinking of arriving early- to mid-week and spending two or so nights in the upper keys, where one day can be mostly at the Everglades, and the other day can be in the water. Then three or four nights over the weekend in the middle keys where snorkeling/boating/kayaking and driving to all sights we find interesting can be done. Then, finally, two or three nights in Key West during the early to middle of the following week, where we can spend a day checking out the island and another day at Dry Tortugas. This might limit our exposure to crowds as much as possible since we'll be in the hotter spots (upper keys, Key West) during the week, and in the middle keys over the weekend.

And, yes, the hope is to have a more fully fleshed-out plan, and to make reservations by the end of this month.
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Re: How to best experience the Florida Keys?

Post by wabbott »

We were there in early April. It was our first time to visit, and I think we would go back if ever the chance presented itself. We liked the drive itself best, especially seeing the remnants of the old Overseas Highway bridges.

We did this one afternoon at Key West, and felt like we got our money's worth.

https://www.dangercharters.com/wind-wine-sunset-sail/

The original Wind & Wine Sunset Sail by Danger Charters lets you experience the spectacular Key West sunset while enjoying fine wines, premium beers, and delicious appetizers aboard an authentic 65ft skipjack sailing schooner. This top-rated sunset cruise leaves Key West in the evening and glides toward the horizon under a cloud of sail to provide an unforgettable adventure at sea.
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Re: How to best experience the Florida Keys?

Post by EdNorton »

November is a good time to visit the Keys but it is particularly windy in November. The boat trip to the dry tortogas is several hours, and if anyone gets seasick, it will be a long day.

Also, beaches are fairly rare in the Keys, there are some beautiful ones like Bahia Honda, but they are not like the wide sand beaches of the rest of Florida.

For young kids, I'd recommend elsewhere in Florida.
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Re: How to best experience the Florida Keys?

Post by Hockey10 »

Gill wrote: Sat Jun 19, 2021 3:12 pm I think the ideal place to stay is Marathon which is about half way through the Keys and enables you to take day trips in either direction. Also would not be too far from the Everglades if you wish to make that trip.
Gill
This is exactly what we did in 2019 based on advice from Gill. It ended up being a great trip. We did a day trip to Key West on one of the days we were staying in Marathon, and it worked out fine. Thanks Gill! :D
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Re: How to best experience the Florida Keys?

Post by Gill »

Hockey10 wrote: Sun Jun 20, 2021 12:37 pm
Gill wrote: Sat Jun 19, 2021 3:12 pm I think the ideal place to stay is Marathon which is about half way through the Keys and enables you to take day trips in either direction. Also would not be too far from the Everglades if you wish to make that trip.
Gill
This is exactly what we did in 2019 based on advice from Gill. It ended up being a great trip. We did a day trip to Key West on one of the days we were staying in Marathon, and it worked out fine. Thanks Gill! :D
Glad you enjoyed the trip and I guess my advice hasn't changed! I've travelled through the Keys by cars, motorcycles and bicycles and always enjoyed the experience. Riding the seven-mile bridge on a bicycle is one I'll never forget!
Gill
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Re: How to best experience the Florida Keys?

Post by BrooklynInvest »

Was just there. Neat place to see but for longer than a day or so a bit raucous for me. Each to their own.

Flew direct from NYC this time and went fishing - lotta fun. The last time I was there, about 15 years prior, I rode my motorcycle down. Beautiful but tough in the summer heat. Wouldn't do it again without abundant air conditioning. Staying outside Key West and visiting for a day or an overnight sounds right to me.
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Re: How to best experience the Florida Keys?

Post by Sandi_k »

We love the Keys, but opted out this year. When I looked for hotels in November (such as the Southernmost Hotel) were asking $750+ per night, when we paid $300 in 2016.

Also keep in mind for family travel - Key West can be RAUNCHY, especially during Fantasy Fest, when public nudity is the norm. For 2021, it's scheduled for October 22-31, but the participants can hang on for another week or so.

We stayed at Tranquility Bay a few years back - a very family-friendly resort in Marathon, with beach houses for rent on the property.

booking.com/hotel/us/tranquility-bay-beach-resort.html
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Re: How to best experience the Florida Keys?

Post by Vanguard Fan 1367 »

pennywise wrote: Sun Jun 20, 2021 9:49 am Don't know last time you used this strategy Vanguard Fan,
I haven't used that strategy for several years.

I drove to and from Islamorada on Labor day some years back. My parents said that never again would they travel north from the Keys on Labor day. The traffic on the northbound (return) trip was pretty bad!

I appreciate your comments on my low budget Keys travelling. I wondered what folks would think.
John Bogle: "It's amazing how difficult it is for a man to understand something if he's paid a small fortune not to understand it."
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