Help formulate itinerary for Florida keys
 

Hello all,

Trying to plan our semi-annual trip with no kids and need your help! With three little ones and stressful jobs - we are prioritizing relaxation, romantic dinners and fun "together time". We are therefore leaning towards traveling to the Florida keys in April for a fun week (5 -8 days) of sunshine.

A bit about us -- couple in mid 30s. We like sightseeing but also a good amount of relaxation time. Our usual pattern is doing activities or sightseeing in morning/afternoon but stopping for early cocktail hour. We like road trips but absolutely don't want to spend the entire trip driving. Husband loves boats and we hope to rent one for a day or two. I love art, gardens and dancing. We appreciate beautiful hotels, foodie type restaurants and a fun nightlife scene.

So, hoping for itinerary ideas.
How many days total do you think we need?
Thinking of flying into Miami and spending 1 or 2 nights?
Then onto key west? Should we stay somewhere in between?
Recommendations and suggestions welcome!!

This is our favorite grown up getaway...

Take ground transportation from Miami airport (no rental car yet) to South Beach... There are dozens of properties along Ocean Dr., but a better choice are the few luxury hotels at the North end of the strip directly on the beach with Collins AV addresses...

These include the Loews, Ritz Carlton, or the Royal Palm... They are amazing and only a short walk from the clubs, restaurants, and shopping...

Everything you want is nearby and you don't have to cross Ocean Dr to hit the beach...

When you are ready after two or three nights, there are rental car agencies nearby for your drive down the Keys... We always left after a tiny breakfast, in late am... This will also keep you out of rush hour traffic... The total drive is 3 to four hours so make it an event by adding a lunch stop... We choose Islamorada for fresh seafood, Cuban food, or the "new place"...

Finish your drive in Key West around check in time, park the rental, and plan on three nights minimum... Consider The Gardens Hotel, Marquesa House, but avoid chain hotels and insist on being in Old Town... If they are booked, try
www.historickeywestinns.com as a back up...

You should always add a bumper night back in South Beach, so you don't have a panic race back to Miami on flight day...

Since we are leaving this morning for Islamorada, curious about where you like to eat there, Gary...

I guess we have booked the worst week of the season, weather wise...sounds like a hurricane outside our place in PBC right now! But we will have fun....even in the rain we love Islamorada. We usually eat at Ma's but they are closed tomorrow, hence my question especially about your " new place.". Thanks.

we are prioritizing relaxation,

Now there is a modern oxymoron.

_______
We are going to the Keys for the first time this March, look forward to the suggestions.

I always hesitate to recommend places unless I have been there within the last year... However tripadvisor just listed their top picks for 2016 this week...

I would fly into Key West and not bother with a car. Key West is walkable and has lots of interesting things to see and do. Stay in Old Town. I prefer The Island City House. If you want, rent a car for the day to do a little exploring outside of the city.

Just had our usual good dinner at Ma's....cracked conch, chowder, and a wahoo dinner plate, followed by the best Key lime pie in the Keys. We are big fans of Ma's for value but they are not on the water in case anyone cares.
But nothing in the area is "cheap;" that dinner just described cost us almost $70 with a glass of wine and tax and tip.

Tomorrow, Wednesday, their closing day, we might cook in the cottage, or try M.E.A.T. We are finished with high-end places in this area after a couple of disappointing experiences over the past few years. My advice in this area is to pay special attention to which fish are local and which come from afar and might be frozen (salmon, halibut, maybe shrimp, etc) If you have access to cooking facilities, even better.

I like Gary's plan, especially if you are going for 8 days. 4 -5 days for Key West is plenty.

We just booked a few days at Merlin's in Key West, anyone familair with it?

We are also spending one night with old friends in Islamorada, and want to thank them by taking them to dinner. Is Ma's OK? Is there another place.

Thank you.

Garyt22 describes an ideal trip. We did it in reverse, and it was a bad idea. His was better.

I would not fly into Key West because the drive is beautiful, in both directions. Maybe if I were a FedEx driver who had to get there no matter what, I would hate it. But on vacation?

IM: Ma's is the type of place that I am almost certain YOU would like. But not "impressive" if you are looking for a "special" place to take friends. It is right on the main road. Most diners are fishermen/women from up north, or locals. The value is the best you are going to find in this pretty pricey area..

They will cook your own fish for $12 a person (check that to make sure) if that is an option..I think Cheeca Lodge, a block north, charges $40 to do that (we asked once for friends who were chartering a boat for a day and they were happy with Ma's)

Knowing your own taste from your posts here I have no doubt you would like Ma's, but just keep in mind that there is no view. Their Key Lime pie is said by many to be the best in the Keys. It's the kind of place where the staff remembers everyone..our wait person even recalled what I had ordered last January and how I had admired her child who was eating there on his birthday.

Tonite Ma's is closed so we have to explore other options or cook in our cottage....I do not put much stock in tripADvisor restaurant reviews but will ask the locals for ideas and report back if I find anything.

There is a Showtime movie, Bloodline, that was filmed at this cottage colony; we've not seen it cause we do not have that service at home.

IMHO parts of the drive to Key West is beautiful, but certainly not the majority of it and depending on the time of year, it can be very crowded and a pain to drive.

That's why I suggested while in Key West, renting a car one day and driving to see some of the attractions.

Thank you EKS. You are right I like restaurants that are good values but we are also adventurous. Have you tried Steve's Key Lime Pie and how does that compare to Ma's?

But we want to thank our hosts which sounds like it will require a little better place, even though they are people who like basic food.

Thanks again.

I understand.

I've tried the Steve's from Red Hook and think Ma's is better...they have a graham cracked crust and top it with meringue and with whipped cream as well. The owner of Ma's if now selling them by mail order.

For fancier, look at Pierre's; I think this is liked to the cottages where we stay:

http://www.moradabay.com/pierres/dinner/

Morada Bay Cafe and Pierre's are where I would suggest. Same property (both are part of Morada Bay Resort) but Morada Bay Cafe's dining room is in the sand on the beach and Pierre's is in a proper building and therefore more formal. But on a beautiful day or beautiful night I'd pick Morada Bay Cafe any day of the week. I've eaten there dozens of times and never had a bad experience. I've eaten at Pierre's twice and it was very good as well.

Ekscrunchy if you are well acquainted with the Keys you'll love Bloodline. Enjoy your stay, I sure miss the keys.

Thank you for the suggestions.

When I think about it again, Ma's might be a good bet, as long as they do not need a view. Wherever you decide, you must stop in there for the Key Lime pie and you can decide how it stacks up to Steve's. I adore that dessert, but it's not easy to find Steve's in my area....I am the better off for that, I guess. I broke my shoulder last summer and been laid off from swimming until the past couple of weeks, and even have to take it easy now, and when I look in the mirror, it seems like the last thing I need is to be doing a Key Lime pie taste test!!!!

The other place, open for dinner only, is Michael's; take a look at their menu. It looks lovely, no water view, though.

http://foodtotalkabout.com/

And here is Pierre's, on the bay side and probably has good view...check out those prices, too. If you want, I can walk over there and take a look for you....

http://www.moradabay.com/pierres/

http://www.moradabay.com/wp-content/...er-10-2015.pdf








Limmy, I will try to watch the show....one of the guys who works here had a part in it. I sure understand how you might miss this place....it's really its own special world down here....

Thanks again, I hope you are doing better.

Our own family Thanksgiving gathering was in a spacious rental on Cujoe Key. About 20 mi. from Key West. We did do sightseeing...recommend Old Town Trolley which circles the island. There are beaches, Butterfly Conservancy, the Aquarium, Hemingway house, Truman little white house, marker at end of U. S. 1. Nice to just stroll down Duvall or around Front St.

Also sunset at Mallory Square parking lot is a nightly local happening. Eateries we enjoyed: Conch Republic Seafood, Grand Cafe, Blue Haven, El Meson de Pepe all good.

But some of the time we just relaxed and chatted and snacked at our Casa Cujoe with its nice swimming pool.

http://sunrisecubancafe.com/Home.php best Cuban and great coffee but https://www.facebook.com/Cafe-moka-t...5628045782928/
has great French food so my husband goes to sunshine and I go to Cafe Moka and we have a picnic outside.
mm92 I think

TortugaSailingAdventures.com in Stock Island provide private custom day and overnight "At Sea" experiences at reasonable rates and has the "Certificate of Excellence" rating with TripAdvisor.

Hello again everyone, thank you for your thoughtful replies.

From past trips we have learned that we enjoy staying in 2 places (3 max). Usually one city stop and one more rural stop - -with the city done first. So GaryT's itinerary sounds perfect. Miami then a leisurely road trip to Key West.

We are looking at 2-3 nights Miami.
3-4 nights Key west.

Right now I am researching itinerary details, hotels and things to do.

We most enjoy upscale hotels with private balcony (with a view) preferably within walking distance to town. Ocean Key looks nice -- although Gary T recommended no chains. Can anyone advise?

I have also been looking at house boat rentals in Key west because the husband loves loves boats. Would this be too isolated?

Key West is one of the handful of places in the US where the character of the Town is based on its architecture... Old Town features grand old mansions, Ship Captains quarters and a distinct style that screams Key West...Even new properties are designed to mirror the Southernmost style.... These "boutique" Hotels and small Inns allow you to experience the Key West "vibe" at a maximum level...

The Gardens Hotel is an estate converted to provide an experience unlike anything available at a chain... There are dozens of similar properties in Old Town that offer the vibe at all price ranges... The major chains were the last to arrive, with multi room properties, but unable to create the feel of KW...

The Ocean Key is a high quality property at the base of Duval Street, featuring balconies overlooking Sunset Celebration and Duval St. , but it's a hotel that could be anywhere in the world with hotel rooms... It can also get crowded down there, and cruise ships often dock there blocking the water view...

Key West is the one place that where you stay matters... There are marriotts and hyatts for your other cities, choose an historic design for this one trip...

Those going to KW often are unaware there is a commercial area outside of Old Town that holds several chain hotels, motels, and time share properties... Avoid this area as a vacation killer...

Do some research on Old Town Key West... And have fun

ok thank you Gary - point taken.

So just to clarify - there is key west and old town. Are these different places? or just different areas? I obviously need to look closer at a map. So chains are outside of old town?

As you enter Key West, you will drive through NewTown which is the commercial area... You will then cross into Old Town, which where you want to be... The spine of Old Town is Duval Street which you can walk end to end in less than 30 minutes...

The charm of KW is there...

Regarding the chain hotels... Some are in Old Town and they are great properties, however you miss the magic of KW by not experiencing the boutique hotels and Inns....

Although my suggestion for flying into Key West was not well received by others in this thread. I did mention to stay in Old Town. There are many Inns and such. My favorite is Island City House. Do not stay in one of the big impersonal hotels.

www.islandcityhouse.com

In old town I really love Marquesa Hotel. Have also had nice stays in at Simonton Court. Marquesa feels special though.

I've never stayed in the Truman Annex area but you might take a look for accommodations there.

Are there any boutique hotels you would recommendation that have balconies? Or view of a harbor?

Marquesa has some rooms with balcony and some ground level rooms with patios. They do not look out to the ocean but are lovely none the less. For ocean view try the Pier House. Pier House is one of the easier places to stay parking-wise if you have a car too. I haven't stayed there myself but I have heard good things. The location is very good and it's one of the few properties on the water that isn't a mega chain resort.

thanks everyone for being so helpful and patient with me!

So now we are seriously considering spending a few nights in Key west and then ending with a few nights in Islamorada (for a really quiet relaxation finale to the trip).

What do you think of this?
Day 1 - early arrival miami / overnight miami
Day 2 - Miami / overnight miami
Day 3 - Leisurely drive to Key West / overnight KW
Day 4 - Key West / overnight KW
Day 5 - Key West / overnight KW
Day 6 - Drive up to Islamorada / overnight Isla
Day 7 - Isla / overnight Isla
Day 8 - overnight Isla
Day 9 - Depart Isla for 5pm flight Miami

SusieQQ, we're flying to Key West from FLL. Just don't have enough time to make the drive (we'll have 3-1/2 days in KW)

steviegene, I think your itinerary looks fine. It would be more direct to fly into key west and out of Miami, moving your overnights in Miami to the end of the trip. But most direct might not be a priority as much as breaking up each move into easy, leisurely segments and in that case your plan works.

As for adding in a couple nights of quiet relaxation, if you are up for a splurge look at Littke Palm Island instead of Islamorada. It really is a splurge ($$$) but a worthy one if budget allows, it's a magical little island. Otherwise a couple nights in Islamorada is a nice contrast to key west and will put you in striking distance of sights & attractions offered in the mid-upper keys. It will no problem making your 5pm flight from Islamorada, easy enough trip.

If you want to stop for a meal between Key West & Islamorada you can't do better than Square Grouper in Cujoe Key, it's my favorite restaurant in all of the keys.

One of my favorite hotels in the US is The Moorings Village on Islamorada. We just returned from 5 nights there and have made our reservations for next year. Accommodations are in private cottages rather than rooms...all are steps from the beach. YOu rarely see other guests except at the pool. There are no on site restaurants but there are some down the street. Not sure if they take two night bookings but you could call them and check and I can give you info on the various cottages....

Thank you again everyone.

A couple more questions if you don't mind.
We are trying to nail down itinerary and have started to get a little nervous about "busyness" of key west. How much of a problem is cruise ship inundation? If anyone has been ---- we love St. John but do not like st Thomas. What kind of speed is key west?

In April it might be more St Thomas-ish. I'm sure I am in the minority here but when I was there last..only on a daytrip from Islamorada, I found it a little crowded for my taste. Undoubtedly gorgeous architecture though, unlike most of the Keys.

My thoughts are the same as Ekscrunchy. Mallory Square area & parts of Duval can be a bit much but there are many quiet blocks dotted with gorgeous historic inns and banyan trees.

Here is a calendar of cruise ships: http://www.cityofkeywest-fl.gov/department/calendar.php

ugh now rethinking everything!
As much as Key West seems fun.... maybe not entirely our speed. REally hate the cruise ship vibe and being buried in seas of people. Wondering if 5 nights in Islamorada would be too boring.
thanks everybody!!

Key West is what you make it. There are many quiet, relaxing Inns away from the crowds. There are plays at the theaters, concerts, good food, boat trips, scooter rentals,etc. It is fun to go once to Mallory Square.

One day in Islamorada would be too long for me.

In terms of transportation, this site has you covered http://www.tampalimousinevip.com/. Just check them out they give free quotes and flexible rates.

First thing, you have to have transportation through and about the city. http://www.miamilimocars.com/ is the best bet to get this done.