Get your beach body ready to enjoy this quintessential winter beach vacation with iconic beaches and outstanding beach activities. Known as “The Gathering Place,” Oahu is home to the largest population of people as well as the best nightlife in Hawaii. The surfing mecca of the world is Oahu’s North Shore, and surfers flock there every winter to witness the best the world has to offer.


Travel tips
  • If you get an offer for free tickets in exchange for couple of hours of your time, know that they are trying to sell timeshare. Unless you don’t mind sitting through a lengthy timeshare sales presentations, beware of high pressure sales tactics if you aren’t in the market for a timeshare.
  • If you’re budget conscious, you can buy a portable grill and cook dinner on the beach. This will not only save money but you can enjoy beach longer.
  • Hawaii has quite strict laws regarding liquor licensing for businesses. Many restaurants avoid alcohol or charge hefty prices. Check if your restaurant allows Bring Your Own Booze (BYOB).
  • During winter, you can expect extremely high surf at many north and west shore beaches.
Recommended daily itinerary

Estimated cost: $2500-$5500 per person

Day 1

First day of the trip, check in to your hotel and get settled.

  • Fly into Honolulu International airport and drive to Kalakaua ave.
  • Checkin to the Lotus Honolulu at Diamond Head. Opposite Kapiolani Park, this polished hotel with views of the Pacific Ocean and Diamond Head volcanic peak is 3 miles from Ala Moana, a shopping mall, and 4 miles from the Honolulu Museum of Art. Explore your hotel and Kapiolani park as you settle down.
  • Enjoy your dinner at Michel’s at the colony surf for a dining experience that captivates the hearts of visitors from all over the world with personalized service and hospitality
Day 2

Lanikai Beach and Kailua Beach Park.

Kailua beach has plenty of soft sand and seclusion for a morning of peaceful, relaxing or swimming. Lanikai Beach used to be about a mile long, but the development of seawalls has caused erosion, making it about a half-mile.

  • Enjoy your breakfast at Nalu Health Bar & Cafe.
  • Drive to Lanikai Beach. Finding Lanikai Beach can be a bit tricky, since there are no posted beach signs. The pedestrian access is located through beach alley ways between the residential homes. The magical aqua blue calm waters here are ideal for swimming, kayaking or paddle boarding. While there are some small patches of reef, this is not a great beach for snorkeling. You can rent kayaks or paddle-boards from Kailua beach adventures.
  • Enjoy your lunch at Champs Sports Bar & Restaurant.
  • Drive to Kailua Beach Park. The turquoise blue water and amazingly soft white powder sand makes it a great beach to relax. While the water is usually calm to swim in, there are usually some small waves to play around in also. Kite Surfers love to take advantage of the winds that blow in this area. Bring your boogie board or just body surf to ride these waves.
  • Enjoy your dinner at TBD by Vikram Garg. We recommend lamb shank.
  • Head back to your hotel to rest up and recharge.
Day 3

Waikiki Beach and Sunset Beach.

The Waikiki area was once a playground for Hawaiian royalty, who enjoyed surfing on longboards in the 1800s. Sunset beach is a beautiful surfing mecca where you can watch big-wave surfers in action during the wintertime.

  • Enjoy your breakfast at Barefoot Beach Cafe. We recommend breakfast burrito.
  • Drive to Ala Moana Blvd. Enjoy waikiki beach sightseeing cruise and explore the Pacific Ocean on a top-rated sightseeing cruise. This glass-bottom boat tour is the perfect introduction to Hawaiian sea life, as the expert captain and crew help spot creatures like green sea turtles (honu), migrating whales, and dolphins. Unlike other catamaran cruises, this one lets you look underwater through clear magnifying port holes.
  • Head over to Paia Fish Market for lunch. We recommend Chicken Pasta.
  • Head over to Sunset Beach, one of the few long stretches of sand that you get to drive right next to, traveling along the Kamehameha Highway. Be careful when entering the ocean in this area, especially when waves are present. It’s best to check in with the lifeguard if you’re unfamiliar with the area to better understand current conditions and advisement on entering certain points of the water. You can head over to Hawaii waves surf school to enjoy surfing. They provide rentals for expert surfers and surf lessons to beginners. Once you are done with surfing, enjoy endless beautiful sunsets to understand how this beach got its name.
  • Enjoy your dinner at Michel’s At the Colony Surf. We recommend island style steamed mahi mahi.
  • Stroll along Main street stopping by main street theater.
  • Head back to your hotel and rest up for the day.
Day 4

Turtle Canyon Snorkel & Sail and Waimanalo Beach

Snorkel with Turtles then Sail along Waikiki coast in a sailboat tour off waikiki, then head over to Oahu’s longest uninterrupted white-sand beach, Waimanalo beach. A large portion the beach is shaded by ironwood trees, which makes for some welcome respite from the sun.

  • Enjoy your breakfast at Bogart’s Café. We recommend avocado sandwich.
  • Take a 11 am Turtle Canyon Snorkel & Sail with Lunch tour with Hanaumabay tours and slip into the refreshing waters of Turtle Canyon off Waikiki to swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life.
  • Head over to Waimanalo beach. Stroll through the white sand beach. It can be a bit chilly during wintertime, so bring a light jacket. You can enjoy swimming in the calm water or bodyboard/boogie board in the small waves that break close to the shore.
  • Enjoy your dinner at Tiki’s Grill & Bar. We recommend fork tender beef short ribs.
Day 5

Last day of the trip

  • Enjoy amenities at your hotel or nearby until your flight time. Pack your bags and get ready to leave thinking about how to make your vacay tan last longer.
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