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CAREFREE Oahu and Maui Vacation Packages
(Nine Day, 2 Island)
More Choices, More Flexibility, More Fun!! All of our packages are designed by agents who live here in the Islands. We give you personal service with the Aloha Spirit. We're right here in Hawaii, helping thousands of people every year enjoy their CAREFREE Hawaiian holiday.
From $2,599.00 per person*
Check out our Hawaii "Carefree" flexible packages. The experience we offer allows you to keep busy, but not too busy that you can't relax. Unlike high end expensive "tour packages" with our all inclusive packages you can choose the property that suites your budget which are carefully selected to make sure they meet our customers needs. We do not use low end properties, or give you gift certificates to all you can eat cheap buffets. We offer you great restaurants located in the hotel or nearby, it's your choice where to eat. We want you to explore and enjoy the islands at your own pace.
Attn: Travel agents! Book this package for your clients
Look at what people are saying about our "Carefee" packages!!!
Kev & Jen Lackersteen (California)
"My wife and I enjoyed our fabulous honeymoon. You organized everything so well, we loved the airport limousine. We enjoyed the welcome pack that included an envelope detailing our restaurant for that evening. It made our holiday so very relaxing. It was nice to finish our days with a reserved table at some of the most popular restaurants in Waikiki and not have to think about where to go. We have only been home for one day and we are recommending you to our friends."
Roy (Boston)
"My wife and I had a spectacular time. The Carefree Package was everything you had promised. We had second row seating at the Polynesian Cultural Center, and the food was excellent. Thank you for making our trip so tremendous. We would highly recommend your service . I could never explain well enough how great of a time we had."
CAREFREE 2-Island Oahu & Maui Vacation Package
DAY 1 - FLOWER LEI GREETING & LIMO AIRPORT PICKUP - Start your trip in style with a personal flower lei greeting and private limo pickup at the airport. Hawaii Welcome Bag with goodies to help you get started on your vacation (1 per booking). Depending when your flight arrives to Hawaii, you can have this first day to relax and unwind at your hotel. Early afternoon flight arrivals, can have an activity or dinner coordinated. Be sure to ask your agent at time of booking for details.

STRETCH LIMO AIRPORT GREETING Welcome Pack
DAY 2 BREAKFAST at hotel RESTAURANT Morning-afternoon: Circle Island Oahu Tour, Evening: Dinner at the hotel or Chinese Cuisine Restaurant nearby the hotel.
This tour is ideal for first-time visitors, but regulars love it, too. On your journey you will see “the best of the best” of Oahu. From the lush, green mountains to the clear blue waters, across the pineapple fields, and beyond. There’s no better way to experience the diversity of this beautiful island. The sights are accompanied by live narration from our friendly tour guides, with interesting cultural and historical information along the way. (And don’t be surprised if you find yourself laughing and singing songs. This tour is anything but boring.) You’ll go to the 1,186-foot Pali Lookout, where King Kamehameha the Great fought his last battle, for a view that will blow you away. Or it may feel like it anyway, with robust winds that often sweep through the mountain pass, so hold on to your hat. World-famous North Shore surfing beaches are also on the tour, along with breathtaking Waimea Bay where giant waves break right on the shore, leaving behind their salty mist. You’ll also catch sight of Aloha Tower, which you may recall from the TV show “Hawaii Five-O,” and the familiar profile of the 750-foot Diamond Head volcano that has become a symbol for Hawaii throughout the years. This Oahu tour is grand indeed, and will not disappoint.
- Diamond Head
- Pali Lookout
- Exclusive Kahala Estates
- Hanauma Bay (closed Tuesdays)
- Halona Point (Blow Hole)
- Byodo-In
- North Shore surfing beaches
- Waimea Bay
- Pineapple fields
- Mormon Temple
DAY 3: BREAKFAST At The hotel RESTAURANT Afternoon-Dinner: Polynesian Cultural Center Ambassador VIP Luau service w/Trans
You'll receive the royal treatment with the Ambassador Luau Package as you enjoy a personalized guided tour of the island villages. Experience firsthand, the cultures of the islands as well as the canoe pageant, IMAX Theater, Laie tour and canoe rides. You'll witness the traditional uncovering of the imu (underground oven) where the main entree, kalua pua'a (roast pig), has been cooking most of the day. Then "eat until you're dizzy," says Cousin Benny the Center's Ambassador of Aloha, as you enjoy many traditional and modern luau favorites in the Alii Luau.
But the highlight of your visit is sure to be "Horizons" the largest Polynesian revue of song and dance in the world featuring over 100 native performers from all corners of the Pacific. Dressed in traditional native costume, these Polynesians share their history, traditions and spirit through song and dance the same way their ancestors did. With the Ambassador Luau Package you'll receive premium seating for this one-of-a- kind show!
DAY 4 SPA DAY w/picnic basket, BREAKFAST At The hotel RESTAURANT, Dinner cruise
This is a perfect day to relax. Enjoy a wonderful relaxing spa treatment at your hotel. In the afternoon you will be treated to a Hawaiian made picnic basket (delivered to your hotel) prepared especially for you to enjoy. Take it to the beach or just enjoy it in your hotel room. WHATEVER! It's your vacation, eat when you want to!
Dinner: Ali’i Kai Sunset Dinner Cruise - Set Sail On The World's Largest Polynesian Catamaran
The Ali`i Kai Makahiki Dinner Cruise is one dinner party you'll never forget. Step aboard this amazing 170- by-50-foot "Ruler of the Sea" for a casual, fun-filled sunset sail and delicious island flavors. Take in panoramic views of the Pacific, world-famous Waikiki and the city of Honolulu as you cruise down the coast. After the sun sets, dine buffet-style and watch a captivating Polynesian show with dancers, drummers and chanters. When the show ends, it's your turn to take to the dance floor as the Ali`i crew encourages passengers to play games and shake their own hips to the live music.
Alii Kai Buffet Dinner Assortment of Fresh Nalo Greens with Choice of Dressings, Italian Pasta Salad with Sun Dried Tomatoes, Carved Roast Sirloin of Beef with Cabernet Sauce and Creamy Horseradish Sauce, Grilled Chicken with Shoyu Ginger Glaze Garnished with Oriental Vegetables, Sautéed Island Mahi-mahi with Macadamia Nut Butter Sauce, Garnished with Spring Vegetables, Pasta with choice of Marinara or Pesto Cream Sauce, Mashed Potatoes, Steamed Rice, Sweet Rolls and Butter, Sliced Tropical Fruits, Assorted Desserts, Kona Coffee
Day 5 Fly to Maui Greeted by Limo for scenic drive to Hotel in Kaanapali DINNER at the HOTEL
Free day to relax and rejuvinate, go to the beach, or WHATEVER!
Day 6 DINNER at the HOTEL
Magnificent Maui
From The Mountains To The Valleys, To The Ocean Lined With Shops.
Appropriately named, this full day tour shows you a few of Maui’s magnificent highlights. In just 37 miles, you’ll go from sea level to 10,023 feet to the top of Mt. Haleakala. The meandering road up the volcano flaunts stunning views of Maui, the Pacific Ocean, and West Maui Mountains, so have your camera ready. Along the way, your tour guide will tell you interesting tidbits, like the fact that this spot is regarded as one of the earth’s powerful energy points. Next, you’ll descend into Iao Valley where you’ll immediately understand why Maui was coined “The Valley Isle.” As you ride up the valley, you quickly realize you’re in a peaceful rainforest. This is where the bright green Iao Needle shoots up from the ground, as if profoundly pointing at the blue sky. Tropical plants, waterfalls, and swimming holes accentuate this verdant wonderland. The final stop of the tour is Lahaina, an old whaling seaport lined with restaurants, shops and galleries. This quaint little town happens to be one of Hawaii’s most popular shopping destinations. Here, tour guides will turn you loose for over two hours of shopping and strolling. The perfect end to a perfect day of Maui sightseeing.
Kula
- Iao Needle
- Wailuku
- Haleakala National Park
- Rare silverswords & protea
- John F. Kennedy Profile
- Lahina Town
- Iao Valley State Park
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Day 7 Discover Kaaanapali Cruise, DINNER at the HOTEL
Two of the most famous beaches in the world are Waikiki and Kaanapali. We happen to prefer Kaanapali. It's also on Maui! And it is the only location where we actually pick up and drop off guests directly from the beach. Kaanapali is ideally located for enjoying the many ocean adventures we offer including sailing, snorkeling, and whale watching.
With those famous Maui Trade Winds just a few hundred yards off shore, our crew wastes no time in hoisting sail and getting into some serious sailing! Some of the best snorkel sites on Maui are only a few miles away and our crew will chose the best ones for the day. And during the winter months from December thru April visiting Humpback whales calf, breed, and frolic nearby.
We provide all the snorkeling equipment and instruction, wet suits for everyone onboard, Breakfast, Lunch, soda and snacks, and that personalized service you've come to expect from Maui's first family of sailing.
Day 8 Free Day, Old Lahain Luau, BREAKFAST at the HOTEL

The Old Lahaina Lu`au takes great pride in presenting an authentic Hawaiian Luau. An evening of Traditional Hawaiian cuisine, music, cultural dances and island crafts. Guests will appreciate a genuine reflection of Hawaii ’s rich history while enjoying an ocean view and sunset.
Day 9 - Time to Pack and go home!! Bummer!! Come again next year STRETCH LIMO transfer to the airport.
Price do NOT include airfare, call 1-800-843-8771 for a personal quote with airfare.
Hotel Combo Choices
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Maui |
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Pacific Beach Hotel
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Royal Lahaina
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Partial Oceanview*
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Oceanview*
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Total
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2699.00 PP
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**room upgrade available, ask your agent
| Oahu |
Maui |
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Marriott Waikiki
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Sheraton Maui
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Partial Oceanview*
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Oceanview*
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Total:
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3299.00
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**Room upgrades available, ask your agent
*Price can change based on availability, dates of travel and black out dates from the hotels. Last minutes bookings subject to service charge, call 1-800-843-8771 for firm quote based on you specific needs.
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