Wednesday, December 05, 2012

Splurge vs Steal #1 - romantic Hawaiian dream vacation!

I'm starting a new blog feature called "Splurge vs Steal"! Each week, I will showcase 2 amazing trips or properties; one will be very high-end, the other more moderate (but still with the same general feel, plenty of little luxuries and special experiences). For my first edition, I'll be showing you Hawaii 2 ways. Today's post will be the splurge trip, tomorrow's, the steal!

Splurge - 14 nights/15 days on 4 incredible islands!
Please don't hesitate to contact me at if you'd like to book this trip or have me fully customize your own dream vacation! 

Day 1:
Upon arriving at the airport in Honolulu (after a relaxing flight in business class, of course), you'll be met at baggage claim, lei'd, and whisked off by private car to begin your 3-night stay at the incomparable Halekulani Hotel.

Champagne and and other treats will await you in your Diamondhead Oceanfront Room (or Ocean Junior Suite, if you'd like a bit more space to spread out). Toast with a glass of bubbly on your lanai, while taking in the incredible view, before heading down to the pool or beach to soak up the late-afternoon rays and watch the sun sink slowly into the sea.

Later that night, enjoy dinner at Halekulani's celebrated Le Mer, a perennial AAA 5-Diamond awardee.

Day 2: 
After a late breakfast at Halekulani's Orchids restaurant, spend the next 5 or 6 hours at the pool or on the beach, swimming, snorkeling, strolling, or just enjoying a good book and umbrella drinks brought right to your lounge chair at the pool.

After so much hard work, you deserve some pampering! So head to Halekulani's beautiful spa for a massage, facial, or any other treatment your heart desires.

That evening, head out into Waikiki to check out one of the area's hot new restaurants. Back at the hotel, enjoy a post-dinner cocktail and live jazz at Lewer's Lounge.

Day 3:
After breakfast at House Without a Key, your driver will pick you up for a private tour of the island. Suggested stops include Diamondhead, Pearl Harbor, the North Shore, and shopping in Waikiki, but the itinerary can be fully customized to your interests!

Back at the Halekulani around 5, freshen up and head back down to House Without a Key, now transformed into a outdoor lounge (overlooking the ocean, no less) with live Hawaiian music and endless Mai Tais.
Wind down your night with room service served on your oceanfront lanai!

Day 4:
After breakfast, you'll be picked up by private car to go back to the airport for your flight to the Big Island. Upon arrival on the BI, you'll be again taken by private car to the spectacular Four Seasons Hualalai, on the island's exclusive Kona-Kohala coast.

After checking into your Oceanfront Deluxe Room, you may never want to leave!
So spend the rest of the day enjoying champagne, room service lunch, and tons of R&R on your private lanai right off the beach.

After the sun goes down, enjoy bathing under the stars in your outdoor lava-rock garden shower! Dinner at the resort's 'Ulu Ocean Grill is the perfect way to cap off a day in the lap of luxury.

Day 5: 
After a fabulous breakfast at 'Ulu, you'll be picked up for the short drive to the helicopter landing pad; it's time to see the island from the sky! Flying over volcanoes, waterfalls, beaches, rainforests, and other natural wonders, you'll literally be on top of the world.
Back at the Four Seasons, enjoy time on the beach, at the pool,  snorkeling and feeding rays in King's Pond, or just relaxing on your open lanai.
 Tonight, enjoy sunset cocktails, live entertainment, and dinner at the resort's open-air Beach Tree restaurant.
 And perhaps a late-night dip...

Day 6:
After an early breakfast, it's time to head out on a luxury fishing boat for a deep-sea adventure! Try your hand at some sport fishing, and reel in a massive marlin, super-sized spearfish, or mammoth mahi-mahi.

Back at the resort, treat yourselves to the Romantic Escape spa package, which includes an aphrodisiac bath, aromatherapy wrap, 80-minute massage in a tropical outdoor (but still private) hale, and wellness activity of your choice. Afterwards, enjoy the whirlpools, saunas, and other spa facilities, or head back to your room to freshen up and relax with a cool drink before dinner.

A private romantic dinner served on the beach is the perfect way to end your stay at this dreamy Hawaiian resort!

Day 7: 
After a tearful goodbye to the Four Seasons Hualalai, and a vow to come back as soon as possible, it's time to leave for the airport. Luckily, you're headed for yet another amazing experience; 5 nights on Maui!

After arriving at the Kahului airport, you'll be whisked to the famed Four Seasons Maui at Wailea to check into your Ocean View Prime Room. Want a few more amenities? Upgrade to a Club-level room to have access to all-day food and drink offerings, an exclusive lounge, and dedicated Club guest concierge!

Spend the afternoon on the Four Seasons'  beautiful beach, where lunch, cocktails, and complimentary evian spritzes are only an "Aloha!" away, thanks to the resort's beach service. Want to burn off some of those pina coladas? Grab some snorkel gear and explore the vibrant world under those warm blue waves.
This evening, enjoy the delectable chef's tasting menu at the resort's Spago outpost.

Day 8:
After breakfast served on your ocean-view terrace, grab the keys to your GPS-equipped convertible, and head off for an incredible drive along the Road to Hana! Winding past rainforests, waterfall pools, beaches, botanical gardens, and other gorgeous sights, there's no end to the photo and exploration opportunities.

When you arrive in Hana, enjoy a late lunch at one of the funky little eateries, then take some time to explore this charming and beautiful town!

Back at the resort, unwind with some cocktails and sushi in the Lobby Lounge, before a late-evening walk along the beach.

Day 9:
Pool day! Rent an Oceanfront Missoni cabana for the day at the adult-only Serenity Pool, and enjoy being spoiled with delicious food, drinks, and poolside massages.

Take an hour or two break in the afternoon for some surfing or stand-up paddle boarding lessons with a local pro.

Dinner and a Hawaiian show at the Old Lahaina Luau is a classic Maui experience; afterwards, snuggle early into your dreamy bed - tomorrow starts before sun-up!

Day 10: 
This morning starts very early, but for good reason! You'll be picked up before dawn by private car and driven to the summit of Haleakala, where you'll enjoy a light snack as you watch the sun rise up over the island, flooding it with incredible color and light.

After breakfast at a traditional Hawaiian restaurant, you'll be taken down to the sea to meet your private charter boat for a day of snorkeling and whale/dolphin/turtle spotting (depending on the time of year). Dock at a secluded beach for a picnic lunch in between snorkel stops, and sail back at sunset, while clinking your "boat drinks" to toast another amazing day!
For dinner this evening, head to one of Maui's numerous notable restaurants, then cap off the evening with live music and dessert at the Lobby Lounge. 

Day 11: 
After a leisurely breakfast, head to the airport for your flight to Kauai. Upon arriving at the Lihue airport, pick up your GPS-equipped Jeep and head for the St. Regis Princeville.
Check into your Ocean View Monarch Suite, and let your butler handle the unpacking. It's time to hit the beach!

Bask in the sun in your comfy lounge chair on the golden sand. Take a stroll hand-in-hand down the shoreline. Snorkel and splash in the clear cerulean sea. Nibble complimentary pineapple skewers as you enjoy that beach read you haven't yet finished. Just luxuriate - you're in paradise!
Tonight, enjoy one of Kauai's restaurants; whether you're in the mood for fine dining or a more casual meal, you'll find a restaurant to suit your taste and mood!

Day 12:
Hopefully, it's Sunday! If so, don't miss brunch at St. Regis' Makana Terrace, with a to-die-for menu offering everything from traditional breakfast items to Hawaiian specialities, from king crab legs to a dessert table overflowing with sweet treats.

Take a break to digest poolside before heading out in your jeep to burn off some of those calories on one of Kauai's famous hiking trails. If you choose the right trail at the right time, you may even be able to enjoy a private romantic interlude under a secluded waterfall!
Back at the resort, enjoy a cocktail on your private terrace before heading to dinner at one of St. Regis's excellent restaurants, then head to the St. Regis bar to catch the end of the Sunday Jazz Jam.

Day 13:
Time to explore some of Kauai's 69 beaches! Grab the picnic lunch the resort staff has packed for you, then take off in your jeep for a day of fun in the sun!

Be sure to get back to the resort before sunset, so you can be part of the classic nightly Champagne Ritual at the St. Regis bar.

Back in the room, take a long soak in your whirlpool tub while looking up at the stars through the oversized ocean-view window. For dinner, it's hard to top the tasting menu at Jean-Georges Vongerichten's Kauai Grill!

Day 14:
To the helipad, Jeeves! Spend this morning high in the sky, on a private helicopter tour. You'll fly over Manawaiopuna Falls (the setting for the film "Jurassic Park"), Waimea Canyon, Mt. Waiale'ale Crater, and the spectacular Na Pali coast. For the adventurous and those who love photography, the doors on the chopper can be removed for unparalleled views of Kauai!
Spend the late morning and early afternoon in a Beach Side Cabana at the St. Regis's enormous infinity pool, indulging in gourmet dishes, tropical drinks, and if you're still a bit peckish, the Afternoon Tea Ritual. A 90-minute couple's massage in your cabana will smooth away any remaining stress, and have you ready for your last evening in paradise.

After sunset, head to the lobby, where your private waitstaff and one of the resort's award-winning chefs will be waiting to escort you to a secluded spot on the beach where a beautiful laid table is set out for you. Here, you'll enjoy a private 4 course dinner (complete with wine pairings!) completely customized to your tastes! If you'd like to supplement the sound of the waves gently lapping on shore, live music can also be arranged. After dinner, linger over your champagne, then talk a long walk down the beach to complete your last night of vacation.

Day 15:
Time to head home - this is always the worst part of any trip. But at least you've made memories to last a lifetime - and you can always come back again soon!

Please don't hesitate to contact me at if you'd like to book this trip or have me fully customize your own dream vacation!

Photos courtesy of the noted resorts and

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