hawaii

Hawaii Trip Planning Timeline

October 12, 2018 by caitylincoln

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You’re planning a trip to Hawaii…wahoo!! How exciting! But it can also be pretty overwhelming…I mean, how do you even know where to start? While you’ll find detailed posts on topics like choosing the best time to go, picking an island, booking accommodations and flights, etc., on my blog, this timeline will let you know exactly when you should be tackling each one of these tasks to insure that you have the most options available for the best prices.

12+ months

If you’re planning this trip over a year in advance, use this time to do preliminary research about when the best time to go will be (for your circumstances) and choosing an island (or two).

Where to Stay in Kauai

July 13, 2018 by caitylincoln

If you’re planning a vacation to Kauai then you’re one lucky dog! It’s one of my favorite Hawaiian islands and probably the prettiest one at that. If you’re very far into the planning process, you’ve probably realized that picking the right place to stay is likely the trickiest (and most important) things you’ll have to do. Where you stay on Kauai can make or break your vacation and there are soooo many options that it can be overwhelming. Not to worry! I’m going to break it down for you, give you an overview of the island.

Side note: After you read up on the lay of the is(land) and know which part you want to stay on, check out these posts for specific recommendations:

7 Kauai budget hotels

12 Kauai beach resorts

20 cool Kauai Airbnb rentals

5 Best Family Friendly Resorts on Kauai

5 best Kauai honeymoon resorts

Top 10 luxury resorts in Hawaii

12 Favorite boutique hotels in Hawaii

Here’s everything you need to know about where to stay in Kauai:

Lay of the Land

Kauai is divided into four major sections (North Shore, East Shore, South Shore, and West Shore). Each section has its pros and cons and own individual personality. Depending on what you’re looking for and what’s most important to you (budget, convenience, stellar views, beautiful beaches, luxury resorts, etc.) one area of the island may be more desirable. Here’s a breakdown of Kauai’s four main areas:

North Shore: In my opinion, the north shore of Kauai is the most gorgeous place on the planet. It has beautiful beaches and the lush green mountainous landscapes that most people’s Hawaiian dreams are made of. As you might guess, it’s so lush because it rains more here than other parts of the island (especially in the winter). The north shore is home to the charming little surf town of Hanalei and some pretty spectacular luxury accommodations. While it’s stunningly gorgeous, it’s also a bit remote if you’re planning on exploring sites on the south and west sides of the island.

East Shore: The east shore is often referred to as the “coconut coast” and is the most developed part of the island. This is where you’ll find the most reasonably priced accommodations and it central location makes it a convenient location from which to explore the north and south shores. There are of course lovely beaches on the coconut coast (hello, this is Hawaii!) but you won’t find any awe inspiring backdrops as you will on the north shore and the amenities are usually not as convenient as those on the south shore. You’ll find more “local” beaches on the east side.

South Shore: Kauai’s south side is the driest and sunniest part of the island, which makes it very popular with tourists. There are plenty of big resorts so you’ll find plenty of shopping and dining options. You’ll also find a nice selection of beaches but expect them to be more crowded than beaches on other parts of the island. The south side is a convenient place from which to explore the west side (Waimea Canyon and Polihole beach) but not so convenient for seeing north shore sites.

West Shore: The west shore is definitely the least visited part of Kauai (except for visitors to Waimea Canyon) and not very many people stay here. It’s very barren, dry, and isolated, and not convenient to seeing the rest of the island. Really the only people who are going to be staying over here are hikers and backpackers.

RELATED: 15 Things to Do on Kauai

How to See the Napali Coast

Where to Eat on Kauai

Where to Stay in Hawaii

June 27, 2018 by caitylincoln

If you’re planning a trip to the Big Island of Hawaii, you’re in for a great time. It’s not the island that most first time visitors to Hawaii choose to visit (most favor Oahu or Maui) and it’s usually because they’re intimidated by its size (you really can’t see the entire island from one central location). Actually, all of the other Hawaiian Islands could fit inside the Big Island TWO TIMES. This is of course why they call it the Big Island. So yes, it can be overwhelming but the Big Island is home to some of the most spectacular sites in the world (the world-not just Hawaii) so it’s a shame to skip it just because the logistics are tougher to figure out. So here’s what you need to know to figure out where to stay in Hawaii:

The island is divided into two sides: Kona side and Hilo side.
The vast majority of visitors stay on the Kona side even though the island’s best attractions are on the Hilo side.
It’s a Big Island so it’s not really possible to stay on one side and drive back and forth to the other, which means if you want to see the whole island, you’ll need to stay in at least two places.

Side note: After you read up on the lay of the is(land) and know which part you want to stay on, check out these posts for recommendations:

25 fantastic Big Island Airbnb rentals

7 Big Island budget hotels

10 Big Island beach resorts

6 best family friendly resorts on the Big Island

5 best Big Island honeymoon resorts

Top 10 luxury resorts in Hawaii

12 favorite boutique hotels in Hawaii

Here’s an overview of the island broken down by area:

Kona Side

Kona side refers to roughly the entire West side of the island, including the town of Kailua-Kona (often referred to just as “Kona.” This is the dryer side of the island (no lush jungles or rainforests here) and it’s mostly barren lava fields as far as the eye can see. But no rain also means the best beaches (the vast majority on the Big Island are found on the Kona side) and therefore all of the resorts and condos. This side of the island is mostly made up of:

Kailua-Kona: This is where the main airport is and it’s a good home base for exploring this side of the island. There aren’t many beaches in Kona but you will find a lot of budget accommodation options. You can easily drive to beaches located north and south of town and you’ll be close to most of the island’s cultural and historic sites. You can also easily daytrip to the Pololu and Waipo valleys from here. One of the downsides of staying in Kona is how touristy it is. This is where the cruise ships dock so you can imagine what that entails but on the upside there are a lot of shopping and dining options.

Where to Stay in Maui

September 12, 2017 by caitylincoln

If you’re reading this, I’m going to assume you’re planning a vacation to Maui—yippee for you! If you’re not planning a trip to Maui, you should be! Seriously though, get on it!

Anyways, if you’re even remotely considering a trip to Maui and wondering where to stay, this post is for you. If you’ve never been before, you might be overwhelmed…which part of the island should you stay on? Are some beaches better than others? Are those fancy resorts really worth the money? Will a condo save you big bucks? I’m going to let you in on everything you need to know!

Side note: After you read up on the lay of the is(land) and know which part you want to stay on, check out these posts for recommendations:

25 awesome Maui Airbnbs

12 Maui budget hotels

16 Maui beach resorts

6 Best Family Friendly Resorts on Maui

5 Best Maui Honeymoon Resorts

Top 10 luxury resorts in Hawaii

12 favorite Hawaii boutique hotels

Guide to Wailea (Where to Stay, Where to Eat, and What to Do)

Guide to Ka’anapali (Where to Stay, Where to Eat, and What to Do)

Lay of the Land, Maui Style

Maui is kind of a big island (we’re talking 10-12 hours of solid driving to go all the way around, which is just a point of reference because NOBODY drives around the entire island in a day) so don’t underestimate its size when you’re planning your trip. It’s divided into four main regions (West Maui, South Maui, East Maui, and the North Shore/Upcountry area) but only has two resort areas. You’ll fly into Kahului (the most sizable city/town) and this is where Wal-Mart, Target, and Costco are located but you likely won’t spend much time in Kahului once you pick up your rental car and groceries.

West Maui: West Maui was originally developed in the 1960s and remains the most popular place to stay and play on Maui. The old whaling village of Lahaina anchors this area and the Ka’anapali resort area is home to the majority of dining and accommodation options on this side of the island. It’s about a 30-40 minute drive from the airport (in Kahului) to the Ka’anapali/Lahaina area in West Maui.

South Maui: South Maui consists of Kihei (a decent sized beach town with plenty of condo options), Wailea (a more upscale, privately planned resort community), and Makena (the sleepy end of the road region in South Maui). The beaches in South Maui tend to get the most sunshine and are generally less crowded than the ones in West Maui. The resorts in Wailea (the Four Seasons, Grand Wailea, Marriot, etc) are only about a 15-20 minute drive from the airport.

East Maui: East Maui is the most remote side of the island (reached by the Road of Hana) and is usually reached as a day trip as accommodations are limited. While most visitors stay in West or South Maui, East Maui isn’t to be missed and the Road to Hana will likely be a highlight of your trip.

North Shore/Upcountry: The North Shore and Upcountry are the most authentic areas of Maui. This is where the locals live and while you likely won’t stay in this part of the island, you should plan plenty of time to explore this part of the island. Paia, Makawao, and a drive upcountry through Kula to Ulupalakua shouldn’t be missed.

Now that you’ve got the lay of the land, you’ll need to decide which part of the island will suit you best. First off, I’ll lay out some pros and cons of the West side vs. the South side before mentioning some more “off-the-beaten-path” options on the North Shore and in Hana.

25 Things to Know Before You Go to Kauai

October 24, 2016 by caitylincoln

UPDATE: In April 2018, Kauai experienced record setting flooding especially on its north shore. As a result, the road west of Hanalei town is currently closed cutting off access to the popular Kalalau Trail, Ke’e beach, and snorkeling at Tunnels. I encourage you to check local news coverage before your trip to obtain the most current conditions, and I will also update this as things reopen.

Kauai is the perfect island if you’re looking for a laid back vacation with plenty of gorgeous backdrops. If you’re planning a trip to Kauai, here are 25 things you should know before you go:

1.Kauai is the oldest of the Hawaiian Islands. It was created by a volcano almost 6 million years ago. It’s also the smallest of the four main Hawaiian Islands, and has a population of just 65,000 people.

2.It’s called the “Garden Isle” but it’s very country. You won’t find big cities or a lot of people on Kauai. You’ll find plenty of lush jungly wilderness to be explored though (we’re talking scenes straight out of Jurassic Park). And a TON of chickens. There are more wild chickens on Kauai than any other Hawaiian Island largely thanks to “Iniki,” a category 5 hurricane, which hit the island in 1992.

3.Hawaii was the 50^th state added to the United States of America. Despite it being a US state, more than one person has asked me if you need a passport to travel there. You don’t. Also, when referring to the contiguous United States, you don’t call it “the states” like you would when traveling internationally. You refer to it as “the mainland.”

4.It may feel like a different country, but remember, you’re still in the US. Hawaii has a very distinct culture and its location in the middle of the Pacific Ocean often makes it feel like a foreign land, so many visitors question how things are done. Here’s the deal, everything works like it does back home, except when it doesn’t : ) Seriously though, your phone service and everything works exactly like it does at home. But you will find yourself subject to the quirks of “island life.” Things move slower (especially on Kauai) so relax and just go with the flow.

Hawaii on a Budget: How to Save $1000 on a Trip to Hawaii

July 7, 2016 by caitylincoln

If you’re tossing around the idea of a Hawaii vacation, you probably know that the dream vacation often comes with a not so dreamy price tag. If you only have a vague idea of the exact numbers, check out this post on how much a trip to Hawaii costs. Once you get over the sticker shock, here are a few ways you can do Hawaii on a budget:

1.Don’t travel during high season. This is the single biggest way to save money on your Hawaiian vacation. High season is around the winter holidays and summer months. If you’re able to travel during the low season (there really is no “off” season in Hawaii), you’ll save a bundle on airfare and accommodations. For more info on the best (and cheapest) time to go to Hawaii, read this post.

2.Be flexible on when you can go and look for deals. If you’re flexible on your dates, you’ll leave yourself open to snagging great airfare or room deals when they become available. Track flights on Google Flights or set some alerts on SkyScanner.

3.Book a package. Sometimes booking a vacation package will score you a big discount as opposed to booking your airfare, hotel, and rental car by themselves. Hawaiian Airlines often runs good specials (I would sign up for their emails) and if you’re a member of Costco, they have travel specials that you can take advantage of.

4.Travel with a group. When you travel with a group of people, even another couple, you’ll be able to split a lot of the costs. Splitting a two or three-bedroom condo (and a rental car) will really cut down on the costs and be much cheaper than a one-bedroom condo or hotel room.

6 Steps to Planning a Hawaii Vacation

When is the Best Time to Go to Hawaii?

Which Hawaiian Island Should You Visit?

5.Stay in a condo or vacation home. Choosing a condo is going to be MUCH cheaper than a comparable resort and many of them have resort like amenities. You’ll likely get much more room for the money and most will come with a kitchen and washer and dryer. If you’re looking for something even cheaper, many locals will rent out their “ohanas” which is usually something like a garage apartment or guest cottage. I’d recommend searching on VRBO or Airbnb (get $40 off your first stay) for these types of set ups.

Wish you had a go to resource for the best spots in Hawaii? I’m talking snorkeling spots, trailheads, hidden beaches, local restaurants, and more! Sign up for my newsletter to access to my library of Hawaii Google Maps. I’ll also send you the latest and greatest Hawaii news, brand new things to do, special weekly deals and more. You don’t want to miss out on this! So sign up below!

6.Choose the most affordable part of the island. No matter what island you’re staying on, there will be parts of it that are more affordable than others. On Maui, Kihei is a much more affordable alternative to Wailea or Ka’anapali. On Oahu, the hotels towards the south/east part of Waikiki (and even a block off the beach) tend to be cheapest. On Kauai, stay in Kapa’a and on the Big Island, stay in Kona for the best prices. Read my detailed guides on where to stay on Maui, Kauai, Oahu, and the Big Island.

7.Use points for airfare and rooms. This, of course, isn’t an option for everyone but if you have miles or points on a credit card or with a specific airline or hotel chain, this is the time to use them! Keep in mind that if you’re booking with points, you might be limited as to specific times and dates and you may have to book pretty far in advance to get anything. Read more tips on how to find cheap airfare to Hawaii here.

8.Book activities directly. If you wait until you arrive on the island, many activities will be booked up and they’re less likely to offer discounts when the tour is almost full and people who waited until the last minute are competing over a few remaining spots. Many companies offer a discount if you book online directly through them. This is because most tours rely heavily on resort concierge desks to promote their tours to the guests. The concierge get a commission for referring guests to the tour company (sometimes up to 40%) so tour companies have to keep their prices high so they walk away with a decent profit on the tour after paying out commissions. So if you go directly to the tour company, they’re often willing to cut you a deal because they don’t have to pay a commission to a concierge for your spot. For example, if a company pays a 40% commission for concierge recommendations, they’ll still come out ahead if they offer you a 20% discount for booking directly. But this way, you also come out ahead. Also, if you go this route, you can do your research on companies ahead of time (I recommend Trip Advisor) and read honest reviews about the tours and pick which one you feel is best for you. If you go with a concierge recommendation, not only are you usually paying more, but 99% of the time, you’re just being recommended the tour provider who pays out the biggest concierge commissions, not necessarily the best one. If the tour provider’s website doesn’t advertise a direct booking special, I would still call and ask for their best price. You never know until you ask! Read about the best paid activities and tours on Maui, Oahu, Kauai, and the Big Island.

9.Go grocery shopping. Everybody knows how expensive food is in Hawaii so every little bit you can avoid buying at your resort or a restaurant helps. Obviously, if you’re staying in a condo or vacation rental, you can buy enough groceries to cook all of your meals, but even if you don’t have a full kitchen, (or don’t want to cook every meal) there are still some things you can stock up on to save you a little cash. I would suggest at least grabbing a case of water, sodas, and liquor to mix your own drinks as well as plenty of snacks. If you have a membership, Costco is usually the best shopping option in the islands. Even buying in bulk, you’ll find their prices are often much cheaper than local grocery stores, plus they also have a pretty big prepared foods section (oh lord, that mac and cheese!). If you’re looking for brands you have at home, all of the islands have Walmart and all but Kauai have Target. Safeway is also a local grocery chain that you’ll find throughout the islands. If you shop there, I suggest signing up for their free loyalty rewards program, as it will usually save you at least $5-10 in one stop.

RELATED: Where to Stay on Maui

Where to Stay on Oahu

Where to Stay on Kauai

Where to Stay on the Big Island

10.Eat like a local. Food gets a bad rap for being super expensive in Hawaii but that’s only if you don’t know where to eat. Anywhere in the resort areas are likely to have higher than normal prices. Even in the resort areas, many restaurants will have two tiers of restaurants, one high-end “steak and fish” option, and a more casual “burgers and tacos” option. If you are in a resort area, take advantage of happy hours! For more reasonable prices, venture away from the resort areas and into the more local towns (hey, it’s still Hawaii and everything is still geared towards tourists). Also, never pass up a food truck, bakery, or little roadside stand. That’s where you’ll usually find the best food. Read about my favorite spots in eat in Hawaii.

11.Plan your splurges. If you do want to have a nice dinner or two out, I suggest planning ahead instead of just blindly walking into a place. Do some research ahead of time to make sure you pick a good place. There are plenty of tourist traps in Hawaii that will cost you an arm and a leg and leave you disappointed. On Maui, Mama’s Fish House or Mill House are must dos for a nice dinner. On Kauai, try the Beach House in Po’ipu. On Oahu, Haleiwa Joe’s (in Kaneohe) is great, and on the Big Island, I like Ulu Ocean Grill.

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How Much Does a Trip to Hawaii Cost?

July 2, 2016 by caitylincoln

How much does a trip to Hawaii cost? This is one of the questions I get asked the most often. While for many people, Hawaii is the ultimate vacation destination, a lot of people don’t even have a vague idea how much a Hawaiian vacation costs. Most conversations go something like this: “I know airfare is really expensive because it’s so far away. And all of those fancy beach resorts can’t be cheap right? And I’ve heard the food is really high. Tell me, how much does it cost anyways?”

Well that’s a loaded question. There are so many factors that can determine the price of a trip to Hawaii least of which would be: what time of year are you going? Where are you flying from? What kind of place do you want to stay at? And are you willing to do less touristy things to save money?

As you can imagine, there’s a pretty large spectrum of what a trip to Hawaii can cost, but here are some general guidelines of what you can expect plus what to budget when you’re planning your trip.

Transportation

Airfare: This is the big one. No matter how you break it down, just getting to Hawaii is usually the most expensive part. As a general ballpark figure, I always assume that a plane ticket to Hawaii will cost me around $1000. That’s flying from the middle of the country (airfare from major Californian cities is often MUCH cheaper). Of course, if you’re flexible with your travel dates and willing to stalk some of the sites that track promotions and deals then you may be able to get that down to $800-$900. And of course your route also determines the price. Flying through Honolulu (even if you’re not staying on Oahu) will often get you a better deal than flying direct from the mainland to Maui, Kauai, or the Big Island. Also, routes that connect through LAX (as opposed to flying direct from Dallas, Chicago, Atlanta, New York, or another Californian city like San Diego or San Francisco) are also often a lot cheaper. This is because you’ll have to jump through a lot more hoops if flying through LAX (changing terminals, rechecking bags, etc.). Read more about how to find cheap airfare & how to survive the long flight to Hawaii.

Rental Car: Rental car pricing in Hawaii can seem insane when you’re first pricing it out but generally it’s anywhere from $20-$80 a day depending on the type of car and how far out you book. Prices during the holiday season can skyrocket but if you’re willing to dig around, you can usually find a pretty good deal. This of course depends on the time of year and type of car. And don’t wait too long to book or during high season you may find yourself with low to no availability. I always book through Hawaii Discount Car Rental to get the best prices.

Cruise to Hawaii: The Best of Hawaii from a Cruise Ship

February 23, 2016 by caitylincoln

For a lot of people, a Hawaiian vacation is THE dream! Visions of swaying palm trees, ukulele music, hula dancers, surfers, and iconic beaches are what everybody thinks of when they imagine Hawaii. And, hey, it’s all there! But for many travelers, choosing an island to visit or knowing how to spend their days on each island can be overwhelming. For the traveler who wants to see everything, a cruise to Hawaii can be the perfect solution…you get to go to all of the islands, you don’t have to worry about inter-island airfare, and your bed follows you around!

So if you’re wondering how to make sure you get to see the best of the islands from a cruise to Hawaii, this post if for you! These ships offer countless excursions…how are you supposed to know which ones to pick? And when is it better to ditch the excursion and head out on your own?

These are my recommendations on how to see the best of Hawaii from a cruise ship. For the purposes of this post, I will be adapting these recommendations to fit the Norwegian Cruise Line’s 7-Night cruise itinerary sailing out of Honolulu as it’s one of the more popular cruise lines but you can still use these daily recommendations no matter which ship you’re on!

Since you’ll be flying in and out of Honolulu (that’s Oahu), here are a few highlights that you should hit on Oahu either before or after your cruise:

hawaii

Lay of the Land

Lay of the Land, Maui Style

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