In honor of the anniversary of our escape from real life, here are the top ten thirteen of our favorite places we’ve visited so far (in reverse chronological order):

1.   Culebra, Puerto Rico – Once we discovered the little secret beach, I was sold. But aside from that, the few shops and restaurants were unique, the snorkeling was the best so far, the anchorage was well-protected and it was easy to get to shore, and anywhere that allows golf carts on all the main roads is a winner to us.
2.   Rincon, Puerto Rico – This little village had just the right mix of cultures: locals, surfers, aging hippies and young hipsters. It was definitely the best surfing we’ve found, though it probably isn’t fair to compare since having a car here made everything exponentially more convenient and accessible for us than usual.
3.   Old San Juan, Puerto Rico – The beautiful 16th century architecture and history of Old San Juan was the perfect reprieve from the uninspired concrete block construction we had become accustomed to seeing. As usual we didn’t do a lot of research before visiting so we were very pleased to find ourselves feeling as if we’d been transported to Europe in the charming walled city.
4.   Luperon, Dominican Republic – Here we felt that we were finally somewhere truly foreign and we loved it. The people were so kind and welcoming, the natural beauty was remarkable, and living with our budget there wouldn’t mean perpetual boredom. We felt like we just scratched the surface of the fun to be had in the country and can’t wait to go back and visit more of the anchorages.
5.   Hawksbill Cay, Exumas, Bahamas – All of the islands in the Exuma Land and Sea Park were a dream to explore, but this one stands out. With only one other boat anchored nearby we walked down the entire beach and through the jungle without seeing a soul. (Okay, so we stumbled upon a group of young sunbathers once we got to the other side of the island, but it was a brief encounter. Get it?) Also, I found one of those elusive perfect yoga spots I’m always searching for.
6.   Norman’s Cay, Exumas, Bahamas – An excellent example of what defines the Bahamas, the clear blue water for snorkeling and fine sand beaches to sink your feet into, this one made us appreciate the fact that all of these gorgeous islands are accessible to us only because we’re on a boat, and therefore the struggle is worth it. (Of course you could just fly there on a private jet if you have heaps of money or whatever.)
7.   Eleuthera, Bahamas – I name the entire main island because the best anchorage is probably Hatchet Bay; a town that is not so great in and of itself. But traveling around the long island we got to poke around in caves, surf, beach comb, and perfect the art of hitchhiking.
8.   Hope Town, Abacos, Bahamas – Yes, one more destination in the Bahamas. This was prettiest town we visited in the Bahamas. Some might call it too touristy and maybe too much like home, but we thought it seemed like a great place for someone to fly in to visit us! It had everything you would want for a relaxing tropical vacation, except we were there a little too early in the year and had to keep moving to get away from the chill.
9.   St Augustine, FL – This was another city we knew nothing about ahead of time, other than hearing that other cruisers really liked it. Even though it sometimes felt like we were in Disney World walking through the town center, the old timey feel was authentic and it was fun to be surrounded by countless options for entertainment.
10. Dismal Swamp, VA; Alligator River, NC; Waccamaw River, SC – These were our favorite stretches of the Intracoastal Waterway and very similar, so I’m taking geographical liberties to combine them into one. Traveling slowly through these three states it was a nice routine to wake up early in the morning, hoist the anchor while drinking our coffee, and peacefully motor along with little to worry about while passing through lovely expanses of swampy forest. The feeling of camaraderie among cruisers was unbeatable and we wished the little group we were traveling with could stick together always.
11.  New York City – This one goes without saying, but visiting by boat made it extra special.
12. Provincetown, Cape Cod – This might just take the cake for the most unique town in the US. We loved all of the meticulously maintained houses, trendy restaurants and bars, and the simple fact of the town’s existence as a celebration of gay culture. The fact that we felt we almost died getting there probably helped too.
13. Maine – Can I just say all of Maine? We wish we would’ve had more of a clue about what we were doing while we were here in order to have seen more of the world-renowned cruising grounds. We would love to go back for another season of endless pristine anchorages, quaint towns, wildlife preserves, and rocky beaches. It was by far the best place we could’ve
hoped to find for initiation into the cruising life.

This list is kind of ridiculous because we’re comparing apples to oranges, and as we thought back on the trip so far, we found we really enjoyed most of the places we’ve stopped. There was something special and memorable about them all. We’re looking forward to revisiting our favorites when we head back through in the winter. Because now that we’ve made it to the Caribbean, hurricane season is upon us and we need to go hide. Our plan is to be in Grenada by July and stay in the vicinity until the end of November. Though a hurricane could still find us in Grenada, the chances are slim.

Once we reached Puerto Rico we really had three options that we drove ourselves crazy considering: sail all the way back to North Carolina or elsewhere on the East Coast by July, make some money and leave again next winter; remain in the hurricane zone through the summer if we found a safe place and jobs to allow us to continue south next season; or continue sailing south now. Considering how long it took to get this far, we aren’t in a hurry to redo all that sailing – albeit in an easier direction – especially because it would mean rushing through all of the islands and not having much time to really enjoy ourselves. The safest anchorages around Puerto Rico and the US Virgin Islands weren’t ones we imagined having much success working out of, so we went with option 3.

The money we’ve set aside for this trip might hold out until we’re able to work again, and we wouldn’t have considered the possibility of moving all the way down to Grenada before we got our tax return! So it’s not that we’ve been doing such a great job sticking to our budget, we’re just willing to hope that things will continue to work out and we’ll discover the means along the way.

2 thoughts on “You’re the Tops”

  1. Hey Guys! I hope this finds you well

    I don't know if this is the best way to get in touch, but my carrier pigeons are all on vacation. I guess i'll try Jon's email too, as a back-up.

    Anyway, i'm going *tentatively* be in Martinique in late June. If that falls close to your route south for the season, it would be great to see you. My conference is 22-24 June, with travel ±1 days around that. If you happen to be in the neighborhood – within a 2 hour puddle-jumper plane ride – it would be awesome to catch up. No stress, as the conference has already changed dates once.

    Let me know your thoughts (facebook or email), and have a great day.

    – Flip

    1. Hey Matt! We are in Dominica and headed to Martinique in a couple days! Jon will email you back about making plans. So glad you got in touch, it would be so much fun to see you!

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