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San Juan, Puerto Rico. Got a bit of everything a group of guys are looking for
Key west #Boys
How's Cancun. That's pretty crazy/young. How's the fishing?
Isla mujeres
Havana
T+c has plenty of fishing and snorkeling and beautiful beaches but is pretty sedate ... mostly wealthy families and older people. Da Conch Shack is lively though if you're just looking to go out one night.
I personally loved Isla Mujeres but didn't think it's a boys time out kinda place. I would suggest Bahamas or Los Cabos from personal experience. Los Cabos has a marine festival of sorts during the summer which is awesome and a fit for guys who like to fish.
I second San Juan. I love Isla Mujeres, but that's not a guys trip location.
Isla can definitely be a guys trip. There are two strip clubs, like 30 bars in playa Norte and it's the sail fish capital of the world. Drinking and driving on golf carts is encouraged and Cancun is a ferry ride away.
I agree with the key west recommendation as my husband has his annual boys trip there every year.
Go to Belize. Key
Negril, Jamaica- best boys trip destination