7-Nights Oahu & Maui Romantic Road Trip - Beach Vacations, Road Trips, Honeymoons & Romance from $3,642

Goway Travel

OFFER ID 1722991

Epic Scenery Romantic independent self drive through Hawaii’s O?ahu and Maui, where sunsets, sea breezes, and island culture create a journey to savour.

Trip Overview:

Begin your Hawaiian journey in vibrant Honolulu, where the soft trade winds carry the scent of plumeria and the Pacific glitters under the sun. Spend your first days exploring O?ahu’s coastline, joining a small group tour along dramatic sea cliffs as the sky shifts through gold and crimson at sunset.

In Waikiki, enjoy unhurried time to swim, shop, and soak up the island rhythm. One evening, the beachfront Royal Hawaiian sets the stage for the ‘Aha ‘Aina luau, where traditional music, dance, and storytelling bring centuries of Polynesian culture to life beneath the stars.

A short flight whisks you to Maui, where palm-lined Ka?anapali Beach welcomes you with its warm sands and clear waters. Set sail in the evening for a serene sunset cruise, gliding past the island’s coast as the horizon melts into soft purples and pinks.

Days at leisure invite you to discover Maui’s charms at your own pace — perhaps driving the winding Road to Hana, snorkelling in Molokini Crater, or simply relaxing beneath swaying palms. As your holiday draws to a close, you’ll carry home the colours, flavours, and aloha spirit that make Hawaii unforgettable.

Highlights:

Begin in Honolulu, where warm trade winds and shimmering Pacific waters introduce Hawaii’s island rhythm.
Explore O?ahu’s rugged coastline and witness golden sunsets over dramatic sea cliffs.
Experience Waikiki’s relaxed charm and an evening of storytelling and dance at the Royal Hawaiian luau.
Fly to Maui to unwind on Ka?anapali Beach and sail into a pastel-hued sunset cruise.
Spend leisurely days discovering Maui’s treasures, from the Road to Hana to Molokini’s crystal-clear waters.

Included Services:

4 nights in deluxe accommodation on Oahu
3 nights in deluxe accommodation on Maui
5 days Intermediate Car Rental with unlimited mileage (Mazda 3 or similar) on Oahu
4 days Intermediate Car Rental with unlimited mileage (Mazda 3 or similar) on Maui
Shared The Beautiful Colors of Hawaii Tour (max. 9 guests)
Aha Aina Luau at the Royal Hawaiian
Shared Deluxe Ka’anapali Sunset Sail (max. 40 guests)
1 dinner

Excluded Services:

Car Rental Insurance
Travel insurance
International and domestic airfare & airfare taxes
Entrances fees to sites not explicitly listed as included
Meals and beverages not mentioned
Gratuities
Items of a personal nature
Passport and Visa fees if applicable

7 nights from $3,642 per person

Itinerary

Day 1: Welcome to Honolulu

Rental Car: Hertz - Honolulu Int'l Apto Honolulu Int'l Ap

Hotel: The Royal Hawaiian (5 Star Rating)

Perfectly situated directly on a private stretch of the famous beach of Waikiki, the luxury hotel enjoys fantastic views over the Pacific Ocean. Thanks to its distinctive architectural style and colour, this iconic landmark is aptly nicknamed “The Pink Palace”. Playground for the rich and famous, it features one of the best spa areas of all of the United States.

The establishment features two restaurants, Surf Lanai, specializing in mainland classic dishes with tropical accents and Azure Restaurant serving the freshest local seafood caught daily. The Mai Tai Bar serves tropical cocktails and nightly entertainment with views of Diamond Head. Guests can swim in one of two outdoor pools, the Malulani Pool and the Helumoa Playground, or relax on the beach. The resort also features a hot tub and water sports rentals. Daily cultural activities are also available to guests.

All rooms boast iPads and offer free Wi-Fi and iPod docks. Guests will also find flat-screen TVs, refrigerators, and room service.

Day 2: The Beautiful Colors of Hawaii Small Group Tour

Discover Oahu's hidden gems on this small group photography tour! Perfect for nature lovers who enjoy a relaxed start and easy walks, this half-day tour takes you to Oahu's natural wonders, iconic movie sites, and picture-perfect spots--all while avoiding major crowds. With personalized attention and a relaxed atmosphere, your expert guide will share island history and photography tips along the way. Start with breathtaking views of Waikiki and Honolulu from hidden lookouts known only to locals. Visit the Pali Lookout, where King Kamehameha united Oahu during the Battle of Nuuanu. Marvel at the towering Ko'olau Mountains as you explore the island's natural beauty. Refuel with a tasty local meal (not included) before continuing your adventure. Walk on the white sands of a true Hawaiian Beach and enjoy the peaceful surroundings. Capture stunning views from Makapu'u & Lanai Lookout, and the famous Halona Blowhole. Savor a famous Leonard's Bakery malasada, a must-try local treat (included). Get expert tips from your local photography guide to capture the best shots and create lasting memories, and soon after, return to Waikiki.

Day 3: At Leisure in Waikiki with Aha Aina Luau at The Royal Hawaiian

Long before Waikiki became a tropical escape, it was home to a community of remarkable grace and artistry. 'Aha 'Aina shares the story of this rich culture through music, traditions, and cuisine in an authentic Honolulu luau experience that journeys from Waikiki's ancient past to the era of The Royal Hawaiian. 'Aha'aina features three captivating acts. Guests begin with traditional Hawaiian activities like kapa-making, poipounding, and tending fishing tools. A conch signals the feast, featuring diverse flavors from Hawaii's plantation-era cultures. As guests explore each station, a storyteller shares the history of native cuisine, lei giving, and culminates with the legend of Helumoa - a performance that brings the tale to life.

Day 4: At Leisure in Waikiki

Day 5: From O’ahu to Maui

Rental Car: Hertz - Kahului Apto Kahului Ap

Hotel: The Ritz-Carlton Maui, Kapalua (5 Star Rating)

The Ritz-Carlton Maui, Kapalua offers an elevated ocean-front retreat set on 54 lush acres along Maui's northwest shoreline. Guests enjoy beautifully renovated guest rooms and suites, featuring private lanais, luxurious marble bathrooms, and serene tropical decor. Rejuvenate in the full-service spa, savor Pacific-inspired cuisine at onsite restaurants, and unwind beside multiple ocean-view pools, including an adults-only sanctuary. Outdoor enthusiasts will appreciate the well-appointed fitness center, tennis courts, and assigned access to two championship golf courses. The resort's calm elegance is reflected in warm, attentive service-creating a refined yet relaxed atmosphere that invites guests to connect with Maui's natural beauty.

Day 6: Deluxe Ka’anapali Sunset Sail

Enjoy stunning panoramic views of the West Maui Mountains, kissed with rainbows, aboard Maui's newest sailing catamaran. Step away from the bustle of a crowded restaurant and slip into sunset at tables set for intimacy and comfort. Allow yourself to be lulled into relaxation while the world-class Trilogy Crew members serve several tasty pupus (appetizers), signature cocktails, and knowledge of Maui's history and marine life. Departing from world-famous Ka'anapali Beach, sip and sail with Maui's oldest and most experienced sailing company!

Day 7: At Leisure on Maui

Day 8: Depart from Maui

Featured Destinations

Maui

Travelers who can go anywhere in the world come back to Maui again and again, because their Maui moments are some of the most treasured of their lives. The majestic leaps of Maui's humpback whales are the perfect symbol for the magic of this island, where natural wonders set your spirit free and the warm aloha of Maui's people fills your heart with a sense of belonging.

Maui's prime resort areas are Kapalua, Kaanapali, Kihei, Wailea and Makena. Strung like jewels on the sunny western and southern shores of Maui, they offer pristine beaches and a wide range of hotel and condominium accommodations. At serene, secluded Hana, you'll discover Hawaii the way it used to be.

The best golf in paradise is yours to enjoy on Maui. There are challenges for players of all skill levels and incredible views no matter where you play, from the public courses to the championship layouts of Maui's Golf Coast. Plus, nowhere else in the world will you find the array of oceansports and activities that Maui offers.

Then there are the 42 miles of world famous beaches, ranging Only on Maui... from the little jewel of Red Sand Beach to the black sand beach at Waianapanapa State Park. The best snorkeling is at Honolua Bay or the small islet of Molokini, a submerged crater.

For the nature enthusiast, Maui has breathtaking hiking trails. The Hawaii Nature Center in Iao Valley is a good starting place. The rangers at Haleakala National Park lead free nature walks, both at the 10,000 foot summit of Maui's awe-inspiring, long-dormant volcano and at Oheo Gulch with its famous Seven Pools.

One of the best ways to experience Upcountry Maui is on horseback. The green pastures and sweeping vistas will remind you of range land in Wyoming. And Makawao town provides a taste of the "Old West."

Discover the fascinating artifacts of Maui's ancient culture at the Bailey House Museum or explore the island's heiau ruins (Hawaiian religious temples). If you get a chance, don't miss the performance of hula kahiko (ancient hula) by one of Maui's hula halau (hula schools).

Oahu

Vacation Details

Valid Date Ranges

11/14/2026 - 12/31/2028

from $3,642 per person

* This departure has been designated a guaranteed departure by the operator, meaning that the minimum number of guests has been met, although still subject to weather and other conditions.

Prices Start At

from $3,642 per person

Length

7 Nights

Air City

Call for airfares from your city.

Vacation Rating

Deluxe
Fine dining, on-site bars or lounges and room service with extended hours are characteristic of deluxe establishments. Guest services usually include valet parking, concierge services, baggage assistance and laundry services. Other on-site facilities often include shops and boutiques, full service spas, full fitness facilities with pools and tennis courts. Business amenities may include available up-to-date technology and support staffs available for services. Attention to detail is apparent in the guestrooms which typically have stylish furnishings, quality bedding and bath products and often provide an evening turn down service.

Remarks

Pricing is dynamic and subject to change based on specific travel dates, room categories and availability. Prices are "from" per person based on twin/double share accommodation and for travel in low season. Seasonal surcharges and blackout dates may apply. Limited seat/spaces and all pricing is subject to change and availability. Rates for single or triple travelers are available on request - please inquire with your Travel Advisor.

All fares are quoted in US Dollars.

OFFER ID

1722991

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Kathleen Stahl Travel Services

529 36th Street
Des Moine, IA 50312
USA

(515) 271-8091