Now that we’ve seen a good chunk of the Caribbean, non-sailors ask us for vacation advice on the regular. We’re always happy for the opportunity to share some of our favorite spots with friends, so I put together this handy post featuring a few places we could see ourselves taking a land-based vacation someday.

Here are 12 vacation ideas, in no particular order:

San Juan, Puerto Rico

This isn’t just a clever ploy to get you to visit us! We obviously love San Juan and think it would be an incredible place for a vacation. It’s got a little of everything – the city of Old San Juan is simply amazing – the prefect blend of culture, art, history, and food – and, as we are now busy discovering, the beach hamlets right outside the old city are pretty fabulous too. I cannot think of another Caribbean island that offers this much variety in one geographic place. And if you can catch a short flight to Culebra (also listed here) for a few days, you won’t be sorry.


Culebra, Spanish Virgin Islands, Puerto Rico

For a totally laid-back, amazingly beautiful experience, hop over to Culebra (via plane from San Juan or ferry from Fajardo). Rent a golf cart to take advantage of all the island’s best beaches and snorkeling spots, of which there are many. Eat tacos at Zaco’s Tacos, our favorite restaurant on the island. Don’t forget to charter a day boat over to neighboring Culebrita for a magical day on an uninhabited island!


Calabash Bay, Long Island, Bahamas

I often tell people that the Bahamas feels otherworldly. Calabash Bay is one of the few places where non-sailors can experience what I mean.  This part of Long Island, Bahamas is so stunningly beautiful, we forgot to take a lot of photos. Whoops. When we visited, we had the entire anchorage to ourselves, along with one of the most gorgeous beaches in the Bahamas. Add to that miles of reef filled with coral and fish to explore right off the shore and a cozy, beautiful little boutique resort with a great happy hour and private villas for rent… now that’s vacation bliss.


Staniel Cay, Bahamas

Staniel Cay is off the beaten path – but those willing to hop a tiny, puddle jumper plane from Nassau to get here are rewarded with riches usually reserved for sailors: crystal clear water, plenty of great snorkeling (including the famous Thunderball Grotto – featured in a James Bond film), interesting beaches (two words: PIG BEACH), and the charming Staniel Cay Yacht Club, which has one of the best full service restaurants in the Exhumas.

There are several options for cottage rental on the island (the Yacht Club has cottages for rent, but you’ll find there are others available with some internet research). Look for a rental that includes the use of a skiff for exploring the surrounding islands to your heart’s content. Our friends Eric and Thea flew here and went cruising with us for a few days, then finished up their trip staying in a cottage on the island and they LOVED it.


St. John, US Virgin Islands

Of all the places on this list, St. John is the only place we’ve actually taken a land vacation ourselves – several in fact. St. John was our go-to beach vacation spot – there was no other place we’d rather spend one of our few, precious weeks off. We love driving our rented Jeep all over the crazy roads, exploring beaches, coral reefs, hiking trails, turtle nesting grounds and fun watering holes all over this crazy, amazing island (most of which is a pristine National Park). Accommodations vary from the extremely budget to luxury, and we had the best time when we rented our own little cottage off VRBO. Go quickly, the New York Times really likes it too.


Bitter End Yacht Club/Saba Rock Island Resort, British Virgin Islands

If you’re into sailing, windsurfing, and/or snorkeling – or you just wish to pop your collar in good company – this nautical resort and this boutique resort just next to it, on the island of Virgin Gorda is the place for you. Whether you prefer a Hobie cat, or a Lazer, or even a J-24, they’ve got a fleet of fun boats available for your sailing pleasure (and an adorable sailing school for those new to the sport). Accommodations are stylin’, the food is delicious, and we love the bar scene right around happy hour at Saba Rock, where salty sailors rub elbows with credit card captains and landlubbers from both resorts alike. PS – there’s awesome snorkeling, right out back. While you’re in the BVI, arrange for a chartered day sail around the BVIs with our friends’ top-rated charter company! I promise you’ll have fun.



Our stay in Anguilla was positively delightful – if you like beaches (we do!) and good food (yup!) – that’s what Anguilla is all about. Also, we appreciate the quiet – there are only a handful of hotels on the island and cruise ships do not stop here. If I were looking for a place to decompress for a week, this would be it. It’s totally chill.


A Taste of France: Grande Case, St. Martin

For a delicious beach vacation at the intersection of fabulous and shabby chic, St. Martin hits all the right notes. There are tons of different lodging options here, but I’ve had my eye on the LOVE Hotel in Grand Case, which features beachside umbrella setups with waiter service for guests, and a fun, modern style that doesn’t take itself too seriously. All along the beautiful beach there are restaurants – serving everything from foie gras terrine to BBQ chicken – and all of it is delish. Once you’ve had your fill, hop on the bus and explore the rest of this multicultural  island – there’s tons to see and do, on both the French side and the Dutch.


Resort Life: Marigot Bay, St. Lucia

While we didn’t visit many of the resort/marina combos scattered around the Caribbean, we were pretty psyched to pull up and spend some time at Capella in Marigot Bay, St. Lucia. We arrived Thanksgiving week and we, along with several friend boats, had the place almost to ourselves. There are tons of great pools, a really nice spa/gym situation, and the service was genuinely awesome. Bonus: they serve light, complimentary snacks poolside throughout the day. But the best reason to stay here, other than to take in the natural beauty of the Piton mountains, is the food. Chefs come to St. Lucia and they bring serious game. We especially loved the upscale Indian place right inside the Capella marina (we ate there three times!) and the hotel’s Thanksgiving dinner was suprisingly well put together and delicious.


Mustique, The Grenadines

Mustique has a reputation for being a playground for the rich and famous, but that’s really only the case between Thanksgiving and New Years. The rest of the time, there are many stylish houses for rent on this seriously quirky island – a cursory search of Air BnB reveals that there are deals to be had. We loved the beaches, the restaurants: Firefly up on the hill (this is also a nice hotel) and the more casual Basil’s Bar in the harbor.  Best of all, Mustique has a stable filled with pedigree horses, and the island is covered with manicured grounds, perfect for an evening ride. We’d love to return here with a group of friends.


Petit St. Vincent

Petit St. Vincent is a beautiful place to splurge on a fabulous resort vacation. The entire island is the resort, and it’s a full-on luxury experience – or so we are told. We visited their bar one evening for a drink (it was their soft opening week for the season and they were welcoming sailors onto the grounds) and were wowed by the clean modern style of the place, something you don’t often seen in the Eastern Caribbean. Best of all, the resort brings guests out to nearby Mopion island, a tiny spit of sand in the middle of the ocean that’s all your own.  It’s kind the kind of place where engagements are sealed on the regular.



Grenada was our home away from home during hurricane season, which gave us four months to explore everything the island has to offer. It’s a beautiful, wild place, filled with rainforests, waterfalls, beaches, and some of the nicest people you’ll ever meet. Grenada has lots of hotel and resort options to fit every budget, but for a unique eco-tourism experience, we recommend Le Phare Bleu (we lived in their marina and loved it!) or True Blue Resort (we hung out here a lot). If you do stay in a resort, be sure to rent a car so you can explore the whole island – there’s tons to see and do.