HAWAII ISLAND HOPPING ADVENTURE
March 17 - 30, 2027
Four Islands, One Spirit of Aloha
An unforgettable Hawaiian adventure with your Sisterhood.
Aloha is more than a greeting — it’s a way of being. It’s the warmth of the sun on your shoulders, the rhythm of waves against the shore, and the feeling of being completely welcomed, exactly as you are. On this extraordinary, women-only journey through four Hawaiian islands, we embrace the true spirit of aloha — together.
Our adventure begins on the iconic shores of Waikiki, where we’ll settle into the island pace and begin to connect not only with Hawaii, but with one another. On the Big Island, we’ll trace the raw, volcanic beauty of the land, from black sand beaches and ancient lava fields to sacred sites and sea turtles basking in the sun.
In Maui, the mood softens as we settle into ocean breezes, swaying palms, and the lush serenity of the ʻĪao Valley. You might choose to journey along the legendary Road to Hāna, or simply let the island hold you in its laid-back charm, with time to explore, reflect, or simply be. And finally, we arrive in Kauaʻi, a place that feels untouched, wild, and deeply spiritual.
This isn’t just a vacation — it’s a journey across islands, across stories, and into Sisterhood. Each island offers its own rhythm, its own wisdom, and its own way of welcoming us in. And through it all, you’ll be traveling with women who laugh easily, listen deeply, and understand the joy of meaningful connection.
Trip Highlights
- From Waikiki’s soft sands to the emotion of Pearl Harbor, Oʻahu blends joy, reverence, royal history, and welcoming island spirit
- Experience the Big Island’s raw beauty where lava meets sea, with volcanoes, black sand beaches, Kona coffee, and sacred stories shared in sisterhood
- Let Maui’s slower pace and lush landscapes invite you into wonder, from ʻĪao Valley cliffs to sunset walks along Kāʻanapali Beach
- Step into Kauaʻi’s dreamlike waterfalls and canyons as the Garden Isle reconnects you to nature, peace, and yourself
- Each island becomes a chapter of laughter, reflection, and lasting bonds with the women traveling beside you
OUR ITINERARY
March 17, 2027
Aloha and welcome to Hawaii! Your island-hopping adventure begins today on the sun-drenched shores of Waikiki Beach, where warm ocean breezes and laid-back island vibes set the tone for an unforgettable journey. The rest of the day is yours to rest, relax and rejuvenate from your long flights. (No meals are included today)
Hotel: Prince Waikiki Honolulu
March 18, 2027
How does a day on the beach, a swim in the pool, or a massage in the spa sound? Today is completely yours to enjoy at leisure with your brand-new Sisters. (Breakfast included)
Hotel: Prince Waikiki Honolulu
March 19, 2027
Today we’ll dive into the heart of Honolulu, getting a feel for the city’s history, culture, and everyday life. As we tour the city together, we’ll see some of O‘ahu’s most recognizable landmarks. Later, we’ll head to Pearl Harbor, one of the most meaningful and memorable stops on the island. At the World War II Valor in the Pacific National Monument, we explore exhibits and artifacts that bring history to life. We’ll travel by naval launch across the harbor to the USS Arizona Memorial, where we’ll pause to reflect and honor those who lost their lives during the attack. (Breakfast and Dinner included)
Hotel: Prince Waikiki Honolulu
March 20, 2027
We’ll head out this morning to visit ʻIolani Palace to learn about Hawaii’s royal past and the events that shaped the islands we know today. It’s a meaningful stop that adds real context to our time in Honolulu. Later, we head into O‘ahu’s rainforest for a stop at the Pali Lookout, where cooler air and sweeping views give us a fresh perspective of the island. (Breakfast included)
Hotel: Prince Waikiki Honolulu
March 21, 2027
This morning, we’ll board our group flight to the Big Island of Hawaii, leaving the buzz of O‘ahu behind for a place shaped by fire, water, and time. After arriving, we’ll stop at Rainbow Falls, where mist and sunlight often create shimmering rainbows. You’ll then have time to explore Hilo on our own with your Sisters before we head along the South Coast to Hawaii Volcanoes National Park, where we’ll learn about Kīlauea, one of the most active volcanoes in the world. We’ll travel past steaming bluffs and take in views of the vast volcanic caldera before continuing on to enjoy views of Kealakekua Bay and stop at an iconic black sand beach, where we might spot a green sea turtle resting along the shore. (Breakfast included)
Hotel: Outrigger Kona Resort & Spa
March 22, 2027
We’ll ease into our day with time to relax at our resort, taking in views of the Big Island’s rugged coastline. Later, we’ll head into Kailua-Kona, a historic seaside town founded by King Kamehameha I. We’ll have time to explore the shops, wander along the waterfront, and grab lunch independently with our new besties before returning to the hotel for a lei-making class with a local expert. In the evening, we’ll enjoy a traditional Polynesian luau, complete with Hawaiian-style dishes, tropical drinks, and lively island entertainment — a fun and festive way to experience local culture. (Breakfast and Dinner included)
Hotel: Outrigger Kona Resort & Sp
March 23, 2027
Today, we begin at Bay View Farm, a family-run coffee farm that’s been harvesting beans since 1984. Touring the farm with a local, we’ll learn how Kona coffee is grown and enjoy a tasting of their freshly brewed coffee. Next, we’ll visit St. Benedict’s Painted Church, built in the 1800s and known for its colorful frescoes that tell stories of Hawaii’s past. We’ll then continue along the rugged coast to Puʻuhonua o Hōnaunau National Historical Park, once a place of refuge in ancient Hawaii for those who broke sacred laws. (Breakfast and Dinner included)
Hotel: Outrigger Kona Resort & Spa
March 24, 2027
This morning, we’ll board our inter-island group flight to Maui, known as the “Valley Isle” and loved for its natural beauty. After arriving, we’ll visit ʻĪao Valley, where we’ll see the dramatic ʻĪao Needle rising nearly 2,000 feet above the valley floor. From there, we’ll travel to the resort area of Kāʻanapali and settle into our beachfront hotel, perfectly located for enjoying Maui’s laid-back pace and ocean views. (Breakfast and Dinner included)
Hotel: Sheraton Maui Resort & Spa
March 25, 2027
Today is a free day to discover why locals say Maui nō ka ʻoi — Maui is the best. The day is yours to spend however you choose.
Perhaps you’d like to travel the legendary Road to Hāna on our optional** full-day guided excursion. Driving along the coast, we’ll pass black sand beaches, lava formations, bamboo forests, eucalyptus groves, and quiet plantation towns. Highlights along the route include Pāʻia Town, Waiʻānapanapa State Park and Black Sand Beach, Kaumahina State Park, and Keʻanae Lookout, each offering a different glimpse of Maui’s natural beauty. (Breakfast included)
Hotel: Sheraton Maui Resort & Spa
March 26, 2027
Spend the day in paradise at our beautiful resort with your Sisters. Or, you may want to take a swim in one of the many beaches along the Maui coast or venture into town for lunch at a nearby restaurant. (Breakfast and Dinner included)
Hotel: Sheraton Maui Resort & Spa
March 27, 2027
This morning, we’ll take a short flight to Kauaʻi, the “Garden Isle” and the oldest island in the Hawaiian chain. Known for its lush landscapes and deep roots in ancient Polynesian culture, Kauaʻi feels worlds away. After arriving, we’ll head to Waimea Canyon, a dramatic landscape carved over thousands of years by rivers and floods. Stretching 10 miles long, a mile wide, and more than 3,500 feet deep, it’s often called the “Grand Canyon of the Pacific” — and it’s just as impressive in person. (Breakfast included)
Hotel: Outrigger Kauai Beach Resort & Spa
March 28, 2027
Today is yours to independently explore this beautiful island with your Sisters. You might prefer to relax on the beach and take advantage of all that our resort offers. (Breakfast included)
Hotel: Outrigger Kauai Beach Resort & Spa
March 29, 2027
Prepare to be awestruck as we step aboard an open-air boat and cruise along the peaceful Wailua River, listening as our captain shares stories of Kauaʻi’s past. We’ll stop at the lush Fern Grotto, where we’ll enjoy a short, guided walk surrounded by tropical greenery. On the return ride, we’ll experience the Hawaiian spirit firsthand as hula dancers join us to demonstrate this traditional art form and share its cultural roots. This evening, we’ll gather for a Farewell Dinner at the island’s first plantation house — a perfect way to reflect on our time together and celebrate an unforgettable journey through Hawaii. (Breakfast and Dinner included)
Hotel: Outrigger Kauai Beach Resort & Spa
March 30, 2027
Today, we bid aloha to Hawaii as our journey comes to an end on Kauaʻi. As we head home, we take with us incredible memories, new friendships, and a lasting connection to the islands. Wherever home may be, Hawaii will always feel like part of our ʻohana. (Breakfast included)
Trip Inclusions
- 13 nights/14 days deluxe oceanfront and ocean view accommodations
- 19 meals (13 breakfasts and 6 Dinners)
- Round-trip transfers between airport and hotels
- Hotel porterage
- 3 Group Flights in Economy class from Honolulu to Hilo, Kona to Maui, and Maui to Kauai
- All sightseeing tours, exclusive experiences and excursions as listed within this itinerary
- Deluxe, private transportation throughout the itinerary
- Private Tour Director
- Sisterhood Travels Group Leader
- Sisterhood Travels Swag
The Art of Staying Flexible
DEPOSITS & PAYMENTS
- Non-refundable deposit due at time of booking: $1000 per person
- 2nd Non-refundable payment due on or before June 1, 2026: $1500 per person
- 3rd Non-refundable payment due on or before September 1 7, 2026: $2000 per person
- Final payment due on or before December 1, 2026
important information
PLEASE READ THIS INFORMATION CAREFULLY
The maximum number of Sisters on this tour will be 26, including your Group Leader. Roommate matching is available. Please note that bookings will close for this tour on October 18, 2026. Any bookings after that date will be on waitlist.
ARRIVALS & DEPARTURES
- Airfare is not included in your pricing. You will fly into Honolulu (HNL) and depart from Kauai (LIH).
- You can arrive at any time on March 17, 2027, and depart at any time on March 30, 2027.
- Check-in time at our arrival hotel is at 3:00 pm.
- All flight arrangements must be submitted to Sisterhood Travels on or before January 17, 2027. If you need help making flight arrangements, or to submit your independent flight arrangements, please click here for Airfare Information.
- Arrival transfers are provided only on March 17th from the Honolulu airport to our hotel. Departure transfers are only provided on March 30th from our hotel to the Kauai airport. If you arrive or depart outside these days and times, or you’re needing transfers or hotels elsewhere, you are responsible for making your own arrangements at your own expense.
- Three (3) inter-island group flights are included in your pricing. Flights are in economy class with no opportunity for upgrades or advanced seating assignments. We will provide you with flight information closer to departure.
ENTRY REQUIREMENTS
- The REAL ID Act standards for identification while travelling is now in effect. This means a standard issued driver’s license used as a form of identification will no longer be accepted for domestic air travel within the United States. Instead, a Real ID compliant form of identification must be presented both at the time of booking air travel and upon checking in at the airport to board any flight. For more information on Real ID, please visit the Department of Homeland Security website.
- You are required to provide us with a copy of your REAL ID on or before October 18, 2026. Any fees associated with changing a group flight reservation resulting from a non-compliant identification will be your responsibility.
GRATUITIES, TRAVEL INSURANCE & OPTIONAL EXPENSES
- Gratuities for your Tour Director, local guides and drivers are not included in your pricing. We will provide you with tipping guidelines for your trip.
- Travel Insurance is strongly recommended and is not included in your pricing. We will send you a quote via email.
- Any optional expenses or expenses related to anything not specifically listed in this itinerary are not included.
- Please don’t schedule any optional excursions on your own for this trip as we cannot promise that you will arrive in time at any location to make your independent excursion. Sisterhood Travels won’t be liable for any expense you incur because of this.
- There are no refunds for unused portions of this tour.
GENERAL
- Wind conditions at Pearl Harbor may result in a boat tour that does not include stopping at the USS Arizona Memorial. This is decided in the moment by the U.S. Navy.
- The Place of Refuge is subject to weather conditions. In rare circumstances where the surf is high, the authorities may close the beach for safety concerns. If beach access is restricted during our tour, we will attempt to move the visit to another day or time but cannot be guaranteed if the park remains closed.
- Dates and times of itinerary as well as hotels listed are subject to change without notice due to operational or logistical reasons, and while sailing, are under the complete control of the Captain.
- Rates are guaranteed once your deposit has been received and your reservation has been confirmed by Sisterhood Travels. Until that point, pricing may change, and any increases in government taxes or fees may still apply.
- We cannot accommodate wheelchairs, assistive devices, scooters, walkers or rollators, or Zimmer-frames. You must be able to ambulate independently with no assistance from devices or others on the trip. It is imperative that you read the activity level description below.
- You will receive an invitation soon after you book your trip for our travel app, “Trip Plans”. You will need to download this app to your smart phone as this is where you will find the most up-to-date, accurate information regarding your itinerary in addition to all of the critical information you need to know.
Need a Roommate?
Cancellation & Refunds
Activity Level:
leisurely
Activity Level: 2 Leisurely
This Hawaii island-hopping journey is best described as a relaxed to moderate activity level experience. It is thoughtfully paced with a balance of guided sightseeing, scenic drives, cultural experiences, and multiple leisure days built in for rest, relaxation, and to enjoy each island at your own pace. While there are several full sightseeing days, the itinerary avoids strenuous hikes and allows ample downtime throughout the journey.
Walking & Standing
Walking is generally light to moderate and spread out over the day. Most sightseeing stops involve short walks on paved paths, boardwalks, or well-maintained trails. You should be comfortable standing and walking for up to 1 to 2 hours at a time, with frequent breaks. No long-distance or strenuous hikes are included. Our accommodations are located on large properties and may require walking longer distances to get around the resorts.
Terrain
Terrain varies throughout the islands and includes paved sidewalks, compact dirt paths, boardwalks, and some uneven or natural surfaces at parks, black sand beaches, historic sites, and scenic overlooks. There may be occasional steps, inclines, or uneven ground, especially in volcanic areas, rainforest lookouts, and coastal sites. Comfortable walking shoes with good traction are recommended.
Transportation & Transfers
This tour includes multiple inter-island flights and several full and partial sightseeing days by motorcoach. Some days involve longer driving distances, particularly on the Big Island and Kauaʻi, where scenic routes connect remote natural landmarks. Coaches are climate-controlled and stops are built in along the way.
Optional Excursion: Road to Hana
Participation is optional and best suited for those comfortable with traveling on winding roads. This excursion may not be suitable for those with motion sickness or back problems.