If you have your own airplane, it is surprisingly easy to fly here yourself. Most pilots check into and out of the US at Key West, Florida and use the Cayman Brac airport as their Port of Entry into and out of the Cayman Islands.
It is not hard at all to get an overflight clearance for flying over Cuba. This can be done through Civil Aviation in Grand Cayman (www.caacayman.com)
The fact that we are located literally 'at the end of the airstrip' means that we get several guests each year who come by private plane.

If you intend on flying to Little Cayman or anywhere else in the Caribbean, there is a guide
available called the Bahamas and Caribbean Pilot's Guide. It is a very
valuablke and informative guide on everything that you need to know
about flying in this region. It was developed by pilots for pilots.
There web site is www.pilotspub.com.

Paul Rosales is part of a flying group who custom built their own airplanes, called RVs. Paul and his group visited us in 2005 and they are scheduled to come back in 2009. Below is his trip report from 2005:

Cayman Islands Trip Report 2005

by Paul A. Rosales

Of all the flying vacations that Victoria and I have flown, one of the BESTvacations ever is the trip we made last year (April '04) flying out of Florida
with 26 GREAT friends (and 15 airplanes) to the Turks & Caicos and Bahamas.
RVer Jim 'Jimmyb' Baker got that trip off the ground (thank you again)!

Not only did we have a fun time flying there from California, I was able to
realize another life-long goal of becoming a SCUBA diver. While in the
Turks & Caicos (British West Indies), I was able to complete the certified
PADI Open Water Diver course in three days and six open-water dives. I
studied the PADI course materials every evening and scored 86% on the test :-)

Victoria and I really enjoyed the four days we spent on Grand Turk at the
Osprey Beach Hotel. Five months after receiving my dive card, I was ready to
fly back to the islands and DIVE! Talk about laid-back & relaxing, ya Mon'!

So in late September 2004, I e-mailed my friend Jimmyb who has flown several
trips over open waters to the islands and is very much 'in-the-know'. I asked
if he'd be interested in flying back to and diving all week out of Grand Turk.
Here's his reply:

I don't think I'd have to be pushed to hard to do something. While you
are thinking about it, why don't you look at going to the Cayman Islands
instead. We could fly over Cuba (the permit is VERY easy to get), and go
to Little Cayman.

It is a small island like Grand Turk, but much less populated. In fact,
it has a grass strip (now paved). Only five places to stay, but all
of them very nice. One place is right across the street from the airstrip,
like one block from where our planes would be parked. The ocean is thirty
feet out the back door of the rooms.

Also, Little Cayman has "Bloody Bay Wall". Look it up on Google. It is one
of the top three dive spots in the world! Jacques Cousteau spent about a month
there once and said it was the best dive sites in the world that he had dove
at that time. It is much closer to the U.S. and not nearly as much over water,
since a bunch of the time you are over Cuba..."Huh...the Cayman Islands...I've heard of them...let's look at a map...ahhh...
there they are...on the south side of CUBA! We'd have to fly over CUBA!?Jimmyb assured me that it wasn't a problem flying over Cuba to the Caymans
as he and his wife Vicki had done it before a couple of times in their Baron.
The ~330nm trip to the Caymans from Key West, Florida was ~250nm shorter
than the ~580nm trip we flew last year from Homestead, Florida to Grand Turk.

He even recommended a nice place they stayed at, Paradise Villas, on Little
Cayman. Two other islands, Cayman Brac, just 12nm east of Little Cayman, and
Grand Cayman, about 80nm southwest of Little Cayman, are the other two islands
that make up the Cayman Islands.

With Jimmyb interested, that was enough for me to start doing some homework
on Paradise Villas, Little Caymans only 100% ocean-front resort. Rebecca
Koss was my contact via e-mail, and she was SUPER at filling me in with
all the details and information on their 12 villas. She also setup our
diving with Paradise Divers (with Dive Masters Rod, Liz and Marc :-)

After some back/forth e-mails with Rebecca and Jimmyb, we decided on a 1-week
stay from May 9-16th, 2005, which is right at the start of the rainy season
but before the hurricane season :-) Another reason for this time frame
was that it was still a comfortable (not hot) time of year and also because
there were 7 (of the 12) villas available to reserve. With myself and Jimmyb
(and wives), that left 5 couples we could invite to join us...

Laird Owens & Christine Johnston, Larry & Gerri Schneider and Gary & Carolyn
Zilik who flew out on the Bahamas trip last year were first on the list.
Jimmyb's long-time friends Sid & Shelly Baldwin followed with Chris & Indira
Kleen of my very own SoCAL RV fliers. We filled more than half the resort with
RVers, and Rebecca marked us down as the 'Little Cayman RVs 2005', excellent!!

One of the first things I did was to renew my US Customs decal required to
enter the USA from a foreign country. Then I checked to see if there was any
authorization paperwork put out by the FAA regarding the Cayman Islands.

After some internet searching, I found FAA Waiver 2127, the same one that
authorizes VFR and IFR flights between the USA and the Bahamas. I flew with it
last year but I didn't realize it also included the Cayman Islands. No other
TSA waivers were needed to make the international flight.

Jimmyb did the legwork on what was required to fly over Cuba, and he found
several USA companies that would take care of the paperwork for a fee ($140+).
He then found that the Cayman Islands Aviation Authority would do the
overflight permits for $50.00...DONE DEAL! Here's the form we needed:
Cuban Overflight Form...that doesn't look too painful :-)

With USA authorization and help from the Aviation Authority, our trip was taking
shape. Other required items were things we already had acquired for our Bahamas
trip: Passports, life jackets, cement rebar (tie-down) stakes for the coral
ground, dive mask and fins, suntan lotion, books, shorts and 12-inch N numbers!

Then it was time to hurry up and wait....it was now October, 2004 and we had to
wait six months...work, work, work, work, work...fast forward to late April, 2005.

The group finalized plans and reservations for our departure point,
Key West (EYW), FL. We were to meet on Saturday, May 7th for two nights then
depart takeoff for the Cayman Islands on Monday, May 9th. Sid & Shelly
were flying in Commercial airlines so we'd have 6 RVs arriving to Key West;
3 from California and 1 each from Arizona, Colorado and Kansas.

A week before departure, we all faxed our Cuban Overflight forms to the Cayman
Islands Aviation Authority, and I received my overflight permit number by fax
the next day. Others in the group had to resubmit as their permits came back
with the wrong name, wrong departure dates, etc. Finally squared that away!

Victoria and I decided on a 3-week vacation so we could visit some friends along
the way, something I very much enjoy doing!

About 2hrs 45min after departure from Key West, we found ourselves letting down
to final approach on RWY 9 at Cayman Brac (MWCB); Chris & Indira glad to be
there; And, of course, a picture of all our planes parked on the ramp, cool!

Clearing Customs at Cayman Brac was not too painful at all. I know we spent
more time waiting to get started than it took to complete as the Customs folks
had not yet arrived. We filled out our arrival forms upon entering Customs.

While we waited, a gentleman walked out to all the planes and sprayed the interior
of each plane with 'something' that would kill the 'bugs' that we could possibly
have brought over with us. The 'bug spray cost was $18.75US. FYI, the exchange
rate at was; $1 US = $0.80 Cayman Islands (multiply Cayman$ by 1.25 to get US$).

Once Customs arrived, they processed us all quickly, and then the pilots were told
to proceed to the tower where we could pay our landing fee ($10US). We also paid
our departure fee early ($25US/person). We could have paid this on the day we
departed for the USA but we took care of it while there in the tower.

All this took about an hour, and then we loaded up and took off for the short flight,
less than 10 minutes, to Little Cayman (no landing fee there ;-)

Here's the approach to Little Cayman (MWCL), RWY 9(?), the runway from each end
and a picture of the ground (texture) you taxi on to get to the grass parking area;

I made it a point to immediately take pictures of the smiling faces of those
who crossed Cuba and beautiful ocean waters, arriving to Little Cayman. Here
you have the Little Cayman RVs 2005: The Bakers, Kleens, Christine Johnston,
& Laird Owens, Rosales', Schneiders, Ziliks and Baldwins (via Cayman Airways);

Sid & Shelly greeted us, and with the planes secured, we made the very short
walk to Paradise Villas. Rebecca Koss, who took our online reservation, was
on the island for a month and checked us all in. She was super, thank you!

By this time, it was 11:30am, 4 hrs after our departing Key West. It turns out
the Caymans do not observe Daylight Savings Time...wow, 10:30am! I tell you that
it didn't take long for some of us to get settled on Island time! No problem 'Mon'!

Jimmyb had told me that our planes would be parked right next to the Villas,
and he wasn't kidding. Here is a picture of the planes (and Paradise Villas'
Office) from our room, and a picture of Paradise Villas from the planes;

Here are pictures of the pool, restaurant next to the pool, and
12 beachfront villas which consist of 6 buildings; 2 one-bedroom villas
with kitchenette & patio per building, all with beachfront access ;-)

And did I forget to mention the Iguanas...They rule the island and share space
with jillions of little sand crabs :-) Be careful not to step on the crabs!

From this point on, I can't begin to put into words all of the wonderful things
we all did and saw for 7 WONDERFUL days. I can show you some pictures of us
relaxing, socializing, eating, diving, smiling, and of course, flying!

RELAXING

SOCIALIZING

EATING

DIVING

SMILING

FLYING

And on the 7th day, our last day on the island, the Kleens and Ziliks flew
a 3-ship with Victoria & I southwest about 75nm to Grand Cayman (MWCG).

We landed at Owen Robert International Airport, secured the planes and went
to the office to pay the $10US landing fee. Could you imagine paying $10
everytime you landed in America...I think I'd owe more than $30,000 in fees!

Chris (who had Cayman Island Driver's License) rented a minivan, and we spent
the day enjoying the island. We had a nice lunch at an ocean-front restaurant,
and the highlight of the day was the time we spent at the Turtle Farm;

From the Turtle Farm, we drove around until we found the town of Hell(no kidding), home to the Islands only official government post office :-)

Though it's been over a year, the damage of Hurricane Ivan from the previous
year was still clearly visible all around the island;

Reluctantly, we headed back to the airport to fly back to Little Cayman
to packup our gear and fly home to the USA the next day...

Laird took this beautiful picture after sunset on our last day...

Monday Morning, May 16th, we woke early, packed the planes, paid our bills,
said our good-byes then flew back to Cayman Brac to clear Customs outbound.
Clearing Customs was again painless, and we had filed our flight plans the
night before. We'd fly the same 12K/10K/8K altitude profiles as before.

We fueled the planes, took some group photos, staged the planes for departure,
and finally waived goodbye to the islands...I was sad we were leaving :-(