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Looking for fly/ride to Key West advice

4K views 32 replies 17 participants last post by  Djtman 
#1 ·
Hey kids,
Looking to plan a trip for me and the wifey to celebrate our 10 year anniversary in the fall. Looking at the first week of November flying into Miami Thursday night, dinner and hotel. Renting at RG at local dealer (do they rent used, as I want nothing to do with the 15s!) and head to key west for the weekend.
I've never rented a bike, or been to key west. Any advice/insight/tips on where to stay, eat, activities would be appreciated. Thanks in advance.
 
#2 ·
Terry, if your wife doesn't want to go, I'll volunteer. Definitely a great place for a 3-5 day get-away. Always a good time atmosphere on Key West. Lots of good food places from bar burger cheap to "just caught today" expensive seafood places. Although I was driving a car, on the times I drove from Homestead down to Key West, I can tell you that the most difficult part of riding a bike down there will be to concentrate on the road and not be gawking off at the water, boats, and bikinis. Very easy to get distracted here and there. Enjoy the trip.
 
#3 ·
Go to Blue Heaven at 729 Thomas St in Key West. Take your time riding down to key west. There are plenty of cool bars to stop at. Stop at Robbie's in Islamorada and feed the Tarpon. As for hotels, they are all expensive. The ighthouse in key west is nice and its across from the Hemingway house. The Key Lime Inn is a mansion that was converted to a hotel.
 
#5 ·
I saw a picture a while back that looked like they had placed guard rails around the Southernmost Point so you couldn't get a bike close enough to take a picture. Does anyone know for sure if that's so?
 
#7 · (Edited)
One of the brides favorite places in the world is Islamorada.

We've stayed at Pelican Cove a couple times over the years. Found it down there scuba diving the wrecks in the 90's. Stayed in a condo near Key Largo the 3rd time down, no rooms south of there that weekend. Lesson learned there was "MAKE RESERVATIONS" prior to blastoff. 250 a night is a common rate if you can see the water,but P/Cove is 50 ft from the gulf side. Key West is a crazy place sometimes. Been twice. We walked out the old Six mile bridge aways, and one night we watched the fishing boats come in with whatever they had caught that day. Watched 5 guys on adventure BMW's head out onto the new 6 mile bridge, last guy in line yanked a wheelie and rode into the sunset..:cool:

On the bucket list to get my bike down there and ride the Overseas Highway someday. Convertibles are fun, but it aint a RoadGlide.

+ one on Card Sound Road
 
#8 ·
Thanks for your insight so far. Any other favorite spots to stay? I'm going to call for reservations later this week.
 
#9 ·
Look into staying in Big Pine Key, much cheaper and very close to Key West. In Key West park the bike and rent a scooter, very cheap and easier to get around on. Go to Hog's Breath Saloon and watch the sunset from Mallory Square, you will regret it if you don't do the square.
 
#11 ·
Lighthouse, key lime in, casa 325 all booked for my dates. Going to keep looking.
 
#12 ·
A $2000 cc deposit for a $99 rental? dfaq? I might just rent a convertible. Any other ideas for lodging? I'm zero for 10 on referrals on where to stay.
 
#13 ·
Try airbnb.com for a place to stay. I've used them all over the world with fantastic results.
 
#14 ·
I have the condo guy's card at home. See if I can scan it or take a pic of it tonight. He has condos avail all up and down the keys, like a clearing house for them. He can do 1 or 2 nite rentals, rather than the week the resorts will charge. If he's still there, should help you out.
 
#17 ·
I'm late to chime in. Don't know what you have booked yet.

But, some riding buddies have done this trip twice out of Boston Logan, as you probably are. After researching:

Fly RT into Orlando. Cheap direct flights because of the mouse.

Rent in Orlando. Dealer there has large rental fleet, good prices.

Drive MC's down east coast to KW. Return on West coast.
 
#18 ·
Bike Rental

2000.00 deposit is S.O.P. for HD rentals. HD rentals will all be 15 model year bikes. Try Eagle Rider if you want a 2013 model RGU, they should still have some in the fleet.

When I do fly'n'rides I use one CC for the bike rental only. Let them put the deposit on that one, I use another CC for gas, accommodation and usually pay cash for meals.

I also take my own rain gear and helmet, personal preference but I know it fits me.

Calgaryglide
 
#22 ·
2000.00 deposit is S.O.P. for HD rentals. HD rentals will all be 15 model year bikes. Try Eagle Rider if you want a 2013 model RGU, they should still have some in the fleet.

When I do fly'n'rides I use one CC for the bike rental only. Let them put the deposit on that one, I use another CC for gas, accommodation and usually pay cash for meals.

I also take my own rain gear and helmet, personal preference but I know it fits me.

Calgaryglide
Tagging this post as we're going to head down there next spring.
Some good tips here. I was just talking to DC3-Mek the other day and we're thinking about putting a ride together down there next spring as well. Course the earlier in the spring we do it the tougher and more expensive it will be to get rooms, so we were thinking late spring like maybe May, but nothings in stone. We'll keep people posted for anyone who'd like to join in.

I never rented from Eagle Rider but one thing I've noticed about them some don't offer unlimited mileage on their rentals. Riding down to Key West from Miami I doubt that'd be a problem but something to consider.
 
#26 ·
Prices are stupid to get and stay there for a few days. Going to the carribean instead.
 
#27 · (Edited)
Have only been there once for a week a long time ago. We pulled the RV down, and stayed in a park. Rented scooters, had a hoot riding the island, and exploring.

There was A LOT of gay activity back then, have no idea what it's like now. But it was obvious enough we saw a bumper sticker on one of the bar windows that read; God created Adam and Eve, not Adam and Steve. It was comforting to have my wife there walking on the beach with me. :wink:

Planning on going back this winter more than likely as the current wife has never been. I enjoyed watching the sunsets with the family, and trying some of the local adult beverages.

Really enjoyed riding the scooter over to the beach before daylight, and watching the sunrise. Total peace, and tranquility, nary a soul out there but me, and just as beautiful as the sunsets.
 
#30 ·
Got a 3 day stay in Punta Cana, DR. It only cost us $750 each including airfare, hotel and all inclusive food and drink! Was going to spend more than that on just airfare/car or bike rental in Key West. They are going to lose money on us!
 
#31 ·
Sounds like a great deal. Take plenty of pix to post.

We've changed our plans ourselves for next May (as of right now anyway). Oldest daughter and her Fiance are now in Monterey, Cali for his school. He's Army and she's prior service. They got a 3 BR house with a view. Looks like we're going to do a Fly and Ride out there.
 
#33 ·
Punta Cana was great. They did have an HD dealer down there, as I saw the shirts, but had no intention of going off resort. We did rent buggies, and thought we were getting ambushed as it was just my wife and I on a 25 mile dirt road until we came up on the place. The guide and his 2 boys took just the 2 of us to some pretty remote areas. And he stopped to chat with dudes with machetes and stuff. It was a little scary.
Food was great, room/beach/staff were excellente, drinks were a little light until I started ordering tanguary and tonics. I'd go back, as it was cheap and they did lose money on us!
 
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