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sell7 Day Two Islander 2026

Overnight Stays: Oahu (3 nights), Maui (3)
Also Visiting: Waikiki, Ka'anapali

Oahu (3 nights) Maui (3)

Perillo’s 2-Island Tour of Oʻahu and Maui is perfect for first-time visitors or anyone looking for a quick, unforgettable taste of Hawaiʻi. You’ll enjoy oceanfront stays, delicious meals at top local restaurants, and all the must-see sights—expertly arranged with Perillo’s signature care and style.

Itinerary

Day 1 - Oahu - Aloha! Lei Greeting and Welcome to Hawaii!

Today you’ll fly to Honolulu on the island of Oahu, one of the single most dreamed of vacation spots in the world. You’ll be met with a cool, aromatic, flower-lei greeting right at the airport!

Our home for the next 3 days, the Grand Dame of Hawaiian accommodations – the Moana Surfrider! (You don’t have to be that old to remember the radio show airing from its courtyard – Hawaii Calls.)

Your Perillo reps will be on-hand to help you to settle into your room in paradise. ALOHA!

Day 2 - Oahu - Breakfast - Pearl Harbor Arizona Memorial - Panoramic Tour of Historical Honolulu & 'Iolani Palace – A La Carte Dinner at Duke’s Waikiki

The brilliant Hawaiian sunrise beckons you to a great breakfast. Next, meet your tour guide for a short familiarization talk on your Hawaiian adventure.

After breakfast we’re off to Pearl Harbor to commemorate the “day that will live in infamy” - December 7, 1941. Few Americans who set foot on the Arizona Memorial can avoid a few goose bumps. We continue on to the historic sightseeing tour of downtown Honolulu, followed by a panoramic tour of the beautiful ‘Iolani Palace, the only true Royal Palace on American soil.

Tonight, enjoy your à la carte dinner at Duke’s Waikiki Restaurant, named after the legendary surfer Duke Kahanamoku. Experience a real Mai Tai (umbrella included) from the Barefoot Bar. Wine, beer or soft drinks are also included.

Included: Breakfast, Dinner

NOTE: While we do plan for and secure U.S.S. Arizona Memorial tickets in advance, access to the memorial is ultimately at the discretion of the U.S. Navy and may be subject to unexpected closures beyond our control. In the rare event of a closure, we will promptly inform your group and provide updates as needed.

Day 3 - Oahu - Breakfast - Day of Leisure - Dinner at Orchids Restaurant

After breakfast, the day is all yours.

It’s said that surfing was invented on Waikiki Beach. The warm shallow water and gentle waves will make a quick surfer out of you too! (Elvis didn’t choose any old beach for his famous movies.)

After a free afternoon we’ll enjoy oceanfront dining at one of the finest restaurants in all Hawaii: Orchids at the Halekulani Hotel. Now is a good time to remember - E mahalo kākou i ka mea loaʻa - Let us be thankful for what we have.

Included: Breakfast, Dinner

Day 4 - Oahu - Flight to Maui - A La Carte Dinner at the Westin Maui Resort & Spa

After breakfast, enjoy your last morning on Oahu to discover the “First Lady of Waikiki”, the Moana Surfrider. How about taking in the Moana’s museum on the 3rd floor? There’s so much history at this hotel!

This afternoon we jet to Maui, the “Valley Island”. In 1778, Captain James Cook arrived in “Mowee” ending the idyllic life of the Polynesian natives. In Cook’s wake came traders, missionaries and whalers.

You’ll love the Westin Maui. It’s fancy but casual, and situated along Ka’anapali Beach, rated as one of the ‘best beaches on earth’ by Condé Nast magazine!

We’ll settle in our room followed by à la carte dinner with wine or soft drinks at the restaurant located at your resort. Of course, gratuities are included.

Included: Breakfast, Dinner

Day 5 - Maui - Full Day of Leisure - Sunset Cocktail/Dinner Cruise

After breakfast, ask your tour director for suggestions today. Try a hula lesson...or how about a ukulele lesson?

Afraid to jump off the world-famous “Black Rock “cliff? Then just watch the kids do it. There’s also fantastic snorkeling along its base—like swimming in the world’s best tropical fish tank!

Later this afternoon, we board our smooth catamaran for a sunset cruise. Enjoy Tradewind sailing with phenomenal views of West Maui, Molokai and Lanai.

Enjoy Mai Tais, beer and soda. Also included is our chef-inspired gourmet dinner featuring fresh Hawaiian fish, beef or a great vegetarian option, plus dessert!

If it’s whale season, mid-December through mid-April, perhaps we’ll be lucky to see a humpback or two.

Included: Breakfast, Dinner

Day 6 - Maui - Morning at Leisure - Hawaiian Luau & Show

Another glorious day in paradise!

After a day of leisure, bring your appetites to our Hawaiian Luau Spectacular! It’s the hottest show on the island. Our luau takes you on a journey through the islands of Polynesia.

Witness the authentic dances and music of Samoa, Fiji, New Zealand, Tahiti and Hawaii. Enjoy an open bar and an all-you-can-eat traditional luau featuring a superb combination of Hawaiian specialties, at one of the best luaus the state of Hawaii has to offer.

Included: Breakfast, Dinner

Day 7 - Maui - Flight Home

Today, our “Two Islander” tour will end with a transfer to Maui’s Kahului Airport. Your tour will end after breakfast this morning. Mahalo, and please join us again soon!

Included: Breakfast

Inclusions

  • 3 Nights – Deluxe Moana Surfrider on Oahu
  • 3 Nights – Deluxe Westin Maui Resort & Spa
  • Lei Greeting at airport
  • Honolulu & Pearl Harbor Tour
  • Sunset Cocktail/Dinner Cruise
  • Authentic Hawaii Luau Dinner & Show
  • Flight to Maui
  • 6 Breakfasts
  • 3 à la carte Dinners with Drinks
  • Resort Fees, Health Club, Free Wi-Fi
  • Bellmen & Restaurant Gratuities
  • Baggage Handling Including tips
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Dates & Rates

Depart - Return Per Person
in a Double
Solo
Traveler
Jun 11 - Jun 17 $4,495 $6,525
Jul 2 - Jul 8 $4,495 $6,525
Jul 23 - Jul 29 Sold Out!
Aug 2 - Aug 8 $4,495 $6,525
Nov 12 - Nov 18 Sold Out!
Dec 3 - Dec 9 $4,495 $6,525

Triple room deduct $600 per person from the Double rate.
Kids 5 to 17 sharing with 2 adults deduct $2300 from the Double Rate.

Hotel Info

Moana Surfrider

Known as “The First Lady of Waikiki,” the Moana Surfrider is a legendary landmark introducing Hawaiian hospitality to the world in 1901. Step back into yesteryear while enjoying contemporary amenities and unique services for an unforgettable vacation.

Honolulu

Westin Maui Resort & Spa

The 2021 US News & World Report lists Ka’anapali Beach as #1 in all America. And that’s just we’re you’ll find the deluxe Westin Maui! Enjoy delicious local cuisine at one of five on-site dining options. Take advantage of an abundance of FREE activities or take the hotel shuttle to nearby West Maui attractions.

Maui

Optional Tour Add-Ons

Please note that each optional tour requires a minimum number of participants; if this minimum is not met, the tour will not operate.

Add-On
Price

Duration: 10 hours
City:

2:00 AM to 12:00 PM

Experience the awe-inspiring spectacle of a sunrise atop Mt. Haleakala, standing tall at 9,740 feet, where the dawn of a new day unfolds in breathtaking splendor. Immerse yourself in the experience while we handle the driving for you in our deluxe touring vehicle. Throughout the tour, our knowledgeable local guide shares captivating Hawaiian history, legends, and insider tips, enriching your exploration. Chilled bottled water and local treats are included, offering a refreshing taste of Hawaii.

As you ascend to the summit district of Haleakala National Park, feel the raw power of being among the clouds, greeted face-to-face by the rising sun. Witness nature's masterpiece as the golden light illuminates the landscape, painting the sky with vibrant hues.

This small group tour on a mini coach is the perfect way to experience the natural wonders and pristine landscape of Maui.

After the mesmerizing sunrise, explore the slopes of Haleakala, where rare Silversword plants thrive, and endemic Nene geese gracefully soar overhead.

Take in the dramatic transformation of the landscape, from the arid desert terrain to lush, fertile farmland, as you descend from the summit area.

Indulge in a delightful breakfast at Cafe O'Lei at the Plantation, a locally and family-owned establishment nestled amidst the tranquil surroundings of the old sugar mill.

Choose from a variety of plated selections, including seasonal fresh fruit, a hearty Plantation Breakfast, or the indulgent Macadamia Nut Pancakes, crafted with local, seasonal ingredients, accompanied by refreshing beverages. Special dietary requirements such as vegetarian, vegan, gluten-free, or nut allergies can be accommodated with advance notice.

Immerse yourself in the beauty of Haleakala National Park, from the sweeping vistas at the Visitor Center Overlook
Areas to the scenic views of Kula and upcountry Maui on the descent. 

The price for adults is $255 and for children under 12, $155. All transfers are included.

This tour needs to be booked in advance, please call us 800-431-1515 to add this to your adventure.

format_quote Testimonials

I have to thank Perillo Tours for an absolutely terrific vacation! The accommodations were wonderful; the side trips were both enjoyable as well as informative but most importantly, Our tour guide, Cousin Burt, was great!

Mrs. I.F.

I just want to say that this Hawaii tour was fantastic.  What made it more fascinating was Paul.  He was exceptional. . .  he is friendly, approachable, very educated on the culture and customs of the island.  The families that toured with us was fantastic and all the accommodations and food were exceptional.  I am so glad I booked with Perillo and will do again and again.  Thank you for making this vacation so memorable.

Mr. N.F.