This six-week arc across the Pacific marries island time with urban wonder. You’ll daydream on Maui’s golden beaches, ride Japan’s shinkansen to storied castles and neon crossroads, sample Singapore’s hawker classics, and unwind amid Bali’s emerald terraces before a sun-drenched finale in Honolulu. It’s paced for a multigenerational crew—grandmother, parents, and kids—with built-in rest days and options for both high-energy and low-impact activities.

From ancient shrines in Kyoto to Mario-powered thrills in Osaka, from Maui’s Haleakalā sunrise to Honolulu’s Pearl Harbor, the journey blends history and fun. June and July bring Japan’s rainy season (tsuyu) shifting into summer festivals; Hawaii and Bali bask in warm weather; Singapore stays equatorial and efficient. Make reservations for high-demand experiences like Haleakalā sunrise, Diamond Head, Hanauma Bay, and popular museums in Japan.

Practical notes: tap-to-pay is widely accepted in Hawaii, Japan, and Singapore; still carry a little cash in Japan and Bali. In Japan, load an IC card (Suica/PASMO) for trains. Pack quick-dry layers, sun protection, and reef-safe sunscreen. With a top-tier budget, you can mix standout hotels with spacious VRBOs, hire private guides where useful, and minimize transit stress.

Myrtle Beach (Pre/Post Ideas at Home)

Before takeoff or after you return, sprinkle in a local family treat. These kid-approved (and Mimi-friendly) options keep the vacation glow going.

• Polynesian Fire Luau and Dinner Show — A colorful, high-energy evening that nods to your Hawaii legs later on.
  Polynesian Fire Luau and Dinner Show Ticket in Myrtle Beach

  

• Catamaran Dolphin Cruise — Easy, memorable, and usually dolphin-filled; great for all ages.
  Catamaran Dolphin Cruise in Myrtle Beach with Barrier Island Stop

  

• Military History Trolley Tour — Gentle pace and compelling stories around the former Air Force base; perfect for Mimi.
  Myrtle Beach Military History Trolley Tour

  

• The Escape Game at Broadway — Team up for puzzles and laughs before jet lag hits.
  The Escape Game at Broadway at the Beach in Myrtle Beach

  

Los Angeles

Days 1–2: Fly to LAX + One Day of Sightseeing

Land in Los Angeles for a short stopover: one full day to stretch your legs, soak in views, and adjust time zones. Aim for city icons that are easy to navigate with kids and a grandparent.

• Top highlights: Griffith Observatory (ramp access and stellar city views), Hollywood Walk of Fame and Dolby Theatre, The Grove and Original Farmers Market for grazing, Santa Monica Pier for sunset and arcade fun.
• Kid-favorite add-on: La Brea Tar Pits (outdoor areas are flat), or the Academy Museum’s movie magic galleries.
• Where to eat: - Breakfast: Republique (French-leaning bakery counter, lines move fast) or Huckleberry in Santa Monica.
  - Lunch: Grand Central Market—try Eggslut (egg sandwiches), Villa Moreliana (slow-cooked carnitas), or Sticky Rice (Thai).
  - Dinner: Jon & Vinny’s (NY-style pies and pastas), Din Tai Fung (xiao long bao—lots of veggies and noodles for kids), or Water Grill (classic seafood near the beach).
• Stay: Search family suites or condos near Santa Monica or West Hollywood: - VRBO Los Angeles - Hotels.com Los Angeles
• Getting there: MYR → LAX (1 stop), ~7–10 hours total. Summer fares typically ~$300–$600 pp. Search: - Trip.com Flights | Kiwi.com Flights

Maui

Days 3–7: Five Nights in Maui (Wailea/Kīhei Base)

Maui blends gentle beaches with volcanic drama. Given West Maui’s 2023 fires, be mindful in Lahaina and support open, local businesses with respect; much of the island—including Wailea, Kīhei, Upcountry, and most of the Road to Hāna—welcomes visitors.

• Family-friendly hits: - Haleakalā Sunrise (reservation required) or a mellower late-morning summit; bring layers and hot cocoa for the kids.
  - Molokini Crater snorkel from Mā‘alaea; look for calmer morning departures.
  - Road to Hāna (partial): Aim for Twin Falls, Ke‘anae Peninsula banana bread, and Waiʻānapanapa State Park’s black sand (timed entry required). Turn back before kids tire.
• Beaches: Wailea Beach (gentle waves), Ulua (snorkel from shore), Big Beach at Mākena (watch for shore break). Bring reef-safe sunscreen.
• Upcountry: Ali‘i Kula Lavender (step-free paths in sections) and Surfing Goat Dairy for playful tastings.
• Where to eat: - Breakfast: Kihei Caffe (hefty plates), Akamai Coffee.
  - Lunch: Paia Fish Market (grilled catch platters), Tin Roof by Sheldon Simeon (kālua pork bowls, mochiko chicken).
  - Dinner: Mama’s Fish House (book well ahead), Lineage (modern local), Monkeypod Kitchen (live music, kid’s menu).
  - Treats: Ululani’s Shave Ice; Coconut Glen’s (vegan ice cream, Road to Hāna).
• Stay: - VRBO Maui - Hotels.com Maui
• Next leg: OGG → Tokyo (HND/NRT) often 10–12.5 hours (sometimes via HNL). Typical summer fares ~$500–$1,000 pp. - Trip.com Flights | Kiwi.com Flights

Tokyo

Days 8–15: Eight Nights in Tokyo (Neighborhoods, Pop Culture, and Day Trips)

Tokyo mixes Edo-era temples with ultra-modern skylines. It’s playground and classroom at once—arcades and anime for the kids, immaculate gardens and museums for everyone, with excellent accessibility on transit.

• Core sights: Asakusa’s Sensō-ji and Nakamise shopping street; Meiji Shrine’s cedar forest; Shibuya Crossing and Shibuya Sky (elevators, amazing views); teamLab Planets (immersive digital art the kids will adore, Toyosu); Ueno Park museums.
• Family day: Tokyo DisneySea’s new Fantasy Springs or Tokyo Disneyland (prebooked dated tickets recommended).
• Local life: Yanaka Ginza’s retro lanes; Kiyosumi Garden for a quiet stroll; Daikanyama’s T-Site books complex and cafes.
• Day trip choices: Kamakura (Great Buddha, beach breezes) or Nikko (UNESCO shrines, forested paths).
• Where to eat: - Breakfast/Coffee: Blue Bottle Aoyama; Bread, Espresso & (Omotesandō); Koffee Mameya (beans to-go).
  - Lunch: Uobei (conveyor-belt style fun); Afuri (yuzu ramen); Tempura Kondo (book ahead).
  - Dinner: Sushi Zanmai (accessible locations), Kyōbashi Tonta (tonkatsu), Toriyoshi (yakitori); crepes in Harajuku for dessert.
• Stay: Family rooms in Shinjuku, Shibuya, or Tokyo Station area: - VRBO Tokyo - Hotels.com Tokyo
• Trains & passes: Load Suica on phones for tap-in/out. For intercity rides, the nationwide JR Pass (price increased) may or may not pencil out; consider point-to-point or regional passes.

Hakone

Days 16–17: Two Nights of Onsen Views

Hakone is your Fuji-framed hot-spring escape. With ropeways and boats doing the climbing, Mimi can enjoy volcanic vistas without steep hikes.

• Do: Lake Ashi sightseeing boat; Hakone Ropeway to Ōwakudani (sulfur vents, black eggs!); Hakone Open-Air Museum (sculptures kids can explore); cedar avenue walk (choose short, flat segments).
• Stay: Consider a ryokan with family-friendly private onsen times and kaiseki dinners. - VRBO Hakone - Hotels.com Hakone
• Getting there: Tokyo → Odawara by shinkansen ~35 min, then Hakone Tozan lines/bus. Total 1.5–2 hours. Buy train tickets: - Trip.com Trains (Japan)

Kyoto

Days 18–23: Six Nights in Kyoto’s Timeless Streets

Kyoto rewards slow travel—lantern lanes, riverside walks, and tea-scented markets. Go early for the big sights, then slip into quiet districts that feel unchanged.

• Musts: Fushimi Inari (sunrise; for Mimi, start mid-mountain via taxi to avoid many steps), Kiyomizu-dera (elevators between areas), Arashiyama Bamboo Grove + riverside boat, Nijo Castle, Philosopher’s Path.
• Hands-on: Family tea ceremony; calligraphy or sweets-making class; cycling along the Kamo River (flat paths).
• Food: - Breakfast/Coffee: % Arabica (Higashiyama), Weekenders Coffee.
  - Lunch: Nishiki Market grazing—oysters at Daiyasu, croquettes, soy donuts; Omen for udon; Honke Owariya (soba, since 1465).
  - Dinner: Katsukura (tonkatsu), Musashi Sushi (family-friendly conveyor), Gion Tanto (home-style obanzai). Dessert at Gion Kinana (kinako ice cream).
• Stay: - VRBO Kyoto - Hotels.com Kyoto
• Getting there: Hakone (Odawara) → Kyoto by shinkansen 2–2.5 hours, ~$80–$110 pp reserved. - Trip.com Trains

Hiroshima & Miyajima

Days 24–25: Two Nights of Reflection and Island Beauty

Hiroshima’s Peace Memorial Park offers moving context, balanced by Miyajima’s serene torii gate floating over the tides.

• Do: Peace Memorial Museum (wheelchair accessible); Okonomimura (kids pick toppings); Ferry to Miyajima for Itsukushima Shrine and easy ropeway ride into the hills.
• Eat: Hiroshima-style okonomiyaki at Nagata-ya; momiji manju sweets; oysters if in season.
• Stay: - VRBO Hiroshima - Hotels.com Hiroshima
• Getting there: Kyoto → Hiroshima by shinkansen ~1h40–2h; then local train/ferry to Miyajima-guchi ~45 min. - Trip.com Trains

Osaka (with Nara Day Trip)

Days 26–29: Four Nights of Street Food and Theme-Park Thrills

Osaka is Japan’s kitchen—loud, friendly, and delicious. It’s also your base for Nara’s temple deer and a day at Universal Studios Japan.

• Do: Dotonbori neon strolls; Kuromon Ichiba market tastings; Osaka Castle (elevators on upper floors); Kaiyukan Aquarium (gentle pace); Universal Studios Japan (Super Nintendo World makes the kids’ day).
• Nara day trip: Feed deer in Nara Park, marvel at Tōdai-ji’s Great Buddha; flat walking between sights.
• Eat: Takoyaki at Aizuya; okonomiyaki at Mizuno; kushikatsu at Daruma (order veggies and chicken for variety); ramen at Ichiran (booth-style fun).
• Stay: - VRBO Osaka - Hotels.com Osaka
• Next leg: KIX → Singapore nonstop ~6.5–7 hours, ~$250–$600 pp in summer. - Trip.com Flights | Kiwi.com Flights

Singapore

Days 30–35: Six Nights of Clean, Green Adventure

Singapore is effortless with kids: spotless MRT, shaded parks, and food courts that turn picky eaters into explorers. Blend gardens, museums, and Sentosa’s beaches.

• Big sights: Gardens by the Bay (Cloud Forest and Flower Dome), Marina Bay Sands SkyPark, ArtScience Museum, Singapore Flyer (fully accessible capsules).
• Sentosa: Beach tram, Adventure Cove Waterpark, S.E.A. Aquarium, and easy beach time at Palawan or Siloso.
• Wildlife: Singapore Zoo + Night Safari (board the tram to minimize walking).
• Hikes: Southern Ridges or MacRitchie Treetop Walk (choose shorter loops for Mimi).
• Eat—Hawker favorites: - Maxwell Food Centre (Tian Tian Hainanese Chicken Rice).
  - Lau Pa Sat (Satay Street after dusk).
  - Old Airport Road (fried Hokkien mee).
  - Katong for laksa; Chinatown Complex for claypot rice and soy beancurd desserts.
• Cafes & treats: % Arabica Arab Street; Tiong Bahru Bakery; Birds of Paradise gelato in Katong.
• Stay: Family rooms near Marina Bay/City Hall or a condo in Tiong Bahru: - VRBO Singapore - Hotels.com Singapore
• Next leg: SIN → Bali (DPS) ~2h45m, ~$100–$250 pp. - Trip.com Flights | Kiwi.com Flights

Bali (Ubud & Nusa Dua)

Days 36–40: Five Nights Split—3 Ubud, 2 Nusa Dua

Bali’s rhythm is gentle and generous. Base in Ubud for temples and terraces, then Nusa Dua for calm beaches and easy sand play.

• Ubud (3 nights): - Tegallalang rice terraces (choose the lower, flatter paths).
  - Tirta Empul water temple (observe or join blessing with guide).
  - Bali Bird Park or a short Ayung River family raft (calm sections).
  - Ubud Palace & evening dance performance.
• Nusa Dua (2 nights): - Chill beach days; morning snorkel; Waterblow lookout (paved path).
  - Optional Nusa Penida snorkel for older kids if seas are calm (longer day).
• Eat: - Ubud: Clear Café (bowls, smoothies), Ibu Oka (babi guling—go early), Naughty Nuri’s (ribs), Warung Biah Biah (Indonesian small plates).
  - Nusa Dua: Bumbu Bali (authentic Balinese set menus), Nusa Dua Night Market snacks.
• Stay: - VRBO Bali - Hotels.com Bali
• Next leg: DPS → Tokyo (HND/NRT) nonstop ~7–8.5 hours, ~$350–$800 pp. - Trip.com Flights | Kiwi.com Flights

Tokyo (Stopover)

Day 41: One Night Reset Near Haneda

After Bali, land in Tokyo for a smooth overnight before heading to Hawaii. Keep it simple: a hotel near Haneda or Shinagawa, ramen dinner, maybe a stroll along the Sumida or in Odaiba for skyline views.

• Eat: Ramen at Ichiran or Afuri; tempura set at Tenya; mochi and melon-pan for the kids.
• Stay: - VRBO Tokyo - Hotels.com Tokyo
• Next leg: Tokyo → Honolulu ~7–8 hours, ~$400–$900 pp. - Trip.com Flights | Kiwi.com Flights

Honolulu (O‘ahu)

Days 42–45: Four Nights in Honolulu—Beaches, History, and Island Vibes

Finish with Waikīkī waves and O‘ahu’s storied past. Build in slow mornings, a bit of hiking, and one big history day.

• Do: - Pearl Harbor: USS Arizona Memorial and museum; reserve tickets ahead; accessible via trams and ramps.
  - Diamond Head hike (timed reservations; go early; railings along the path).
  - Hanauma Bay snorkeling (reservations; closed Tuesdays).
  - North Shore drive: Food trucks in Hale‘iwa, turtles at Laniakea (view from a respectful distance), sunset at Sunset Beach.
• Beach time: Waikīkī and family-friendly Ala Moana Beach Park with calm waters.
• Eat: - Breakfast: Island Vintage Coffee (acai bowls), Leonard’s Bakery malasadas (best warm).
  - Lunch: Marukame Udon (watch noodles being made), The Pig & The Lady (Vietnamese-inspired), Giovanni’s Shrimp Truck (North Shore).
  - Dinner: Helena’s Hawaiian Food (pipikaula short ribs), Zippy’s (local comfort), Roy’s for a celebratory final night.
• Stay: - VRBO Honolulu - Hotels.com Honolulu
• Homeward bound: HNL → MYR (1–2 stops), ~12–16+ hours total, ~$500–$900 pp. - Trip.com Flights | Kiwi.com Flights

Suggested 45-Day Flow (At a Glance)

• Days 1–2: Los Angeles (2 nights)
• Days 3–7: Maui (5 nights)
• Days 8–15: Tokyo (8 nights)
• Days 16–17: Hakone (2 nights)
• Days 18–23: Kyoto (6 nights)
• Days 24–25: Hiroshima & Miyajima (2 nights)
• Days 26–29: Osaka (4 nights, incl. Nara day trip)
• Days 30–35: Singapore (6 nights)
• Days 36–40: Bali (5 nights; 3 Ubud + 2 Nusa Dua)
• Day 41: Tokyo stopover (1 night)
• Days 42–45: Honolulu (4 nights) → Fly home

Logistics Tips for a Multigenerational Crew

• Transit: Use trains in Japan (elevators widely available). Book morning trains/flights to maintain energy.
• Pacing: Alternate big days (theme parks, long walks) with gentler ones (gardens, beach). Build in hotel pool time.
• Reservations: Secure Haleakalā sunrise, Diamond Head, Hanauma Bay, and popular Tokyo/Osaka attractions several weeks in advance.
• Luggage: Consider luggage-forwarding in Japan between cities to keep train days effortless for Mimi and the kids.

From Maui’s volcanic dawn to Kyoto’s lantern-lit evenings and Honolulu’s soft twilights, this route balances play, culture, and rest. With smart travel windows and family-ready picks, it’s the rare itinerary that thrills kids, delights parents, and stays comfortable for Mimi.