Romantic Sailing Experience in St. Augustine: Sweetheart Head Over Heels Package
Difficulty
easy
Duration
1–2 hours
Fitness Level
Suitable for all fitness levels; minimal physical effort required.
Overview
Experience a romantic afternoon sailing the historic coastal waters of St. Augustine, Florida. The Sweetheart - Head Over Heels Package offers couples a serene, intimate journey that blends maritime heritage with personalized comfort.
Sweetheart - Head Over Heels Package
3 hours - Starting at $2,150.00 for 2
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Adventure Photos
About This Adventure
Description:
Snuggle up under a blanket built for two and experience the most unique and romantic sailing experience ever! Set sail on a private luxury yacht while toasting each other with a bottle of bubbly and soaking in the sights on a 3-hour sail along the beautiful intracoastal waterway and Matanzas Bay. Enjoy quality time with your special someone while a private chef prepares an upscale 5-course dinner, then wine and dine together as the sea shimmers around you.
Your exclusive 3-Hour Charter Experience will include an upscale 5 Course Dinner prepared by our Private Chef, house wine to include 2 bottles of house sparkling wine.
To enhance your sailing experience we offer a variety of beer, wine, and canned cocktails for those 21+, water, and soft drinks are also available as well as warm cozy blankets are available for purchase in our office.
Convenient and free parking is available at the marina.
More to Know
Food and beverages are available for purchase.
Please wear shoes with non-marking soles (deck shoes, tennis shoes, white-soled shoes). Avoid hard soles, high heels and black rubber-soled shoes.
All alcohol is required to be purchased in the office prior to departure. No red wines are available.
Please NO spray tanning products as these products can stain the boat.
Smoking of any substance is not allowed on board.
No pets on board.
Adventure Tips
Arrive early to check in and settle
Give yourself time to get oriented so your sailing experience starts stress-free.
Bring layers for changing coastal weather
Evenings on the water can get cool; dress in layers to stay comfortable.
Use reef-safe sunscreen
Protect your skin without harming sensitive marine ecosystems.
Secure your valuables
Keep phones and cameras safe and dry with waterproof pouches or zip-lock bags.
Local Insights
Wildlife
- Dolphins often seen near shore
- Brown pelicans and osprey hunting along the coast
History
St. Augustine is the oldest continuously inhabited European-established settlement in the continental U.S., founded in 1565.
Conservation
Operators emphasize eco-friendly practices such as minimizing fuel use and promoting wildlife respect to protect coastal ecosystems.
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Adventure Hotspots in St. Augustine
Frequently Asked Questions
Recommended Gear
Light jacket or windbreaker
Spring coastal breezes can be cool, so bring a lightweight jacket.
spring specific
Sun hat
Protect your face during sunny afternoon sails.
summer specific
Comfortable shoes with grip
Non-slip shoes help maintain footing on wet boat surfaces.
fall specific
Warm layers
Even mild winters require some warm clothing on the breezy water.
winter specific