ITINERARY FOR THE WEEKEND OF DECEMBER 28 - DECEMBER 29, 2024

New Year’s Eve in Kailua: Scenic Adventures and Relaxation Await

Celebrate New Year’s Eve in Kailua with a blend of scenic adventures and relaxation. With pleasant weather and a mix of sun and clouds, indulge in wine tasting at Oahu’s only winery and paddleboard tours to the Mokulua Islands for an unforgettable experience.

A Toast to New Beginnings: Wine Tasting at Oahu’s Only Winery

As the sun casts its golden glow over Kailua, the perfect way to start your New Year’s Eve adventure is with a visit to Oahu’s only winery. Nestled in the serene landscape of 201 Kapaa Quarry Place, this hidden gem offers a delightful escape into the world of New World wines. With a focus on organic practices and minimal preservatives, the winery promises a tasting experience that is both refreshing and enlightening.

Join a 90-minute wine sampling session, available at various times throughout the day, including 11:00 AM, 2:00 PM, and 5:00 PM. As you sip on six different wines, you’ll be guided by knowledgeable hosts who share the art of winemaking with passion and charm. The cozy atmosphere, coupled with the exquisite flavors, makes for an indulgent start to your day.

“Highly Recommend - They were very nice and the selection was great! The guy who served us was very kind and answered all of our questions.” (Reviewed on 2024-07-12)

Whether you’re a seasoned wine enthusiast or a curious novice, this experience is sure to leave a lasting impression. Wine Tasting

Paddle into Paradise: Lanikai to Mokulua Islands

As the morning unfolds, embrace the spirit of adventure with a stand-up paddleboard tour from Lanikai to the Mokulua Islands. This heavenly sea adventure, available from 9:00 AM to 1:00 PM, invites you to explore the celestial beauty of Hawaii’s waters.

Departing from the quaint village of Lanikai, you’ll glide across the serene bay, surrounded by the breathtaking views of the Kualoa Mountains and the pristine white sands. The journey to the Mokulua Islands is not just a paddle; it’s a voyage into the heart of Hawaii’s natural splendor.

“Sensational fun! - Truly, can’t recommend this tour enough! The guide was so fun, professional, and knowledgeable… Not to mention knew just how to give us the best, Hawaiian paddleboard experience!” (Reviewed on 2024-03-25)

With no prior experience needed, this tour is perfect for families and thrill-seekers alike. Let the gentle waves and the warm sun guide you to a place of pure bliss. Paddleboard Tour

Sunset Serenity: Reflecting on a Day Well Spent

As the day draws to a close, the skies over Kailua transform into a canvas of vibrant hues, setting the stage for a tranquil evening. After a day of exploration and indulgence, take a moment to reflect on the experiences that have enriched your soul.

Consider returning to the winery for an evening tasting session at 6:30 PM, where the ambiance is even more enchanting under the starlit sky. The nearly full moon adds a touch of magic to the night, making it an ideal time to savor the last sips of the day.

The gentle breeze, the sound of the ocean, and the warmth of the Hawaiian spirit create a perfect backdrop for welcoming the New Year. Whether you’re toasting with a glass of wine or simply soaking in the beauty around you, Kailua offers a celebration that is both serene and unforgettable.

As you prepare to bid farewell to the old year and embrace the new, let the memories of Kailua’s scenic adventures and relaxation linger in your heart. Here’s to new beginnings and the promise of more exquisite journeys to come.

Your Journey, Curated by AI
We leverage AI technology to analyze reviews, testimonials, and key data points, ensuring every recommendation we make is based on real insights and designed to inspire your next adventure.
About the Author
Author Image
Henry St. James
Henry delivers exquisite journeys through France and Italy, analyzing vineyard conditions, restaurant reviews, and seasonal trends to offer travelers the best wine-tasting experiences and culinary delights, all informed by data.
Popular in Kailua
SEASONAL

March into Adventure: Kailua’s Clear Skies and Outdoor Wonders Await

March into adventure with Kailua’s clear skies and outdoor wonders. Discover stunning beaches, vibrant culture, and thrilling activities perfect for the season.

Dante Escobar
Mar 1, 2025
Beach Adventures in the Caribbean
SEASONAL

Spring Awakening in Kailua: Discover Sacred Sites and Scenic Beauty

Experience the awakening of spring in Kailua, Hawaii, with perfect weather for exploring its sacred sites and stunning landscapes. Discover the island’s rich cultural heritage and natural beauty through immersive tours and outdoor adventures.

Yuto Saito
Feb 22, 2025
Cultural Experiences Worldwide
SEASONAL

Presidents’ Day Weekend in Kailua: Scenic Tours and Cultural Adventures Await

Celebrate Presidents’ Day weekend in Kailua, Hawaii, where scenic beauty and rich history await. With pleasant weather and exciting tours, it’s the perfect time to explore the island’s cultural and natural wonders.

Dante Escobar
Feb 15, 2025
Beach Adventures in the Caribbean
SEASONAL

Weekend Escape: Exploring Kailua’s Natural Beauty Through Kayaking and Paddleboarding

Experience the perfect weekend getaway in Kailua, Hawaii, with pleasant weather and thrilling outdoor adventures. From kayaking to stand up paddleboarding, discover the natural beauty and vibrant culture of this Hawaiian paradise.

Layla Hart
Feb 8, 2025
Water Activities Worldwide
SEASONAL

Valentine’s Day Preparations: Romantic Adventures Await in Kailua

With clear skies and comfortable temperatures, Kailua offers the perfect setting for romantic adventures this Valentine’s Day. Discover breathtaking helicopter views and eco-friendly kayak tours, creating unforgettable memories with your loved one.

Elena Marquez
Feb 1, 2025
Romantic Getaways for Couples in the USA and Caribbean
SEASONAL

Rainy Weekend Retreat: Discover Kailua’s Hidden Gems and Indoor Delights

Experience the perfect blend of indoor and outdoor adventures in Kailua, Hawaii, this weekend. With a mix of overcast skies and potential rainstorms, embrace the island’s natural beauty and cultural richness through self-guided tours, wine tastings, and historical explorations. Don’t miss out on this unique opportunity to unwind and explore!

Dante Escobar
Jan 25, 2025
Beach Adventures in the Caribbean
SEASONAL

Mid-January Escapades in Kailua: Kayaking, Culture, and Clear Skies Await!

Experience the best of Kailua this mid-January with clear skies and perfect temperatures. Dive into thrilling kayak tours and explore Oahu’s hidden gems with a self-guided audio tour. Don’t miss out on these unforgettable outdoor adventures!

Dante Escobar
Jan 18, 2025
Beach Adventures in the Caribbean
SEASONAL

Rainy Day Adventures in Kailua: Embrace the Elements with Unique Experiences

Discover the hidden beauty of Kailua, Hawaii, on a rainy weekend with unique adventures that embrace the elements. From ocean safety training to exploring sacred sites, this itinerary offers a perfect blend of excitement and cultural immersion.

Layla Hart
Jan 11, 2025
Water Activities Worldwide
SEASONAL

Post-Holiday Serenity: Kayaking and Wine Tasting in Kailua, Hawaii

Escape the post-holiday hustle with a serene retreat in Kailua, Hawaii. With perfect weather for kayaking and wine tasting, this weekend promises relaxation and adventure in equal measure.

Layla Hart
Jan 4, 2025
Water Activities Worldwide
Activities in Kailua