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sell7 Day Two Islander 2026

7 Days / 6 Nights   Starting at $4495 PP (Land Rate)

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 – 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.

Later, we will visit the Martin & MacArthur warehouse, home to Hawaii’s premier handcrafted Koa wood furniture and gifts. You’ll get a behind-the-scenes look at how skilled local artisans transform this rare, native wood into heirloom-quality pieces. Koa wood holds deep cultural significance in Hawaiʻi, traditionally used by royalty and prized for its beauty and strength.

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. B, D

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.  B, D

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

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. B, D

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

After breakfast, ask your tour leader 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. B, D

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. B, D

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. We hope to see you on another Perillo Tour to Italy, Spain, Portugal, Ireland or Hawaii again! As the Hawaiians say, “Mahalo Nui Loa!” (Thank you very much).

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
  • Flight to Maui
  • 6 Breakfasts
  • 5 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
Mar 12 - Mar 18 $4,495 $6,525
May 21 - May 27 $4,495 $6,525
Jun 11 - Jun 17 $4,495 $6,525
Jul 2 - Jul 8 $4,495 $6,525
Jul 23 - Jul 29 $4,495 $6,525
Aug 2 - Aug 8 $4,495 $6,525
Nov 12 - Nov 18 $4,495 $6,525
Dec 3 - Dec 9 $4,495 $6,525

Triple room deduct $600 per person from the Double rate.
Kids under 12 sharing with 2 adults deduct $2300 from the Double Rate.

Hotel Info

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

Air Info

For a seamless travel experience from start-to-finish, we strongly recommend taking advantage of Perillo's flights. By booking your air with Perillo, your round trip airport transfers in Hawaii will be included, provided you arrive and depart on scheduled tour dates.

Affordable Upgrades

Treat yourself to the luxury and comfort of flying First Class or Business Elite on United Airlines or American Airlines.

At an astonishingly affordable surcharge, this is the perfect opportunity to travel in the lap of luxury.

Call for Perillo's exclusive rate.

Arranging your own air?

If you are purchasing your own flights (not through Perillo Tours), you should arrange to fly into Honolulu and return from the last island of your tour, accordingly:

  • The "Three Islander" ends on Kauai.
  • The "Four Islander" ends on Kona.

Don't worry about your inter-island flights as they are all included in the above "Land-Only" rates.

Perillo Tours passengers traveling on the scheduled arrival and departure dates shown in our brochure will be transferred from airport to hotel. Passengers arriving prior to the scheduled tour date will need to make their own transfer arrangements. Please call 800-431-1515 to make the necessary arrangements with the help of our staff. Click here for airport transfer information.

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format_quote Testimonials

This is the second Perillo tour we have taken in the past 2 years.

The Hawaiian trip was outstanding. The choice of the hotel and all the amenities provided far exceeded our expectations. A real good price performer.

We will definitely use Perillo in the future.

Mr K.K.

My husband and I enjoyed a wonderful trip to Hawaii in April 2025 hosted by Cousin Bert. The hotels and sponsored dinners were fabulous. It was great to get a taste of Hawaiian culture with the fun luau and also the movie tour. It was so nice to have our luggage delivered to our rooms and the schedule was not super tight, which was perfect for us.

Above all, wanted to “raise a glass” to the magnificent job done by Cousin Bert. He easily handled our transportation between islands and hotel check-ins. Above all he was so pleasant, kind, knowledgeable, and most entertaining throughout our 10 day tour! He made it so much fun!
I would highly recommend this trip to anyone who has always wanted to visit Hawaii.

Thanks to all of you at Perillo who worked hard to make this an enjoyable trip for us.

Mrs. C.F.