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FAQ How To Choose A Boat Charter in Key West

Updated: Feb 4

These facts, feelings, and recommendations are from my many years living and working in the Key West charter industry on both sailing and power boats. I hope this article can bring a bit of insight into the charter boat world and help visitors to Key West sift through the overwhelming amount of boat excursions to choose from.


At a glance, I'm sure attempting to book a boat charter in Key West seems daunting. Don't worry. I'm going to attempt to simplify it a bit...or at least give you some facts and help you think through it. Stick with me.


So let's start here - Key West has quite a number of boats to choose from if you are looking to adventure out into the wild blue.


Sandbar charters, dolphin watching, sunset cruises, snorkeling charters, eco tours, fishing charters... eco tours w/dolphin watching, eco tours with mangrove kayaking, sandbar charters on a private boat, sandbar charters on a tiki boat, sunset sails, sunset sail boats that legitimately sail, sunset sail boats that advertise sailing but don't truly sail sail, tiki boat tours, round tiki boats, rectangle tiki boats, dolphin watching on big boats, dolphin watching on small boats, snorkel boats that choose calm seas with good visibility, snorkel boats that do backcountry snorkeling, snorkel boats that take you to the barrier reef no matter how large the chop and visibility just to say you did it and have the vomit bag to prove it...


Did that feel overwhelming? Ok, I'm sorry. Let's break it down some.


First off, you obviously need to figure out what it is you want to see/do/experience. Getting out on the water is the number one thing to do in Key West in my opinion. Don't just ask yourself what boat charters are the best in Key West but rather how many boat charters should I book while in Key West?


My answer: get out on the water as much as you can.


Key West is not known for its beaches. We're just not. Sure, we have them but they aren't the most picturesque that you would imagine. My favorite beach in Key West is Fort Zachary Taylor...which is more of a sand/pebble beach but a great place to snorkel off the beach, watch the sunset, grill out if you'd like (yes, grills available), and you don't experience as much stagnant ocean water on that side of the island - making it a great spot to actually venture in for a swim. However, this is one of the very few spots around Key West to snorkel off the beach - and it's limited. If you want to find out why Key West is known for snorkeling, then you most certainly need to book a snorkel boat charter. None of Key West's beaches even come close to matching the experience you get chartering a boat.


What Key West is definitely known for, however, are sandbars. Surrounded by crystal blue waters, sandbars populate the waters of the Florida Keys with shallow sanctuaries filled with sand. Key West is home to dozens of these beautiful sandbars engulfed in paradise...and they are only accessible by boat.


Sandbar boat charter key west
Photo credit: Captain Nikki, sandbar charter in Key West

Before we get on with the FAQs, I have to talk about dolphin watching tours. The Florida Keys are unique in the fact that we have a super pod of around 200-250 Atlantic bottlenose dolphins that live here year-round. Eight years later running dolphin watching tours and I still get excited every single time I see them. They are highly protected, therefore no feeding or swimming with them is allowed in the wild, so a boat is the best option for encountering these local dolphins in their natural habitat.


You can find dolphins all year long around the waters of Key West, but do be aware that winter time it can get a little trickier to locate them. This is only because weather conditions tend to be windier this time of year. High winds can cause the ocean to be a bit choppier than usual, which makes dolphin watching a little tougher. Yes, we do still find them in the winter months and even windy days, but calm seas like you tend to find closer to Key West summer months most definitely makes spotting dolphins easier.


Bottlenose dolphins in Key West
Photo credit: Captain Nikki, Dolphin Playground in Key West

Ok, so here are some frequently asked questions about choosing a boat charter in Key West. I will attempt to be unbiased and give some answers, but share my own recommendations at the very end.


What kind of boat charters are in Key West?

Sandbar excursions

Snorkeling

Scuba diving

Dolphin watching

Sunset cruises

Eco tours

Novelty tiki boats

Sailing

Fishing

Sightseeing


First, narrow down what it is you wish to experience.


How do you choose from so many charter companies?

After prioritizing what it is you wish to do while visiting Key West, consider these things. Boat type? Trip duration? Price? Public vs private? What type of vibe would you like?


Public or private?

There are public boat charters in Key West offering general admission tickets on boats with capacities everywhere from 6 passengers to 126 passengers. Price range typically correlates with the capacity. If you don't mind sharing a boat with a large group, then you can find boat charters a little cheaper in Key West. If you don't necessarily wish to book a private charter, but also don't want to be crowded on a boat with a bunch of other passengers, you are in luck. There are public charters capping their occupancy at 65, 49, 30, 25, 22, 14, and even just 6 guests.


Want a boat all to yourself? There are plenty of private boat charters to choose from in Key West. Depending on what you are looking for, you can charter just about any sized boat in Key West for a private experience from basic to luxury, and even find inexpensive private options on smaller boats such as this.


Can I / should I rent my own boat?

I'm not sugarcoating this one and just going to say - no. As a USCG licensed captain, someone who knows the waters of Key West, and just a local boater constantly witnessing dangerous boating habits, just do yourself a favor and charter a boat with a local captain. The Florida Keys are known for incredibly shallow waters and sandbars covering the area. If you do not live in the Florida Keys and/or are inexperienced and unfamiliar with the waters down here, don't risk it. Let someone else navigate, take you to the cool spots, dodge the sandbars, and let you enjoy that cooler full of cold ones while you relax safely on your vacation. I am a huge advocate on boater safety and not testing Mother Nature.


I get seasick? What kind of boat should I go on?

This is a tough one since obviously people's sensitivity to seasickness can greatly vary. I now predominantly run power boat charters, but I ran catamaran charters for many years. I have seen passengers on flat calm days on a catamaran barfing their lunch up when there were literally zero waves. It just all depends. You know your body more than anyone. Some say catamarans are the best for seasickness because they're sturdy vessels, but get on a smaller catamaran on not-so-gentle seas and you may say otherwise.


So I'll say it again - it all depends. I'm no expert in this, but if you are quite prone to seasickness, I would personally try to book my charter on a calm day if possible, take the seasick pills, don the bands, or whatever I could do. I recommend you just choose the charter that you like the best if you can tolerate the sea at all, because there are also perks to power boats gliding through the ocean quickly, keeping you cooler with the wind in your face and that pukey feeling at bay. Sorry if this doesn't help much...again, this is a tough one. Definitely don't show up to the boat and ask "Should I take my Dramamine?" because a) no one else knows your body as well as you, and b) it's likely too lately at that point anyways.


Big vs small charter companies in Key West?

Key West has a few very large watersports companies. Some of us in the charter industry joke that they are like the "Walmart of watersports." I'll refrain from listing them, but they're pretty obvious. They offer many different types of charters at various price ranges. Then there are "the other guys" (I'm simplifying this, but it's pretty spot on). Typically, you will find a little more intimate setting with the smaller watersports companies. Keep this in mind when you choose a boat charter in Key West. Whatever the vibe or experience you are looking for, maybe this little tidbit will help you decide what is best for you.


What is the best sunset cruise?

Sunset cruise boat charters are one of the most popular tours in Key West! Sure you can watch one of the world famous Key West sunsets at Mallory Square or Fort Zach, but there's nothing like the experience you get watching it on a boat. From catamaran champagne cruises, sailing on an old schooner, party boats, gliding across the crystal blue waters on a power boat, or even cruising around on a floating tiki boat - there are so many sunset cruises in Key West to choose from. The sunset view may be the same, but the boat vibes can vary significantly. Be sure you book an appropriate charter for the vibe you wish to experience. Want a party vibe? Romantic? Premier sailing? Private? Relaxed and chill? Sunset with a side of activities? There is something for everyone.


Sunset sailing schooner in Key West
Photo credit: Captain Nikki, sunset sail in Key West

What is the best time of year for sailing in Key West?

You can sail just about any time of year in Key West given some decent wind, but keep in mind closer to summer months is when the winds tend to be lower. The best time for stronger winds and better sailing conditions is January through April. This time of year is when beautiful sailing vessels that operate summers up north, make the trek south to Key West for the winter/spring to grace us with their majestic sailing charters. If you are visiting Key West anytime between November and May, one of my all-time favorite seasonal schooners is the 105-foot-long elegant America 2.0. If a premier sailing experience tickles your fancy - do it. I had the opportunity to crew on this boat one winter and even sail aboard it one summer through New York harbor, and I have to admit it is an absolute must do.


What is the best time of year for boating in Key West?

Summertime is hands down the best boating weather in Key West. If you want to almost guarantee crystal clear water with incredible visibility for snorkeling or scuba diving - this is an optimum time of year. The winds tend to remain low and the conditions of the ocean are more favorable than not. The water is warmer and dolphins are even easier to spot. Many summer days the water is crystal clear and calm as a lake - you wouldn't even believe you were on the ocean.


All-in-all, weather and water conditions in Key West can change drastically all throughout the year, even daily, sometimes hourly. Nothing is guaranteed. Even throughout the winter, spring, and fall months you can experience these same perfect summer-like conditions. It all just depends on what Mother Nature is feeling like at that time. However, the cool thing about boating in Key West is that many times despite uncontrollable weather, there are various spots on both the Atlantic and Gulf of Mexico side to choose from that a knowledgeable captain can take you to find the calm seas, favorable snorkeling conditions, decent fishing, and better chances to find dolphins.


Which boat charters go to the Dry Tortugas?

Well, the Dry Tortugas National Park is 70 miles from Key West, so not many. Oftentimes people don't realize how far it really is in the middle of the ocean. For the most part, visitors take the Dry Tortugas ferry or a seaplane to get there. There are some private boats and fishing charters that go out there as well, but it's definitely uncommon for the average charter company to take a vessel out that far.


What do you recommend?

I recommend getting on the water in Key West as much as you can! There are lots of charters to suite everyone's vacation goals.


I will always be partial to smaller group public or private charters because I feel people get a much more quality bang for their buck. You might pay a little more, but it's worth it. Less crowded, more intimate, and a captain/crew that is able to interact with you more personally. This makes a huge difference for people specifically nervous about snorkeling when you have a captain/crew more one-on-one teaching and attentive when you are in the water. And don't forget...if it's less crowded on the boat, it'll also be less crowded in the water when you all go to jump in and snorkel. The vibe is just so different.


Private charter is definitely the way to go if you want to customize a day on the water to your liking. Spending your bachelorette party in Key West? Planning a family vacation? Getting away for a quick girls' weekend? Wish to have the coolest, most unique micro wedding at sea or even on a sandbar? Popping the question with a romantic Key West sunset as a prop? Dreaming of the most beautiful way to honor your loved one with an ashes memorial at sea? Private charters don't have to be expensive. Check out these options for amazing and affordable private charters.

Next best thing to a private charter experience - small group, semi-private boat charters! Let's narrow this down a little... if you were only going to get on the water twice, I would say book one daytime charter and one sunset cruise. Pick an adventure you would like to experience on the water, whether it be a sandbar excursion, dolphin watching, snorkel adventure, or whatnot. Then pick a sunset cruise. Witnessing a beautiful world famous Key West sunset on the water is just a must. And if you only want to do one sunset cruise, I recommend this. Sailing into the sunset in Key West...it doesn't get much better.


I hope this article in some way helps simplify your charter booking in Key West! Please feel free to contact me with any questions or comments about boat trips or just general questions at all to assist with planning your Key West vacation!


I love giving people insight and helping in whatever way I can...even if you simply want to know where I've discovered the best espresso martinis on the island. Pro tips, if you will.



Want to book a private charter with Captain Nikki? BOOK HERE and request her!


More about Captain Nikki click here.

Captain Nikki winter in Key West
Captain Nikki, photo taken January in Key West (perfect boating conditions)















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