Hawaii · Planned start to finish
At Traveland, we plan personal journeys across the Hawaiian Islands, from the volcanoes of Hawaiʻi Island and the heights of Haleakalā to Kauaʻi’s canyons and the history of Oʻahu. We take care of the research, bookings and logistics, from the first conversation to your flight home, so your time goes into enjoying the trip, not planning it. We are a family-owned travel agency in Connecticut, planning trips since 1978 as a member of the Signature Travel Network.
Since 1978Family-owned and operated
Signature Travel NetworkMember agency
Orange & BridgeportTwo Connecticut offices
Every detail handledSo you can simply enjoy the trip
The islands
Six islands, six distinct worlds. Each has its own landscapes, pace and heritage sites, and we help you choose the right pairing for your time and interests.
The largest island is home to Hawaiʻi Volcanoes National Park, Akaka Falls, Puʻuhonua o Hōnaunau and the calm waters of Kealakekua Bay.
Sunrise above the clouds at Haleakalā National Park, the green walls of ʻĪao Valley, farm-to-table dining and long, restful beaches.
Waimea Canyon, Kilauea Point Lighthouse and lush valleys make the Garden Isle a place to breathe deeply and slow down.
Pearl Harbor, ʻIolani Palace, the Bishop Museum and Diamond Head, with Honolulu’s energy and the legendary surf of the North Shore.
A small, quiet island known for secluded shores, rugged landscapes and a relaxed, private feel.
Towering sea cliffs, the Kalaupapa Lookout and a strong sense of Hawaiian culture and community.
Six islands. Six distinct worlds.
We handle the details. You enjoy the journey.
Experiences
Every journey begins with what matters most to you.
Palaces, sacred places and memorials that tell the story of the islands.
Guided ways to experience volcanoes, forests and reefs with care.
Lessons on gentle waves or front-row seats to the North Shore’s giants.
Oceanfront courses on every major island.
Lighthouses, lookouts and wildlife refuges along dramatic shorelines.
Working with us
01
Tell us how you like to travel, who is coming, and what you hope to feel. There is no charge to begin.
02
We design the route, hotels, transfers and experiences, then refine them with you, so you skip the hours of research and comparison.
03
We book the flights, stays, cruises and tours and keep track of every confirmation, so all you have to do is enjoy the journey.
Timing
Hawaii is warm all year. April to May and September to October are often quieter, while winter brings big surf and humpback whales.
Pleasant weather and fewer visitors between spring break and summer.
Dry, sunny days and calmer seas on most north-facing shores.
Warm ocean, quieter beaches and good value in September and October.
Humpback whale season and big North Shore surf, with more rain on windward coasts.
Questions
Hawaii is warm year-round. April to May and September to October are often quieter. Winter, roughly December to April, is humpback whale season and brings big surf to north shores, while summer is typically drier.
Many first-time visitors pair Oʻahu, for history and Honolulu, with Maui, for beaches and Haleakalā. Travelers seeking quiet often choose Kauaʻi, and those drawn to volcanoes choose Hawaiʻi Island.
Two islands in ten days or three islands in two weeks allows time to settle in without rushing. Short inter-island flights connect the main islands.
No. Hawaii is a U.S. state, so U.S. citizens flying from the mainland do not need a passport. You will need a REAL ID-compliant license or another accepted ID for domestic flights.
Humpback whales visit Hawaiian waters in winter, generally from December through April, and are often seen off Maui.
Yes. Calm beaches, snorkeling, easy hikes and cultural sites make every island a strong choice for families and multigenerational trips.
Planning a trip like this can take many hours of research, comparison and booking. We do that work for you, draw on decades of experience to get the details right, and keep every confirmation in one place, so you can spend that time looking forward to the journey.
We are a family-owned travel agency in Connecticut, with offices at 564 Racebrook Road in Orange (203-929-6000) and 4270 Main Street in Bridgeport (203-371-1114).
Inquire
Tell us a little about the Hawaii journey you have in mind. One of our advisors will reply personally.
Choose a time for a call with one of our advisors.
Orange
564 Racebrook Road, Orange, CT 06477
203-929-6000
Bridgeport
4270 Main Street, Bridgeport, CT 06606
203-371-1114
Monday to Friday, 9am to 6pm
info@traveland.net
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