Tall agenda!

I don’t know how far you want to travel. I really liked Stowe, VT. The downtown is smallish, but very nice. Many good restaurants there. I highly recommend the history tour at the Von Trapp lodge. You can also your Ben and Jerry’s factory in Stowe. You can try to time it when they have an event going on. When I was there it was British car weekend, and Saturday night they closed the streets and had a “Beatles” band and everyone was out walking around, listening to the music, checking out each other’s cars.

There are all sorts of little towns along the Hudson as you travel north from NYC. You can go to the Castle in Tarrytown (I don’t think I’ve ever been there) Hyde Park and see the FDR Museum and home and Eleanor’s cottage. Also, while there tour the Culinary Institute and get some food in the Italian cafe (the regular restaurants there are quite expensive). The tour is led by students so you get interesting info not only about the school, but also about their experience. More north of there is Rhinebeck where Chelsea Clinton got married. Another to research up there on the other side of the Hudson is Woodstock. I have not been there in 30 years, so I have no idea what it is like now, but it used to be a very artsy little town. The Catskills to the south and west are a nice change of scenery if you want to be up in the mountain air. All of this is within 2.5 hours of NYC.

Ballroom dancing just look up Fred Astaire dance studios near you. Or, google ballroom dancing near you.

Since you want to mingle you might consider a singles cruise. They leave out of Jersey and NYC. Last minute cruises can be inexpensive if you have a lot of flexibility. There are week ling to Bermuda and north to Canada out of the ports near you. There must be 4 and 5 days cruises to various other ports also. The ports usually have lots of shopping in small towns. The ship usually has a disco, pool, events to participate in, restaurants, etc.

As to Kayaking near you, I immediately think of the Adirondacks in upper New York state. They are beautiful with more than 3,000 lakes and ponds, and 30,000 miles of rivers and streams. According to this site there are many kayak rentals up there and they offer many of the other activities on your list. Here are discriptions and photos of what they claim are the 9 best places to kayak in the Park.

We have a guy here, @Luckyguy, who lives up in there. You might want to either invite him to answer this question, or PM him directly. He’s an expert on the area and might even know of which hotels and casinos offer what you are hunting for and even where to find the interesting little villages you mention above. You could make it a one-stop shopping thing, or a frequent weekend destination.

You might revisit Cape May for a weekend of introductory sailing lessons through one of the hotels or yacht clubs. Outward Bound is up there and you can find out more about what they offer in Cape May and elsewhere here. This might be the start of something interesting and long-term for both of you. I’m a big proponent of sailing, as is another member here, @CWOTUS, who might know the northeast. Maybe there is a circumnavigation in your future.

Welcome to Fluther.

Sorry, Scotty, I got you confused with a new guy on another question. I take back the Welcome to Fluther. Lol.

What I know of: Take a drive up to Hunter Mountain, Ellenville, Margaretville NY. Charming little towns if you like rural areas. Hunter Mountain is a ski mountain and in the summer they have festivals, for example, Native American, German, etc.

Take a day and go to Mohonk Mountain House in New Paltz. You have to pay to hike on the grounds, but it’s great. The whole area is great.

Cape Cod is great and a whole different atmosphere – New England at its best. A little farther is the coast of Maine. So beautiful. Vermont is beautiful, too. Not coastal, but really nice towns and great stuff to do.

Drive down to Virginia and see Williamsburg if you like history. Busch Gardens is great if you like amusement parks.

Take a ride west in Pennsylvania. There’s a coal mine you can tour and it’s very educational and also fun. I’ll google it and let you know the name of it. Amish country, Lancaster County PA is also a whole different thing to see.

NY Hudson Valley – Lyndhurst in Tarrytown, Roosevelt’s home and Vanderbilt mansion in Hyde Park, plus a bunch of other historical mansions in the area. If you’re into history, that’s for you. If you’re not, then maybe not so much.

Some of the best times I’ve had in my life have been journeys where we meandered and with little definite plan – just drive, stop, chill, drive some more.

I live near Asbury Park and it is a happening beach town these days – even in the winter. Great live music at the bars and clubs, a biergarten, art house movie theater, great Japanese restaurant (owned by friends of mine) and a fun boardwalk. Langosta Lounge is a bar/restuarant that has music most nights and a music and brunch thing on Sundays. A new boutique hotel is opening soon. If you like quaint towns, Ocean Grove right next door to AP is a Methodist camp meeting town and on the National Register of Historic Places. It has some cute small shops and restaurants, B&Bs, and wonderful Victorian restaurants and a quieter boardwalk. Sandy Hook National Seashore is a great park for beachwalking and there is a nude beach there – although not a sex scene particularly.

For canoing and kayaking, you could try either the Pine Barrens rivers such as the Wading River and the Otsego. I think there is a place called Mick’s Canoe Rentals that probably rents both and will transport you. On the Delaware River above the Gap, Kittatiny Canoe Rentals should rent out both. Stokes State Forest near there is a great place for hiking and camping.

Eidts: I meant “Victorian buildings” not “Victorian restaurants” and it’s the Oswego River not the Otsego.

Actually yeah let me rescind what I said about NJ, PA and NYC. Just give me anything and everything. New England area – whatever.

You could go to old town Alexandria outside of DC. If you’ve never been to DC you can see some of those sights too.