Looking for 7 day trip from Boston to Hawaii
#1
Original Poster
Joined: Feb 2025
Posts: 15
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Looking for 7 day trip from Boston to Hawaii
2 teens & 1 adult parent
7 day trip including travel days
end of March ( spring break )
- Love nature
- beaches to see ( not the type to lie down in a beach all day.. )
- mountains, volcanoes ( if any close to visit - safe spots only )
- ferry rides or train rides through scenic pathways
- some shopping for gifts for friends and family
Suggestions needed for
1. Where to fly and what to see.. ( Thinking mainland & Maui )
2. Where to stay
Thanks
7 day trip including travel days
end of March ( spring break )
- Love nature
- beaches to see ( not the type to lie down in a beach all day.. )
- mountains, volcanoes ( if any close to visit - safe spots only )
- ferry rides or train rides through scenic pathways
- some shopping for gifts for friends and family
Suggestions needed for
1. Where to fly and what to see.. ( Thinking mainland & Maui )
2. Where to stay
Thanks
#2
Joined: May 2022
Posts: 565
Likes: 0
It takes 12 hours to fly nonstop to Honolulu (main island), so you are down to five days of vacation. Maui has Haleakaia National Park with its volcano and subtropical forest. Alot of people go whale-watching on cruises in Maui in March.
#4
Joined: May 2023
Posts: 640
Likes: 0
You don't indicate where you are flying from so hard to recommend best airline. You can do a search on websites like Kayak to see what your options are. In the past I've flown to Hawaii from NY changing planes in both LA and SF however Hawaiian Airlines now flies direct to Honolulu and you can get connecting flights there. Others I know have changed planes in Phoenix. Last time we flew United from the West Coast to Maui and then return flight. Most return flights are red-eye flights as it is a long trip to get to Hawaii.
#5
Joined: May 2023
Posts: 640
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Oh sorry I just saw that you plan to fly from Boston. You can go to kayak.com or other travel sites to research as well as the websites for major carriers that fly in and out of Boston and these days things are very changeable with airline schedules. Just make sure to leave sufficient time for changing planes and avoid going through Chicago for starters.
#6
Joined: Jan 2003
Posts: 98,176
Likes: 12
From Logan (BOS) to Oahu (HNL) there is a nonstop flight available by Delta. As mentioned in the first post a 11-1/2 hour flight.
There are other airline choices with a connecting flight like Hawaiian, Alaska, American, JetBlue, etc.
1. Where to fly and what to see.. ( Thinking mainland & Maui )
What do you mean by "mainland"?
aloha, suze
There are other airline choices with a connecting flight like Hawaiian, Alaska, American, JetBlue, etc.
1. Where to fly and what to see.. ( Thinking mainland & Maui )
What do you mean by "mainland"?
aloha, suze
#7
Joined: May 2022
Posts: 565
Likes: 0
Maybe aim for some place closer such as Sarasota, Florida. It's only 3.5 hours nonstop to nearby Tampa. It features a vibrant downtown with an equally vibrant bookstore and cafe culture. Attractions include the Selby Botanical Gardens (with 6,000 orchids), Ringling Museum of Art, Circus Museum, and Towles Court Artist Colony. Nearby are lovely powdery white-sand beaches (such as South Lido Park Beach). Bicycle or walk on the Legacy Trail to Venice. Take a wildlife cruise and view dolphins and manatees. There are many nature preserves in the Sarasota County.
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#9
Original Poster
Joined: Feb 2025
Posts: 15
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flying to HNL (couldnt find any redeye so entire day now gone in flight) - stay for 2 days. Then to Maui for 3 days
then to somewhere in Kona 2 nights ( I meant that as mainland Hawaii - goes to show how much I know about Hawaii ) and leaving to HNL and return ( This will be a all night flight )
With this itinerary, any 'must-see' and 'not to miss' ? There is so much out there i see, but trying to wrap around what is what is confusing.
Should we rent a car in Maui & also in Kona..
Thanks again to everyone that took the time to reply and trying to help! Appreciate it.
On another note, How do you "like" messages in this forum? I only see a report post option below the name on the left side of one's message.
then to somewhere in Kona 2 nights ( I meant that as mainland Hawaii - goes to show how much I know about Hawaii ) and leaving to HNL and return ( This will be a all night flight )
With this itinerary, any 'must-see' and 'not to miss' ? There is so much out there i see, but trying to wrap around what is what is confusing.
Should we rent a car in Maui & also in Kona..
Thanks again to everyone that took the time to reply and trying to help! Appreciate it.
On another note, How do you "like" messages in this forum? I only see a report post option below the name on the left side of one's message.
#10

Joined: Dec 2009
Posts: 2,157
Likes: 0
there is a nonstop flight available by Delta
I’d take the nonstop and spend the 5 days in Honolulu. There’s enough there to occupy you. Skip Kona entirely, there’s little to see or do there, and although less busy than Maui or Oahu the traffic may be even worse. If an active volcano is a must fly in and out of Hilo— do not go to Kona.
#12
Joined: May 2023
Posts: 640
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Well to each his own. It is a short trip and you can't do it all. There is enough to see and do on Oahu or split with Maui. Save the Big Island for a future trip as it is very interesting and it is also big as essentially it is an island the size of the state of CT. Yes you will need a car in Maui as there isn't public transportation options as there are in other places. It is definitely worth it to drive up to the top of the volcano but be prepared as it is super windy and cold. While Maui isn't as large as the Big Island, because of the volcano, there is limited road options and so you will spend time just driving the same roads to go from place to place.
On Oahu I would certainly think that Pearl Harbor is the principal attraction. It is so interesting, well done and very moving. We were there prior to the reservation system but got there just after nine and definitely spent most of the morning there.
On Oahu I would certainly think that Pearl Harbor is the principal attraction. It is so interesting, well done and very moving. We were there prior to the reservation system but got there just after nine and definitely spent most of the morning there.
#13
Joined: Mar 2025
Posts: 2
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Looking at your 7-day trip to Hawaii from Boston with teens, I'd recommend keeping your Oahu (2 days) and Maui (3 days) plan but consider replacing Kona with Hilo if you want to see volcanoes, definitely rent cars on both Maui and Big Island, and prioritize Pearl Harbor, Haleakala National Park for sunrise/sunset, Road to Hana, and whale watching (it's peak season in March).
#14
Joined: Jan 2003
Posts: 98,176
Likes: 12
flying to HNL stay for 2 days. Then to Maui for 3 days then to somewhere in Kona 2 nights ( I meant that as mainland Hawaii - goes to show how much I know about Hawaii ) and leaving to HNL and return.
Sorry but I think that's a crazy itinerary. If you stick to that plan, you will be spesnding most of your time checking in and out of hotels, renting and returning cars, sitting in airports waiting, taking flights... than you will have for sight-seeing, touring around, and relaxing. Takes at least half a day to change islands, and you're doing it three times in less than a week. Really eats up your free time with this plan.
Corrrect... Island of Hawaii aka Big Island is never called "the mainland" (that is the term for USA, contiguous 48 states).
Seven days is super short for coming all the way from 'back east'. I would suggest to book a nonstop flight and only go to Oahu (or if you could find a non-stop only to Maui would be another idea).
aloha suze
Sorry but I think that's a crazy itinerary. If you stick to that plan, you will be spesnding most of your time checking in and out of hotels, renting and returning cars, sitting in airports waiting, taking flights... than you will have for sight-seeing, touring around, and relaxing. Takes at least half a day to change islands, and you're doing it three times in less than a week. Really eats up your free time with this plan.
Corrrect... Island of Hawaii aka Big Island is never called "the mainland" (that is the term for USA, contiguous 48 states).
Seven days is super short for coming all the way from 'back east'. I would suggest to book a nonstop flight and only go to Oahu (or if you could find a non-stop only to Maui would be another idea).
aloha suze
Last edited by suze; Mar 6th, 2025 at 11:05 AM.
#15
Joined: May 2022
Posts: 565
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As someone mentioned it takes 20 hours from door to door. Then the return trip of 20 hours, so your time is limited. I would skip the Big Island and split your time between Oahu and Maui. As I mentioned there is a volcano on that island.
#16

Joined: Dec 2009
Posts: 2,157
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Road to Hana
#17
Original Poster
Joined: Feb 2025
Posts: 15
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Yeah I hear the crazy hopping in and out
Leaving 21st - reaching evening. ( day flight HNL )
not planning to rent a car
22 - Pearl Harbor ( did not reserve. Thanks for that tip Madam397 ) Once finalized will try to get that booked .
23 - Was hoping to see something before hopping on to a flight to Maui. but if door to door is 5hrs time then guess we cant plan anything.. Any suggestions here. Havent looked at flight availability also. And flights from Maui to Hilo is via HNL
24, 25 - Maui ( wondering what to cover. RTH is good but also dangerous ( not sure some forum referred to this as too adventurous and danger - tough route? )
26 - to Hilo volcano village (so probably all day on travel door to door? ) could we do anything else at all?
27,28 - Hilo
29 - Return to HNL ( evening flight to BOS )
I wish it doesnt become too hectic either. It is a well long due and deserved fun trip for the children..so looking for some veteran travelers to jump in and point out if this tentative itinerary ( except the in-flight & outflight to HNL ) makes sense. grateful for your time and thoughts!
Leaving 21st - reaching evening. ( day flight HNL )
not planning to rent a car
22 - Pearl Harbor ( did not reserve. Thanks for that tip Madam397 ) Once finalized will try to get that booked .
23 - Was hoping to see something before hopping on to a flight to Maui. but if door to door is 5hrs time then guess we cant plan anything.. Any suggestions here. Havent looked at flight availability also. And flights from Maui to Hilo is via HNL
24, 25 - Maui ( wondering what to cover. RTH is good but also dangerous ( not sure some forum referred to this as too adventurous and danger - tough route? )
26 - to Hilo volcano village (so probably all day on travel door to door? ) could we do anything else at all?
27,28 - Hilo
29 - Return to HNL ( evening flight to BOS )
I wish it doesnt become too hectic either. It is a well long due and deserved fun trip for the children..so looking for some veteran travelers to jump in and point out if this tentative itinerary ( except the in-flight & outflight to HNL ) makes sense. grateful for your time and thoughts!
#18

Joined: Dec 2005
Posts: 1,342
Likes: 0
My Hawaii experience has been one trip staying for a few days on Waikiki Beach (meeting), a couple of trips to Maui, (one a meeting at Kaanapali) and a family trip loved by all to the Big Island.
I would think twice about Maui when you can so much more easily get to gorgeous beaches in the Caribbean.
I would think twice about Maui when you can so much more easily get to gorgeous beaches in the Caribbean.
#19
Joined: Nov 2013
Posts: 3,250
Likes: 0
you've changed your original 7 day plan which included travel. You are now planning chaos with little return. No time to get to feel and understand the magic. That said the Caribbean or Florida will not give you Aloha spirit. It is not something that can be replicated. I want you and your kids to have the best. I would book Hawaiin from Boston to Honolulu and then head over to Maui and connect back thru Honolulu for a direct flight home. Good luck
#20
Joined: May 2023
Posts: 640
Likes: 0
Road to Hana
Agree with Post #16.. Only would do this if I was in Maui for 7-10 days. In my experience, it is an extremely long day's drive. First you need to drive to where the Road to Hana begins and that takes a fair amount of time depending on where you are staying on the other side of the island. Unless the roadway has been upgraded, it was not in good shape when we did this drive and there isn't any shoulder, making the one-way bridges not pleasant when your side of the road has to back up for oncoming traffic and some of that oncoming traffic might be a school bus, a lumber truck, a soda delivery truck, a construction vehicle and all of the above. Most of the sites are not visible from the road and there may be only 1 or 2 spots to pull over as well as No Trespassing signs. The one rest area has minimal parking spots. Hana itself is a tiny town and the interesting sites are not in Hana. We had ice cream there and walked on a small beach as the adjoining pier was closed because in disrepair. After all this.. you get to do the drive back as the road dead-ends there. In addition there could be a downpour along the way,
Agree with Post #16.. Only would do this if I was in Maui for 7-10 days. In my experience, it is an extremely long day's drive. First you need to drive to where the Road to Hana begins and that takes a fair amount of time depending on where you are staying on the other side of the island. Unless the roadway has been upgraded, it was not in good shape when we did this drive and there isn't any shoulder, making the one-way bridges not pleasant when your side of the road has to back up for oncoming traffic and some of that oncoming traffic might be a school bus, a lumber truck, a soda delivery truck, a construction vehicle and all of the above. Most of the sites are not visible from the road and there may be only 1 or 2 spots to pull over as well as No Trespassing signs. The one rest area has minimal parking spots. Hana itself is a tiny town and the interesting sites are not in Hana. We had ice cream there and walked on a small beach as the adjoining pier was closed because in disrepair. After all this.. you get to do the drive back as the road dead-ends there. In addition there could be a downpour along the way,

