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14-Night Relaxing Beachfront Escape: Ultimate Unwind Itinerary
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14-Night Relaxing Beachfront Escape: Ultimate Unwind Itinerary
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Day 1: Tofino Arrival
Tofino, Canada on May 19, 2025
10:00am
Check-in at Long Beach Lodge Resort
Arrive and check into your beachfront lodge located right on Long Beach, perfect for immediate ocean views and relaxing sounds of the Pacific.
CAD0, 0h30m
12:00pm
Lunch at Shelter Restaurant
Enjoy freshly caught local seafood in a cozy oceanfront setting; open daily from 11am to 9pm.
CAD30, 1h
2:00pm
Relax on Long Beach
Spend your afternoon unwinding on the expansive sandy beach, ideal for walking or simply soaking up the peaceful ambiance.
CAD0, 3h
6:30pm
Dinner at Wolf in the Fog
Dine on Pacific Northwest inspired dishes using local ingredients in an artsy, lively atmosphere; open 5pm to 9pm.
CAD50, 2h
Find Hotels in Tofino
Day 2: Tofino Exploration
Tofino, Canada on May 20, 2025
8:00am
Breakfast at Rhoda's Bakery
Start your day with fresh pastries and coffee at this beloved local bakery, opens at 7am.
CAD15, 1h
9:30am
Hot Springs Cove Tour
Take a boat or seaplane tour to Hot Springs Cove for a natural hot spring soak, surrounded by rainforest; tours typically last 5 hours and depart in the morning.
CAD120, 5h
3:30pm
Evening walk on Chesterman Beach
Enjoy a calm stroll on Chesterman Beach, famous for beautiful sunsets and tide pools.
CAD0, 1.5h
6:30pm
Dinner at The Pointe Restaurant
Enjoy upscale dining right on the water at the Wickaninnish Inn; exquisite views and locally sourced menu items, open until 9pm.
CAD60, 2h
Find Hotels in Tofino
Day 3: Travel to Parksville
Parksville, Canada on May 21, 2025
9:00am
Breakfast at shelter Restaurant to go
Grab a hearty breakfast to take for your travel day before checking out.
CAD15, 1h
10:30am
Drive to Parksville
Drive approx. 3.5 hours south from Tofino to the quieter, gentle sandy beaches of Parksville on Vancouver Island’s east coast.
CAD0, 3h30m
2:00pm
Check-in at Pacific Shores Resort
Settle into your beachfront condo resort offering private beach access and spectacular views of the Strait of Georgia.
CAD0, 0h30m
4:00pm
Afternoon on Parksville Beach
Unwind barefoot on the wide sandy beach and explore tide pools in this calm, family-friendly environment.
CAD0, 2h
6:30pm
Dinner at The Beach Club Resort Restaurant
Enjoy casual beachfront dining with fresh Pacific Northwest dishes; open until 9pm.
CAD40, 2h
Find Hotels in Parksville
Day 4: Parksville Relaxation
Parksville, Canada on May 22, 2025
8:00am
Breakfast at Wholefoods Market
Pick up organic and fresh breakfast items near your resort for a relaxed morning.
CAD10, 0h45m
9:00am
Explore Rathtrevor Beach Provincial Park
Take a leisurely walk or enjoy birdwatching in this beautiful beach park during low tide; park open daily dawn to dusk.
CAD0, 3h
12:30pm
Lunch at The Bayside Restaurant
Eat fresh seafood with views over the bay; open 11am to 3pm.
CAD25, 1h
2:00pm
Spa afternoon at Resort
Indulge in a beachfront spa treatment at your resort to fully unwind in paradise.
CAD100, 2h
6:30pm
Dinner at Morgan’s Bistro
Enjoy a farm-to-table dinner with a cozy atmosphere; open 5pm to 9pm.
CAD45, 2h
Find Hotels in Parksville
Day 5: Travel to Maui
Maui, Hawaii, USA on May 23, 2025
7:00am
Early breakfast and checkout
Enjoy a quick breakfast and prepare for your flight from Vancouver Island to Maui International Airport.
CAD20, 1h
9:00am
Travel to Vancouver International Airport then fly to Maui
Take a ferry or drive to Vancouver Airport and fly approx. 6 hours to Maui, Hawaii.
CAD600, 8h
6:30pm
Check-in at Wailea Beach Resort
Arrive and settle into your luxurious oceanfront resort perfectly situated on Wailea’s stunning beaches.
USD0, 0h30m
7:30pm
Dinner at Monkeypod Kitchen
Enjoy cuisine with fresh island ingredients and lively ambiance; open until 10pm.
USD50, 1.5h
Find Hotels in Maui
Day 6: Maui Relaxation
Wailea, Maui, Hawaii, USA on May 24, 2025
7:30am
Breakfast at Kihei Caffe
Start your day with local Hawaiian breakfast dishes and strong coffee; open from 6am.
USD15, 1h
9:00am
Relax at Wailea Beach
Spend the morning soaking up the sun and swimming at the pristine Wailea Beach, known for calm waters and beautiful sand.
USD0, 3h
12:30pm
Lunch at The Restaurant at Hotel Wailea
Enjoy gourmet lunch with ocean views in a tranquil setting; open from 11:30am to 2:30pm.
USD40, 1.5h
2:30pm
Spa treatment at resort
Pamper yourself with a beachfront massage at the resort’s spa, perfect for ultimate relaxation.
USD120, 2h
6:30pm
Dinner at Ferraro's Bar e Ristorante
Dine on Mediterranean cuisine with gorgeous sunset views; open until 9:30pm.
USD60, 2h
Find Hotels in Wailea
Day 7: Explore Hana Coast
Hana, Maui, Hawaii, USA on May 25, 2025
7:00am
Breakfast at resort
Enjoy a leisurely breakfast with ocean views before departing on your day trip.
USD25, 1h
8:00am
Road to Hana Tour
Embark on the scenic Road to Hana drive including waterfalls, black sand beaches, and rainforest hikes; plan for a full day adventure.
USD150, 10h
6:00pm
Dinner upon return at The Gazebo
Enjoy famous pancakes and casual Hawaiian food; open until 3pm - if dinner options closed, order takeout during lunch on trip.
USD20, 0h30m
Find Hotels in Hana
Day 8: Maui Leisure Day
Wailea, Maui, Hawaii, USA on May 26, 2025
8:00am
Breakfast at Trio
Start with breakfast in Kihei with fresh, local produce; open 8am to 3pm.
USD20, 1h
9:30am
Snorkelling at Molokini Crater
Take a morning boat tour to the famous Molokini Crater for snorkeling among vibrant marine life; tours depart early and last about 4 hours.
USD120, 4h
2:00pm
Relax at resort pool and beach
Spend the afternoon relaxing at your resort’s lagoon pool or beach with a tropical drink in hand.
USD0, 3h
6:30pm
Dinner at Mama’s Fish House
Enjoy island fresh seafood with oceanfront ambiance; reservations recommended, open 5pm to 9pm.
USD80, 2h
Find Hotels in Wailea
Day 9: Travel to Oahu
Waikiki, Oahu, Hawaii, USA on May 27, 2025
7:00am
Breakfast at resort
Relax over breakfast in paradise before heading to the airport.
USD25, 1h
9:00am
Flight from Maui to Oahu
Quick 45-minute flight to Honolulu, Oahu.
USD100, 1h
11:00am
Check-in at Halekulani Hotel Waikiki
Arrive and check into this iconic oceanfront luxury hotel right on Waikiki Beach.
USD0, 0h30m
12:30pm
Lunch at Duke’s Waikiki
Enjoy casual beachfront dining famous for fresh fish and the Hula Pie dessert; open 10am to 10pm.
USD35, 1h
2:00pm
Relax at Waikiki Beach
Spend the afternoon lounging or swimming at bustling Waikiki Beach with stunning views of Diamond Head.
USD0, 3h
6:30pm
Dinner at House Without A Key
Dine while enjoying live Hawaiian music and sunset views; open 5pm to 9:30pm.
USD55, 2h
Find Hotels in Waikiki
Day 10: Oahu Relaxation & Culture
Honolulu, Oahu, Hawaii, USA on May 28, 2025
8:00am
Breakfast at Koko Head Café
Enjoy innovative all-day breakfast dishes at this popular spot; opens 7am.
USD20, 1h
9:30am
Morning at Lanikai Beach
Travel to and relax at Lanikai Beach, known for powdery white sand and clear turquoise waters.
USD0, 3h
1:00pm
Lunch at Uahi Island Grill
Casual Hawaiian food with local flavors; open 11am-9pm.
USD25, 1h
2:30pm
Visit Iolani Palace
Tour the only royal palace on US soil with informative guided tours; open 9am to 4pm, closed Mondays.
USD30, 2h
6:30pm
Dinner at Alan Wong's Honolulu
Experience Hawaiian regional cuisine by a top chef; open 5:30pm to 9pm, reservations recommended.
USD100, 2h
Find Hotels in Honolulu
Day 11: Travel to Big Island
Kailua-Kona, Big Island, Hawaii, USA on May 29, 2025
7:00am
Breakfast at hotel
Enjoy a calm breakfast on Waikiki Beach before your flight.
USD25, 1h
9:00am
Flight to Kona International Airport
Short 45-minute flight to Kona on the Big Island.
USD90, 1h
11:00am
Check-in at Royal Kona Resort
Settle into a beachfront resort known for incredible ocean views and tranquil sunsets in Kailua-Kona.
USD0, 0h30m
12:30pm
Lunch at Kona Brewing Company
Savor fresh pub fare and locally brewed beer with indoor/outdoor seating; open 11am-9pm.
USD30, 1h
2:00pm
Relax at Magic Sands Beach
Enjoy soft white sand and great snorkeling at nearby Magic Sands Beach.
USD0, 2h
6:30pm
Dinner at Huggo’s
Dine ripe seafood dishes with oceanfront ambiance and sunset views; open 5pm to 9pm.
USD55, 2h
Find Hotels in Kailua-Kona
Day 12: Big Island Leisure
Kailua-Kona, Big Island, Hawaii, USA on May 30, 2025
8:00am
Breakfast at Island Lava Java
Enjoy fresh coffee and island-inspired breakfast dishes with ocean views.
USD20, 1h
9:30am
Snorkeling or swim at Kahalu’u Beach Park
Spend the morning snorkeling in calm waters filled with vibrant sea life; park open daylight hours.
USD0, 3h
1:00pm
Lunch at Umekes Fishmarket Bar & Grill
Treat yourself to fresh poke bowls and grilled seafood with casual island vibes.
USD25, 1h
2:30pm
Afternoon at resort pool and beach
Relax on the resort’s beach or by the pool with a tropical cocktail.
USD0, 3h
6:30pm
Dinner at Kona Canoe Club
Upscale dining with fresh seafood near the pier; open 5pm to 9pm.
USD60, 2h
Find Hotels in Kailua-Kona
Day 13: Big Island Sunset Chill
Kailua-Kona, Big Island, Hawaii, USA on May 31, 2025
8:00am
Breakfast at Kona Coffee & Tea
Relish Kona’s legendary coffee and breakfast sandwiches in a casual setting.
USD15, 1h
9:30am
Visit Pu'uhonua O Honaunau National Historical Park
Explore this sacred place of refuge with cultural significance and beautiful coastal scenery; park open 7:45am to 5pm.
USD25, 3h
1:00pm
Lunch at The Painted Church Café
Enjoy cafe style lunches and local coffee near the historic Painted Church.
USD20, 1h
2:30pm
Resort relaxation and beach time
Spend your last afternoon soaking up the sun and sounds of the ocean.
USD0, 3h
6:30pm
Farewell dinner at Lava Lava Beach Club
Dine barefoot on the sand with spectacular ocean views and delicious island cuisine; open 5pm to 9pm.
USD70, 2h
Find Hotels in Kailua-Kona
Day 14: Departure
Kailua-Kona, Big Island, Hawaii, USA on June 1, 2025
7:00am
Breakfast at resort
Enjoy your last breakfast with ocean views and reflect on your relaxing stay.
USD25, 1h
9:00am
Check-out and travel to airport
Prepare for departure and travel to Kona International Airport for your flight home.
USD0, 1h
Find Hotels in Kailua-Kona
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Itinerary created by
Plantrip Team
May 19, 2025
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