Sunset Half Day

Our Most popular #SailStiletto experience

…for a reason. The sunset half day sail is a 4 hour experience with enough time for jumping in, laying out, and still catching the sunset show. Timed perfectly so your group can enjoy the best of an Outer Banks stiletto sailing experience, your charter will end up right at civil twilight just after the most magnificent sunset colors shine.

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Frequently Asked Questions

Is gratuity included in my charter fee?

Gratuity is not included in your charter fee. Customary gratuity is 15%.

Can I bring more than 6 total guests?

Sorry, we can only accommodate groups of 6. We hope to add additional boats, so please check back next season and look into our Flotilla options.

When should I arrive at the dock?

Please arrive 10 to 15 minutes before your charter begins. You will find the start time of your charter on your receipt.

Can Children come on the boat?

Of course. We love Kids, and have 3 of our own. Please bring your own lifejackets for children. Safety is so important to little ones, and according to the US Coast Guard regulations they are required to wear a life jacket at all times on the boat. The life vest should be comfortable enough that they will wear it and fit them appropriately.

Can I bring a cooler and drinks?

Please bring water and drinks. Alcoholic beverages are allowed, but your captain reserves the right to stop serving if a guest becomes a danger or annoyance to the other guests.

Please do not bring a cooler. We have a cooler and ice is provided. Whether you are an adult or a child, it is a good idea to bring along a lidded cup to prevent messy spills.

If you are on a private charter, you may bring food of whatever sort you like. If you are on a shared charter feel free to bring “neat” snacks.

What do I need to bring with me on my charter?

  • Dress in layers for morning and evening charters. Early mornings and evenings can be chilly with the breeze particularly if you are wet from swimming.
  • Sunblock and a hat are essential even on cloudy days
  • Camera, phone, waterproof protection for your devices
  • Please wear boat safe shoes or plan to stay barefoot. You may not wear street shoes on the boat.
  • If you are susceptible to seasickness, plan to take motion sickness medication before your trip.

Phillips Boatworks Charter Terms & Conditions

Advance Reservations

You may book a charter up to 12 weeks in advance.

If you reserve your charter more than 3 days in advance, our system prompts you to pay a set reservation fee which reserves the charter for your party. Three days prior to our sail, the final balance becomes due. You will receive an invoice with a link which you can click to pay the final charter fee.

If you book within 3 days of your charter, a full charter fee is required upon reservation.

Weather Policy

We sail in 0-20 knots, and light, spotted showers. We do not sail over 25knots or when it is lightening. While this is our general guideline, all charters are held at the captain’s discretion and he considers all factors.

If the charter you have reserved is cancelled due to inclement weather, we will do our best to reschedule your sail during your stay here on the Outer Banks. If for some reason, we cannot agree a time to make up the charter, we will refund your charter fee.

Beverage Policy

We provide a cooler with ice. You may bring alcoholic beverages on board. We reserve the right to terminate your charter with no refund if members of your party become unsafe due to excessive alcohol consumption. Underage members of your party may not drink while on board the sailboat.

Private Bookings Only

Due to current Covid-19, we do not offer per person charters at this time.


Children are very welcome aboard, but per the coast guard children under 12 must be in a life jacket while on board the sailboat. You must bring an appropriately sized life jacket for each child. We do not have the boat equipped with child sized life jackets.

The boat is stocked with coast guard required adult lifejackets. The adult life jackets we supply are not particularly comfortable to wear. If you feel you need to wear a lifejacket while on board, please bring one that is comfortable for wearing.