Caribbean Climbing Travel Guide

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We have 4 adults that want to charter a sail boat for 7-10 days somewhere warm and sunny in January. No more than 7hrs flight from Detroit, MI. Ideas? Suggestions? Cost?
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We have several families who have daughters that are high school seniors this year and have younger brothers who are 13. We normally do a relaxing beach trip for spring break but this year we want lots of fun and excitment to celebrate the girls senior year. The question is cruise? If so, which one? Or, do we do a resort instead? If so, where? Like to stay under $6,000 for a family of 4 for the week. Thoughts?
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So I am a 25 years old bringing a new girlfriend on vacation looking for something that will be romantic yet with a great nightlife. any ideas a good place to go in the carribean.(something economical prefferably)
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Attractions

Klein Bonaire

Off Bonaire
PO Box 68
Bonaire, Netherlands Antilles

Description: Klein Bonaire is a small uninhabited islet located just offshore from the mainland, and offers excellent snorkeling for both advanced and beginning divers. ... Read More

Expert Rated & Recommended

Dickenson Bay Beach

Dickenson Bay
Antigua, Antigua and Barbuda

Description: On a quiet day, Dickenson Bay Beach fills with swimmers and surfers by 11 a.m. Some credit the... Read More

Expert Rated & Recommended