BY JENNIFER BABSON

  KEY WEST - Geographically speaking, many of the Florida Keys have always been closer to Havana than to Miami.

  Now a group of elected and municipal leaders from the Keys is trying to become one of the first government delegations from South Florida to visit Cuba
  since Fidel Castro took power 43 years ago.

  They say they want to prepare the Keys -- Key West is, after all, only 90 miles away from the island -- for an eventual opening of U.S. trade and tourism.

  ''The purpose is to fact-find and prepare ourselves for that date,'' said the trip's organizer, Monroe County Mayor Charles ''Sonny'' McCoy, a former mayor
  of Key West who in 1978 water-skied to Cuba, trailed by journalists.

  Once again, McCoy says, he will travel the Straits of Florida, this time by boat.

  Others who are expected to make the two-day trip next month include Key West Mayor Jimmy Weekley, City Manager Julio Avael, Port Director Raymond
  Archer and County Attorney Jim Hendrick.

  Like many longtime residents of the Lower Keys, McCoy, Weekley and Avael claim both Cuban and Keys roots that run deep.

  Among the issues the delegation hopes to address: the logistics of one day resuming air service, ferry transport and cruise ship travel between Key West
  and Cuba.

  First, though, the Monroe County Commission will consider a resolution this week authorizing the delegation to seek a license from the Treasury
  Department.

  The U.S. government curtails travel to the island by banning most Americans from spending money in Cuba. Exiles, journalists and those on cultural,
  fact-finding or educational missions are allowed, however, under certain circumstances.

  County commissioners will consider McCoy's resolution, ''for the purposes of exploring cultural, educational and future economic ties,'' on Wednesday --
  coincidentally the anniversary of the disastrous 1961 Bay of Pigs invasion.

  It's certainly not the kind of venture you would see government discussing in Miami-Dade or Broward counties, says Dario Moreno, a political science
  professor at Florida International University.

  ''I haven't seen a political delegation from South Florida go down there since Castro,'' Moreno said. ``It shows how different the Keys are.''

  LONG HISTORY

  The ties between Cuba and Key West span centuries and generations.

  In the 1800s, Cubans who flocked to Key West's cigar factories fashioned a vibrant outpost symbolized by the city's majestic San Carlos Institute -- a pit
  stop for patriot José Martí as he raised money for the war of independence from Spain.

  And Florida's first Cuban-American legislator, in 1896, came not from Miami but from Key West, Moreno said.

  But Key West resident Arturo Cobo, a veteran of the Bay of Pigs and a participant in the 1980 Mariel boatlift, said Friday the visit won't sit well with many
  longtime residents.

  ''The way I see it, this is an insult,'' Cobo said. ``This is going to divide the officials in Key West and the Cuban exile community. This is bad judgment.''

  START NOW

  But Weekley says Keys officials feel the need to get a handle now on future possibilities for cooperation with Cuba as other U.S. delegations have
  stepped up efforts to forge their own ties.

  ''I think it's time to move on. Eventually Cuba is going to open again. Castro is not going to live forever,'' Weekley said. ``There are some positive
  opportunities that will occur with Cuba's opening for the city and the county. We need to start looking at what's available and talking about it and not
  waiting until the last minute.''

  Boats leave daily from Key West to Cuba -- ferrying fishermen, tourists visiting on the sly and others who want to glimpse a nearby country that has been
  off limits for four decades.

  ''They are our neighbors, and we need to start communicating about how we can start working together when Cuba does open,'' Weekley said.

  McCoy and Weekley say they envision a return to the era before Castro when planes made what has now become a 30-minute hop to Havana, and boats
  transported goods, cars and people back and forth every day.

  Monroe County's approach toward Cuba is definitely unlike the one favored on the mainland, county attorney Hendrick says, taking a poke at Miami.

  ''We have a much different historical connection with Cuba than does the Miami area,'' Hendrick said. ``We are not prisoners of rhetoric here.''