Serving Customers ALL OVER THE USA since 2020
Hawaii Vacations for Families, Honeymooners, Couples & Multi-Generational Trips
Curated Getaways for Honeymoons, Anniversaries, Family Vacations, & Couples
Hawaii is one of the world’s most extraordinary destinations — and one of the most rewarding to plan right. With four distinct islands, dozens of resorts, hundreds of activities, and a spirit of aloha unlike anywhere else on Earth, a Hawaii vacation has the potential to be absolutely unforgettable. At Voyage & Trails, we specialize in creating personalized Hawaii vacation packages for Midwest families, couples, and multi-generational groups — handling every detail from your departure out of O’Hare to your return home. Whether this is your first trip to the islands or your tenth, we’ll make sure you’re on the right island, at the right resort, at the right time of year.
Why Choose Voyage and Trails for you Hawaiian Vacation?
Planning a Hawaii trip from the Midwest involves a lot of moving pieces — long flights, inter-island logistics, car rentals, activity bookings, and navigating which island (or islands!) is the right fit for your family. That’s exactly where Voyage & Trails comes in. As a Chicago-area travel agency specializing in family vacations, we’ve done the research so you don’t have to. We know which resorts are truly family-friendly, which tours are worth the price, and how to build an itinerary that doesn’t leave you exhausted.
We handle everything — flights, hotels, inter-island travel, car rentals, luau reservations, helicopter tours, and more — so that from the moment you leave O’Hare to the moment you land back home, the only thing you need to worry about is making memories. And because we work with you personally, your Hawaii trip is never a cookie-cutter package — it’s built around your family, your budget, and your travel style.
What we take care of for your Hawaii trip
What we take care of for your Hawaii trip:
- Flights from Chicago and surrounding Midwest airports
- Inter-island flights and logistics when visiting multiple islands
- Resort and vacation rental selection matched to your travel style and budget
- Car rentals on each island
- Activity and tour bookings — luaus, snorkel cruises, helicopter tours, whale watching, and more
- Dining and restaurant recommendations
- Travel insurance options
- Ongoing support while you’re traveling
Let’s Start Planning Your Hawaii Vacation
Planning a Hawaii vacation should feel exciting — not overwhelming. At Voyage & Trails, we’re here to simplify the process and guide you every step of the way. Hawaii trips involve a lot of details: flights, island choices, resorts, car rentals, inter-island travel, activity bookings, dining, and travel protection. We take care of everything behind the scenes so you can focus on the best part — looking forward to your trip.
Whether you’re dreaming of a family adventure across all four islands, a romantic honeymoon in Maui, or a multi-generational trip celebrating a milestone, our team works closely with trusted Hawaii travel partners to create a seamless, personalized experience designed just for you.
Wherever your Hawaii story is headed, we’re ready to help you bring it to life.
Choosing Your Hawaii Island
One of the most common questions we get is: ‘Which island should we visit?’ The truth is, every Hawaiian island has its own personality — and the right one depends on what kind of experience you’re looking for. Here’s a quick guide to help you decide.
Oahu — Best for First-Time Visitors & History
Oahu is Hawaii’s most visited island, home to Waikiki Beach, Pearl Harbor, Diamond Head, and the legendary North Shore. It has the widest range of accommodations, dining, and activities — making it the easiest first-time choice. Families will love Hanauma Bay for snorkeling, and Disney’s Aulani Resort at Ko Olina is one of the best family resorts in the country.
Maui — Best for Romance, Adventure & Scenery
Maui is our most requested island for honeymooners and couples. The Road to Hana, Haleakala sunrise, Molokini Crater snorkeling, and whale watching season (December through April) make Maui one of the most diverse and beautiful destinations in the world. Resorts in Ka’anapali and Wailea offer world-class luxury.
Kauai — Best for Nature Lovers & Dramatic Scenery
Kauai is Hawaii’s most lush and undeveloped island. The Na Pali Coast, Waimea Canyon, and Poipu Beach make it a stunning destination for families and adventurers who want to experience Hawaii away from the crowds. A helicopter tour over Kauai is one of the single most breathtaking experiences in all of Hawaii.
Big Island — Best for Unique Once-in-a-Lifetime Experiences
The Big Island is unlike any other place on Earth. Walk across ancient lava fields at Hawaii Volcanoes National Park, snorkel with manta rays at night, stargaze from Mauna Kea — the world’s tallest mountain from base to summit — and swim with sea turtles at black sand beaches. No two days look the same on the Big Island.
Not Sure Which Island is Right for You?
We'll ask you a few quick questions about your travel style, budget, and must-have experiences — and give you a personalized recommendation. That's what we're here for.
Who We Plan Hawaii Trips For
Hawaii Vacations for Every Traveler
We plan Hawaii trips for all kinds of travelers. Here’s who we love helping most:
Hawaii Family Vacations
Hawaii is one of the best family vacation destinations in the world. Calm lagoons for little swimmers, sea turtles on every snorkel beach, Disney’s Aulani Resort, luaus, pineapple farms, helicopter rides, and the sheer wonder of watching a volcano up close — kids of all ages are captivated by Hawaii. We help families choose the right island combination, the right resort, and the right activities for every age in the group.
Hawaii Honeymoons & Romance Travel
Few destinations rival Hawaii for a honeymoon. Overwater bungalows at the Four Seasons Maui, private sunset cruises along the Na Pali Coast, a candlelit dinner on the beach in Wailea — Hawaii delivers romance effortlessly. We specialize in planning seamless honeymoon experiences where every detail is handled and every moment feels like it was designed just for you.
Multi-Generational Hawaii Trips
Bringing grandparents, parents, and kids to Hawaii together is one of our specialties. We know which resorts offer the right mix of activities for different ages, how to structure an itinerary that keeps everyone happy, and how to manage the logistics of traveling with a larger group across multiple generations.
Anniversary & Milestone Celebrations
Whether it’s your 10th or 40th anniversary, Hawaii is one of the most meaningful places on Earth to celebrate a milestone. We help couples plan anniversary trips that go beyond a standard vacation — with special touches, upgrades, and experiences that make the trip feel truly celebratory.
So Many Ways To Experience Hawaii
Island Hopping — Visit More Than One Island
Many of our clients visit two or more islands in a single trip. Inter-island flights are short (30–45 minutes) and affordable, and combining islands allows you to experience everything Hawaii has to offer. Our most popular combinations:
- Oahu + Maui — The most popular combo. History and city energy paired with beaches and adventure. Perfect for first-timers.
- Maui + Big Island — For families and couples who want dramatic scenery, world-class snorkeling, and the volcanoes.
- Oahu + Kauai — Busy and vibrant meets quiet and lush. A great contrast for families who want both experiences.
- All 4 Islands — For a 14+ night trip, the ultimate Hawaiian experience. We build seamless multi-island itineraries that flow naturally from one island to the next.
We book inter-island flights as part of your complete Hawaii package — no extra coordination needed on your end. We handle the full logistics of moving between islands so your trip feels seamless.
When Is the Best Time to Visit Hawaii?
Hawaii is a year-round destination with warm weather on every island throughout the year. That said, timing matters — and we’ll help you choose the best travel window based on your budget, travel goals, and calendar.
- April & May (Shoulder Season) — Excellent weather, fewer crowds, slightly lower prices than peak. One of our top recommendations.
- June, July & August (Summer Family Season) — Busy and warm, great for families with school-aged kids. Book early — resorts fill fast.
- September & October (Best Value Season) — Fewest crowds, lowest prices, beautiful weather. Our #1 recommendation for budget-conscious travelers.
- December – March (Peak Season) — Whale watching season in Maui (January–March), holiday travel, higher prices. North Shore surf peaks. Book 4–6 months ahead.
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At Voyage and Trails, we believe great trips start with real experience. We take the time to explore destinations, partners, and experiences firsthand so we can confidently guide you to the right fit. Whether you’re planning a romantic getaway, a river cruise, or a corporate incentive trip, our goal is simple — to make sure your journey is seamless, memorable, and truly exceptional.
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Our Services
Many of our travel experts have years of hands-on experience creating unforgettable journeys. At Voyage and Trails, we handle every detail of your trip — from accommodations, flights, and transfers to tours, activities, travel insurance, and contracts.
Whatever your travel style or destination, we take care of everything so you can focus on enjoying the experience. Every itinerary is personalized, seamless, and designed to make your journey effortless and memorable.
Romance Travel
Destination weddings, Anniversaries, vow renewals, honeymoons, engagements, elopements, retie the knot, babymoons, proposal trips and more
Group Travel
Corporate retreats and incentive travel, seniors-only river cruises, friends and family getaways, milestone anniversary celebrations, and so much more — all thoughtfully planned to bring people together.
Family
From all-inclusive resorts and unforgettable cruises to Hawaii, Europe, African safaris, and the exotic islands of Fiji and beyond, there are endless travel possibilities for families to explore together.
Disney
Adventures by Disney, Disney Cruise Lines, Disney World, Disneyland, Disney Resorts, Aulani, Universal, MyDisneyExperience, Disney Genie, characters dining, and more
Cruises
Ocean cruises, river cruises, private yachts, and expedition adventures — with so many options, we help you choose the perfect way to explore the world by sea.
Europe
We know Europe — and we love it. Paris, London, Rome, Florence, Barcelona, the Swiss Alps, Prague, Amsterdam, Venice, Athens, Vienna, Madrid… where will you go next?
And SO Much More!!
We create custom travel itineraries and trips, and we know travel – Whether it’s Universal, river cruises, safaris, yacht charters, Australia, Thailand and more!
Our Amazing Team Is Ready To Make Your Vacation A Success
Our Most Popular Locations and Brands
Experiences All Over The World
Click on a location below to learn more. We recognize that vacations are not just an investment, but often the highlights of our lives, and we take that responsibility seriously. We want to ensure you have the best experience.