I just completed (February 2020) a great adventure of island hopping the Caribbean in N271TM - my Aviat Husky taildragger. What a great time. Our itinerary is below and I'm sharing this with other Husky owners so they can contemplate blazing their own trails through the Caribbean (warm) instead of Alaska (cold) on their tundra tires.
Why a Husky? Well-built and especially well protected for corrosion. I was really happy. N271TM celebrated its first birthday during this adventure as the Husky has traveled from the Wyoming factory to the Caribbean, back up to New England and Canada and then back to the Caribbean for this trip. Next will be Oshkosh this summer.
It was surprisingly easy to do the trip. I flied IFR a lot using Foreflight - typically filing the day prior to the flight and every time ATC in all the islands had my flight plan. I could have done VFR the whole way, but IFR afforded me the luxury of picking my track and altitude and I didn't have to change because of any puffy white clouds along the route.
GenDecs were a bit of a pain. Probably used 50 on the trip. Some locations required 3 on arrival and 3 to depart (customs, immigration and tower). But no departure taxes as we were crew! Didn't use an FBO except Signature in Nevis and that wasn't a problem. Signature was a little expensive but saved me a bundle on hotel. Landing fees, overnight parking etc was incredibly inexpensive for the most part. Bring lots of small denomination USD for this.
Fuel wasn't available everywhere but it was available enough. I never went below 20 gallons in the tank. Ranged from $5/gallon in St Thomas to just over $10 in Nevis and the rest were typically between $7 and $9 per gallon.
Played it by ear for the most part and always found good hotels and rental cars everywhere. And this is the high season.
We landed at 16 different islands on the trip, went to 17 islands (St John USVI doesn't have an airport so we took the ferry from St Thomas). And we stopped at three of the islands twice (St Maarten, Vieques and PR); once in each direction.
San Juan, PR Isla Grande TJIG 05 Feb
Vieques - TJVQ 05 to 07 Feb
Culebra - TJCP 07 Feb
St. Thomas, USVI - TIST 07 to 10 Feb including spending three day in St. John with Terry Mulcahey
Grand Case - French St. Martin - TFFG 10 Feb for lunch
St Barts - TFFJ 10 Feb to 13 Feb - visiting the other Caribbean Husky driver - Eric Stubbe
St Eustatius - TNCE 13 to 14 Feb
Nevis -TKPN 14 to 17 Feb
Marie Galante - Guadeloupe - TFFM 17 to 19 Feb
Martinique - more fuel ?? - TFFF 9/gal avgas, but worth it! 19 Feb
Castries, St. Lucia - meeting an old University classmate - TLPC 19 Feb to 22 Feb
Mustique - will Mick Jagger be in residence? - TVSM - 22 Feb - only overflew - they don't want you there and make it difficult/impossible to go
Canouan - TVSC for lunch 22 Feb
Bequia - TVSB 22 Feb to 25 Feb
St Vincent - TVSA - 25 to 27 Feb
Antigua - TAPA - 27 Feb to 1 Mar
Barbuda - TAPH - 1 Mar for lunch - very beautiful but nowhere for lunch on a Sunday
Grand Case - ST Martin - TFFG - our second time here - for dinner and overnight
Vieques - TJVQ - 02 to 02 Mar
Ending at San Juan Isla Grande so MJ Agostini could catch JetBlue back to BDL and cold weather on 04 March.