Can I bring alcohol on the cruise?

Yes, guests are encouraged to bring their own beverages to enjoy during the sail, with the exception of glass containers for safety.

Is the cruise suitable for children?

Yes, the cruise is family-friendly, but children should be comfortable on a boat and supervised at all times.

Comfortable, weather-appropriate clothing with sun protection is recommended; layers are helpful for varying conditions.

Are there restrooms on board?

Yes, the vessel is equipped with restrooms for guests’ convenience.

How early should I arrive?

Arrive at least 15 minutes before your scheduled departure to allow for boarding and settling in.

What if the weather is bad?

The cruise may be rescheduled or canceled if weather conditions are unsafe; you will be notified in advance.

Romantic Sailing with North Shore Sailing Adventures in Haleiwa | Private | Sailing

Haleiwa, on the North Shore of Oahu, Hawaii, is renowned for its legendary surf breaks and vibrant coastal scenery. Amidst this oceanic playground, North Shore Sailing Adventures offers a standout experience designed for couples and small groups seeking an intimate escape on the water. Their signature TBR Romance Cruise is a 3-hour private sail that turns any special occasion into a cherished memory. Imagine gliding across crystalline waters aboard a well-equipped vessel, with unobstructed views of the Pacific’s vast horizon and the lush North Shore coastline. The cruise is tailored for up to six guests, perfect for honeymoons, engagements, or simply celebrating a moment together. Bring along your favorite food and beverages to personalize this floating sanctuary, adding a touch of your own romance to the journey.

What makes North Shore Sailing Adventures unique is their ability to craft a bespoke experience in a setting packed with natural beauty and cultural significance. The North Shore’s rugged volcanic coastline, with its dramatic sea cliffs and hidden coves, forms an unforgettable backdrop. Plus, the calming motion of sailing offers a welcome respite from busy travel routines. It’s a standout addition to any Hawaii trip—combining adventure, luxury, and intimacy.

This experience not only captures the spirit of Hawaiian waters but also offers an escape that fosters connection and relaxation. Whether celebrating an anniversary, proposing, or simply craving quality time, the TBR Romance Cruise delivers an authentic and memorable Seaside escape crafted for romance and discovery.

About North Shore Sailing Adventures

North Shore Sailing Adventures is a private sailing operator based in Haleiwa, Hawaii, offering small-group charters along Oahu’s North Shore. The company provides a range of private trips—including the TBR Romance Cruise, Sunset Sailing Adventure, TBR Half-Day Private Charter, Full Day Private Charter: Waimea Bay, Sailing Adventure, Dolphin Watching Adventure, and Whale Watching Adventure—designed for up to six guests per vessel. Trips range from three-hour sunset and romance cruises to four-hour whale watching and half-day sails, plus a six-hour full-day charter to Waimea Bay for swimming, snorkeling, and anchoring in calm waters.

Crews provide real sailing experiences and on some trips naturalist-style commentary and a hydrophone for listening to whales. Whale watching is available during Oahu’s humpback season (November through April). Guests are invited to bring their own food and beverages on many private charters for personalized celebrations such as honeymoons, engagements, and family outings.

Safety and comfort are central: trips are private charters accommodating up to six passengers to maintain an intimate experience, and activities include snorkeling, wildlife viewing, and relaxation on the water. Bookings typically cover private time aboard a sailing vessel with options for sunset, wildlife-focused, and full-day itineraries. North Shore Sailing Adventures positions itself as a local operator focused on personalized, small-group sailing experiences that showcase the natural beauty of Oahu’s North Shore while providing informative and memorable outings for visitors and residents alike. Reservations are available online or by phone via The Adventure Collective listing; itineraries can be customized to match guest interests and schedules.