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A Hands-on Sailing Experience

On our charters, you can take the helm, sit back and relax in our fully covered cockpit, lounge on our foredeck or take it all in from our aft deck’s more private seating. Our well-appointed yacht, first-class service and experienced crew will give you a tour of the historic Virginia Beach waterfront that will be refreshing, relaxing and hard to top! Once you see Virginia Beach's resort and famous sites from our perspective, it might be difficult to go back to the hustle & bustle of everyday life.

Like all sailboats, we will sail where the wind takes us. However, our trek on a typical summer day with typical summer winds will take us out on an angle from Rudee Inlet at the southern end of the Virginia Beach resort strip to the historic point where the Atlantic Ocean meets the Chesapeake Bay. This is called First Landing State Park and is the site where the Jamestown Settlers originally landed 400 years ago before making their way up to the Jamestown Settlement.

Catch an up close glimpse of marine life as you sail. Dolphins love to play alongside Iggy Biggy. It is the shape of the sailboat’s hull that draws them near and tempts them to play so close. At times, it is like they are putting on a show just for you!

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Our Breakfast Sailing Experience

Breakfast Sails are 2 hours and depart daily at 9:30am.

Please arrive at the slip no later than 9:15am. Our Breakfast sail includes freshly-squeezed orange juice, fresh-brewed coffee, fresh fruit, and breakfast baked goods. If you plan on bringing your own beverages, please make sure that they are in plastic or cans. No red wine, glass bottles, open cups or thermoses please. Please contact us through our reservations number for more information. 757-358-5800

Our Sunset Sailing Experience

Sunset Sails are 2 hours and depart daily at 6:00pm.

Please arrive at the slip no later than 5:45 PM. On our Sunset sail you will be served refreshing beverages, as well as bottled water and soft drinks. If you plan on bringing your own beverages, please make sure that they are in plastic or cans. No red wine, glass bottles, open cups or thermoses please. Please contact us through our reservations number for more information. 757-358-5800

RESERVATIONS 757-358-5800


Reservations recommended and are accepted beginning in late April. Due to the limited number of passengers that we accept for each charter and our high level of customer service, reservations cannot be made online. Reservations must be made through our reservations phone number. 757-358-5800

In order to hold your reservations, a credit card is required. We accept Visa, MasterCard, American Express and Discover Card. When you arrive, you may charge your sail to your card or pay cash. Your card will be charged in the event that you are a ‘no show’ or have not followed the cancellation policy as outlined.

Children: Please let us know the age of all children in your party when making your reservation. We do have an age limitation that must be met. We do not allow infants or young toddlers to sail with us for safety reasons.

Private 2-hour charter for 2-6 guests is available. Please call for more information


Cancellations must be made at least 48 hours in advance of your sail. If you do not cancel 48 hours before your sail, you will be refunded only in the event that we cancel the sail. We want you to enjoy your sail so in the event of heavy rain, thick fog, high winds or if threatening weather appears imminent, we will cancel. However, we will sail if it is merely overcast or even if it just looks like rain. We frequently experience summer thunderstorms at the oceanfront. Even though you might witness a heavy downpour and dark skies from your hotel room… just wait 30 minutes. These storms are usually just a short respite from the heat. A decision to cancel is usually made by us only shortly before your sail is scheduled to depart.

Check In

Each charter is 2 hours long and departs from the Oceanfront Marina at 416 Southside Road just south of the Rudee Inlet Bridge. Iggy Biggy is in slip 11. You will be greeted at Iggy Biggy by a crewmember, checked in, and your payment will be processed. We ask that you arrive 15 minutes prior to your scheduled charter time so we can get you checked in and no one will miss the sail. We cannot stress enough – BE ON TIME to check in! If you will miss the boat, you will still be charged for your tickets and there will be no refund!

Tips & Safety

Bring appropriate gear for going on the water. A lightweight jacket might be a good idea for a breezy morning. We have a full canvas top over our cockpit, but we still recommend sunscreen. Please do not bring tanning oil as it makes the decks slippery and dangerous. Non-greasy lotion is best. If you are going to wear a hat, make sure that it will stay on your head securely. Big, floppy brimmed hats tend to fly away easily… so make sure yours has a chin strap. Please wear boating shoes or white soled athletic shoes. If you do not have either, we welcome bare feet! Running shoes, sneakers, hiking boots and soft soled sandals with black soles will leave black marks on our decks that are hard to remove. You can certainly take your shoes off just before boarding the boat and we can store them safely for you until the end of your sail.

Your safety and enjoyment are our primary concerns. All of our captains are very experienced and hold a current license from the United States Coast Guard.

Iggy Biggy is well appointed and well equipped to handle any emergency. Luckily, the owners’ children, in need of a Band Aid or two, have been our biggest concern so far.

As your departure day and time approaches, it is always wise to keep an eye on the weather. For the most accurate forecasts we recommend accuweather.com. You can simply enter in the zip code for Virginia Beach (23451) and you will get hourly forecasts specifically for our area. We, of course, cannot ever guarantee a forecast, but accuweather.com is highly recommended by sailing charter companies in other areas of the country as well.

If anyone in your party has a problem with motion sickness, this is not the time to try out a new remedy. We cannot turn the charter around to accommodate a seasick passenger unless you are chartering the entire sail and want to forfeit the trip.

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