Our Most popular #SailStiletto experience
…for a reason. The sunset half day sail is a 4 hour experience with enough time for pulling up to the beach jumping in for a swim, hopping on a board for a paddle, soaking up the sun, and for the grand finale…come back aboard your sailboat and sail into the sunset. 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.
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?
Each boat can only take up to 6 guests. If you have a larger group, book a flotilla. We can accommodate up to 12 guests with a Flotilla Sail, where we sail two identical boats together. Such a fun experience, many options for extra fun with two boats. Check out our flotilla sailing.
- Click here to book our second boat: https://stiletto-classic-catamarans.com/
- Click here to learn more about multiple boat charters: https://phillipsboatworks.com/charters/adding-a-second-stiletto-27-to-our-outer-banks-sailing-fleet/
When should I arrive at the dock?
Please arrive just a few minutes before your charter begins. You will find the start time of your charter on your receipt. Often, particularly in the heat of the summer season, our skippers are often taking a water break and will arrive just a few minutes before your charter. It only takes a couple minutes to board and shove off.
Where do we meet the boat and captain?
Most of our charters leave from the Buxton Harbor Hatteras Sailing Center at 48962 NC-12, Hatteras, NC 27953. However, sometimes due to the weather we may depart from other locations. Your skipper will be in touch with you before your charter if there is any weather related start location change. Note: Our boat shop and sail repair are in a different location, but we are usually around 😉
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?
- Hats, sunglasses, drinks, water shoes or boat safe shoes
- 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
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.
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.
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.