Menu

Top 10 Best Hawaii Sailing Trips

Found 97 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 5
 

BYOB Friday Night Fireworks Cruise

(4.2 of 5 reviews)

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights and be in awe with this unobstructed view of fireworks from the water! With plenty of... More

Free Cancellation
Start From $138.95
 
BYOB Friday Night Fireworks Cruise Likely to Sell Out

BYOB Friday Night Fireworks Cruise

  • Hawaii
  • Exellent5 reviews4.2

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....

    Free Cancellation
    Start From $138.95
 
 

Friday Night Waikiki Fireworks Sail

(3 of 1 review)

Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a spectacular Hawaiian sunset and the Friday Night Fireworks onboard a luxury private yacht.... More

Free Cancellation
Private Tour
Start From $699.00
 
Friday Night Waikiki Fireworks Sail Likely to Sell Out

Friday Night Waikiki Fireworks Sail

  • Hawaii

Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a....

    Free Cancellation
    Private Tour
    Start From $699.00
 
 

Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii

(4.9 of 10 reviews)

Welcome to the only place in Hawaii where the spirit of ancient Hawaiian seafaring meets modern expectations on the pristine waters of the Kona coast. Immerse yourself in a unique and unforgettable experience as we invite you to j... More

Free Cancellation
Private Tour
Start From $125.00
 
Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii Likely to Sell Out

Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii

  • Hawaii
  • Superb10 reviews4.9

Welcome to the only place in Hawaii where the spirit of ancient Hawaiian seafaring meets modern expe....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Private Whale Watching Sailing Adventure

(3.5 of 2 reviews)

From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback whales. Departing near Waikiki, enjoy a leisurely sail against the majestic backdrop of Diamond Head as you scan the water for maj... More

Free Cancellation
Private Tour
Start From $695.00
 
Private Whale Watching Sailing Adventure Likely to Sell Out

Private Whale Watching Sailing Adventure

  • Hawaii
  • Good2 reviews3.5

From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback ....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

2hr Luxury Private Sailing Catamaran for 7-12 People

(3.5 of 2 reviews)

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More

Free Cancellation
Private Tour
Start From $1,495.00
 
2hr Luxury Private Sailing Catamaran for 7-12 People Likely to Sell Out

2hr Luxury Private Sailing Catamaran for 7-12 People

  • Hawaii
  • Good2 reviews3.5

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....

    Free Cancellation
    Private Tour
    Start From $1,495.00
 
 

Moana’s Luxury semi-private Sunset Cruise on Nalu

(4.3 of 6 reviews)

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback Whale watching at no additional cost. Dolphins, Sea turtle... More

Free Cancellation
Private Tour
Start From $121.99
 
Moana’s Luxury semi-private Sunset Cruise on Nalu Likely to Sell Out

Moana’s Luxury semi-private Sunset Cruise on Nalu

  • Hawaii
  • Exellent6 reviews4.3

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizabl....

    Free Cancellation
    Private Tour
    Start From $121.99
 
 

Private South Shore Sail Charter

(5 of 2 reviews)

Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and enjoy complimentary drinks while getting the ocean breeze, some Hawaiian sunshine, and even a splash or two! Experience the south ... More

Free Cancellation
Private Tour
Start From $1,000.00
 
Private South Shore Sail Charter Likely to Sell Out

Private South Shore Sail Charter

  • Hawaii
  • Superb2 reviews5

Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and ....

    Free Cancellation
    Private Tour
    Start From $1,000.00
 
 

Private Swim and Sail Charter (Kewalo Harbor)

(5 of 2 reviews)

A beautiful ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). This experience is customization in its duration and activity *Viewing marine life is not guaranteed but we do... More

Free Cancellation
Private Tour
Start From $1,800.00
 
Private Swim and Sail Charter (Kewalo Harbor) Likely to Sell Out

Private Swim and Sail Charter (Kewalo Harbor)

  • Hawaii
  • Superb2 reviews5

A beautiful ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and....

    Free Cancellation
    Private Tour
    Start From $1,800.00
 
 

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

(5 of 2 reviews)

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More

Free Cancellation
Private Tour
Start From $1,595.00
 
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People Likely to Sell Out

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

  • Hawaii
  • Superb2 reviews5

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....

    Free Cancellation
    Private Tour
    Start From $1,595.00
 
 

Afternoon Ali'i Adventure

(5 of 4 reviews)

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. ... More

Free Cancellation
Private Tour
Start From $276.00
 
Afternoon Ali'i Adventure Likely to Sell Out

Afternoon Ali'i Adventure

  • Hawaii
  • Superb4 reviews5

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....

    Free Cancellation
    Private Tour
    Start From $276.00
 
 

Private Morning Ceremony Sailing Charter

(5 of 4 reviews)

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, and more. We offer this experience at a discounted rate to accommodate groups wanting to do private charters in the morning to celeb... More

Free Cancellation
Private Tour
Start From $1,000.00
 
Private Morning Ceremony Sailing Charter Likely to Sell Out

Private Morning Ceremony Sailing Charter

  • Hawaii
  • Superb4 reviews5

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, an....

    Free Cancellation
    Private Tour
    Start From $1,000.00
 
 

Kanoa Yacht Charter: 2-Hour Sail off Waikiki

(5 of 4 reviews)

Start your luxurious voyage at Kewalo Basin Harbor, located at 1025 Ala Moana Blvd - Pier E, Slip 223. With prime parking on-site, your journey begins the moment you arrive. For those without wheels, don't fret! The dock is a quic... More

Free Cancellation
Private Tour
Start From $2,000.00
 
Kanoa Yacht Charter: 2-Hour Sail off Waikiki Likely to Sell Out

Kanoa Yacht Charter: 2-Hour Sail off Waikiki

  • Hawaii
  • Superb4 reviews5

Start your luxurious voyage at Kewalo Basin Harbor, located at 1025 Ala Moana Blvd - Pier E, Slip 22....

    Free Cancellation
    Private Tour
    Start From $2,000.00
 
 

Private Luxury Sailboat Charters of Honolulu

(5 of 4 reviews)

Oahu’s private luxury sailboat charter, Sailing Beauty, is operated by a mother and son team. While aboard this fully renovated 41' vessel, view the most treasured maritime life and landscapes of Oahu on a Day Sail and create gr... More

Free Cancellation
Private Tour
Start From $699.00
 
Private Luxury Sailboat Charters of Honolulu Likely to Sell Out

Private Luxury Sailboat Charters of Honolulu

  • Hawaii
  • Superb4 reviews5

Oahu’s private luxury sailboat charter, Sailing Beauty, is operated by a mother and son team. Whil....

    Free Cancellation
    Private Tour
    Start From $699.00
 
 

Waikiki private Day Tour and Sunset sail for couples

(5 of 12 reviews)

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples on their honeymoon, celebrating an Anniversary, or just in love, celebrating ... More

Free Cancellation
Private Tour
Start From $300.00
 
Waikiki private Day Tour and Sunset sail for couples Likely to Sell Out

Waikiki private Day Tour and Sunset sail for couples

  • Hawaii
  • Superb12 reviews5

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This privat....

    Free Cancellation
    Private Tour
    Start From $300.00
 
 

Private Cruise Swim with Dolphin

(5 of 12 reviews)

Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and anniversaries. An Impressive Swimming Experience with Wild Dolphins at the West Coast of Oahu. Learning about the ecosystem of wil... More

Free Cancellation
Private Tour
Start From $3,769.63
 
Private Cruise Swim with Dolphin Likely to Sell Out

Private Cruise Swim with Dolphin

  • Hawaii
  • Superb12 reviews5

Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and ....

    Free Cancellation
    Private Tour
    Start From $3,769.63
 
 

Waikiki Sunset Cruise and Iconic Views with Swimming

(5 of 12 reviews)

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide along the iconic Gold Coast as the sun sets, painting the sky with vibrant co... More

Special Offer
Free Cancellation
Private Tour
Start From $43.20
(Saving 20% ) $54.00
 
-20% Waikiki Sunset Cruise and Iconic Views with Swimming Likely to Sell Out

Waikiki Sunset Cruise and Iconic Views with Swimming

  • Hawaii
  • Superb12 reviews5

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $43.20
    (Saving 20% ) $54.00
 
 

Private Charter Snorkel Sail Adventure off Kaanapali Beach

(5 of 12 reviews)

PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘H... More

Free Cancellation
Private Tour
Start From $6,301.24
 
Private Charter Snorkel Sail Adventure off Kaanapali Beach Likely to Sell Out

Private Charter Snorkel Sail Adventure off Kaanapali Beach

  • Hawaii
  • Superb12 reviews5

PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant wi....

    Free Cancellation
    Private Tour
    Start From $6,301.24
 
3 4 5
Booking.com
Booking.com
Booking.com