Matt and Britney Weidert

Matt Weidert

Key West Bareboat Charter | Sailing Adventure to the Dry Tortgas

Today I am excited to share a spontaneous adventure that started with a simple conversation between friends some time ago. We wanted to meet again since we hadn't seen each other for a while and we discussed the idea of an impromptu getaway. Within hours of talking, we got carried away and booked a sailing vacation, with only 10 days to prepare for this unexpected trip.

We looked at a couple nearby destinations, such as Miami, the Bahamas, or the Caribbean. Ultimately, we settled on a Key West bareboat charter with a visit offshore to the Dry Tortugas National Park..

It had everything we were looking for in a short guys trip: close to home, excellent fishing prospects, long days on the water, pre-Civil War era fort exploration, and a bit of nightlife on Duval St in Key West.

Planning and our last-minute booking

This was the first sailing trip we booked during hurricane season.. After checking the long-range weather models routinely on Tropical Tidbits, it looked like we had a clear weather window - so we went for it. We were careful to avoid the fate of Ernest Hemingway who was marooned at Fort Jefferson for 17 days when a tropical storm moved through!

There are not many options for a bareboat yacht charter to the Dry Tortugas. I found one, but it was not a great option - a Dream Yacht Charter (they have since closed the base) 2018 Bali 4.3 with a flybridge, but no AC!

Yes, I'm spoiled. But this was a guys trip and we decided to rough it even though this was August in south Florida. Better to go and sweat than not go at all.

I wrote more about what to expect in this post.

Boat trouble a-brewing

Enjoying the morning breeze at the poolside dock at Stock Island Yacht Club & Marina

We arrived early on Wednesday and had a few hours to kill before boarding at 5pm. We got our first taste of the Florida sun as we explored downtown Key West and secured some souvenirs for the kiddos back home.

Garbo's, made famous by the Diner's Drive in and Dives, was a welcome respite from the heat. Check out the Umamiburger or Mahi Tacos and pair with a cold beer from the attached Hanks Saloon. The live music was already jamming.
Cold beer and fish tacos at Garbo's and Hanks Saloon

Check in went smoothly and it was a luxury to have a well-established food delivery program available through Instacart. Prices were high, but it's much cheaper than you'd pay on a bareboat trip in the Caribbean.

After stowing away our provisions and gear, we moved the catamaran over to the pool dock where we could better take advantage of the prevailing breeze (no shore power AC either since the boat was 220v).

We enjoyed the pool, showers, and restaurant available to charterers at the Stock Island Yacht Club and Marina. They also have a small store a short distance walk from the main building.

Unfortunately, the next morning we learned that an engine water pump was failing and the inverter was busted. We could live with the inverter, but a replacement would be needed for the pump. 

When the pump didn't arrive on time, we decided to salvage the day and sailed down to the coral reef in Western Sambos for a swim and snorkel. We spent the night at anchor outside of Stock Island to soak in as much breeze as possible.

Sailing to Dry Tortugas - our catamaran finally gets underway

Epic sunset over Marquesas Keys at Boca Grande

We received a call from DYC the next morning with a new plan - they just had a Nautitech 40 check back in that was available during out trip. After an inspection, cleaning, and swapping out of our gear, we were ready to get west - towards the Dry Tortugas at last! We jammed some sailing tunes and got underway.

Side note: I hadn't been on a boat type quite like the Nautitech 40 - it has two helm stations at deck level. This made visibility for the helmsman especially difficult. After the challenge of dodging lobster trap buoys throughout the trip, let's just say I won't charter a boat like this in the future (unless of course it's my only option).

Given the late departure, we spent our first night anchored off Boca Grande. The remaining 50 nautical miles to Fort Jefferson at Garden Key we would tackle the next day. You can enjoy spectacular sunsets here over the Marquesas Keys. 

What to expect from the Key West Bareboat Charter cruising grounds

If you choose this anchorage, expect to swing with the changing tide, so make sure you get that anchor set well. This is one of the reasons the Florida Keys or Key West requires more sailing experience and isn't considered a beginner bareboat charter cruising ground. These are some other reasons - I go into more depth in this separate post about what to expect.
  • Few protected anchorages
  • Mostly anchoring, limited moorings available
  • Longer passages
  • Trickier navigation with shallow areas and hazards to avoid (such as lobster buoys!)
    • Dodging the lobster trap buoys was very frustrating - here's my advice: charter a boat with good visibility from the helm station and go farther south on your route to the park (time and weather permitting)
    • I asked the operator of the Yankee Freedom (high speed catamaran that takes tourists to the park daily) if there was a better route to avoid the buoys - they confirmed there is no better route than the one we took
  • Less predictable weather - shiftier trade winds, hurricane season, and cold fronts in the winter

Fishing en route to the Dry Tortugas

Little Tunny
Being a guys trip and all, we took the fishing seriously!! We brought our own gear and tackle. Ilander skirt lures were rigged with ballyhoo. Most of the time we fished in 30-60 feet of water, but we also ran south past the reef to deeper water (300+ feet) in search of tuna, mahi, and wahoo.

We trolled with two rods - one with the ballyhoo towards the surface, and the second with a diving artificial lure (Rapala X-rap Magnum for example).

We weren't able to go too far offshore because of the ground we had to cover, so we had to settle for fish caught in the shallower depths. This time of year when the water is warmer, the pelagic species are generally going to be farther out towards the Gulf Stream - apparently out of reach for us on this trip.

If you want to learn more about how we fish, check out our sailboat fishing guide.

Our track, with an attempt to reach deeper water on the westward passage | Pins are where we landed fish

Dry Tortugas fishing totals - I give us a C+

It was a decent haul, but we didn't do as well as expected. Sadly, nothing was caught that we wanted to make fish tacos out of. Here are the totals for the trip.
  • 3 barracuda (one of which was the biggest I've ever caught...and I seem to catch a lot of them)
  • 2 king mackerels 
  • 1 little tunny
If you do fish, be aware of the the fishing regulations for the Dry Tortugas National Park - certain areas are restricted and you should stow your gear before arriving. If you do have any fish aboard, radio the Park Rangers on Channel 16 to report your catch before entering the park boundaries.

Within a mile of the Garden Key, fishing is permitted from a boat.

Exploring Fort Jefferson and Garden Key

Exploring Fort Jefferson after the crowds from the Yankee Freedom had left | We had the place to ourselves

Adventure was the objective for this trip, and what could answer more than a long journey to the least visited lower 48 National Park with plenty of history?

We arrived at the Garden Key anchorage and found that we had the it all to ourselves (one boat later arrived)! Excellent. The crowds from the daily Yankee Freedom ferry were also gone so the fort was empty.

Before going ashore, I dove on the anchor and was visited by the largest barracuda I've ever seen. I'm sure he makes the anchorage his home - he hung around under the boat during our entire visit. I was also hoping to see some of the goliath groupers during the day, but they only showed up after dark.
Fort Jefferson

Heading ashore at Dingy Beach

We took the dingy in at, yes, Dingy Beach (there is a sign, you can't miss it), and walked over to the boat pier to get our permit - it's free. All you need to do is pay your entrance fee. The office also posts daily weather reports for the boating community.

Following the self-guided tour, we enjoyed learning about Fort Jefferson such as the construction, purpose, and famous prisoners including Dr. Mudd. Atop the fort next to a monster Parrot Rifle, it was fun to see our catamaran lying peacefully in the anchorage below.

You can also camp at the fort - and we spent some time mingling with a few of the campers. Most had taken fishing boats to the fort, enjoying the bountiful waters surrounding the National Park. We were jealous of their fresh catches!

Unfortunately, the very next day we had to begin the return trip to Key West since we lost a day with the boat issues. Next time we return, we'll make sure we have more time for adventuring and exploration in the park, including Loggerhead Key.

Homeward bound - back to civilization

Dodging isolated squalls on our return to Key West

With the prevailing trades blowing in our teeth and a long distance to cover, we had to motor much of the way back. Such is the reality of a catamaran charter trip with firm travel dates.

We spent another night at Boca Grande with a mesmerizing sunset, one of the most magical I've seen. There was a massive thunderstorm complex to our north that put on quite the lightning show for hours and hours. 
We thought it was coming closer at times, but thankfully it stayed away. This made the perfect backdrop for a showing of Master and Commander, which we enjoyed with our projector after sunset cocktails. 

I slept on the catamaran trampoline out front each night, and this was the only time I was scared away below decks due to the approaching storms!

Our last day and a change in plans

On our way back to the marina, we enjoyed some more fishing and snorkeling at Western Dry Rocks. Check the state park and fishing regulations, but fishing and lobstering was permitted at this location during our visit. Unfortunately, I came up empty handed on the spiny lobster this time.

After swinging by the fuel dock in the afternoon at the Stock Island Yacht Club and Marina, we decided to debark and find a hotel. Our flights didn't leave until the next evening, so it allowed us a refuge to hang out for the next 24 hours.

We chose the Perry Hotel, a welcome respite from the heat at neighboring Stock Island Marina. We enjoyed showers, a poolside happy hour, and of course - some AC! It was the perfect place to wind down and share sea stories from our Key West sailing charter trip.

Poolside happy hour at the Perry Hotel

Not qualified to do a Key West bareboat charter on your own yet?

Check out our starter guide here if it's something you are interested in. 

Can you still take a similar trip in Key West? Yes! Crewed charters are available. Ask your charter company and they can help pair you with a skipper for the Florida Keys. You can also look into a power catamaran option if you have some boat know-how.

You may also stay in Key West and take some day trips. Day charters aboard catamarans are available for reef snorkeling and sunset cruises. The high-speed ferry Yankee Freedom also leaves Key West daily at 8:00am to bring you to the Dry Tortugas. You'll be back by 5:00pm.

When is your next yacht charter?
Consider booking with the Yacht Warriors.

Charter. Beyond.

Get fresh ideas for your next yacht charter trip - insider guides, sailing itineraries, planning tips, and more. Subscribe and receive my free BVI Trip Planning Document.

    Genuine sea stories
    From hidden coves to the best anchorages, I share my first-hand experiences to enrich your next voyage.
    Exclusive insights, twice a month
    Our newsletter is your gateway to the secrets of successful chartering, delivered at no cost. Plus, the freedom to unsubscribe anytime.