Island to Island Charters: a Top Shelf Experience Exploring Key West’s Waters

It’s rare that we ever do a charter when we’re planning a tour. Island to Island Charters changed that for us and now we understand the fun and value of booking this sort of experience. Going out into the backwaters of Key West with Island to Island Charters is so very different from the snorkeling tours that we normally enjoy. The captain tailors the tour and your destinations based on your small group and what you’re interested in, and it’s just so special to see your family or friends experience the Keys like this.

There are quite a few boat charter companies in the Key West, and we’ve been out with a few now, but our day with Captain Ally at Island to Island will always be a favorite for us. Read on and see what you can expect and how best to plan for an exciting Key West charter trip like this. If you have any questions about Island to Island Charters or visiting Key West, please leave a comment or send us a note. We’re always happy to share more!

Highlights of Island to Island Charters in Key West

One of my best tips for anyone planning a Florida Keys vacation is to weigh out their costs and activities and see what they value the most or what to do the most. I will say that chartering a boat with a captain for a guided sandbar day in Key West is one of the best investments you can make in your vacation. Captain Ally with Island to Island Charters is one of the kindest people we’ve met in Key West and she knows her backwaters! Taking our family out to explore and enjoy some of the most beautiful and secluded parts of the Lower Keys, Island to Island Charters was a completely different experience than any other tour we’ve done from Key West. I absolutely loved our charter boat experience through Lazy Dog Adventures out of Hurricane Hole, but that was without kids (our choice) and going out with Island to Island Charters and seeing how much our kids enjoyed it was extra special.

If you haven’t had a sandbar charter or a Key West boating experience before, in general it’s just a blast getting out into the quiet mangrove islands and passageways far from the city. When you’re booking the boat just for you and your family, you get to determine what sort of sights and experiences you want to have on the water. Getting to drift with a pod of dolphins and then following spotted eagle rays through the sandbars are two of the most memorable Florida Keys experiences our family has had, and our kids recount the adventure often. Island to Island Charters is just such a win for adding a really special adventure to your trip.

Book a 4 hour charter or 6 hour charter here

Tips for a Great Backwaters Charter Trip

If you’re new to exploring the backwaters of Key West or if this is your first time in the Florida Keys, when you’re planning your day with Island to Island Charters, let the captain lead the trip. She’ll make sure she understands everyone’s interests and what’s the most important experience you want to have, and from there you can just trust the you’ll get to explore some beautiful, unique, unforgettable places. You might’ve gotten suggestions from other people about where your sandbar charter should go, and for sure bring those ideas up to the captain as you talk about your excursion, but ultimately just go with the flow. The combination of changing tides, weather, wildlife and how busy the area is will guide the destinations you get to visit with Island to Island charters.

While it’s difficult for me to relate to anyone that doesn’t want to be in the water at all times, I know that swimming, especially in open water, isn’t something everyone is interested in. I would strongly recommend using this experience out in the backwaters and sandbars to get past that if you’re able and to enjoy the beautiful water. The coolness against the heat of Key West paired with the calm flow, even if you’re swimming in a current, is really something. You kind of detach from reality for a while as you’re floating in this clear, turquoise water. If you’re hesitant to do a snorkeling trip out to a reef, this is a great opportunity to work on that fear or skill set. Do what’s right for you though, and don’t traumatize yourself on vacation.

There is some unique snorkeling when you’re exploring with Island to Island Charters though. While it might not seem like a sandbar is a great place to see interesting things underwater, there are a surprising amount of fish and rays here. When you anchor near mangrove islands, being able to snorkel in the channels are explore these sheltered places is really cool and different.

Being Prepared for an Island to Island Charters Day

You know me and what I’m going to say: REEF SAFE SUNBLOCK. Even if you’re somebody that doesn’t tend to wear sunscreen, it’s very important when you’re out on the water in the sandbars. Island to Island Charters tends to have some reef safe sunblock available on the boat for you if you forgot, but the best thing to do is to apply it to everyone before you’re out on the water. This gives the sunblock time to set and absorb so it can be the most effective. You’ll want to arrive in your swimwear, maybe with a coverup if you like, and then bring towels for everyone as well. When you’re onboard, shoes come off, so it doesn’t matter what sort of footwear you show up in, as it’s not staying on. Everyone should have a hat of some sort that will stay on in the wind, and then, of course, sunglasses.

Note: even though we’re talking about a lot of sun protection, Island to Island Charters’ boat has a larger bimini (shade) than many other small charter boats, so there is lots of shade, but the sun still bounces off the water.

When you’re putting together your day bag for going out with Island to Island Charters, be sure to bring a camera, both for above and underwater shots. I like to bring my big DSLR when we go out on a charter from Key West because there is so much wildlife to photograph. I also bring a waterproof case for my phone, as it’s my primary underwater camera. I don’t travel with a GoPro anymore because it’s very inconsistent for me with how well it works, but if you have good luck with that product, you’ll have opportunities to use it whenever the boat temporarily anchors out in the backwaters of Key West.

Parking for Island to Island Charters – Garrison Bight Marina

Island to Island Charters goes out from Garrison Bight Marina. THIS IS NOT IN THE HISTORIC SEAPORT where Key West Eco and Sunset Watersports go from. Garrison Bight Marina is located on the way into town from Roosevelt Blvd. A lot of fishing charters go out from here, so expect parking to be tight if you’re doing a morning backwaters charter with Island to Island. If you’re going out in the afternoon, many of the morning fishing boats have usually come back by your departure time, so parking is easier. I recommend just doing an Uber or taxi from your Key West hotel so you don’t have to stress about either finding parking or running over on your time.