Captain Dan’s Around the Island Tours


What is the cost of the cruise?

Around The Island Tour (2-3 hours)

$40 per person for adults, and $35 per person for children under 12.


Money Back Guaranteed Pony Tour (2-3 hours)

$50 per person.

We also offer a $5 off discount per person for payments made by cash or check.

How does the "Money Back Guaranteed Pony Tour" work?

I guarantee that you will see ponies at a distance of 100 yards or less, or your trip is free. My goal is to get just a few feet away from the ponies, and I will scour the coast to make that happen. The guaranteed pony tour will not necessarily go “around the island”, it may not see the Assateague Lighthouse, or the pony swim lane, etc. We are just seeking out ponies until the guarantee is satisfied. If time allows, we may be able to continue in an “Around the Island Tour” route, but not necessarily. We do not guarantee ponies on our Around the Island Tour, although we do see them over 90 percent of the time. Our fee for the Money Back Guaranteed Pony Tour is $50 per person. In 2013 I had 5 Guaranteed Pony Tours in which did not collect my fee. I did indeed find ponies, but they were too far away to satisfy the conditions of my guarantee.

What does the “Around the Island Tour” consist of?

Captain Dan’s Around the Island Tour is a 2 to 3 hour trip that goes all the way around the entire island of Chincoteague. Most of the trip is spent sailing between Chincoteague and Assateague Island. We travel over 25 miles of unique coast line never passing the same area twice. You will see every stretch of coastline of Chincoteague, and Assateague’s entire bayside coastline in Virginia, all the while searching for Wild Ponies, Dolphins, Bald Eagles and more. But our trip is not just a sightseeing trip; Captain Dan and Captain Ray explain the history of the Islands, the economy, the people, and the wildlife. Of course the wild ponies are a big attraction, and we can explain the entire evolution of annual Chincoteague Volunteer Fireman’s Carnival and Pony Swim and Auction, from the origins of the ponies back in 1750 to the modern-day events. Oysters and clams are a big part of our way of life and we explain those industries too. There is so much to talk about that it helps to tell your captain what your interests are. Dan and Ray are both direct decendents of one of Chincoteague’s original settlers John Merry Jester, who settled the island in 1780. See our “Trip Description” page for more details.

Where is your dock?

We load from the floating dock, in the Robert Reed Downtown Park. Parking is available behind and adjacent to Don’s Seafood Restaurant (4113 Main Street, Chincoteague VA 23336). Once you park, walk out to the water and down to your left until you see the aluminum ramp sloping down to the floating dock. The boat arrives 10-15 minutes prior to departure. If you happen to be staying at the Hampton Inn, or Comfort Suites, you can hop on at our boat slip on the south side of the Hampton Inn, a very short walk from either hotel. Hotel guest wait next to out “Hotel Boarding Area” sign. Please arrive 15 minutes prior to departure time.

How many passengers will be on the boat?

We carry no more than 6 passengers per boat; with two boats we can accommodate groups of up to 12 people. We like to be able to personally address any of your questions or concerns about our islands, and our way of life.  Each guest is guaranteed as much face time with the captain as they need. Some trips are a total Q & A experience, where our guests steer the discussion in whatever direction they want. If you desire a private tour, you can book the empty seats on the boat at the child rate.

What information is required to make a reservation?

When you call or email to place your reservation, Miss Abby will need to know:

1.      The date and preferred time of day for your cruise

2.      The number of passengers in your party. (Include all persons, children and infants)

3.      Visa or Master Card number to hold the reservation (unused numbers are shredded weekly, charged numbers are shredded after payment is processed.)

4.      A cell phone number we can reach you on the day of your cruise. This is only used to contact you in the event complications arise on the day of your cruise.  Mostly used during bad weather to reschedule, or if you are not at the dock at your departure time.

Why do you need my credit card number if I will be paying in cash?

Your credit card is used to hold your seats on the boat. When you call and make the reservation, we don’t allow anyone else to book your seats. The credit card is only charged if you fail to show-up for your trip, without calling us 24 hours in advance to let us know you won’t be cruising with us. You will not be charged for inclement weather cancellations (see inclement weather policy below). If you are uncomfortable about giving credit card information out over the phone, I recommend getting a Visa gift card at your local bank or retailer. That is what we do when we go on vacation.

What about inclement weather, do you go out in the rain?

All trips are weather permitting; we do not cruise in dangerous weather (including high winds, high seas, heavy rain and/or lightning).  Weather is difficult to nail down in advance, even within 12 hours forecasts change drastically. April, May, October, November, you can expect it to be a bit cool. I say that it’s going to feel a good 15 to 20 degrees cooler on the boat, since we will be in the wind. You’ll want to bundle up if temperatures are below 70 degrees. Windbreakers will keep you warmer than heavy coats that the air can move through.


As for inclement weather. We run on a strict “GREEN, YELLOW, RED” weather condition policy.


GREEN: Great weather, calm seas, all conditions working together for a great trip. We are going!


YELLOW: Conditions may not be the most comfortable, but are still safe. This would include light rain, or potential for light rain. Winds that cause sea spray to blow over the side, extreme cold, etc.  In most cases, a condition yellow trip will be wet, and there is no “a little wet” on the boat. Some folks bring ponchos and rain gear; some don’t care if the weather is warm. I will either call you, or meet you on the dock and discuss this with you. If you feel as though the conditions are more than you want to endure, you are free to back out of the trip, at no cost to you.


RED: Condition Red is deemed unsafe by the captain, and we will not leave the dock. This is when the conditions are, or have the potential to develop: heavy rain, high winds, high seas, thunderstorms, lightning, tornados, etc. You will not be charged for a condition red cancelation.


Judgment of conditions is made by each captain, and we err on the side of caution. Your safety is my personal responsibility, and I take that responsibility very seriously. I want you to have fun, and enjoy yourself. Rest assured I will keep you safe. 95% of the time we are in condition GREEN.


Again, we will not take you out in bad weather, so if a thunderstorm comes up at noon, please don’t call and cancel your sunset trip. In all likelihood, the storm will have cleared, and the weather will be great.

Is the boat covered?

Yes! Both of our boats feature retractable double canopies so there is plenty of shade for all passengers. We also have the option of shading one half of the boat and leaving the other half un-shaded for those guests that want to work on their sun-tan. When the canopies are open, and we are underway, we say that the temperature on the boat feels 15 to 25 degrees cooler than on the land. A midday boat ride is a great way to beat the summertime heat. However these canopies do virtually nothing for rain, do not expect them to keep you dry in the event of rain.

Do you charge for infants?

Yes, since we only carry 6 passengers per boat, infants do count as a passenger.  For passenger counts the Coast Guard includes infants. Infants must be included in the total passenger count, and that cannot exceed 6 passengers per boat. If pregnant women deliver on the boat, they will be charged for the newborn child (hopefully it doesn’t put us over 6 passengers).

Will there be mosquitoes on the boat?

It’s extremely rare that we encounter mosquitoes on the boat. You can bring your bug spray if you want, however it’s not like it is when you walk one of the nature trails.

What’s the best time of day to see the wild ponies?

We have not found any time of day that’s better for seeing any of the wildlife; it just really depends on what your schedule is like. We see ponies all day, every day; it’s very rare to have a trip where we don’t see them at all. Same thing with dolphin, there are times of the year when dolphin viewing is better, but not times of the day.  In 2012 our first dolphin sighting was on 04/11 on the 12pm trip. The dolphins really move in from the end of May until the end of October. In the month of October we see dolphin on almost every trip.  I should also mention on our sunset trip the sun doesn’t set until the last 20-30 minutes of the trip, so dolphin and pony viewing is just as good as any other trip of the day. Birding, however, is better at low tide. About 2 hours before low tide at the beach is a good birding trip.

What type of boat is it?

Captain Dan’s Around the Island Tours uses 2, 25 foot Sweetwater pontoon boats. They utilize a flat deck and cushioned seats for your comfort. Designed to carry up to 15 passengers, we only ever carry 6 per boat.  So there is plenty of room to spread out and get comfortable.  Our boats are also equipped with double canopies to keep you in the shade on hot days.

Is a restroom available?

The boats are equipped with a restroom. The restroom is a camping potty with a dressing room curtain around it It is adequate to provide the necessary privacy and and serve its function, but it is not elaborate.

Can we bring food and drinks on the boat?

Certainly, all food and drink are welcome on board Captain Dan’s boats. Keep in mind that the wind will be moving by at 15 mph or greater, so paper and plastic wrappings should be tucked away or kept to a minimum. Also keep in mind that there may be other guests on board during the trip, so please be mindful of other with regards to you eating and drinking

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