Top Oahu Wine Tasting Tours

What makes this experience truly unique is that it takes wine tasting completely out of the traditional setting and places it on the open ocean along Oʻahu’s coastline. Instead of a bar or vineyard, guests enjoy a moving coastal journey where every moment changes with the light, water, and scenery. The experience blends a guided tasting of four craft wines, a locally distilled Hawaiian rum, and artisan chocolate from Lonohana Chocolate, creating a layered tasting experience that feels both elevated and distinctly island-inspired. What sets it apart further is the combination of ocean adventure and cultural immersion. Guests may encounter Hawaiian green sea turtles, dolphins, and seasonal whales while sipping, and select departures feature live performances by local artists, adding an authentic sense of place. It’s a rare balance of relaxation, discovery, and connection—designed to feel social and memorable without being crowded or formal.

Highlights: • Intimate sunset cruise just minutes from Waikiki • Curated Artisan wine tasting! • Complimentary local samplings from the island of Oahu • Live performances onboard • Optional ocean swim with stunning Diamond Head views • Breathtaking twilight and ocean scenery • Possible wildlife sightings: sea turtles, dolphins, and seasonal whales • Warm, knowledgeable, and welcoming staff and crew family

We've created a fair marketed up to 6 group size priced tour. There are 3 options. (North). North Shore, Dole pineapple, Haleiwa Town for Hawaii grown beef burgers or Garlic Shrimp, Turtle searching at the Beach, Kohana Rum distillery factory. (Central). Tantalus hills for some incredible panoramic view of Honolulu, Leonard’s Hawaiian Malasada doughnuts, Breathtaking ocean scenic driving along towards Sandy Beach, back to Downtowns Iolani Queens Palace and Kamehameha statue, A few breweries to choose from that's around Kakaako town. (East). Breathtaking Coastal scenic driving, Stopping by Kailua beach and Kailua town for some food. Laniakia breweries would be next or to have some red wine to pair along with chocolate at the Manoa chocolate factory. Swap the crowd and hassle of big bus. This exclusive experience takes your party around Honolulu, the North Shore, or Kailua with hotel pickup included. Settle in for a scenic drive filled with history and sights tailored to your interests.