January 19-29, 2026
11 days / 10 nights

4 nights in Oahu
3 nights Days in West Maui
2 nights in Hana, Maui
1 night near Maui Airport

An Active, Yet Relaxed Adventure for Women Over 50

Hawaii isn’t just about beaches—it’s about experiencing the islands on foot, feeling the ocean breeze on a coastal trail, and stepping into lush rainforests where waterfalls cascade into hidden pools. This trip is designed for women who love to explore but want a comfortable pace, breathtaking scenery, and time to relax along the way.

Over the course of this journey, you’ll walk scenic trails with panoramic ocean views, explore volcanic landscapes, and follow rainforest paths to stunning waterfalls. Every day is thoughtfully planned to blend active discovery with relaxation, ensuring you experience the best of Hawaii without feeling rushed or overwhelmed.

No extreme hikes. No pressure. Just incredible landscapes, rewarding walks, and unforgettable moments shared with like-minded women.

What to Expect:

✔ Scenic coastal walks & easy-to-moderate trails – All under 3 miles round trip – with one exception on day 9
✔ Incredible landscapes – Waterfalls, volcanic craters, lush valleys & ocean views
✔ Relaxation & adventure balanced perfectly – Time to unwind at beautiful resorts
✔ Small group paced – you won’t feel left behind
✔ Authentic Hawaiian experiences – Enjoy local cuisine, culture & history

If you love walking in beautiful places, discovering new landscapes, and embracing adventure without feeling overwhelmed, then this is the perfect trip for you.

10 Reasons to Join us:

• Two Islands, Two Unique Experiences – Explore both Oahu and Maui, each offering stunning landscapes, coastal beauty, and rich culture.
• Walk Hawaii’s Most Scenic Trails – Hike Diamond Head, Makapu’u Lighthouse, Lanikai Pillbox, Pipiwai Trail, and more, designed for a comfortable pace.
• Coastal Views Like No Other – Enjoy breathtaking walks along rugged cliffs, sandy shores, and panoramic ocean vistas with stops at Ka’ena Point, Kapalua Coastal Trail, and Dragon’s Teeth.
• Step Into a Tropical Rainforest – Discover lush green valleys and towering waterfalls on the Manoa Falls Trail and Waimea Valley, where you can swim in a natural pool.
• Sunrise Over a Volcano – Witness an unforgettable sunrise from the top of Diamond Head in Oahu and Haleakalā Crater in Maui, two of Hawaii’s most iconic summits.
• Unwind on World-Class Beaches – Relax on Lanikai Beach, Waimea Bay, and Napili Bay, where soft white sand meets crystal-clear waters.
• Stay in Beautiful Oceanfront Resorts – Enjoy beachfront accommodations in both Waikiki and Maui, waking up to ocean breezes and stunning views.
• Authentic Hawaiian Cuisine – Savor fresh seafood, tropical fruits, and traditional Hawaiian plate lunches, with a stop at a famous North Shore shrimp truck.
• Adventure at a Relaxed Pace – Designed for women over 50 who love to walk, explore, and take in the scenery without extreme hikes or long distances.
• New Like Minded Friends for Life!

Day 1: Welcome to Paradise – A Relaxed Arrival in Oahu

This journey begins with a warm Hawaiian welcome as you arrive in Honolulu, Oahu. From the moment you step off the plane, the scent of tropical flowers and the gentle ocean breeze set the tone for an unforgettable getaway.

After a smooth transfer you’ll have time to settle in, unpack, and refresh before experiencing your first breathtaking Hawaiian sunset.

This evening, take a leisurely stroll along Waikiki Beach, where the golden sands meet the gentle waves. Relax with a cocktail in hand, soaking in the view of Diamond Head as the sky turns shades of pink and orange.

For dinner, indulge in fresh, locally sourced food at one of the island’s top restaurants before heading back to the resort for a restful night’s sleep.

Why This Day is the Perfect Start to Your Hawaiian Escape:

• Seamless Arrival & Effortless Check-In – A stress-free start to your vacation
• Luxury at a Premier Beachfront Resort – Enjoy ocean breezes and world-class amenities
• Sunset Walk Along Waikiki Beach – A picturesque introduction to Hawaii’s beauty
• Authentic Hawaiian Cuisine – Fresh seafood and tropical flavors to begin your journey

Day 2: Coastal Beauty & Rainforest Tranquility – Makapu’u Lighthouse & Manoa Falls

Today, experience two of Oahu’s most breathtaking natural landscapes—the coastal cliffs of Makapu’u and the lush rainforest of Manoa Valley. These trails, both under 2 miles round trip, are designed for maximum scenic reward.

Your early morning begins with a scenic drive along the southeastern coast, stopping at lookouts before reaching the Makapu’u Lighthouse Trail (2 miles round trip, gradual incline, paved path). Walk along the cliffs, where the ocean stretches endlessly before you, and during winter months, keep an eye out for humpback whales breaching offshore.

After a break, we’ll head into the heart of Manoa Valley, a rainforest oasis where towering banyan trees and thick bamboo groves line the Manoa Falls Trail (1.6 miles round trip, dirt path, gentle incline). At the end of the trail, the stunning 150-foot waterfall cascades down volcanic rock, surrounded by lush greenery.

Following the hikes, enjoy a well-earned Hawaiian plate lunch before returning to the resort for a relaxed afternoon by the pool or beach.

• Hike Two of Oahu’s Most Stunning Trails – Experience both coastal and rainforest beauty in one day
• Walk at a Comfortable Pace – Short, scenic trails designed for enjoyment, not endurance
• Seasonal Whale Watching Opportunity – Makapu’u’s elevated views make spotting whales a possibility
• Experience the Magic of a Hidden Waterfall – Manoa Falls is straight out of a tropical dream

Day 3: Hawaii’s Iconic Landmarks & Unforgettable Natural Beauty – Diamond Head, Waimea Valley & North Shore

Today is a perfect mix of breathtaking landscapes, Hawaiian history, and world-famous island flavors. Begin the morning with a rewarding climb to Oahu’s most iconic viewpoint, walk through a lush valley once reserved for Hawaiian royalty, indulge in legendary North Shore cuisine, and end the day with relaxation on a golden sand beach.

Hike to the Summit of Diamond Head – Oahu’s Most Famous View

Start the morning with a sunrise climb up Diamond Head (1.8 miles round trip, moderate incline, well-maintained trail). This ancient volcanic crater, formed over 300,000 years ago, is one of Hawaii’s most recognizable landmarks. The trail winds past lava rock tunnels, military lookouts, and historic bunkers before reaching the summit, where you’ll be rewarded with a breathtaking panoramic view of Waikiki, the coastline, and the vast Pacific Ocean. The morning light casts a golden glow over the island, making it one of the most unforgettable moments of the trip.

Step Into Hawaiian History at Waimea Valley – A Sacred, Tropical Sanctuary

We will take a break the day slows down with a peaceful walk through Waimea Valley (1.5 miles round trip, paved path, mostly flat), a place of deep cultural and spiritual significance. Stroll through a lush botanical garden filled with rare tropical plants, towering banyan trees, and reconstructed ancient Hawaiian temples. The path leads to Waimea Falls, a stunning 45-foot waterfall nestled in the rainforest. Here, you’ll have the option to take a refreshing dip in the natural pool at its base, a truly unique way to experience Hawaii’s raw beauty.

Experience a True Hawaiian Classic – North Shore’s Famous Shrimp Trucks

No visit to the North Shore is complete without trying Hawaii’s most famous roadside meal. Enjoy lunch at a legendary shrimp truck, where you’ll savor garlic butter shrimp, fresh from the ocean, served with rice and tropical slaw. These casual roadside stops are an island tradition, offering a meal that’s as authentic as it is delicious.

Unwind at Waimea Bay – A Beach with Towering Cliffs & Crystal-Clear Waters

After lunch, it’s time to slow down and soak in Hawaii’s beachside beauty. Waimea Bay is a stunning golden sand beach framed by dramatic cliffs and turquoise waters. Depending on the season, you’ll experience either calm, swimmable waters perfect for floating and relaxing, or towering waves that attract world-class surfers. Whether you choose to take a refreshing swim, walk along the shore, or simply sit back and enjoy the view, this is Hawaiian paradise at its finest.

Highlights

• Diamond Head’s Panoramic Views are Worth Every Step – This short, rewarding climb offers a once-in-a-lifetime view of the Pacific and Waikiki, making it one of the most photographed spots in Hawaii.
• Waimea Valley is More Than Just a Walk – It’s a Step Into Hawaiian History – The paved, gentle path winds through a sacred valley filled with Hawaiian legends, botanical gardens, and peaceful surroundings.
• Waimea Falls is a Picture-Perfect Waterfall, and You Can Swim In It – Unlike most waterfalls, this one welcomes visitors to wade into its natural pool for an optional, refreshing dip.
• Lunch is an Experience, Not Just a Meal – The North Shore’s shrimp trucks are famous worldwide, and this is a true Hawaiian foodie moment you won’t forget.
• Waimea Bay is the Perfect End to the Day – Whether you want to swim, relax in the sun, or simply enjoy the view, this is one of Oahu’s most breathtaking beaches.

Day 4: Coastal Views & Secluded Shores – Ka’ena Point & Lanikai Beach – A Slice of Paradise

Today offers some of the most jaw-dropping ocean views in all of Hawaii, paired with unforgettable coastal walks and a chance to relax on one of the world’s most beautiful beaches. You’ll start the morning with a short, scenic climb to an incredible island viewpoint, then explore one of Oahu’s most untouched coastal preserves before ending the day at a postcard-perfect beach with soft white sand and crystal-clear waters.

Ka’ena Point – A Remote and Wild Hawaiian Landscape

After a well-earned break, head to Ka’ena Point (3 miles round trip, flat coastal path, unpaved), an untouched nature preserve at the westernmost tip of Oahu. This rugged, windswept coastline feels like a completely different side of Hawaii—far from the crowds, peaceful, and breathtakingly raw. The trail follows an old railway path along the rocky cliffs, leading to the remote tip of the island where Hawaiian monk seals often sunbathe, seabirds nest along the cliffs, and waves crash against lava rock formations.

This is a place where Hawaii’s natural beauty is truly untouched, making it a must-see for those who want to experience the island beyond the resorts.

Sunset at Lanikai Beach – A Slice of Paradise

The rest of the afternoon is all about relaxation at Lanikai Beach, a spot that is consistently ranked as one of the most beautiful beaches in the world. With its powder-soft sand, crystal-clear water, and gently rolling waves, it’s the perfect place to take a refreshing dip, go for a leisurely shoreline walk, or simply sit back and soak up the tropical beauty.

Why This Day is Perfect

• Experience One of Oahu’s Last Wild Coastal Areas – Ka’ena Point is an untouched, remote landscape where nature takes center stage, far from the crowds and the usual tourist spots.
• Spot Hawaii’s Unique Wildlife Up Close – This area is home to endangered Hawaiian monk seals, nesting seabirds, and, during the winter months, migrating humpback whales.
• Relax and watch the sunset on One of the World’s Best Beaches – Lanikai Beach is the definition of tropical perfection, with its clear waters and pristine shoreline, making it the ideal place to unwind.

Day 5: Island Hop to Maui – A New Landscape Awaits

Today, you’ll trade Oahu’s bustling energy for Maui’s stunning, laid-back landscapes, known for dramatic coastlines, lush valleys, and some of the most breathtaking sunsets in the world. After a short flight, settle into your oceanfront resort on Maui’s famous Kaanapali Beach, where you’ll unwind and prepare for the next chapter of your Hawaiian adventure.

Morning on Oahu – A Relaxed Start Before Departure

Enjoy a leisurely breakfast at the resort before transferring to the airport for your quick 40-minute flight to Maui. The flight itself offers incredible aerial views of the islands, giving you a preview of the beauty that awaits.

Arrival in Maui – Welcome to the Valley Isle

Upon landing, pick up your private transfer or rental car and head to one of Maui’s most celebrated dining spots for a special welcome lunch. Mama’s Fish House, an iconic oceanfront restaurant, is the perfect way to kick off your time on the island, offering fresh, locally caught seafood served with stunning ocean views.

Check-In at Your Oceanfront Resort 

This afternoon, arrive at the Outrigger Kaanapali Beach Resort, a stunning property located on one of Maui’s most picturesque coastlines. Take time to settle in, explore the resort, and enjoy the warm ocean breeze from your private lanai.

Why This Day is Perfect

• Seamless Travel with a Short & Scenic Flight – The 40-minute flight between Oahu and Maui is quick, comfortable, and offers stunning aerial views of the islands.
• Stay in an Oceanfront Resort on Maui’s Most Famous Beach – Wake up each morning to the sound of the ocean and enjoy a prime location with easy access to everything Maui has to offer.
• Experience One of Maui’s Most Magical Sunsets – Black Rock Beach offers a rare and breathtaking sunset experience, complete with the iconic Hawaiian cliff-diving tradition.

Day 6: Maui’s Stunning Coastline & Hidden Valleys – Kapalua Coastal Trail, Iao Valley & Napili Bay

Today is all about immersing yourself in the breathtaking landscapes of West and Central Maui, from dramatic coastal cliffs and lush valleys to pristine beaches. You’ll begin the day with a scenic oceanfront walk, explore a sacred valley filled with history and towering peaks, and end with time to relax at one of Maui’s most picturesque beaches.

Kapalua Coastal Trail – A Walk Along Maui’s Most Dramatic Shoreline

Your morning starts with the Kapalua Coastal Trail (1.5 miles in-and-out trip, mostly flat, coastal path), a stunning walk along Maui’s rugged northern coastline. This scenic, well-maintained trail takes you past golden beaches, jagged lava rock formations, and turquoise tide pools with endless ocean views. As you walk, keep an eye out for sea turtles bobbing in the waves and, if visiting during the winter months, humpback whales breaching offshore.

Iao Valley – A Walk Through Hawaii’s Sacred Green Heart

In the afternoon, travel to Iao Valley State Park (1 mile round trip, paved path, gradual incline), a place of deep cultural significance in Hawaiian history. Here, you’ll walk through lush, mist-covered mountains, passing through dense rainforest and crystal-clear streams.

At the heart of the valley stands the Iao Needle, a 1,200-foot emerald spire rising dramatically from the valley floor. This sacred landmark has been a spiritual and historical site for centuries, once the location of one of Hawaii’s most legendary battles.

The peaceful, jungle-like setting of Iao Valley feels like stepping back in time, offering a quiet, meditative experience in nature.

Sunset at Kapalua Bay – A Perfect End to the Day

Return to the resort for some time to relax before heading out for a stunning sunset at Kapalua Bay. This intimate, sheltered beach is one of the best places on the island to watch the sky transform into fiery shades of pink and gold.

Why This Day is Perfect

• Walk One of Maui’s Most Scenic Oceanfront Trails – The Kapalua Coastal Trail is a breathtaking, relaxed walk that offers the best of Maui’s rugged shoreline.
• Step Into Hawaii’s Ancient Past at Iao Valley – This isn’t just a scenic walk—it’s a chance to experience a site that has shaped Hawaiian history and legend.
• End the Day with an Unforgettable Maui Sunset – Watching the sunset from Kapalua Bay is a truly magical experience, with golden light reflecting off the waves.

Day 7: Sunrise Above the Clouds & A Relaxing Coastal Escape – Haleakalā Crater, Maluaka Beach & Sea Turtles

Today blends adventure with relaxation, beginning with one of the most breathtaking sunrises in the world at Haleakalā, followed by a leisurely brunch near Maluaka Beach and a peaceful afternoon watching sea turtles along Maui’s golden shores. After a few days of scenic hikes, today offers the perfect balance of awe-inspiring views and restful beach time.

Haleakalā Sunrise & Crater Rim Walk – Witness Hawaii from Above the Clouds

The day begins before dawn as you depart the resort at 3:30 AM to reach Haleakalā National Park in time for sunrise. As you arrive at the summit, you’ll feel the crisp mountain air and watch the first light of the day rise above a sea of clouds. The fiery reds, oranges, and pinks stretching across the sky make this one of the most unforgettable sunrises in the world.

After sunrise, take a short, scenic walk along the Haleakalā Crater Rim (1-mile loop, mostly flat, volcanic terrain). The landscape here is otherworldly—red and black lava rock, massive cinder cones, and a vast, open crater stretching as far as the eye can see. Walking along the rim, you’ll experience silence like nowhere else on the island, a stillness that makes you feel completely immersed in the vastness of nature.

Brunch with a View – A Leisurely Meal in South Maui

After your morning above the clouds, descend back toward the coast and head to South Maui near Maluaka Beach for a well-earned, relaxing brunch.

Maluaka Beach & Sea Turtle Watching – A Peaceful Afternoon by the Ocean

After brunch, it’s time for a slow, tranquil afternoon at Maluaka Beach, one of Maui’s most beautiful golden-sand beaches. Known for its calm, crystal-clear waters and stunning views of Molokini Crater, this is the perfect spot to dip your toes in the ocean, take a relaxing stroll, or simply lay back and enjoy the peaceful atmosphere.

Just a short walk from here is Turtle Town, one of Maui’s best places to spot Hawaiian green sea turtles in their natural habitat. These gentle giants often rest along the shoreline or glide effortlessly through the water nearby. Watching them bask on the sand or swim in the shallow waters is a magical, serene experience that truly connects you to the beauty of Maui’s marine life.

Return to the Resort for a Relaxing Evening

After a peaceful afternoon on the beach, return to the resort for an evening of leisure. Whether you choose to relax by the pool, take a sunset stroll along Kaanapali Beach, or enjoy a cocktail at a beachfront lounge.

Why This Day is a Perfect Balance of Adventure & Relaxation:

• Experience the Most Spectacular Sunrise in Hawaii – Watching the sun rise above the Haleakalā crater is one of the most awe-inspiring moments of the trip.
• Walk Along the Crater Rim for a Unique Perspective – This short, scenic hike offers unparalleled views of Hawaii’s volcanic landscape, without a strenuous trek.
• See Hawaiian Sea Turtles Up Close in Their Natural Habitat – Maluaka Beach and Turtle Town offer a rare chance to observe these majestic creatures up close, in a peaceful setting.
• Unwind on One of Maui’s Most Beautiful Beaches – Soft golden sand, gentle waves, and a stunning ocean view make this the ideal spot for a tranquil afternoon.

Day 8: The Legendary Road to Hana – A Journey Into Maui’s Untouched Beauty

📍 Check out of Outrigger Kaanapali Beach Resort, Check in at Hana-Maui Resort

Today, you’ll experience one of the most breathtaking and scenic drives in the world—the Road to Hana. This winding coastal route will take you through lush rainforests, cascading waterfalls, black sand beaches, and hidden tropical gems. The best part? You won’t be rushing back to the resort at the end of the day—you’ll check into the luxurious Hana-Maui Resort, allowing you to fully soak in the beauty of East Maui at a relaxed pace.

Early Morning: Depart West Maui & Begin the Road to Hana

After checking out of the resort, the adventure begins as you leave West Maui’s dry coastline and head toward the lush, waterfall-lined roads of East Maui. With over 600 turns and 59 bridges, the Road to Hana is as much about the journey as it is about the destination.

Your first stop:

• Twin Falls (1.5 miles round trip, unpaved, gentle incline) – One of the first waterfalls along the Hana Highway, offering a short walk to beautiful cascading pools where you can stretch your legs and take in the rainforest surroundings.

Midday: Ke‘anae Peninsula & Black Sand Beaches

• Ke‘anae Peninsula Viewpoint – A stunning coastal stop where waves crash against jagged lava rock, offering some of the best photo opportunities along the drive. This area is a quiet reminder of old Hawaii, with taro fields and a historic stone church built in 1856.
• Banana Bread Stop at Aunty Sandy’s – No trip to Hana is complete without trying warm, freshly baked banana bread, a Maui tradition that’s been served here for decades.

Continuing along the highway, you’ll arrive at one of the most iconic stops of the journey:

• Wai‘anapanapa State Park – Walk Along the Famous Black Sand Beach

Afternoon: Arrival in Hana & Relaxation at the Resort

After exploring Hana’s stunning coastline, check in to the Hana-Maui Resort, a peaceful retreat surrounded by lush tropical gardens with sweeping ocean views.

Spend the afternoon relaxing and unwinding after the scenic drive— sipping a cocktail on your private lanai, taking a dip in the infinity pool, or simply listening to the sound of the waves.

Why This Day is a Must:

• Experience One of the Most Beautiful Drives in the World—At a Relaxed Pace – Unlike rushed day trips to Hana, staying overnight means you can truly take in the stunning views and stop as often as you like.
• Visit Maui’s Most Unique Natural Wonders – See a jet-black volcanic sand beach, dramatic sea arches, and waterfalls hidden in the rainforest.
• Enjoy a Taste of Old Hawaii – Ke‘anae Peninsula’s taro fields and Aunty Sandy’s famous banana bread are simple yet authentic experiences that capture the charm of East Maui.
• Stay in One of the Most Peaceful Resorts on the Island – The Hana-Maui Resort offers a quiet, luxurious escape, surrounded by lush greenery and ocean views.
• End the Day with a Beautiful, Crowd-Free Sunset – Unlike West Maui’s busy beaches, Hana’s coastline offers a serene, untouched beauty perfect for unwinding after a day of adventure.

Day 9: The Heart of Hana – Waterfalls, Rainforests & Hidden Beaches

📍 Staying at: Hana-Maui Resort

Today, you’ll explore some of the most stunning natural wonders of East Maui, from towering waterfalls and dense bamboo forests to hidden beaches untouched by crowds. With no need to rush back to the other side of the island, you’ll have the freedom to fully immerse yourself in the beauty and tranquility of Hana.

Morning: Pipiwai Trail & Waimoku Falls – Maui’s Most Breathtaking Rainforest Hike

Begin the day with a short drive to Haleakalā National Park’s Kipahulu District, home to the Pipiwai Trail (2 miles in, 2 miles out with a long break at the waterfall, moderate difficulty, rainforest path, wooden at times and flat).

This trail is one of the most awe-inspiring hikes in all of Hawaii, leading you through:

• A massive banyan tree with sprawling roots, perfect for an unforgettable photo.
• A dense bamboo forest, where towering stalks create a tunnel of green that sways and sings in the breeze.
• Waimoku Falls, a staggering 400-foot waterfall that cascades down a sheer lava rock wall. Standing beneath this towering natural wonder is a once-in-a-lifetime experience.

Take your time soaking in the sounds of nature—flowing streams, rustling bamboo, and the distant roar of waterfalls.

Day 10: The Scenic Journey Back – A Leisurely Return to Central Maui

📍 Check out of Hana-Maui Resort, Check in at Airport Hotel

After two nights in Hana’s peaceful rainforest retreat, today’s journey takes you back toward Central Maui. Unlike the drive in, today’s pace is relaxed and unhurried, allowing time to revisit favorite spots, take in new scenic views, and enjoy a final taste of East Maui’s untouched beauty.

Morning: Sunrise Over Hana & Coastal Lookouts

Start the morning with a slow, peaceful breakfast at the resort, overlooking the ocean. The early light in Hana is magical—soft, golden, and free from crowds.

• Koki Beach – An Optional Quiet Morning Stroll – This stunning red-sand beach, framed by dramatic cliffs, is the perfect spot for a final glimpse of Hana’s wild coastline.

Midday: A Leisurely Drive Back with Stops Along the Way

The return trip offers a chance to revisit favorite spots along the Road to Hana, without the pressure of making it to a hotel check-in.

Evening: Check into Your Airport Hotel & A Farewell Dinner

After a scenic, easy-paced day, check into a comfortable hotel near Kahului Airport, ensuring a stress-free departure tomorrow.

For your final evening in Maui, enjoy a farewell dinner at one of the island’s top restaurants, reminiscing about the incredible journey. 

Why This Day is the Perfect:

• A Relaxed, Scenic Drive Back from Hana – No need to rush—this is the perfect way to take in one last look at Maui’s east side.
• Time to Revisit Your Favorite Stops – If there’s a black sand beach, lookout, or fruit stand you loved, today is the perfect chance to see it again.
• Stress-Free Check-In at an Airport Hotel – Stay close to the airport for a smooth departure, with no early-morning travel hassle.
• Celebrate the End of an Unforgettable Journey – A farewell dinner is the perfect way to reflect on the adventure and enjoy one last taste of Maui’s incredible flavors.

Day 11: Depart from Maui to Home

📍 Check out of Airport Hotel

• Depart at your leisure from Kahului Airport, Maui