Tailor-Made Holiday

Sail the Hawaiian Islands

Discover the wonders of these remote, volcanic islands from the comfort of an exclusive yacht

10 days

from £4,840pp (excluding flights)

On-board a boutique 36-passenger yacht, sail through remote waters to the islands of Molokai, Lanai, Maui and Big Island. It is possible to navigate in both directions, either beginning or ending on Big Island. 

  • Exclusive yacht getaway for an unforgettable adventure
  • Evening pa‘ina (feast) and Hawaiian jam session with Molokai locals
  • Snorkel among coral gardens, giant manta rays andlook for humpback whales
  • Explore giant sea cliffs by kayak, paddle board or skiff

Why travel on a private yacht?

This voyage is well-suited to those who aspire to experience the more remote areas of the Hawaiian Islands and partake in a more authentic tour of the archipelago. A small boat is carried onboard the yacht, enabling passengers to navigate even closer to the dramatic coast of Lanai.

Life in the Hawaiian Islands

Notably, this itinerary often ventures on to land in hopes of discovering the history of the ancient islands through traditional feasts, local music and dancing. Passengers can snorkel, paddle board and kayak amongst the myriad of sea life that is native to the volcanic shores, or simply relax on deck and observe dolphins and green sea turtles from this unique vantage point.

Extending your adventure

It is possible to add additional nights before and/or after the boat journey to allow for further exploration of the inland areas. Please speak to one of our experts to discuss further possibilities, which include discovering the volcanoes of Big Island or taking in the drama of Kauai.

For a more detailed itinerary with great ideas on what to do and where to stay, please get in touch with our experts.

Price Excluding Flights £Flight cost from 
£ 4840 £ 1070

Itinerary at a glance

Collapse all
Day 1

Day at leisure in Honolulu

You will be staying at The Modern Hotel Honolulu, room only

Day 2

Fly Honolulu to Molokai

Transfer from Molokai Airport to the Safari Explorer

On arrival at Molokai Airport you will be met by a representative from the yacht who will drive you to their hospitality area on the island. Later, board the Safari Explorer with champagne in hand and receive a warm greeting from the Captain and crew.

First night on-board the Safari Explorer
You will have time to settle in to your cabin before sitting down this evening to your first dinner aboard the yacht. The guides will give a presentation full of information about the week ahead, and there will be time for you to ask any last-minute questions that you might have.

You will be staying at Safari Explorer, full board

Day 3

Explore Molokai
Spend the day on Molokai meeting locals and learning about the traditions of the Hawaiian people. In the evening, enjoy one of Hawaii's cultural treasures, a pa'ina (feast) held at the Molokai Museum. Discover the history of this ancient homeland as you experience singing, dancing, traditional cuisine and Hawaiian décor.

You will be staying at Safari Explorer, full board

Day 4

Discover the smallest inhabited island in Hawaii
Wake up to views of the tranquil island of Lanai, the smallest inhabited island in Hawaii, and prepare for a full day of water and land-based excursions. Enormous sea cliffs line the coastline and ancient volcanic plugs, home to a wide variety of marine life, protrude above the surface of the ocean. You can explore these calm waters by floating atop the surf with a snorkel or by heading out in a paddle board or small boat. Ask the onboard guides about the offshore wreck of a WWII tanker that rests off the coast of Shipwreck Beach.

On land, hike to Puu Pehe, otherwise known as Sweetheart Rock, an ocean rock formation steeped in folklore that rises majestically 25 metres out of the sea and towers above the crashing surf. Learn about the history of Lanai and its historical plantation days, during which time it produced 75% of the world's pineapples. It will also be possible to visit to the quaint Lanai Culture and Heritage Centre to absorb the history and traditional culture of colloquially known "Pineapple Island".

You will be staying at Safari Explorer, full board

Day 5

Drift on the Olowalu Reef
In ancient times, the community of Olowalu on the west of the island of Maui was known throughout the Hawaiian Islands as a place of sanctuary, or pu?u honua, however it also has a turbulent and poignant history. Today, the community of Olowalu is home to one of the most unique ocean reef systems in all the Hawaiian Islands, known locally as Turtle Reef.

Snorkel in this known sea turtle habitat among hundred-year-old coral gardens that are swarming with an abundance of tropical marine life. Sail through the Humpback Whale National Marine Sanctuary, a designated expanse of shallow warm waters that surround the main Hawaiian Islands, and learn from the guides about one of the world's most important protected marine habitats. From the decks, search for humpback whales, spinner dolphins, Hawaiian monk seals and reef fish.

You will be staying at Safari Explorer, full board

Day 6

Captain's Choice Exploration
Today, the Captain will purposefully navigate to a site that uncovers more of what the Hawaiian Islands have to offer. Dramatic volcanic backdrops, marine life sightings, and opportunities to embark on kayak explorations are all possibilities.

You will be staying at Safari Explorer, full board

Day 7

Anchor at Honomalino Bay
Located on the south-western shoreline of Hawaii's Big Island, Honomalino Bay is a scenic clear-water gem that is rarely frequented by crowds. Fringed by coconut palms, the Bay provides an ideal backdrop for a morning of marine-based activities as it is teeming with a diversity of colourful corals, sponges, and tropical fish.

This evening the Safari Explorer will anchor at an offshore location for a thrilling night-time snorkelling adventure with giant manta rays.

Hawaii Island isn't just big, it's still growing. The Island of Hawaii is the youngest island in the Hawaiian chain and is also by far the biggest, providing a vast canvas of environments to discover a variety of unrivaled natural wonders. This is the home of one of the world's most active volcanoes (Kilauea), the tallest sea mountain in the world at more than 33,000 feet (Maunakea), the most massive mountain in the world (Maunaloa) and the largest park in the state (Hawaii Volcanoes National Park). All but two of the world's climate zones generate everything from lush rain forests to volcanic deserts, snow-capped mountaintops to beautiful black sand beaches.

You will be staying at Safari Explorer, full board

Day 8

Step ashore at Kailua-Kona
Board a small boat and travel over the surf to Kealakekua Bay, the site where Captain Cook was slain in 1779, to partake in some stunning snorkelling off the pebble beaches.

Later, visit the seaside town of Kailua-Kona, where the Hualalai volcano meets the ocean, to explore this lively settlement and uncover its charm at a leisurely pace. You might like to purchase some of the world-renowned Kona coffee before heading back to the yacht.

This evening marks the end of the voyage and is celebrated with a splendid Captain's Dinner and photographic recap of your adventure.

You will be staying at Safari Explorer, full board

Day 9

Disembark at Kawaihae Harbor
Bid farewell to the Captain and crew as you disembark at Kawaihae Harbour on the north-western coast of Big Island. With an interesting history of its own, this humble community once served as the seat of the Kingdom of Hawaii island during the ancient reign of King Alapa?inuiakauaua.

Transfer from Kawaihae Harbour to Kona Airport

On disembarkation, you will be driven from Kawaihae Harbour to Kona Airport for your onward flight to Honolulu.

Fly Big Island Hawaii to Honolulu

You will be staying at The Modern Hotel Honolulu, room only

Day 10

Day at leisure in Honolulu


Below you can see some of the wonderful places we recommend you stay on your journey.

The Modern Hotel Honolulu

The Modern Hotel Honolulu

The Modern in Honolulu is a stylish high-rise hotel with a contemporary decor, conveniently located just minutes from Waikiki beach....

View Accommodation

Safari Explorer

Safari Explorer

A nimble 36-passenger yacht that cuts through the gentle surf of the Pacific Ocean at a maximum cruising speed of 10 knots, the 45-metre-long Safari Explorer is capable of navigating to the wildest edges of the Hawaiian Islands....

View Accommodation

For a more detailed itinerary with great ideas on what to do and where to stay, please get in touch with our experts.

Destination Experts

Our experts have unrivalled firsthand knowledge of USA

Paul Bird, Travel Expert

Read More

Roxy Dukes, Travel Expert

"Roxy filled us with enthusiasm and came up with some great ideas for a trip. We liked the idea of a slightly 'off the beaten track experience' and some private bespoke activities and that's exactly what we've had. Thank you!"

"Roxy created a wonderfully interesting route which was the basis for a super trip. She also chose lovely places for us to stay and interesting activities for us to participate in, introducing us to the idea of private guided experiences which we thoroughly enjoyed."

Read More

Sue Grimwood, Travel Expert

"It was tremendously helpful to be able to speak to someone who had been to Antarctica before - Sue had been on the ship we had booked, so was able to give us some very useful information. We felt that at every stage of the booking process that we were in safe hands. "

""I was uncharacteristically worried about this trip - neurotic some might say - and I was given 110% support and help with everything. I had been disappointed by not being able to get a space on the 2014 trip and so Sue was stuck with me for 2 years - a testament to her patience and professionalism. I was confident in Sue - she knows Antarctica and speaks from experience, that is worth a huge amount. Emails, which I would send were responded to almost immediately.""

Read More

For a more detailed itinerary with great ideas on what to do and where to stay, please get in touch with our experts.

Enquire about this holiday:
Speak to a USA holiday expert:

Tailor-Made Holiday Ideas

Booking a Tailor-made holiday gives you the flexibility to customise your journey, travelling when and where suits you.

Holiday Ideas in USA

You are unique, so we believe your holiday should be too.

We listen to what you want and create a personalised itinerary tailored around you.

Your holiday. Your experience. Your way.

Can’t find what you’re looking for?

Call our Travel Experts on +01285 880 980
Start Your Journey


  • Established for over 25 years creating journeys across 100 destinations worldwide
  • Exclusive access to the best private guides


  • We negotiate the best rates with hotels and expert guides
  • Be protected from fluctuations in exchange rates


  • Each time you travel with us we donate £5 to a local charity in the UK and £10 to an international charity

Fully Protected

  • Your monies are financially protected
  • 24/7 Emergency UK contact whilst abroad

Featured in the Press

Financial Times
The Telegraph
Sunday Times logo

Our Partners

African Parks
Galapagos Conservation Trsut
Restless Development
Save The Rhino
Tusk Trust
World Land Trsut
Gorilla Doctors

© Steppes Travel, 51 Castle St, Cirencester, GL7 1QD, United Kingdom