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.

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


Afternoon Pony Tour (2-3 hours)

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

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

To make our Afternoon "Pony Tour" available daily, and more affordable, we have removed our money back guarantee.

Private Tour (2-3 hours)

$200 for parties of 4 or less

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 descendents of one of Chincoteague’s original settlers John Merry Jester, who settled the island in 1780. See our “Trip Description” page for more details. This trip sees the wild ponies over 90% of the time, dolphin about 50% of the time (from mid-June to mid-October), and bald eagles about 75% of the time.

How does the afternoon "Pony Tour" work?

We modified our "Pony Tour" for the 2017 season, to make it more available and affordable. The basic strategy is to manage our time differently, bypass some of the other attractions, and use that time to explore areas that we do not typically have time to search on our "Around the Island Tour". This tour takes no specific route, but may travel up to 40 miles in 2.5 hours. We have been using this route and time management technique since 2012, and over 90% of the time we are able to find at least one pony at a distance of 100 yards or less. To make this trip available daily, we have removed our money back guarantee, and lowered the price to our standard fee. It is the same route we used to run for our guaranteed pony tour. This trip may be aboard our larger 14 passenger boat.

What is a Private Tour?

 If we have more than one group on the boat, we try to get a feel for what everybody wants to see and talk about, and divvy our time up between those interests. Some guests have specific interests, and would like to focus the trip on that. Our private tour is designed to cater to those interests. In 2015, Capt. Ray had a couple who wanted to learn how to get from Captain's Cove to Chincoteague, and they booked a private trip to learn the way. In 2012, Capt. Dan had a couple of bird watchers who wanted to just look for birds, and they booked a private trip to focus on their birds. Some folks just want to keep it a private trip, but cover our standard route, and we can do that too.

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, let us know when you book, and 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. Be sure to let us know you want to be picked up there, otherwise we will be waiting for you in town.

How many passengers will be on the boat?

Our primary boats 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.

In 2015 we purchased a larger boat, capable of carrying 14 passengers, our plan is to use this boat for our afternoon "Pony Tour", by request for larger groups, and when our other boats are down for maintenance.

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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