The Perfect 7-Day Maui Itinerary for Bay Area Families

Your complete guide from SJC to the Valley Isle — with kids in tow.


Photo by Karsten Winegeart on Unsplash

If you’re a Bay Area family dreaming of warm turquoise water, jungle waterfalls, and an escape from the grind — Maui is your island. Better yet, direct flights from San Jose (SJC) mean you can be sipping a mai tai on a Kaanapali beach in under 6 hours. No connections, no chaos, just aloha.

This 7-day itinerary is designed with families in mind: a smart mix of adventure, relaxation, culture, and kid-friendly fun — without trying to cram in everything at once.


Before You Leave the Bay Area

Flights from SJC to Maui

Southwest, United, and Alaska Airlines all offer direct flights from San Jose to Kahului Airport (OGG) on Maui. Flight time is roughly 5.5 to 6 hours. Pro tip: book morning departures so you land with plenty of afternoon daylight to enjoy.

💡 Travel Agent Tip: Families of 4+ should book at least 4–6 months out, especially for summer and holiday travel. Hawaii routes fill fast from the Bay Area.

Best Time to Visit

Maui is gorgeous year-round, but Bay Area families tend to travel during summer (June–August) and the holiday break (December–January). April through early June is our favorite “sweet spot” — whale season overlaps (through May), crowds are thinner, and prices drop slightly after spring break.

What to Pack

Bay Area weather has nothing in common with Maui, so pack accordingly:

  • Reef-safe sunscreen (required in Hawaii — chemical sunscreens are banned)
  • Light layers for Haleakala sunrise (it gets cold — around 40°F at the summit)
  • Water shoes for snorkeling and rocky beaches
  • A light rain jacket — Maui’s north and east sides can get showers
  • Kids’ snorkel gear (or rent locally — we can arrange)

Your 7-Day Maui Itinerary

Day 1 — Arrival & Settle In (West Maui / Kaanapali)

You’ve landed. Breathe in that warm plumeria-scented air and remind yourself: you’re in Maui.

After picking up your rental car at OGG (I recommend an SUV or minivan for families), head straight to your resort in Kaanapali or Wailea — two of the best family-friendly areas on the island.

  • Check in and hit the pool — the kids have been on a plane for 6 hours, they’ve earned it
  • Stroll the Kaanapali Beachfront Walk for a casual first sunset
  • Dinner at Hula Grill on the beach — open-air seating, fresh fish, great for families

🌅 Don’t Miss: The cliff-diving ceremony at Black Rock (Pu’u Keka’a) at sunset — a nightly Kaanapali tradition that kids absolutely love.


Day 2 — Snorkel, Sea Turtles & Lahaina Town

Start the morning with Maui’s #1 family activity: snorkeling. Head to Kapalua Bay or Napili Bay — both calm, protected, and teeming with sea turtles and tropical fish.

  • Morning snorkel at Kapalua Bay (one of the best beginner snorkel spots on the island)
  • Lunch in Lahaina — the historic former capital of Hawaii, packed with restaurants, galleries, and shops along Front Street
  • Stop by the famous 150-year-old Banyan Tree in Lahaina Court Square — the kids will want to climb it

📸 Photo Op: The Banyan Tree in Lahaina is the largest in the US — a must-see and perfect for a family photo.


Day 3 — Road to Hana (The Full Experience)

No Maui trip is complete without the Road to Hana — one of the most breathtaking drives in the world. Leave early (7 AM or before) and take your time. It’s a 64-mile winding coastal highway with 600 turns and 59 bridges. It’s not about the destination — it’s about the stops.

  • Twin Falls — easy 20-minute hike, waterfalls, perfect for kids
  • Wai’anapanapa State Park — stunning black sand beach (reserve entry in advance at gostateparks.hawaii.gov)
  • Garden of Eden Arboretum — lush botanical gardens and a Jurassic Park filming location
  • Keanae Peninsula lookout — dramatic lava coastline and taro fields
  • Hana town — grab banana bread from Aunty Sandy’s roadside stand (a Maui institution)

💡 Travel Agent Tip: You do NOT need to drive back the same way. Continue past Hana and loop around the backside of the island (Highway 31) for more stunning views — just note some rental car companies prohibit this, so check your agreement or let me arrange the right rental for you.


Day 4 — Haleakala Sunrise & Upcountry Maui

This is the day that will make your whole trip unforgettable. Rising at 2:30 AM might sound brutal, but watching the sunrise from 10,023 feet above the clouds at Haleakala summit is one of those once-in-a-lifetime moments.

  • Book your Haleakala sunrise reservation in advance at recreation.gov (they sell out weeks ahead)
  • Dress in layers — it’s cold at the summit, even in summer
  • After sunrise, explore Upcountry Maui — the cool, green farming community above Kula
  • Stop at Surfing Goat Dairy for a farm tour the kids will love
  • Lunch at Kula Lodge for gorgeous views over the valley

⚠️ Important: The drive from Kaanapali to the Haleakala summit takes about 1.5–2 hours. Set multiple alarms. It’s worth every groggy minute.


Day 5 — Molokini Crater Snorkel & Afternoon at the Beach

Today is all about the water. A snorkel boat trip to Molokini Crater — a partially submerged volcanic crater just off the coast — is one of the best snorkeling experiences in all of Hawaii.

  • Book a morning Molokini snorkel tour (we can arrange this through our preferred vendors)
  • Water visibility frequently exceeds 100 feet — expect sharks, rays, and hundreds of fish species
  • Most tours also stop at Turtle Town on the way back
  • Spend the afternoon at Wailea Beach or Big Beach (Makena) — one of Maui’s most beautiful white sand stretches

💡 Travel Agent Tip: Morning tours leave around 6:30–7 AM when the water is calmest. Afternoon winds can make for rough seas — especially for kids prone to seasickness.


Day 6 — West Maui Mountains & Kaanapali Beach Day

Take a slower pace today. West Maui is stunning and often overlooked — but the waterfalls, valleys, and viewpoints here are spectacular.

  • Drive through Iao Valley State Monument — home of the iconic Iao Needle, a 1,200-foot green rock pinnacle
  • Stop in Wailuku town — charming, non-touristy, with great local plate lunch spots
  • Afternoon beach day at Kaanapali — paddleboards, snorkel gear, or just relax
  • Dinner at Monkeypod Kitchen — a Bay Area family favorite every time we send clients

🍽️ Eat Like a Local: Don’t leave Maui without trying a plate lunch. Two scoop rice, mac salad, and kalua pork — that’s Hawaii comfort food.


Day 7 — Last Morning Magic & Fly Home

Your last morning is precious. Don’t waste it in a hotel room.

  • Early sunrise walk on the beach — quiet, peaceful, and a perfect goodbye to the island
  • Grab shave ice at Ululani’s (the best on the island — multiple locations)
  • Last swim or snorkel if time permits
  • Return your rental car and head to OGG — give yourself 2 hours before departure

Most afternoon flights from OGG land back in SJC by early evening, getting you home in time for the Bay Area fog — and about a week of post-vacation blues.


Practical Family Travel Info

Getting Around

A rental car is essential. Maui has no real public transit, and you’ll want the freedom to explore on your own schedule. Book early — cars sell out fast in summer and over the holidays.

Where to Stay

  • Kaanapali (West Maui) — iconic resort strip, walking distance to Lahaina, great beach, calm water
  • Wailea (South Maui) — more upscale, beautiful beaches, excellent restaurants, more consistent weather
  • Kihei (South Maui) — best value for budget-conscious families; vacation rentals with full kitchens are a great option

Budgeting for Your Trip

Here’s a rough daily guide for a family of four:

  • Budget: $300–$450/day (vacation rental, grocery shopping, mix of free and paid activities)
  • Mid-range: $500–$750/day (resort hotel, mix of dining out and groceries, 1–2 paid activities)
  • Luxury: $1,000+/day (beachfront resort, fine dining, private tours and charters)

💡 Travel Agent Tip: I can package flights, hotels, and car rental together to save you money — and we have preferred rates with top Maui resorts. Reach out before you book anything on your own.


Ready to Book Your Maui Family Vacation?

This itinerary barely scratches the surface of what Maui has to offer — and every family trip is different. Whether you want more beach days, a helicopter tour over the volcanoes, or a private sunset sail, we can customize this trip to fit your family perfectly.

As a Bay Area travel specialist, I know Maui well — and we know the specific needs of families flying out of SJC. Let me handle the details so you can focus on making memories.

📞 Contact me today to start planning your Maui getaway.

Your Bay Area travel agency — proudly serving San Jose and the greater Bay Area.

Jamaica, After the Storm: Why Travel Matters More Than Ever

When Hurricane Melissa tore across Jamaica as a powerful Category 5 storm, it left behind more than damaged buildings and flooded roads. It left a nation grieving for what was lost and fighting bravely to protect what remains. Yet even in the hardest days, the spirit of Jamaica continues to shine through its people, its music, its culture, and its deep sense of community.

This is a moment when travel to Jamaica becomes more than a vacation choice. It becomes an act of meaningful support.

A Nation Hurt but Never Defeated

Hurricane Melissa brought widespread destruction to parts of the island. Homes were damaged, power and communication lines were lost, and several communities were left cut off while emergency teams worked tirelessly to reach them. In many areas, families are still rebuilding, repairing, and trying to regain a sense of normalcy.

But if there is one thing Jamaica has always been known for, it is resilience. From the first moments after the storm, neighbors helped neighbors, local businesses came together to share supplies, and communities rallied around one another. Jamaica is hurting, but Jamaica is far from broken.

Why Tourism Is Essential to Jamaica’s Recovery

Tourism is not simply an industry in Jamaica. It is the foundation of thousands of livelihoods. When travelers return to the island, they support:

  • Hotel staff who depend on steady shifts
  • Taxi drivers and tour guides who earn by the day
  • Local restaurants and small eateries that rely on visitors
  • Craft vendors and artisans who pour their culture into their work
  • Farmers and fishermen who supply resorts and restaurants

When tourism slows, every one of these groups feels the impact. And when a hurricane causes major damage, the absence of visitors only deepens the hardship.

Your trip does far more than fill a hotel room. It helps a local family get through a difficult time. It gives a small business a chance to recover. It sends a message that the world has not forgotten Jamaica.

Jamaica’s Rebuilding Efforts Are Already Underway

Despite the challenges, Jamaica is moving forward quickly and with determination. Recovery crews are repairing roads, restoring power, and supporting the tourism sector so that travelers can safely return. Many hotels and resorts are reopening or preparing to open soon, and countless local businesses are ready and eager to welcome guests again.

Visiting during this time does not mean stepping into an unsafe environment. It means supporting a country that is actively rebuilding and grateful for your presence.

Why Traveling to Jamaica Now Makes a Difference

Your visit provides immediate economic relief.
Every meal, every tour, every purchase directly helps the island’s recovery.

Your presence gives hope.
When visitors return, it shows Jamaica that people around the world believe in its ability to rise from hardship.

You help protect jobs and families.
Tourism revenue ensures that workers can provide for their households while the nation rebuilds.

You experience Jamaica’s true heart.
Traveling now offers a deeper connection to the island, its people, and its culture. You become part of the story of resilience and renewal.

How to Travel Responsibly and Respectfully

  • Choose accommodations that are fully open and operating safely
  • Support local guides, restaurants, and small businesses
  • Tip generously when you can
  • Approach your trip with patience as some areas continue to recover
  • Consider contributing to local relief or rebuilding programs

A Final Reflection

Jamaica has always been a place where visitors feel welcomed, embraced, and at home. After Hurricane Melissa, the island is leaning on that same spirit of warmth and unity to move forward. By choosing to visit now, you become part of that healing. You help rebuild not just structures but lives, families, and futures.

Jamaica will dance again, sing again, and celebrate again. And your support can help bring that day a little closer.

First-Time Trip to Jamaica? Here’s Everything You Need to Know!

Planning your first trip to Jamaica? You’re in for an unforgettable island escape filled with tropical vibes, vibrant culture, and unmatched hospitality. From stunning beaches to lush mountains, reggae rhythms to rich cuisine—Jamaica is more than a destination, it’s a feeling. Here’s your ultimate guide packed with tips, must-do experiences, and why booking with expert Travel Advisor Krystal Hall will make your journey smooth, safe, and stress-free.


Arrival Tips: Start Smart with Club Mobay

One of the best-kept secrets for travelers flying into Montego Bay’s Sangster International Airport (MBJ) is Club Mobay—a VIP fast-track service that makes your arrival and departure a breeze.

Why You’ll Love It:

  • Expedited immigration and customs to skip the long lines
  • Welcome lounge with snacks, drinks, and Wi-Fi while your bags are handled
  • Departure lounge with food, drinks, showers, and even a kid’s play area before your flight home

Pro Tip: Club Mobay can get booked up—Krystal Hall can arrange it in advance for a seamless experience.


Top Travel Tips for First-Time Visitors

1. Currency
The Jamaican Dollar (JMD) is the official currency, but US Dollars are widely accepted at resorts and tourist areas. Just bring small bills for tips and local purchases.

2. Safety
Stick to trusted excursions and resort recommendations. Booking with a professional advisor ensures vetted, reputable experiences.

3. Weather
It’s always warm, but pack light layers for breezy evenings and occasional rain showers.

4. Power Outlets
Jamaica uses the same plug types as the U.S. (Type A/B) and the voltage is 110V—no adapter needed.

5. Culture
Respect the pace. “Island time” is real—embrace the laid-back lifestyle and friendly vibes.


Can’t-Miss Excursions and Activities

Whether you’re craving adventure, culture, or relaxation, Jamaica has something for everyone. These are top-rated excursions perfect for first-timers:

Dunn’s River Falls (Ocho Rios)
Climb the iconic cascading waterfall—an exhilarating and photo-worthy experience.

Luminous Lagoon (Falmouth)
Swim in this glowing bioluminescent bay at night. One of only a few in the world.

Blue Hole & Secret Falls
A lush jungle escape where you can cliff-jump, rope-swing, and swim in bright blue waters.

Catamaran Cruise to Rick’s Café (Negril)
Dance, snorkel, and sip rum punch on the Caribbean Sea—then watch cliff divers and the sunset at this legendary spot.

Local Flavors Tour
Taste your way through jerk chicken shacks, fresh fruits, and a real Jamaican patty. A must for food lovers.


Why Book With Krystal Hall?

Traveling to a new country can feel overwhelming, but not when you have the right expert by your side.

Why Krystal?

  • Extensive first-hand experience with Jamaica’s best resorts, excursions, and hidden gems
  • VIP access to exclusive perks, upgrades, and travel promotions
  • Personalized planning tailored to your travel style—honeymoons, families, girls’ trips, or destination weddings
  • Seamless booking of Club Mobay, airport transfers, and excursions before you even take off

Final Words

Your first trip to Jamaica should be full of joy—not stress. By planning ahead and working with a seasoned expert like Krystal Hall, you’ll enjoy a worry-free vacation where all you have to do is relax and say, “Yeah mon, no problem.”

Ready to book your Jamaican getaway?
Contact Krystal Hall today and let the island magic begin.

Krystal@VincentVacations.com

Romance in Montego Bay: Escape to Secrets St. James & Secrets Wild Orchid

If you’ve been dreaming of a luxury escape wrapped in romance, where the ocean breeze meets warm Jamaican hospitality, look no further than Secrets St. James and Secrets Wild Orchid in Montego Bay. These neighboring adults-only resorts are designed with love in mind—offering couples the perfect setting to unwind, reconnect, and celebrate life’s most beautiful moments.

A Romantic All-Inclusive Oasis

Tucked along a private peninsula with the Caribbean Sea on three sides, both Secrets St. James and Secrets Wild Orchid share a sprawling property that blends British colonial elegance with modern, chic Caribbean flair. Think poolside cabanas, ocean-view suites with whirlpool tubs, gourmet dining under the stars, and beachside fire pits—all included with your stay.

Whether you’re celebrating a honeymoon, anniversary, or planning a surprise romantic getaway, these sister resorts offer the Unlimited-Luxury® experience that includes:

  • 24-hour room service
  • Top-shelf spirits at multiple bars and lounges
  • Seven à la carte restaurants with globally inspired cuisine
  • Daily activities and nightly entertainment
  • Access to a world-class spa and wellness center

And the best part? Guests at one resort enjoy full access to the other. Two resorts for the price of one love story.

Picture-Perfect Wedding Destination

If a destination wedding is in your future, Secrets St. James and Wild Orchid are two of the most sought-after wedding venues in the Caribbean. With a variety of customizable wedding packages, an on-site wedding coordinator, and stunning ceremony locations (beach, gazebo, or garden), your big day can be as effortless as it is unforgettable.

Imagine exchanging vows with your toes in the sand, surrounded by your closest family and friends, then dancing the night away under the stars with the ocean as your backdrop. It’s pure Jamaican magic.

Beyond the Resort: Activities in Montego Bay

While it may be hard to tear yourself away from the tranquility of the resort, Montego Bay offers a variety of nearby activities perfect for couples:

  • Sunset Catamaran Cruises: Sip champagne as you sail along the coast, taking in breathtaking sunset views.
  • Dunn’s River Falls: Take a day trip to this iconic natural waterfall, and climb hand-in-hand up the cool, terraced rocks.
  • River Rafting on the Martha Brae: Glide down a scenic river on a bamboo raft—ideal for slow moments and stunning photo ops.
  • Hip Strip (Gloucester Avenue): For nightlife, local eats, and duty-free shopping, the Hip Strip is the place to go.
  • Rose Hall Great House: Explore this beautifully restored plantation with a hint of mystery and historic charm.

The Perfect Escape for Two

Whether you’re newly engaged, celebrating your forever love, or just in need of a peaceful escape with your partner, Secrets St. James and Secrets Wild Orchid offer the ultimate romantic retreat in Jamaica. With unparalleled service, breathtaking scenery, and a vibe made for love, this is the place where memories are made.

Ready to say “I do” in paradise or just need some well-deserved time for two? Secrets Montego Bay is calling.

Escape to Paradise: Tensing Pen in Negril, Jamaica

Escape to Paradise: Tensing Pen in Negril, Jamaica
When I was invited as a special guest of the Jamaica Tourism Board, I knew I was in for something memorable — but Tensing Pen in Negril completely exceeded all expectations. Perched on Negril’s dramatic West End cliffs, this boutique resort is a hidden gem that feels like the perfect blend of nature, comfort, and island soul. And if that’s not enough, they also have resident Rhodesian Ridgeback dogs that might just steal your heart.

Cliffside Bliss
Tensing Pen is not your typical beachfront resort — and that’s what makes it magical. Instead of sand, you’ll find dramatic limestone cliffs that plunge into crystal-clear Caribbean water. Cottages and bungalows are hand-built with local wood and stone, giving everything a rustic-yet-romantic vibe.

During my stay, I spent mornings sipping Blue Mountain coffee with a sea breeze on my face, and evenings watching the sun melt into the horizon from the resort’s iconic wooden bridge. Every corner felt like a postcard come to life.

Meet the Ridgebacks
Now let’s talk about the true VIPs of the property — the Rhodesian Ridgeback dogs. These majestic pups are part of the Tensing Pen family, casually lounging around the resort like they own the place (and honestly, they kinda do).

They’re gentle, affectionate, and love a good scratch behind the ears. As an animal lover, getting to know these sweet dogs was a highlight of my stay — it gave the entire experience a cozy, homey vibe that’s rare at luxury resorts.

Wellness Meets Island Soul
From yoga sessions in an open-air pavilion to massages in a thatched hut above the sea, the wellness experience at Tensing Pen is all about connecting with nature. I left every treatment and sunrise stretch feeling completely recharged.

Local Flavors with a View
Tensing Pen’s on-site restaurant, The Lodge, serves up fresh, locally inspired meals in a laid-back open-air setting. From spicy jerk chicken to catch-of-the-day grilled to perfection, every meal was full of flavor — and the views of the Caribbean Sea made it taste even better.

What to Do Nearby
While Tensing Pen feels like a world of its own, Negril has plenty to explore just minutes away:

Rick’s Café – A Negril icon! Whether you’re cliff-jumping or just enjoying the music and drinks, it’s a must-visit — and super close to Tensing Pen.

Seven Mile Beach – A short taxi ride away, this beach is perfect for a lazy afternoon with reggae beats, coconut cocktails, and barefoot strolls.

Mayfield Falls & YS Falls – These lush waterfalls offer a peaceful break from the sun and sand, with river tubing and natural pools to explore.

Local Culture – Don’t skip the nearby craft markets or roadside jerk shacks. The energy, the colors, and the people are what make Jamaica unforgettable.

Final Thoughts: Why I’ll Be Back
As a travel advisor and a guest of the Jamaica Tourism Board, I’ve had the privilege of experiencing many beautiful properties — but Tensing Pen left a lasting impression. It’s romantic without being fussy, luxurious without losing its island authenticity, and so full of charm that even the dogs are unforgettable.

Whether you’re planning a honeymoon, a romantic escape, or just need a cliffside moment of peace, Tensing Pen delivers something truly special — and I can’t wait to return.

Pro Tip: Book early — with limited cottages and a loyal following, Tensing Pen fills up fast. And yes, bring treats for the Ridgebacks. You’ll thank me later.