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Hemingway Water Shuttle

4.9 (27 reviews)

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Tobipitu R.

Family run business. Really friendly, took the time to get all passengers familiar with Marco Island and some of the history. We ran into some dolphins and captain stopped for us to take pictures and appreciate the moment. Their dog Jack was onboard - adorable!

John David F.

What a great time! We did the Keewaydin Island trip! The two people running the trip were very nice people. My girlfriend and I were in town for vacation and had arrived only about an hour or so earlier. We were at lunch a few minutes away talking about things to do when we came across this one. In our mind, there was no way we could get to the 1:30 trip in time. But with a call and a little patience on the Hemingway's side, they accommodated us for the trip. They stop the boat and talk about things with the island as well as some wildlife and sea creatures (dolphins, turtles, etc). Once we got to the island we were blown away by how private-esque it seemed. Thanks so much for accommodating us and making the first excursion we went on during our vacation in Marco Island, one of our favorites!

Captain Jack
Randi M.

We were looking for something to do in Marco and came across Keewaydin Island. I booked this online 2 days before and it was an easy process. We were staying in an Airbnb right behind the marina so it was easy peasy for us. The ride to Keewaydin was slow so we could see the marine life and enjoy Capt. Jack!! Val rolls out a ramp to walk off the boat once you get to the island. The island is gorgeous and a perfect relaxing/shelling spot. Make sure you bring plenty of sunscreen!! I'm already planning our next trip to Marco, and you can be sure Hemingway Shuttle will be on that trip.

Highly recommend owners are super friendly and always stop the boat so we can see the dolphins and captain Jack is the cutest captain ever Thank you Hemingway I had an amazing time...

Looking out headed north ... I think :)
Daniel O.

It was great. They are very accommodating as you are allowed to bring your dogs on board. They know the area well and are full of interesting tidbits about Marco and Keewaydin. It's a quick 30 minute ride and there are frickin' dolphins swimming alongside you. I highly recommend it

Christina B.

Another awesome trip out to Keewaydin Island for my shelling! Something very magical about going out to a private and serene island! Steve and Val are very knowledgeable about the local area and wildlife! Thx Riley the dog for helping find all those dolphins! Make sure you bring your appetite! There's a food boat, Best Burgers, that serves up a great burger! And a ice cream boat for everyone! See you again guys!!

We had a fabulous trip! Captain Jack kept an eye out for dolphins the whole time. Val was very knowledgeable about the area and made sure to point out everything. Captain Steve got us to the perfect shelling spot. Highly recommend!

Our Captains: Steve and Val Hemingway

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6 years ago

The nicest couple. They are happy to help in any way to make your trip the best it can be.

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8 years ago

Great way to get to Keewaydin! The whole grew was so friendly and great guides. Highly recommend!

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Ask the Community - Hemingway Water Shuttle

Review Highlights - Hemingway Water Shuttle

“So glad my husband booked this excursion to Keewaydin Island with Hemingway Water Shuttle, which is the easiest way to get to the island.”

Mentioned in 7 reviews

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Key West Express

Key West Express

(12 reviews)

My friend and I took the Key West Express down to KW this past week, and returned the following day…read morealso on the ferry. Overall, the experience was fantastic. We got to the Rose Marina in Marco Island slightly before 7am in order to board the ferry. They scan the code either on your printed ticket or your phone and check your ID...have those ready and the process goes really quickly. Onboard, there are lots of seats on the main level inside. On the upper level, half the seats are inside and half are outside. There are restrooms on both levels. We opted for inside on the main level with the galley and had a very comfortable ride. We had Dramamine and Sea-Bands with us, but you can purchase Dramamine onboard the ship and they will tell you if the ride is expected to be a little rocky. They played a movie (Captain Ron...classic) on the way down, with captions on the TV screens. A lot of people read or slept. The food from the galley wasn't great, so plan to bring some of your own if you need snacks on the three hour trip. On the return trip, we did have a really rowdy group of adults who played a radio really loudly the whole ride back, which was pretty annoying. Other people also seemed annoyed by this group, but no one said anything, nor did the crew ask them to lower the volume. That would have made the return trip a better ride. But still, it was such a smooth and easy trip both ways, and SO MUCH better than flying!

I don't normally take the time to write reviews unless service was exceptional or awful. this one…read moreis due to above and beyond every step of the way. from the time we got there staff could not of been nicer. ease of the entire experience, and this includes a canceled trip due to weather. refunded and actually got to talk to someone on the phone. honestly just great all the way around.

Conrad Joe Charters

Conrad Joe Charters

(3 reviews)

Tony and Ellen were fantastic hosts! Conrad Joe was clean, modern, spacious and just the way to…read morecelebrate the Fourth of July! My now fiancé had been working secretly with Ellen for months planning a 5 hour sunset Fourth of July cruise for the two of us. When I walked onto the boat I even thought Tony and Ellen were family friends I've never met as they were so welcoming and treated us as if they've known us for years. I was nervous at first as since it was a surprise I hadn't packed any food or sunscreen and to my excitement Ellen had taken care of it all! She had variety of healthy appetizers set for us as well as sandwich platter and a bottle of sparkling wine. Although we did bring beer and a bottle of champagne I thought it was sweet of them to supply us with another bottle. They took us to the dome homes and gave us a brief history on the architecture and location of the now abandoned yet oddly beautiful landmarks. We cruised around and took in the Florida sunset as we anchored up in the perfect location for the fireworks off of Marco Island. Since Tony has extensive expierince with boating and the local area, he knew exactly where to take us to be close enough for a great view, but far enough from the boating masses. They also had a co-captain on board (Calvin)who shared stories of his life travels and casually snapped some amazing photos of my fiancé and I, memories I would not have been able to capture. We have already booked our trip back to Naples, and will be reaching out to Ellen and Tony for another visit!

There is not a better sunset experience on Marco Island than cruising with Tony and Ellen aboard…read morethe Conrad Joe. Tony is a master captain and Ellen is the consummate hostess. They provide an amazing cruise, fantastic snacks and beverages, and wonderful company. Don't miss out on this trip!

Hemingway Water Shuttle - boatcharters - Updated October 2026

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