(Closed) Key West vacation! Advice?

posted 5 years ago in Travel
Post # 4
405 posts
Helper bee
  • Wedding: July 2013

Sorry cant help. I was in the same boat as you and fell in love with the Checca Lodge or something like that in Islamorada but it was pricey and after reading reviews I changed my mind and we found a better deal elsewhere. Im thinking maybe try a Hampton Inn or something and look up the special offers or deals you may qualify for.

Post # 6
720 posts
Busy bee
  • Wedding: October 2012

I spent a lovely 3 days there including NYE in 2010-2011. It was wonderful! We drove from Miami and the drive was nowhere near as scary as we thought it’d be. The weather, in December/January was quite warm though not hot. The people were all really nice. The nightlife was obviously great, though tended to be an older/middle-aged crowd. The lodging prices were indeed high, we had a deal for a boat b&b.

For sightseeing, do NOT miss this: http://www.hemingwayhome.com

For food, do NOT miss this: http://www.pepescafe.net/

Post # 7
1458 posts
Bumble bee
  • Wedding: January 2015

July is usually the slower season, so you definitely could get something for less than $200 a night. I would recommend getting a hotel near a higher mile marker, as long as you don’t mind that it won’t bebeachfront. All the sandy beaches in Key West are man-made anyway, so it doesn’t matter too much.


I love the keys for the snorkeling, so I can only really recommend you where to snorkel πŸ™‚ John Pennekamp park (not quite in key west, further up the keys) is wonderful and they have awesome boat tours that come with the snorkel gear so you don’t have to buy your own.


Depending on how long you’re in Key West, think about making a day trip out to the dry tortugas. There are boat tours and plane tours, obviously with the plane being way more expensive. The snorkeling is phenomenal, and the fort is amazing. It is one of my favorite places on earth! It is SO HOT in July though. Ridiculously, swelteringly hot. Stay hydrated!


Post # 8
634 posts
Busy bee
  • Wedding: October 2013

@prettyinpink11:  We stayed in a Bed & Breakfast which was reasonable.  Maybe you should look into those.

Post # 9
9954 posts
Buzzing Beekeeper
  • Wedding: December 2012

Hi @prettyinpink11:  Mr TTR and I LOVE the Keys, infact that is where we Eloped to for our Destination Wedding… just the 2 of us marrying on the Beach.

The Keys are spectacular year-round… BUT July will be super-hot and humid !!  You can fly in, or drive down along the Overseas Highway (one of the prettiest drives in America).  If you fly in to somewhere else in Southern Florida than KW, I suggest Fort Lauderdale over Miami if you have a choice, Miami Airport is a zoo !!

The Overseas Highway is gorgeous.  Be sure to have your camera at the ready, cause you’ll take photos as you go.  And plan twice as long for the drive vs what you read on Google Maps, because you’ll want to stop here and there along the way… and it is a 2 lane road, one southbound and one northbound, so if there is any accident or delay… it will be slow going (or traffic on a weekend etc)

Accommodations in The Keys are expensive… because it is just like going to the Caribbean (but all the comforts of home).  $ 200 or under will be tough, but do-able (most Hotels we’ve found start at about $ 250 or $ 300… depending on WHERE you are in The Keys, proximity to the Waterfront, Beaches, or in KW Duval Street).

If you stay in KW consider looking not at the Brand Name Hotels but the smaller private Hotels, Guest Houses, B&Bs etc.  And as I said the farther off Duval the less you’ll pay.  BUT it is nice to be within walking distance… because parking a car is a nightmare !!  Getting around the island can also be done by Tour Trolly (good way for an overview and getting around at least one day with their hop-on & hop-off service), or you can rent a Bike, Scooter or Moke.  Or get around by cab or pedi-cab.

Mr TTR and I like the Southernmost Hotel Group which is at the far east end of Duval… near the Southernmost Marker… but it isn’t cheap accommodations (I’d call it moderate).  Stay in the Southernmost Hotel (vs Southernmost on the Beach) and you can still enjoy all the benefits of the Resort.  Rooms are clean, and the staff great !!

When you are on TripAdvisor, be sure and check out not only the Reviews Section for Accommodations (Hotels, B&Bs, Rentals etc) – Restaurants – and Things to Do… but also check in on the Forums (like the Boards we have here on WBee) you can chat with Destination Experts and Locals and get great info / feedback and any Questions you have answered personally.

Hope this helps,

PS… Here is a post that I did for another Bee… it has a TON of great info in it.


PPS… I have oodles of info to share… you can always drop me a PM (personal message) here on WBee


Post # 11
9954 posts
Buzzing Beekeeper
  • Wedding: December 2012

TO @prettyinpink11:  glad to help the Destination Experts in Key West are AWESOME… a fun bunch.  And extremely helpful… they were fantastic when Mr TTR and I were planning our first trip there 5 or so years ago.  Lol, I don’t know if they still do it (check the Forums to see) but once upon a time they had a weekly meet up with Visitors at a local Bar for Happy Hour.  It was fun to go and have a drink with some of the locals and folks you had met thru chatting on-line with while planning your vacation.

The Keys & KW has a HUGE LOYAL following (of which Mr TTR and I now count ourselves part of… definitely suffer happily from “Keys Disease”).  We now try to get down to The Keys every couple of years… it was an easy decision to marry there.  And well the Sunrises & Sunsets are phenomenal.  Places like The Southernmost Hotel on the Beach, actually a spot that can afford you views of both of them…

LOVE The Keys.  Truly a unique destination… the second you drive away from the Florida it is like you’ve enterred another world (definitely more Caribbean than NA).  Quickly can understand WHY at one time these guys wanted to be a “seperate” country (look up the entertaining history of The Conch Republic).

Hope this helps,

PS… KW is known for its party atmosphere but there is sooo much else going on there… so be sure to learn as much as you can.  Food & Drink is excellent (including a strong Cuban influence) – History – Culture – Water Activities – Music & The Arts (be it the local theatre scene, the Drag Queen Review, or just the fact that KW has always been a draw for the talented amongst us… Ernest Hemingway, Tennessee Williams, Robert Frost, John James Audubon, Truman Capote, Calvin Klein, Ralph Lauren, Judy Blume, Jimmy Buffet and Kenny Chesney to name but a few).  Taking the Old Town Trolley Tour is one way to get a good introduction to the city, its people & history.. and where things are etc… and as I said it offers hop-on & hop-off services too.

PPS… Lol, we LOVE Fort Myers too… the day we arrived in KW we left Fort Myers Beach in the morning… drove across the REAL Alligator Alley (Hwy 41) and then made our way south from Homestead (via Card Sound Road to Key Largo… and then onto KW).  Made 2 favourite pitstops… Alabama Jacks (Card Sound Road) for lunch… and Holiday Isle Tiki Bar (Islamorada) for a cocktail… then back on the road pulling into KW in plenty of time to catch the Sunset.


Post # 13
9954 posts
Buzzing Beekeeper
  • Wedding: December 2012

TO @prettyinpink11:  funny you should mention that…

Our next trip to Florida we are going to focus on the Gulf Coast Islands… so Cedar Key – Clearwater Beach thru to St Pete Beach (we’ve done this a couple of times previously) – Terre Verde – Mullet Key – Longboat Key – Siesta Key – Manasota Key – Boca Grande – Pine Island – Sanibel & Captiva Islands – Lovers Key – and Marco Island.

Lol, all in the pursuit of sunshine & happiness… and finding the right place to spend part of of our Winters in the not too distant years to come.

PS… Good luck with the SIUP.  May a little “Keys Romance” come your way… truly a wonderful place to vacation (propose ?), marry or honeymoon… definitely one of our faves.


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