Wailea and Kaanapali on Maui are beautiful. viewing sunrise or sunset from Haleakala is lovely. I have challenges with smoke and fire so would not at all be interested in potential fire season. I believe there are wineries and lavender farms you could tour on Maui.
I think both options are great!
If youâre coming from New York, Maui is a long way to go for just 5 days. Iâd allow more time for that. I have a friend who lives in New York and she went to Hawaii with her husband. They flew to San Francisco, spent a night there and then flew to Hawaii the next day.
Napa would be fun. You could also tack on some other stuffâŠlike the Russian River, Bodega Bay, etc. Itâs a neat part of the state.
Santa Barbara is fun. You can fly right into Santa Barbara, I know theyâve expanded their airport and added a lot more flightsâŠthough if youâre coming from New York it would probably be just as cost effective to fly into LAX, rent a car and drive to Santa Barbara. The wineries near Santa Barbara are in the Santa Ynez Valley which is just north of Santa Barbara, itâs a beautiful area and definitely worth visiting if youâre in Santa Barbara. Central California is a beautiful part of the state.
There is a winery on Maui as well as an organic vodka distillery - both offer tours. And yes a lovely lavender farm as well.
OP since you mentioned St John, if you liked it there you might want to consider Grand Cayman or Turks and Caicos, 2 other very nice Caribbean islands.
I think a lot of this depends on how long youâre staying, how willing you are to put up with the extended travel time, and your affinity to wine/wineries.
Iâve been to Maui three times and Napa/Sonoma twice, and Maui is the easy choice for me, all else being equal. There will be plenty to do other than swimming. We visited an Upcountry winery, if you need a fix (though nowhere near the scale of one in Napa).
EDIT: reading further/maybe I missed it - I wouldnât select Maui if the time period is 5 days. Youâll lose a day compared to Napa, for starters. Weâve never made the time investment for less than 12 days (at least 2 islands).
You might want to consider Iowa City. Thatâs where weâre likely headed in June!
If you are looking for closer alternativesâŠwhat about Sanibel, Marco IslandâŠor someplace like that?
Some ideas/suggestions to consider:
Maui:
- if youâre coming from the east coast, 5 days is too short. Needs to be at least a 10 day trip in order to make it worthwhile.
- Maui is NOT just about laying around on the beach. It CAN be that sort of trip, but it doesnât HAVE to be if youâre interested in other stuff.
- a lot of people talk about doing the road to Hana, but honestly, itâs a huge pain in the neck in my opinion and is only worth doing one timeâŠand if youâre only there for 5 days total, donât waste your time on that.
- there are a lot of amazing locally-owned eateries all over Maui that are worth trying.
- thereâs a great aquarium on the island, too.
- in Kahului every Saturday, thereâs a swap meet in the morning. Very cheap to get in. Great way to get some locally-grown produce and other stuff at decent prices.
Napa:
Iâd pass on this and go to the Santa Barbara area instead, but thatâs just my personal preference. In the Napa/Sonoma area, youâd be easy driving distance to Muir Woods (remember, that youâll need a reservation to get into Muir Woods, though). If you spend a day in SF, donât leave ANYTHING inside your rental car. At all. Bad car break ins all the time in SF now.
Santa Barbara
- Fly into & out of LAX and rent a car.
- Carpinteria is a small-ish coastal town on the way to SB. cute walkable downtown area with some shops & restaurants. Easy beach access.
- cheaper prices in Goleta for places to stay overnight in the Santa Barbara area.
- often on weekends along the main beach near Stearns Wharf, thereâs local artisans selling arts and crafts stuff.
- thereâs a fancy Ritz Carlton resort just north of Goleta
- Gaviota state beach north of Goleta is a really cool spot
- if you take 101 to hwy 246 to get to Santa Ynez, youâll pass through Solvang, which is a fun stop for a couple of hoursâ worth of browsing in Scandinavian shops.
- if you take Hwy 154 from Santa Ynez back to SB, youâll pass by Cold Spring Tavern, which has been around since 1868. itâs a really cool spot. Open for lunch or dinner. I think you need reservations for dinner, though.
As an east coast person, I recommend the sfo or lax overnight stop over for HI with an early morning departure from CA. Itâs better to arrive midday than late at night and still have to negotiate getting to hotel. And it reduces worry about connections.
A HI travel almost pro tip here⊠it does not matter pandemic or not, picking up a rental car in Hawaii during peak travel season can be a nightmare. The agencies have always been and still are understaffed, so lines are extremely long. Does not matter what company or island! Joining a loyalty program like Budgetâs Fastbreak saves a lot of time upon arrival! The last thing you want after a long flight is to wait 2 hours to get your rental.
I also agree that breaking up that long travel into 2 segments is worth it. I do not recommend LA or SF for this because it would take a long time to pick up luggage and then Uber to the hotel. The best airport for this would be San Jose. Compact, efficient, not crowded. Hotels have free shuttles. The next best, IMO, is SeaTac. Plenty of flights to Maui and hotels within walking distance.
My H likes wine caves and when we went to CA we toured two wineries with cavesâDel Dotto in Napa and Bella Winery in Healdsburg. We loved the tours for both.
I thought of this thread when I saw the USA article:
And hereâs the full ânoâ list:
DH and I are going to Maui for the first time next month. Actually, itâs my first time, but heâs been before. Flying from Boston for our 25th wedding anniversary. Weâre staying 7 nights which is a long vacation for us. DH has travelled all over the world for work and I tag along when Iâm free. Itâs always much shorter than 7 days.
Feel free to message me before/after our Maui trip in late February and Iâd be happy to share info on hotels, restaurants, activities.
We also went to Napa for 5 days for a friendâs 50th birthday a few years ago. Itâs was a great couples/friends trip with a group of 9 people. Lots of fun to explore the area and go to vineyards, wineries, restaurants, the spa, a wine cave, hiking, etc. Great specific suggestions in this thread for activities.
We visited Napa in June and did have to change one day of planned activities in order to avoid an area with an active fire.
Napa was really an exceptional friends trip, but Maui seems more special for our anniversary.
In Maui, if that is the destination chosen, I recommend staying in Wailea. Kihei and Kaanapali tend to attract families with little ones and the younger crowd, so busy and noisy. Wailea is more expensive and therefore generally less crowded/more quiet⊠If you are a Hyatt loyalty member, Andaz is worth checking out. We never stayed there (used our points at the Marriott next door which was a construction zone so dirt cheap ) , just ate breakfast at their restaurant which was fabulous! We returned for dinner and werenât disappointed. The beach by Andaz is not huge but nice.
Emphasizing this. Itâs not just Maui, though the water crisis there seems to have pushed it over the edge and onto this list. Tourism in Hawaii is extractive and harmful to the native population and ecosystem. It drives up cost of living and homelessness, two already-major problems for the islands. Anyone considering a pleasure trip should read this article (originally published in the Honolulu Civil Beat) and reconsider.