What It Was Like Multi-Day Open-Water Sailing: Key West To Dry Tortugas

May 22, 2021

Growing up in Kansas, who would have ever guessed that I’d discover a deep love of sailing??  But after an impromptu weekend sailing in Sweden some years ago, I’ve made it my mission to seek out as many opportunities to be on the water as possible.  And I finally did a multi-day open-water trip, sailing from Key West to Dry Tortugas National Park.

What it Was Like Open-Water Sailing Key West to Dry Tortugas | Ever wondered what a multi-day sailing trip on the open water is like? I did a 5-day trip from Key West to Dry Tortugas National Park and back...absolutely loved it, but not without its challenges. Here is my experience & some amazing pics! #sailing #boating #openwater #drytortugas #keywest

I’m going to do a separate post on the trip itself, including my brief time in Key West on both ends, my time in Dry Tortugas National Park, and more.

But this is more about just the open water sailing piece…what it was like being out in the ocean with nothing but sky and waves for company.

If you’re contemplating your own multi-day open water sailing trip (especially from Key West to Dry Tortugas), this post may be useful.  And more than anything it’s kind of a photo essay to inspire and excite.

Sun & blue skies aboard the Halia - about my open-water sailing Key West to Dry Tortugas

Get inspired by every part of my sailing adventure!

Exploring Historic Fort Jefferson In Dry Tortugas National Park

Idyllic, Remote Loggerhead Key: Exploring Lesser-Known Dry Tortugas

Captain John met me at a restaurant in Key West and brought his dinghy to the shore to pick me up.  We loaded up my carry-on suitcase and beach tote and then I slipped off my shoes, waded into the water, and climbed into the dinghy….the first time of MANY.

Tip:  You really REALLY want to pack light for a sailing trip.  First, getting your things in and out of the dinghy is no joke (and they’ll get a bit wet regardless).  Second, there’s very limited room in the boat’s sleeping area.  I’m going to do a whole other post on what to pack (and leave home) for this type of trip.

What it Was Like Open-Water Sailing Key West to Dry Tortugas | Ever wondered what a multi-day sailing trip on the open water is like? I did a 5-day trip from Key West to Dry Tortugas National Park and back...absolutely loved it, but not without its challenges. Here is my experience & some amazing pics! #sailing #boating #openwater #drytortugas #keywest

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Tip:  One thing to be prepared for is that there is NO cell signal at all once you get a bit past Key West.  It might *look* like you have a bar of signal for a few hours, but nothing can actually get in and out, and then it’s dead air.  Make sure you’ve prepared the loved ones in your life for that…my mom was FREAKING OUT.

What it Was Like Open-Water Sailing Key West to Dry Tortugas | Ever wondered what a multi-day sailing trip on the open water is like? I did a 5-day trip from Key West to Dry Tortugas National Park and back...absolutely loved it, but not without its challenges. Here is my experience & some amazing pics! #sailing #boating #openwater #drytortugas #keywest

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Our first stop of the trip, a few hours in, was the tiny uninhabited Boca Grande Key.  We dropped anchor for the night and then Captain John took me ashore in the dinghy.  I had an hour or so to just chill, take pictures, and watch the beginnings of the sunrise.

I was the only person around and I enjoyed the quiet.  I took some photos but then just sat and read for a while, since there isn’t really a ton to see or do on the island.  I was also getting bitten liked crazy by the “no-see-ums,” suuuuuper tiny little flies with quite a painful bite (for some people).

One advantage of a sailing trip like this is you get to experience places totally alone...no crowds

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Back on the boat, Captain John prepared delicious fresh yellow tail snapper, rice, and veggies for dinner, and we basked in the sunset.

I stayed up on deck even after it got dark…1) because the night sky was beautiful, but also 2) because anytime I went belowdecks, I was SWEATTTTIIIINNNGG.  So much sweat.  I’d brought a sweatshirt and jacket in case it got cool at night, but I never needed them down here in the Caribbean.

I laid in the hammock and swayed in the wind while it got dark.  I watched a full moon and the stars come out…just absolutely magical.  Nothing but the sound of wind and waves, and no real light pollution to spoil it.  This is one of the amazing things you can experience on an open-water sailing trip (Key West to Dry Tortugas, at least, but most trips really).

It was the only night I was able to get in the hammock, as the wind was too strong the other nights (according to the captain it would just pitch me out in to the water!).  I didn’t last *too* long though because I was super tired and knew I’d wake up early.

Sunset aboard a sailboat is so special - open-water sailing Key West to Dry Tortugas

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I awoke to the sway and lapping of the boat and a pale sunrise.  Captain John made coffee and prepared a beautiful fruit plate for me to start the day, a ritual he would repeat daily.  After a while he also made me a GIANT burrito of scrambled eggs and cheese.  So much food!

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We raised anchor and took off for a long day of sailing, all the way out to Dry Tortugas National Park.  The wind and seas REALLY weren’t our friend, and John had to fight them the whole way (and we had to use the motor most of the time).

The wind was going the wrong direction and we had “confused” seas…there were tons of active systems out in the Gulf and that seemed to be causing it.  All in all it was definitely not a smooth day—quite jostly, and I felt like all my organs were in the wrong place at the end.

This is one of those things about sailing that is just time and chance—I’ve had absolutely idyllic sailing trips, but then you have some where Mother Nature won’t give you an inch.  And this was unfortunately one of those trips.

What it Was Like Open-Water Sailing Key West to Dry Tortugas | Ever wondered what a multi-day sailing trip on the open water is like? I did a 5-day trip from Key West to Dry Tortugas National Park and back...absolutely loved it, but not without its challenges. Here is my experience & some amazing pics!

The seas were rough & winds fought us for most of our trip

I read and got sun all day.  It was SO hot!  The heat index was 110 F (from 95 F temp and 90% humidity), and I could not get enough water, no matter how much I drank.  And despite my best efforts I did get pretty sunbaked.  One of those “so intense of a tan it’s kind of like a burn” things.

But then the COOLEST THING EVER happened.  A couple different times, schools of dolphins came and swam with us for a while.

They’d wind back and forth beneath the boat’s bow, doing little leaps out of the water, and generally being so cute and playful!  I’ve never gotten to see them up close like this, and it was amazing…I could seriously have reached out and touched them if I’d wanted!!

Schools of dolphins just came and swam with the boat for a while! What to expect on a multi-day sailing trip Key West to Dry Tortugas

What it Was Like Open-Water Sailing Key West to Dry Tortugas | Ever wondered what a multi-day sailing trip on the open water is like? I did a 5-day trip from Key West to Dry Tortugas National Park and back...absolutely loved it, but not without its challenges. Here is my experience & some amazing pics!

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Finally, around late afternoon, we got our first glimpse of Fort Jefferson.  It just appears out of the water, this one tiny little speck, but is actually a big, super cool fort in the middle of the ocean.

We found our anchor spot for the night and then Captain John took me in the dinghy to the fort.

What it Was Like Open-Water Sailing Key West to Dry Tortugas | Ever wondered what a multi-day sailing trip on the open water is like? I did a 5-day trip from Key West to Dry Tortugas National Park and back...absolutely loved it, but not without its challenges. Here is my experience & some amazing pics!

You can read more about my Fort Jefferson experience here!

I had a couple hours left to my own devices, so started with a spot of snorkeling…the snorkeling out here is awesome!

Then I got to explore Fort Jefferson basically completely on my own…all the day trippers who either take a sea plane or the ferry from Key West were gone, and I had the entire place to myself.  I mean, how often do you get to say you have an entire national park all to yourself??  AND FOR SUNSET, no less.

I had Fort Jefferson all to myself for sunset because I'd chartered the boat instead of day tripped

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After dinner (burgers!) a thunderstorm rolled through so we went belowdecks to watch a movie, and made it an early night.  I could easily have kept just reading my Kindle though 🙂

The next morning, after some rum-soaked flaming french toast (and yes, rum in my coffee), we took a lovely sail over to Loggerhead Key (about 6 miles away).

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This is one of those amazing things about charter sailing yourself rather than doing a a tour because it gives you such FREEDOM.  Almost no one gets to experience Loggerhead Key.

Though it’s within Dry Tortugas National Park, most people just visit on a day trip tour to Fort Jefferson by sea plane or ferry, and so miss out on the rest of the park.

As you approach the island, the view is super cool, with the lighthouse jutting toward the sky and a broken building on the beach, surrounded by vivid turquoise waters.

What it Was Like Open-Water Sailing Key West to Dry Tortugas | Ever wondered what a multi-day sailing trip on the open water is like? I did a 5-day trip from Key West to Dry Tortugas National Park and back...absolutely loved it, but not without its challenges. Here is my experience & some amazing pics!

Before heading ashore, I did a little more snorkeling…there’s a cool wreck here but since the waters were too choppy I couldn’t do that and so just snorkeled a bit right on the reef.

It was my second chance trying out my new (super affordable) prescription snorkel mask (you have to follow up with the company to get your actual prescription added & it ups the cost; Get Wet Store is the seller).  As my eyes are crazy awful, this mask was a gamechanger.

Snorkeling in a national park...why I loved my multi-day open-water sailing trip Key West to Dry Tortugas

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I was ready for lunch after that!  You can see how the boat is at an angle due to the waves—this was our reality constantly from the force of the waves!  Definitely not a “smooth sailing” kind of trip…

Anchored at a 45 degree angle due to the waves - what it was like sailing Key West to Dry Tortugas

What it Was Like Open-Water Sailing Key West to Dry Tortugas | Ever wondered what a multi-day sailing trip on the open water is like? I did a 5-day trip from Key West to Dry Tortugas National Park and back...absolutely loved it, but not without its challenges. Here is my experience & some amazing pics!

After lunch, Captain John took me ashore in the dinghy, being SUPER careful to not hit the reef.  He had to take a couple different approaches to find the break in the reef.  Everyone here is very careful about preserving the wildlife and this amazing barrier reef.

I had a few hours to explore the island, and I started out taking a bunch of pictures and laying on the beach, but then a freak thunderstorm rolled through.  It didn’t last long, but I was soaked so walked toward the center of the island…unfortunately a terrible patch of burrs got my bare foot *right* before I hit the sidewalk.  OW OW OW!  Lesson learned, wear shoes.

With my sandals now on, I walked all over the island, seeing different beautiful beaches and running into a grand total of two people (who live there, as part of the national park).  Then another rainstorm came through…I thought I’d just wait it out, but Captain John sped up to take me back to the boat because it was looking like a nastier storm.

See more about my time on the gorgeous, deserted Loggerhead Key here!

What it Was Like Open-Water Sailing Key West to Dry Tortugas | Ever wondered what a multi-day sailing trip on the open water is like? I did a 5-day trip from Key West to Dry Tortugas National Park and back...absolutely loved it, but not without its challenges. Here is my experience & some amazing pics!

Pristine, deserted beach at Loggerhead Key

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After another beautiful sunset all to myself back at Fort Jefferson, we were up and at ’em the next morning, ready to head back toward Key West!

And MAN, the waves and wind just would not cooperate.  Poor Captain John fought and fought and fought…we motored most of the way and still had to fight for every tiny bit of progress.  We couldn’t even make it quite as far as we’d planned for anchoring at night, had to stop at Marquesa Key instead.

He said it was his worst day of sailing in 30 years of experience…for me it was a physically challenging day getting thrown around by the waves and inhaling the fumes of the motor, but otherwise okay and thank goodness I don’t get seasick!

What it Was Like Open-Water Sailing Key West to Dry Tortugas | Ever wondered what a multi-day sailing trip on the open water is like? I did a 5-day trip from Key West to Dry Tortugas National Park and back...absolutely loved it, but not without its challenges. Here is my experience & some amazing pics!

So hopefully that gives you an idea of what it was like sailing from Key West to Dry Tortugas National Park.  My video editing skills aren’t amazing, but I cut together all my little snippets of video from the trip, just to give you a sense of the experience—the motion really makes it!

I rented Captain John’s sailboat (with him, obvs) on Airbnb…I’m not sure if he’s still doing these multi-day trips, but worth finding out!

Other boat adventures you’ll love:

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What it Was Like Open-Water Sailing Key West to Dry Tortugas | Ever wondered what a multi-day sailing trip on the open water is like? I did a 5-day trip from Key West to Dry Tortugas National Park and back...absolutely loved it, but not without its challenges. Here is my experience & some amazing pics! #sailing #boating #openwater #drytortugas #keywest

Comments (2)

  • MERCER M FAULKNER

    June 12, 2021 at 2:00 pm

    Jessica: I enjoyed your sailing comments re the Dry Tortugas. We live in Kansas and travel a fair amt. We love Key West or any beach will do. If you don’t mind, would you share the cost to underwrite your stick boat adventure? MMF

    1. Jessica

      June 13, 2021 at 1:12 pm

      Hi Mercer! I can’t remember the exact amount but I think it was around $5,000. I was honestly a bit surprised by the cost, compared to some of my similar sailing adventures internationally. It was “all inclusive” in that it included all the sailing stuff, food and drink on board, etc. (though not entrance into the national park…I had a park pass). Though I suppose in most cases the cost is for multiple people, which evens it out a bit. But maybe this is a pretty normal cost (and given that we had to motor so much, I’m sure the fuel costs were much higher than he’d anticipated).

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