We want to go on vacation oct or nov and are coming from Portland and want sunshine which island would be the best?

October and November is still hurricane season in the Caribbean and while historically over the last 150 years more storms occur in October than November there's no way to predict NOW if there will be any major storms in the Caribbean during either month and even if there were it's impossible to tell if any particulars storm will affect any given island.

If there are no storms in the area the weather for any Caribbean Island will generally be "good" but here again there are never any guarantees when it comes to predicting the weather.

All that said, the islands of Aruba, Curacao and Bonaire are pretty fare south and generally considered to be pretty free from major hurricanes. They are also arid islands meaning they get less rain than the lush mountainous islands so they'll be your best bets. To confuse you even more, I've been to numerous Caribbean islands in October and November and have had near perfect weather. The thing is, it's not the island that controls the weather but rather where the wind currents steer are steering the weather fronts the week or so you'll be traveling and you won't know that until a few days prior to your trip.

Honestly, no one can guarantee sunshine, that's up to mother nature.

Bermuda is lovely during that time

I thing Bermuda would be too cool that time of year...especially if you want to do any swimming.
Look into Aruba and Curacao.

Bermuda would likely not be too cool if it is mid-Oct to Nov.1 based on 2 visits. Curacau has a windy season in Sept. and October that ends by veryearly Nov. Aruba always has that 12-14 mile breeze and in Oct. it can be up to 20mph. From one visit and word from others it drops down to 14mph in Nov. I . We were in Bonaire in August and they do not have the Aruba breeze though it is quite close for some reason.

Definitely look into travel insurance. And remember that as RoamsAround said, there are no guarantees. We've had two trips to Bermuda in the fall cancelled due to possible hurricanes. And Aruba, which has a reputation for being one of the driest islands, had an unusually rainy November in 2011.

ABC "Blue Sky Isles" out of the storm belt best
for Carib cntraveler.com good recent articles. Hyatt Palm
Eagle Beach Aruba my fav. My fav island in fall princesresortshawaii.com Hapuna Prince Mauna Kea
Kohala Coast less than 1 inch of rain per month
konaweb.com $1kpp for me last priceline.com 4 hours direct to Kona from LAX.

Trip Cover wise for storms for Carib in fall...

stayhawaii.com would be my choice in fall especially from PDX

We have been to various Islands the first week of a November and the weather was fine. The exception was 2005 when Hurricane Wilma creamed the Yucatan Peninsula of Mexico. Our trip to Cozumel was cancelled and we re-booked to St. Lucia thanks to the hurricane insurance we purchased. It still rained in St. Lucia (think of the distance between the two. Wow), but it was fine and we had an amazing trip. To date, St. Lucia is still DH's favorite Island.

I have read over the last 2-3 years of Aruba having tropical storms in Oct/Nov and rain showers in December, so you never know.

If you can wait until the first week of December, you will find better weather, better prices and lower crowds. We typically go somewhere that time every year and have had no issues.

been to Bermuda the past two Octobers (end) and into November. This past year '11 - we were hot every day (we stayed 10 days). The ocean temp was 80 - pretty warm for swimming! And we swam in 2010 as well - again quite warm.

We spent the middle of November in St Vincent and the Grenadines last year - particularly Bequia and it was wonderful. Great weather, great time. Just know to push your trip as far into November as you can as the dry season typically starts in December, but mid to late November can be very nice. Going in october can be very risky as it is typically one of the rainiest months in the Caribbean. The mosquitos in September and October can be oppressive. Push it as late as you can!