Hawaii Vacation Packages

Day 2: Hit the Beach

From Honolulu, it’s a little over 20 minutes’ drive southwest to Hanauma Bay, famed for its incredible snorkeling. About 30 minutes’ drive northwest is Waimanalo, the island’s longest beach where you can try surfing on a traditional outrigger canoe.

In the evening, there is nothing more Hawaiian – or more romantic – than listening to live music and watching a hula dance at sunset. In Waikiki, there’s a free Kuhio Beach Hula Show held three times a week at the Hula Mound along Kalakaua Ave.

Day 3: Driving Tour

We suggest heading for the Windward Coast first; it’s just a 30-minute drive east from Honolulu but feels a world away. There’s enough to do in this area to fill a whole day; however, you could also spend just a few hours here then drive another 50 minutes to Hawaii’s North Shore, known for its surfing and laidback atmosphere. 

• From Honolulu, hit the Pali Highway that winds east through the Koolau mountain range. After about 15 minutes, you will reach the Nuuanu Pali Lookout. Pause here for dazzling views
• Just below the lookout is a hidden gem, the Likeke Falls. You can get to this two-tiered beauty by taking a 10-15 minute hike up from the Ko’olau Golf Course parking lot, which is just a 10-minute drive from the Pali Lookout
• Drive east on the Pali Highway for just over 15 minutes to reach the spectacular natural beauty of the Windward Coast and Kailua Beach
• Stay in the town of Kailua to swim, surf and go on the Pillbox Hike. At sunset, head back to Honolulu for dinner or end your day with an unforgettable horse ride along Kailua’s North Beach at sunset

Day 4: Maui

After 3 days on Oahu, it’s time to hop on a flight to Maui. Flights between Oahu and Maui are frequent and take around 40 minutes. To get the most out of your time on Maui, pick up a rental car at the airport to have the freedom to explore.

• Spend the morning settling into your hotel, lounging by the pool and gazing at the far-reaching sea views
• In the afternoon, hop in your rental car to cruise along the magnificent Hana Highway. Stop at the lookouts for romantic views, pass by coursing waterfalls including the beautiful Wailua Falls, and be sure to stop for a swim at Pailoa Bay, a black sand beach with a lava tube
• In the evening, join a luau and sample kālua pua'a, a traditional meal of roasted pork cooked in an underground oven. Choices for luau include Old Lahaina Lu’au and the Grand Wailea Lū’au

Where to stay: Options in Kihei include smaller boutique hotels such as the luxurious, adults-only Hotel Wailea, Relais & Chateaux, or larger resorts such as Fairmont Kea Lani Maui, which has an adults-only swimming pool and excellent selection of bars and restaurants.

Day 5: Maui

You will need a car to travel from your hotel to the starting points of these guided adventures, so we recommend renting a car for your daytrip around Maui.

• Makena Beach is one of Maui’s most picturesque beaches – and it’s where you can begin a guided kayaking tour. Spend the morning paddling above the reef, which is protected by two lava walls. Keep watch for green sea turtles, Hawaiian spinner dolphins and maybe even monk seals
• Head back to dry land for a short trip over to Ukumehame Beach Park where you can try your hand at a couples’ surf lesson

For your last night, we recommend a sunset cruise with one of the many companies that depart from nearby Maalaea harbor to end your 5-day getaway. In the evening, catch a flight from Maui back to Oahu to make your connection home.