1 year Florida to Trinidad and Tobago

[blackc2004]

Hello! I am starting to plan for a work sabbatical in 2025. I want to take one year off and sail from Florida to Trinidad and Tobago. I have been sailing for about 4 years now and have taken 101,103,104,105,106,114 through ASA. I've done a charter in French Polynesia, The BVI's and have one upcoming in Greece in September 2024. I sail monthly on the San Francisco Bay in a 30-40' monohulls.

Planning to buy a 40-45' catamaran.

1. Thoughts on when to leave Florida or timing of the trip in general (IE where would I need to be by June for Hurricane season)?
2. Top highlights of this route?
3. Favorite or must stop places?
4. Ability to do this trip with a dog/any major country restrictions for a dog?
5. What would you use to start planning the full route / Cruising guide suggestions?
6. Any other suggestions/Ideas?

[Zanshin]

The direct route non-stop from southern Florida to Trinidad is going to take only 11 days total sailing assuming a 5knot average speed, you will have a long time to do this and enjoy each set of islands/countries on the way. The first legs are upwind, often called "the thorny path" but once in St. Martin the rest of the legs will be much easier and faster. Basically look at the chart, you'll be doing an arc down the island chain. With your time frame, you can afford to wait for good weather windows while heading east, that makes life a lot easier.
With a 40-45 catamaran and active cruising, you can be in the western Caribbean during the season if you keep a watch out for the tropical waves and at the first sign of potential hurricanes and storms forming you can escape to the south. Even if you were in St. Martin, far to the north, you could make it to Grenada in 3-4 days sailing and motorsailing, and with modern weather reporting that is sufficient time. All the other islands will have correspondingly shorter "escape" times to the south.
Each country has different rules for dogs and other pets. I'd make a list of all the countries on the route and check out their websites or use noonsite.com or a similar site for information.

I've been sailing up and down the chain from the USVI to Grenada for a long time, and each country has highlights that make a visit and stay worthwhile. I've skipped Saba because I've never been in the area when the weather was calm enough to warrant the trip. But one day I'll make it there as well.

I wouldn't make a full trip plan, that will just lead to frustration. Once you get started you'll find a place you like and stay longer, or dislike and want to leave earlier. Then you'll talk to fellow cruisers at happy hour and find out about a place worth visiting that wasn't on your radar. Or equipment fails and you need to backtrack to St. Martin for cheap replacements. The rough course is set out for you, roughly east then southeast.

Once you reach the windward and leewards, there are only 2 1/2 passages where you can't see an island. All passages are less than a day and many can be done by leaving at sunrise and arriving before sunset. The exceptions are the Mona passage between Hispaniola and Puerto Rico and the Anegada passage from the BVI to St. Martin. The 1/2 is from St. Barths to Antigua - but if visibility is good you'll still see St. Kitts/Nevis before losing sight of St. Barths and locating Antigua.

[blackc2004]

Awesome thanks so much! This makes me feel better about starting to really plan up for the next year.

Now it's just a matter of starting to get charts, decide some basic locations and then figuring out when/where to buy a boat!

[SailingHarmonie]

If you insure the boat your underwriters will have a significant say in where you’ll be during hurricane season. With most it’s north of Florida, or Grenada and south.