Best Wintertime Sailing Trips

By | July 23, 2022

Looking for a place where you won’t need your DST800 Airmar temperature sensor in the winter? Check out these suggestions for a wintertime sailing trip. The water will be warm, you can make your friends jealous with “wish you were here” postcards, and most importantly, you can return to work with a tan in the middle of February. What more could you want in a winter vacation?

Best Wintertime Sailing Trips

Florida Keys

Of course the Florida Keys make a list of best wintertime sailing trips. It’s the obvious choice because the temperature in the Keys rarely drops below 60 degrees Fahrenheit at night, which is perfect for sleeping. During the day, the weather is usually warmer than that, but not as hot and stuffy as it is in the summer. You’ll avoid the humidity of the summer months but get all of the excitement and adventure that Florida has to offer.

You’ll always be close to marine services for fuel, parts, food, and fun, as most of the Keys are well populated. This isn’t a trip for someone who really wants to get away from the big city, but if climate is the most important consideration for your trip, you really can’t go wrong with the Florida Keys. Plus, if you’re sailing from the U.S., you won’t even need a passport.

The Bahamas

The culture in The Bahamas is second to none, especially if you’re looking for authentic Caribbean food, reggae music, and a laid-back atmosphere. You will truly feel like you’re on vacation when you sail to The Bahamas, no matter how you decide to spend your time. The pristine beaches, picturesque landscapes, and warm weather make this a top destination for winter sailors.

The Bahamas can be a bit crowded in the winter months with northerners who are trying to escape the cold and it’s a popular place for spring breakers in the latter part of winter as well (yes, spring breaks often occur before the actual start of spring). But you can find secluded areas of the islands that will give you respite from the crowds for as long as you need.


For decades, Cuba was off-limits to U.S. travelers, but all that’s changed now and it should definitely be one of your top considerations for a wintertime sailing trip. If you’re a history buff, access to Cuba will give you all the historical adventures you can handle, many of which Americans haven’t been able to experience for years. You’ll probably be the first in your circle to visit these sites, which certainly is worth bragging about.

You’ll always be close to resources and amenities when traveling to Cuba, making it a great choice for a long sailing trip. It is a little more complicated to travel to Cuba than the other destinations on this list, but as long as you plan ahead, you’ll have no problem getting there and experiencing this relative enigma.


Of course, there are many other warm weather locations that are ideal for sailors looking to get away from the cold in the winter. But, the three destinations listed here are going to give you exactly what you want from a winter sailing trip.