Thanks for all the help on the forum. Here's how it went. Hopefully this helps others in their planning.
We chose Saint Kitts merely by default due to it being one of the few locations in the Caribbean we could get to using airline miles semi-last minute. We lucked out in that regards. Such a great destination with just enough touristy amenities without it being an overly tourist manufactured island (like many are). Our beach vacation history outside of the continental USA before this trip has been all the islands of Hawaii, Grand Cayman, Dominican Republic, Bahamas, and Mexico.
Unfortunately, for us to get to Saint Kitts on miles required an overnight in Miami on the way there and on the way back. We booked a 2 bedroom villa at the Marriott after researching some rental properties on the island. We received a “book 4 nights and get 3 free” promotion due to it being the offseason. The Marriott was wonderful. It has the usual resort amenities (pools, beach, restaurants, casino, etc…). It was a nice place to relax when not exploring the island. The villa was awesome. We saved a bundle eating most of our meals in instead of dining out 2 or 3 times a day.
Day 1: We picked up the rental car from Thrifty. I highly recommend renting a car. The first thing they showed me was where the spare and jack are located. I checked out our nice bald tires and grimaced. It was pretty pricey, but we more than made up for the cost as opposed to using a taxi. We went to the grocery store about 4 different times, to/from the airport, Cockleshell beach 3 times, Shipwreck beach twice, Nevis once, around the island once, to the port once, miscellaneous errands numerous times, Frigate bay 3 times…and that is just off the top of my head. I estimate the taxi trips would have cost at least $700 (not that we would of taken a taxi as often as we used the rental car). Our first day we just settled in at the Marriott and purchased groceries. Grocery prices I would say are about 25% - 40% higher than at home. Of course that all depends on what you are buying. Chips, soda, etc… were more expensive than the meats/cheeses/veggies. I did find the IGA to have a better selection than the Rams, which they also had much more no-name brand stuff that was available for reasonable prices. I found it amusing that a can of soda was about the same price as a bottle of beer. Liquor prices were really good which made rum the flavor of choice for the trip.
Day 2: Went on a short run to the Caribbean side of the island and zig zagged my way back through back roads and the golf course. I love to explore new places with a run. Then we went to Shipwreck beach in the morning because that seemed to be most recommended. No one was there when we arrived at 10:00am (likely since it was offseason). We found the beach a little narrow. I “think” it may be a favorite because it is a pretty short/cheap taxi ride from the Marriott. We headed to Cockleshell beach next. This was my favorite of the beaches we went to…calm water, nice beach bar, water activities, beautiful views, and good sized beach. We spent the morning there and our 3 year old daughter loved the shells to pick through and calm water to get in and out of (over and over again). We did have an “incident” with one of the monkeys in the cage there. It snuck up and grabbed our daughter’s hair and pulled it. It made for some drama with the monkeys all hollering followed by our daughter screaming and sobbing for awhile. No harm, but it did put the kibosh on her wanting to be near any of the monkeys on the trip. We rented a 2 person kayak and paddled around the bay for a ½ hour which was fun. Once it got to be nap-time we went back to the Marriott. I got in the routine of using their fitness center during the afternoon during nap time. For a resort it was really nice. I’ve been to full service gyms that have worse/less equipment. We cooked dinner for the evening (we ate in most every evening but 2 dinners on the trip and a couple lunches). The villas have 4 different thermostats. This was great for accommodating the temperature for each person’s preferences which made for great sleep.
Day 3: We drove to the Turtle Beach area. We never really found turtle beach (I think unless it was a beach that was very seaweeded over at the end of a dirt road). We did end up driving to the very end of a road that got really steep really fast. It was the most nerve-racking driving of the trip. I really thought our compact car wasn’t going to make it up the high grade at some points, and then boulders were scattered about on the road that I dodged along the way up. I was near turning around (out of fear) until we reached the top with great views of the island/ocean below. I couldn’t quite figure out what the deal is with that road. I guess it was built for a future subdivision of luxury homes on a cliff, but it was definitely not cleared of rocks / boulders regularly. Anyways with Turtle Beach being a bust we headed back to Cockleshell for more sun and relaxation. Continued the day with another trip to the gym, pool time and relaxation at the Marriott
Day 4: We decided to drive around the island. The drive started through Basettere which got the blood flowing while navigating the tight traffic. Driving on the island isn’t particularly difficult, but the rules of the road are a little different than the USA…and not just driving on the other side of the road. For instance, stopping suddenly to talk to a friend on the street (while blocking traffic) is perfectly acceptable and other drivers just need to wait. The speed limit is pretty much your comfort limit with driving fast while navigating random pot holes. The drive along the island was fun to see the different little towns. I pretty much kept my eyes fixated on the road but I know the passengers got to absorb the island. We made a stop at Brimstone Fortress ($8 per person). Neat fort that is well preserved with great views of the island and surrounding islands. Knee gave out on me exploring the fort which put a damper on future runs on the island as well as the consideration of hiking the volcano. We didn’t stop many places along our tour around the island due to not doing the research ahead of time so I’m sure we missed a lot of hidden gems. Stopped at Thrifty rental car on the way back to see about getting a car in Nevis, but no luck with the culture festival going on. That evening we attempted to see the sunset from a point on the way to Cockleshell beach but last minute clouds blocked the sun. Did see quite a bunch of monkeys scurrying about though at a road leading to an undeveloped subdivision on the cliffs. There were monkey sitings throughout the trip.
Day 5: We decided to take the car ferry to get to Nevis. Wasn’t my preference from what I heard about it running late and potential over-charge issues. The car ferry was quite a “trip”. The lady handling the registering of vehicles wasn’t too popular with many of the locals. She was trying to organize everyone, and people were getting aggravated. We were some of very few tourists using the car ferry. Getting on the car ferry was a bit nerve-racking. They don’t spare an inch on getting every possible car on that thing. I was one of the first on and was boxed in the back (had to climb out the window to get out of the vehicle). Cost for this was $80 round trip for 3 of us (plus child). Everyone seemed to warn us that driving on Nevis was a bit crazy. I found it easier than driving on Saint Kitts. But we did not stray much from the main road around the island so that could be why. Nevis was cool to see, but wouldn’t be a must-return place. We stopped at the culture festival and had some chicken, ribs and rice. Stopped and swam at a couple different beaches. Grabbed a drink at Sunshine’s bar with (can’t remember the name) must-try drink. The ferry was running way behind but we got there early enough to not have to wait more than about an hour each way. For dinner we tried the Pizza shack at the Marriott which was very good.
Day 6: We went to Port Zante since it was a cruise ship day. Did a little shopping and walked around Downtown Baseterre a bit. The cruise ship ports all kind of seem the same to me from each one I’ve ever been to. Did the “picture with the monkey in the diaper” thing. Then we decided to check out the beach at Majors bay. It was nice with great views. My wife and I swam out to the abandoned ship wreck. The snorkeling was pretty good in this area (best I’d seen yet on the island). A little creepy with the murky water around there and being a bit off from the beach so we didn’t stay long. Also our waterproof camera decided to stop working at this point so no pics of the ship wreckage which would of been nice. Knee was feeling a little better and we wanted to do a little jungle hiking. It seemed recommended to not try doing that solo. So we asked a taxi driver outside the Marriott how much he would charge to take us. $120 for three of us plus a child seemed reasonable so we set it up with him for the next day.
Day 7: Met our guide this morning for the hike. He took us a round-about way and showed us some areas off the beaten path. Some of the places we had already seen by car, some we hadn’t. He eventually took us to the jungle hike which literally started right where we had parked a couple days earlier while exploring the island. Had we only known. The hike was fairly short. Probably a little over a mile round trip (which was good since I was carrying a 3 year old most of the way with a bum knee). It was nice to know that he knew his way in and out of the jungle (although I think most could of followed this trail in and back out safely). He did show us different thing like almonds we ate, how to make ear rings out of some parts of the tree, etc… It was definitely worth doing if one does not have a car to explore. But I don’t think it was quite worth the $120 (plus tip) on top of our rental car price to see many things we already had seen. He took us to Romney Manor which we walked around a bit. In the evening we went to Jam Rock for dinner and had very spicy jerk chicken and jerk pork. Beautiful views of the Caribbean sunset from here. We also went to the casino and used our $10 promo coupons (plus free spin for bonus money) we each got for our stay. I thought the casino was pretty nice for a resort casino. We spent the rest of our evening packing up to head home the next afternoon.
Day 8: Spent the morning soaking up the last of our sun at the Marriott beach and pool before heading to the airport to head home.
Overall: Great island. Great resort. Great people. I wish people in America were ½ as friendly as everyone was on Saint Kitts. Almost everyone we talked to seemed like old acquaintances that we were catching up with. Really hope we make it back here sometime in the near future.