We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Trip to Maui from Boston - HELP

worcester, ma
Level Contributor
50 posts
Save Topic
Trip to Maui from Boston - HELP

Family of five is strongly considering traveling to Hawaii this July from Boston. Any tips on where to get started in planning this would be much appreciated!

Iowa City
Level Contributor
886 posts
4 reviews
Save Reply
1. Re: Trip to Maui from Boston - HELP

Any tips on where to get started in planning this would be much appreciated!

I'm, not sur what you are asking-but, try www.kayak.com, it will give you options, and then take you to the airlines website. You can also look for air-hotel combination. Are you a member of any Frequent Flyer Programs-that may influence your airlines choice. I assume you have some ideas about what island, what price range etc., if not, get a book or two, then come back and ask specific questions. Good luck

Destination Expert
for Maui
Level Contributor
4,706 posts
9 reviews
Save Reply
2. Re: Trip to Maui from Boston - HELP

Assuming since you posted this on the Maui forum that you want to stay on Maui. It would help to know what your accommodations budgets is and what you are looking for in a vacation. Do you like to crash poolside or on the beach and relax? Or do you like to fill your days with activities? What are the ages of your kids?

Generally speaking the vacation areas are split into several focused areas. West Maui is home to the historic whaling village of Lahaina which is now full of restaurants, shops, galleries and historical sites. just up the road is Ka'anapali, a loveley stretch of white sand beach and a collection of resort hotels and condo complexes like the Sheraton, Westin, Hyatt and others. Most are high rise complexes, some with elaborate pools. Also in West Maui are Kapalua and Napili Bays where you'll find great snorkeling and swimming, and a number of terrific condos and hotels. West Maui is a lively area with many activities to participate in from ziplines to paragliding to ocean excursions.

South Maui is a bit more quiet and laid back. The resorts in Makena and Wailea are large, elaborate, a bit more pricey, and sit on some primo beaches. South Maui is also home to Kihei, which is about as close as you can come to a "breach town" in Maui. Many of the condo complexes here are less expensive (read older and smaller), but can be great bargains for families. Also, many - but not all - of he Kihei condos sit across a busy road from the beach rather than right on it. A consideration if you have young kids.

Here is a great site where you can do some reasearch...


When you click on a property, you'll see an aerial photo with review, rack rate pricing (you can do better) and a link to the resort's web site.

Lot's of deals flying around these days, and some only pop up for a few days and then disappear. Most places seem to be offering discounts like 3 or 4th night free. So it's important to do your research. Places like the Sheraton have deals for Club members that don't show on their regular site so it's worth joining the Starwood Club.

Level Contributor
50 posts
62 reviews
Save Reply
3. Re: Trip to Maui from Boston - HELP

I booked everything from Travelocity.com and saved big time. I stayed in Kihei because it was centralized and cheaper. During peak season, I've heard the street going through Kihei can become overwhelming, but I still liked its proximity to everything. I've seen all the Hawaiian Islands and Maui is by far the best. Haleakala Crater is incredible regardless of the time of day, BUT it's known to get very cold at any time of year. If you go to the Iao Valley, get there early or you won't get a good parking space. The Lahaina Luau was awesome, but they don't have guys spinning the fiery sticks. Black Rock Beach is great for snorkeling: reefs, fish, giant turtles, rays. If you don't take a helicopter ride of the Wall of Tears (high waterfalls), you will regret it; I recommend bluehawaiian.com for helicopter rides. The Hana Highway is very narrow, crowded, and takes forever to drive, although I recommend you stop at Nahiku for an awesome photo stop if you do go. The highway on the northwest side of the island is even more treacherous between the Blow Hole and Kahalui; I do NOT recommend it. Hope you have as great a time as I did!

Level Contributor
50 posts
62 reviews
Save Reply
4. Re: Trip to Maui from Boston - HELP

Correction: I mean try Alexair at www.helitour.com for a helicopter ride, not Blue Hawaiian. The reason is because Alexair is the only one where you can talk to the pilot with headsets and microphone. That way you can ask questions.

boston, ma
Destination Expert
for Western Ireland
Level Contributor
1,477 posts
15 reviews
Save Reply
5. Re: Trip to Maui from Boston - HELP

Greetings from your Metrowest neighbor. Happy St. Pat's Day. How was your parade?

We visited Maui 2 summers ago and absolutely loved it. I'll speak to the flight from the East coast. We traveled on 3 airplane flights and were dead on arrival in Maui. See if you can find a better arrangement without extremely long layovers. Once you get there it will be well worth the long flight. You might wake up at 4:00 a.m. the next morning like we did because your body thinks it is 10 a.m.

As others have mentioned you will have to choose accomodations in either West Maui (Kaanapali area) or South Maui. We chose to go through vrbo.com and rent a beautiful condo in Kihei from a private owner. You will be closer to the airport and Haleakala but about 45 minutes from Lahaina and Kaanapali. South Maui has its own beautiful beaches also.

We also decided we couldn't leave Hawaii without seeing the Arizona Memorial on Oahu. So we hopped a short inter-island flight from 9 a.m. until 9 p.m. and spent the day on Oahu. Again it was well worth the trip.

We made the drive to Hana but don't think we will spend a whole day of our vacation on the Road to Hana if we were to visit again.

Have a great time.

Boston, MA
Level Contributor
231 posts
88 reviews
Save Reply
6. Re: Trip to Maui from Boston - HELP

As another local poster, who has been planning a trip from Boston, let me recommend looking at United Airlines for flights. They had reasonably good prices, and they use SFO mostly for the stopover. Plus you can fly direct to Maui. It's not too bad a flight schedule BOS_SFO-OGG.

Maui, Hawaii
Level Contributor
8,395 posts
186 reviews
Save Reply
7. Re: Trip to Maui from Boston - HELP


There is Mauii visitors Bureau. check their website

new hampshisre
4 posts
1 review
Save Reply
8. Re: Trip to Maui from Boston - HELP

Hello Mass Neighbor:

My family and another family just booked last week to Honolulu although the other family is planning on renewing their vows on Maui. I got a great deal on airfare out of Manchester. At least $200 cheaper than Boston. Airfares were lowest on Wednesday. Check out Bestfares.com for comparisons between MHT and BOS. WE are flying into Honolulu for $561 roundtrip then taking a quick island hopper over to Maui for $49.00.

When on the islands, we look to booking a house so as to maximize the $$$ especially when traveling in a group.

Good luck.

9. Re: Trip to Maui from Boston - HELP

-:- Message from TripAdvisor staff -:-

This topic has been closed to new posts due to inactivity. We hope you'll join the conversation by posting to an open topic or starting a new one.

To review the TripAdvisor Forums Posting Guidelines, please follow this link: http://www.tripadvisor.com/pages/forums_posting_guidelines.html

We remove posts that do not follow our posting guidelines, and we reserve the right to remove any post for any reason.

Removed on: 21 October 2009, 20:19