Interesting you being in Hawaii and asking for vacation trip suggestions. I live in Florida and there are so many great vacation destinations for me in my own home state right in my own backyard. Maybe consider doing something in your own beautiful home state of Hawaii…do something new in a part of Hawaii you have never really explored before. Sometimes the best things are right under our own nose!
http://www.mackinacisland.org/
But it is pronounced MAK-in-aw.
If Japan’s a possibility, it is lovely in the Spring. If you don’t speak/read Japanese, suggest learning to read katakana, which is used for non-Japanese words, like coffee, shampoo. (quick anecdote- at the bath in an inn, I couldn’t distinguish between shampoo & conditioner… you can imagine the result)
As you’re interested in higher education, although a tour, how about those exotic sounding ones with experts in the field. For example, I’m always getting brochures for the ones sponsored by the Metropolitan Museum or alma maters of my family. Years ago, my father-in-law went on a cruise to the Antarctic sponsored by the Smithsonian.
Even if you don’t want the tour route, the websites for educational tours, like those above or eco-tours, might provide inspiration.
Whatever you go take a relaxing trip. I would love to be in one of the Vancouver/British Columbia islands, I think we just had a thread recently. Personally I need to do a train trip in Canada West to East for my husband when I retire, he loves train ride. I still have to decide when to go. Not too cold I hope but I think it would be beautiful to see the snow.
These threads alwsys get us dreaming. With your budget and the fact you travel lot- and haven’t been back to Europe- I’d consider Rome, Florence, Venice. Or any two of those. You can do as little as you like, just hang some days, visit local markets, have a coffee somewhere and people watch. Rome can be a lot of walking, but I suspect you’d pick a nice hotel that always has taxis near. Train from Rome up. Go before the tourist crush, which means be coming back by mid-May. Nothing beats off-season. If you’re really adventurous, rent a car to visit some small historical or farming towns.
What do you really like to to? You and DH bond on these trips, balance the museums/good dining with pure downtime? Or the sort of “get my money’s worth” travelers? Cuz if you can handle laid back, hands down, for an anniversary, I’d be thinking Greece, any sunbaked island, mopeds, maybe a VRBO where we could some days cook, feel like we live there.
I would go to Tuscany in a heartbeat. Rent a villa and explore the Italian towns, take a cooking course. You can have busy sightseeing days followed by relaxing “sit at the villa and drink wine” days. 
Speaking of Rome, I had planned for at least a week in Tuscany, rent some nice villas with a swimming pool and enjoying the relaxing pace, kind of living like Sting(in one of his DVD) for a week. I had planned to see Florence before and Rome after this week in Tuscany. Unfortunately, it was cancelled due to various reasons but I might do that again next year.
I agree with the Tuscany suggestion! I’d stay in Florence for 5 days and then stay in the country for 5 days. Rather than renting a villa, I’d stay at a Relais & Chateuax type property. I’ve planned whole trips just based on what Relais & Chateaux places looked most appealing. I like being able to see, and mingle, with the other guests. So when traveling as a couple and not a huge group I prefer an inn over renting a house.
Fiends do 5-6 weeks in Tuscany every May-June. They rent a villa and collect enough friends (or friends of friends, you could latch on) who come in for a week or two, fill the extra rooms, share costs, hike, cook, drink wine, tour ruins, eat at wayside places, and all. Her timing is too cold to swim in an unheated pool. They usually stay a week in an agritourismo or B&B’s, depending. I could never go with them because of the girls’ schedules. Go for it, Dr G!
@lookingfoward, I had planned for similar trip before kid #2 was born but things happened and she is near 20 and I have not made that trip. I was thinking of a villa because I wanted my kids to come and experience it with me, plus with the Euros down, it was not as expensive. But, I’m still nervous about driving there so I hope it happens next year, not sure I like to be anywhere without a car.
I can highly recommend this place for four or five nights in the Tuscan countryside:
Combined with 5 nights in Florence and then maybe a 4 nights in a place in the lakes, that would be a perfect 30th anniversary celebration.
They rent a car for the whole time. A lot of the villas she chooses are slightly out of the way. And frankly, they couldn’t afford the level they want to accomplish if they took a small place for themselves only.
Nottelling: wow.
We went to Capetown for our 30th (as part of a larger trip). It was spectacular!
If you want to see some absolutely spectacular scenery I suggest you to take the road trip from Banff to lake Louise to Jasper National park in Canada. June is a wonderful month to go- the nites may be a bit cool but the days should be lovely!
Wow–these are all amazing ideas. Keep them coming!
I had planned a trip to Europe for S’s graduation in 2010, but the fallout from the Icelandic volcano and an infection made me switch it forva train and road trip from LA to Seattle, Ranier and back down the national parks for 3 weeks.
There is a WONDERFUL train trip from Vancouver to Banff that winds through the Canadian Rockies ! The combination of the train and road trip would be a fantastic vacation!. Check into when the summer performance season starts at the Banff School of Fine Arts and see some unbelievably talented Canadian performances there as well. I love the town of Banff- touristy but still kind of fun. And the Banff Springs Hotel is a elegant world class hotel!
When in-laws were close to or past retirement age, they enjoyed leisurely trips to New Zealand, South Pacific islands, which included Tonga, and Portugal.
If you enjoy train travel and like planning your own itinerary, highly recommend first class Eurail pass or passes for specific countries. Have thoroughly enjoyed traveling in France, Italy, & Switzerland this way. Would travel longer distances with the pass, then have a base, e.g. Florence, from which to make short trips with other modes of transport, unless we had unlimited days with the pass.
I can highly recommend the Grand Hotel on Mackinac Island. H and I are celebrating #33 there this summer with 3 of our 4 kids. Excellent food, incredible views of the Mackinac Bridge, Lake Huron, and Lake Michigan, no cars, quaint shops, lots of history and natural rock formations. But…5 days is plenty.
My parents celebrated their 50th there with all 18 family members.
Mackinac Island is lovely; it’s beautiful and quaint and small. You can see the entire island in just a few days, which is fine if you just want to relax, but if you’re interested in seeing sights or being on the move, then it’s not the place for you. If you go, stay at the Grand Hotel. (I worked on the island every summer when I was in college.)
http://www.grandhotel.com/specials/new-2015-packages/mothers-day-weekend/
What about Iceland? It’s a nice place, lots of hot springs, friendly people.
My husband and son went to New Zealand last year for two or three weeks. They just did the North Island. My sister went with her family the previous year and did both North and South Islands. All were very happy with their trips.