Hi All… hoping I can get some help and advice here. My wife and a I were planning a fly and ride from Miami to Key West. Flying in from Boston first week of March next year. We have a couple of questions that we hope you can help with.
1. Is this a good time of year, weather-wise to make this trip?
2. We’re on a limited schedule so does it seem reasonable to pick the bike up in Miami and make it all the way to Key West in one day? We were planning on spending the second day just riding around the keys and then heading back on the third day to return the bike.

I’ve done a fair amount of fly and rides but I’ve never ridden the Keys so I have no idea what to expect. Hence why I’m asking here
Any advice, insights, must sees, hotel/restaurant recommendations are of course always welcome too!!
Thanks so much in advance!!! Totally looking forward to getting out of the New England winter for a few days in Feb!

 

We have done the ride several times, coming from NY.

March is an excellent time of year, it will be summer VS our winter in the Northeast. From Miami it is only a one day ride. It is slow going and sometimes you can get into some traffic, but overall it is a beautiful ride. One day is more than enough. Depending when you leave and how many times you stop, you could be in KW for lunch.

Key West is a party town. If that is your scene, get a hotel walking distance to Mallory Square and Duval street. After you check in, park the bike and go for a walk. Good times will follow immediately. Be in Mallory Square for sunset.

See more of the Keys on the way home the next day. Have fun.

 

NH eh? Used to live just south of Keene in Rindge. GREAT state for riding as you know.

When going to the Keys my friend (and I have been there MORE F'n times than I can count) there are a bunch of fun things....

As you go south outta Miami and are in Florida City 'juss b4 you head into the Keyes, on the LEFT SIDE there is "Card Sound Road" only locals really know abt it. It is 6 - 7 miles longer but WAAAAY NICER a ride. And NO real traffic to talk abt.
.Careful my friend, it is a sharp left. It is pretty straight. When it starts to curve SLOW DOWN. 'juss b4 the bridge ($1) on the right is Alabama Jacks. Biker Place. After u go over the bridge which is SHARP HIGH and makes u think the bridge does not continue and u will just fall off. LOL!

Anyway, at the end take a RIGHT.

Abt 23.5MM (Mile Marker) on the RIGHT is Boondocks Grill. GREAT PLACE to eat/brew. NVR had a bad meal thee. SO GOOD I brought my wife down there.

7 MM (easy to miss) on the RIGHT is a skydiving sign but there is a BAT Housing thingy - NVM, I think it blew down in a hurricane.

You MUST go to the most southern place The BOUY in the USA.
.It is at the corner of WHITEHEAD and SOUTH streets.
.FAMOUS PIX taking area.

You will see the also famous Duval street in the above PIX., YOU want the OTHER END of Duval St. That is where Mallory Sq is and 211 Duval is Irish Kevins Pub. <-- 1 of 'me FAV pubs.

The 7 mile bridge (which is really not 7 miles) ...... well, if u r 2 on a bike make sure the pillion gal takes PIXs. Really nice.

Wahoo's Bar and Grill below.
/IS on the south side of Isalmorada. OCEAN side. (Right side as you leave the keys.) Try to sit in the area I marked. You can order food there, drinks... OVERLOOKING the Atlantic and boats. NICE!

Used to have REALY lobster sandwih which was PHENOMENAL. Sadly they do not anymore. Grrrrrrrrrrr.

Anyway.........the above will get u started.

Oh, Blue Heaven Restaurant is famous down there, Ernest Hemmingways place (near the bouy) etc..........

It is EXPENSIVE to stay in the keys anywhere. Prepare for that if u would. But u will make GREAT memories there.

...............enjoy!

 

WOW Guys!!!

I cannot thank you enough for your suggestions and insights! Both you guys are making us wanna go even more now!!! Not really much into partying these days more so than just pulling up to a good bar with good food and enjoying some downtime. I know by February, we'll be chomping at the bit to get the heck outta NH.

See.... THIS is what makes this forum so awesome!

Thanks again!

 

Hey DinoM, I fixed it for you above. No worries. No charge.

Hey, when you address the MOM (Member Of the Month) Architect, you are supposed to address him bowing and "Your Majesty". .... 'juss say'n.
..

Awww, come over here Architect.

Ok, time for a group hug...........
Can't catch me. Peeeeeooooooowwwwww...........

 

LMAO!!! Thanks again gents! Still don't know how to put those emoji things in the message... oh wait.... is this it?
If you happen to be down in the Keys first week of March and see a big Greek dude on a Road Glide Ultra with a beautiful redhead on the back, looking kinda lost, just yell Dino!!! First round is on me!!!!

 

Depending on your dates, if you are there the week after Daytona Bike Week, you may run into lots and lots of bikes in the Keys, the Survivor's Party.

I recommend stopping at Alabama Jack's on the way down.

We also like:

For lunch: https://www.bobalusrestaurantandbar.com/menus.html

For dinner: https://blueheavenkw.com/

On the way down or up:

http://www.burdineswaterfront.com/
https://boondocksus.com/
http://www.kikissandbar.com/

In Key West, hard to find a bad bar or a bad meal. Duval street is the tourist strip, great bars and music, probably not the best place for dinner. Off the main drag, lots and I mean lots of great places to eat.

And in town, stop for a drink:

https://www.hogsbreath.com/

 

Super Bowl Weekend 2021 my wife and I and a buddy did exactly what you are planning . Ride from Miami to Key West is a piece of cake in one day. Have rain gear for the inevitable afternoon sun-shower. Since you are planning a March trip, you should be OK since you are outside of hurricane season. One day down, one day back and one day sightseeing is OK if you arrive as early as possible and depart as late as possible. Have fun.

 

Miami to key west is only about 3 hours .
nice ride do it all the time but from Lauderdale.
Last chance saloon . across from the entrance to cardsound rd.. Gilberts, caribean club ect are some of the northern stops

 

Oh yeah, talking abt hogsbreath, in back (or front depending upon how u enter the place) they have some NICE T's there. Cheap crap but nonetheless, some of the graphics are nice.

Out back, where the T's are, u can cross over the street there and go to Peterson HD. Clothes only.

Yuppers, finally stopped there ONCE. With my wife. (Once was 'nuff.)

Upon leaving, I fumigated myself.............. 'juss say'n but YES, worth a trip in. WEAR A MASK ANYTIME U GO THERE.