Expert Tips for the Best 

Trip to Hawaii

by Daria Dimitroff
May 2024
Wailea Beach Resort, an under-the-radar gem on Maui great for families and couples
I'm a luxury travel advisor and Hawaii is one of my agency's specialties so, even if you have been to the islands a bunch of times, using me to book your trip is better.
I’m an expert in the destinations I sell. I travel to them myself. I save you time and give you personalized adviceI curate unique excursions and experiences. I get you a better value, including perks. I have clout and connections on the ground to ensure you are taken care of. I customize your trip, and I’m a real human who delivers exceptional white-glove service and takes care of you before, during, and after your journey.
Here are some examples of the common queries I get from clients headed to Hawaii, and how my expertise, knowledge and contacts can help.

Which Island(s)?
Probably the most common questions I get are about which island(s) to visit and whether it makes sense to visit more than one island
I know all of the islands intimately, having been to them all and designed Hawaii trips for many clients. I interview my clients about what they want, and then explain which islands would be best for them and why. 
All of the islands are a bit different, but I know the pros and cons of each and which are best for the type of vacation you are dreaming about.
I also explain whether it makes sense to visit more than one island, how long it takes to get in between the islands and more.

Weather Conditions and When to Visit
I help every client make the best choice for them about when to visit the islands. I know which times of year are best to visit for avoiding crowds, getting the best value and enjoying superb weather.
I also know which time of year is best to stay on which parts of the islands. Weather reports and what you see on apps (a lot of rain) can be confusing if you aren't an expert like me, but I will give you personal advice based on what you are seeking in terms of temperature, rainfall, surf conditions and more.

Best Way to Get There
I know the best options for getting to each Hawaiian island, and which airlines have the most comfortable first-class offerings. I guide my clients to the best choice for them.

Best Places to Stay
I know the best accommodations from resorts to boutique hotels on all the islands depending on the vibe you want. I will also steer you clear of overrated places. The best location on each island varies with the time of year, so I've got you covered there too.
I have special relationships with all the finest hotels and resorts on all the islands and get extra perks for my clients that you can't access when booking on your own. (Click here for a list of my partner hotels and resorts in Hawaii, and the extra perks I get my clients.)
I know which hotels and resorts are the best for groups, honeymooners, families, food, beaches, girls trips, bachelor parties, spas and more.

Insight into Activities, Sites & Tours
I know all of the top sites, tours and activities for each island (and which ones to avoid) like the best luaus, snorkel companies, boating experiences, and more. 
I give my clients tips about how to avoid crowds and advice about off-the-beaten-path experiences you won't find on the top 10 lists.
I also know what the options are for when and how to visit all of the top sites (for example whether a sunrise bike ride is the only way to see Haleakela).
I give expert advice about which activities can be done at which times of year.
I advise my clients about which activities, parks, restaurants, and other experiences require reservations or tickets and how far in advance you need to make those reservations
I give my clients tips about the best events, festivals, and more.
I curate private experiences like a yacht charter for a day, a photographer, a private dinner on the beach, a chef at your villa, and more. 
Turtle Bay, one of the best resorts on Oahu. Great for everyone from multi-generational groups to honeymooners.
Best Beaches & Pools
I give tips to my clients about the best resort pools and best beaches on each island for different interests like surfers, kids (calm waters), and more. I can also share information about the ocean temperature for swimming.

Better Dining & Food Experiences
I give personalized restaurant recommendations, make reservations for my clients, and arrange custom experiences like a sunset dinner on a beach, a private chef in your villa, a food tour, and more.

Packing & Dress Codes
I advise my clients about expected attire in the islands and share packing tips.

Best Transportation
I know whether you need to rent a car (depending on where you are staying and what you want to do) and what to do if you don't feel like driving, and I make all of the arrangements.
I know how long it takes to get around and between the islands.

Value
I know when, where, and how to reserve your trip to get you the best value from airfare and rental cars to hotels and resorts. I also advise my clients about what their budget should be to get a 4- or 5-star experience and how this varies by time of year.

Personalized Travel
All of my clients are different, and I assist with the best Hawaii experience, whether you are a big multigenerational group, a couple, a bachelor party, single, a large family with kids, experience mobility issues, or don't fit neatly into a box.

Maui After the Fire
I know which parts of Maui are open and able to handle tourists right now.

Contact me to plan your next trip and find out how much better it is to use a travel advisor who's an expert on Hawaii! 🌈  I specialize in bespoke luxury travel, group trips, and exclusive cruise experiences. 
Ko'a Kea Resort, a great boutique property for couples in Poipu, Kauai
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Daria Dimitroff
Founder • Travel Advisor 
Journeys of a Lifetime
415.939.5773

CST# 2143380-40