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How to Find Affordable Sailboat Rentals in the Florida Keys

January 9, 2019

The Florida Keys is a great area to spend any vacation, but what can you do besides lounging around the beach? If you’ve always wanted to spend some time on the ocean, you should consider sailboat rentals in the Florida Keys during your vacation time! However, if you’ve never sailed before or have never rented a sailboat in the Florida Keys, this guide can help you get sorted. To affordably rent a sailboat on your vacation, here are a few steps you should take. 

Know Your Budget

Going on vacation can cost plenty of money, to enjoy attractions such as sailing, it’s essential that you take a hard look at your budget to determine what you can afford. It’s easy to overspend once you’re enjoying time on the beach, whether it be food, services, or attractions. However, you should try to avoid tourist traps that try to guzzle your hard earned cash. While planning your trip to the Florida Keys, you should take account of activities you want to enjoy with your family or spouse, such as sailboat rentals. This way, you have plenty of money to enjoy your vacation.

Figure Out Where You’re Staying

The Florida Keys is a reasonably large area. To find the best sailboat rentals, you should figure out where you’re staying and find businesses that are nearby. Especially, if there’s a particular area that you want to be spending time with friends and family, it’s best to know the area of the Keys that you’re renting a room at. Plus, you typically want to spend less time driving around the Florida Keys in a hot car. However, you should also see if your hotel or motel has any exclusive offers to vacationers for sailboat rentals since some do partner with local businesses and have special promotions, depending on the season.

Take Online Learning Before the Trip

A lot of sailboat rental companies will charge you additionally if you need a staff member in the boat with you if you don’t already know how to sail. To avoid this extra expense, you should consider taking some online (or in-person) learning before renting a sailboat, this way, you will know how to operate the boom, rudder, sail, etc. Although this may seem like a lot of work on your part, free online learning sure beats needing to spend an extra $50 to $100 for staff to do the sailing for you. Plus, it’s so much more fun to do it on your own! Not to mention, a skill set to impress your friends and family with. 

Compare Different Rental Providers in the Area

The easiest way to find the most affordable sailboat rentals in the Florida Keys is to compare a few different rental providers in the area. You can do this by getting a few personal recommendations, but also use online resources like Google and Yelp as well. Once you have a handful of rental providers that you’re considering, you should compare their credentials, rental prices, and customer reviews to determine which one you want to go with. After a little research, you should be able to narrow down your options to a sailboat rental or two that you want to use for your vacation. 

Bring a Friend with You

When browsing a few different sailboat rental providers in person, you should really consider bringing a friend. Not only to make your afternoon a little less boring but also to get a second opinion before you make any final decisions. Also, if the friend you’re bringing is going sailing with you, it’s often for the best to get their opinion for which company they would like to use and which boat they would prefer sailing in with you. However, this doesn’t just stop at a friend, if you’re going sailing with your family, you should bring them, or if you’re going by yourself, you should check with a few rental companies to see if you can join a group to make your day on the water more interesting.

Take Advantage of Current Promotions

There’s no doubt that sailboat rentals can get pretty expensive, especially during some of the busier vacation times of the year, such as winter. But are there any ways you can help lower your sailboat rental bill so that it doesn’t crush your savings for the trip? Fortunately, one of the best savings you can take advantage of are current promotions that sailboat rental companies are having. Fortunately, if you have a Groupon, you can search for local sailboat rental discounts and apply a promo code or two to your order for hourly rentals during your vacation time. Or, you can check out the website of local sailboat rental companies and see what kind of promotions they’re offering for your vacation dates. 

Book Far in Advance

When preparing to book your sailboat rental this winter, you should do so far in advance. This will help you save as much money as possible during the booking process and give you plenty of availability options. When you book it a few weeks to a few days in advance, you might notice much higher rates for your rental and fewer available rental times open. Although you may not be able to book a few months in advance, you should generally work on scheduling a few weeks before your trip to ensure you aren’t paying surge pricing for sailboat rentals.

You don’t necessarily need to spend a lot of time and effort to find affordable sailboat rentals in the Florida Keys. Hopefully, you are now able to rent a sailboat for your upcoming vacation on the cheaper side thanks to this helpful guide. If you’re looking for a great sailboat rental provider, you should consider affordable and reputable sailboat rental provider, Calypso Sailing. Request a sailboat or snorkeling session today directly on our site at Our team of knowledgeable staff is eager to make your vacation one to remember! Not to mention, our large selection of catamarans, monohulls, and charters, will give you and your family plenty of fun on the water.