Choosing the Right Island

Old May 17th, 2016, 11:15 AM
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Choosing the Right Island

Hi Everyone! My husband and I are looking to plan our next 5-6 night vacation and I was hoping to get some advice on which island would best suit us. We don't have any set dates yet - these are flexible depending on whatever time is best for the island we end up choosing.

We are looking for something relatively easy to get to from the Philadelphia/NJ/NY area and would like to keep the trip (airfare/accommodations/food) under $5,000. We are in our early 30's and have never been to the Caribbean. We would like this vacation to be mostly relaxing on beautiful beaches with turquoise waters, with some exploring around the island mixed in. Snorkeling off the beach is important to us, but having "the best" snorkeling will not make or break our trip. We are not fans of all-inclusives and would prefer staying at a nice hotel/villa with a pool that is on or generally close to the beach where we have the opportunity to come and go as we please. We are definitely looking for something laid back, but love good food and would like to be able to do something in the evenings. We aren't looking for crazy nightlife, but grabbing a drink or two and listening to some live music, or walking around a little downtown area would be perfect.

We are open to any suggestions, but so far we are seriously considering the following: St. John, Bermuda (I know this technically isn't in the Caribbean), Anguilla, Virgin Gorda, and Exuma (swimming pigs sounds like fun!). Grenada also sounds interesting. I know these islands are all fairly different from one another, but I'd love to hear your thoughts on which may be the best option for us and when would be the best time to go. Thank you for your help!
bridetobe2013 is offline  
Old May 17th, 2016, 03:14 PM
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Easy Peasy...Jost Van Dyke! This is a tiny island off of St. Thomas and Tortola. Its simply amazing and I can't say enough good things about it. Its small enough for you to see the whole island and close enough to other islands for you to hop around a bit. You should speak to Bonnie at White Bay Villas ( This island has everything you'll need to get around and feel resort/stampede free. You can rent a jeep for the week and come and go as you please, you can rent a dinghy and visit the other islands just the two of you. What's great about Bonnie is she will send you an entire packet of how to travel, how to get to the island, how to rent your jeep, even where to grocery shop on the island. For it to be an "on the go" island, its set up really well for you to never want to leave! There are NO resorts on the island and is so low key, but PLENTY to do. The restaurants are 5-star, the bars are entirely accessible, the drinks are amazing and you can visit Foxy's for a bit of nightlife later on. You will LOVE this island and ou can thank me later
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Old May 17th, 2016, 07:03 PM
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Check out rental villas on Mahoe Bay, Virgin Gorda. It's an enclave of privately owned beachfront and beach access rental villas (many offer reduced prices if renting to a couple) on a wonderful 3/4 mile long light golden sand beach lapped by gin clear calm waters. There's a very good "triple" snorkeling reef that starts just 100'' or so off shore that runs the entire length of the beach. The location has a western exposure so you get views of neighboring islands and cays as well as the setting sun. In short it doesn't get much better anywhere in the Caribbean.

Island itself is quiet and laid back but with a variety of very good restaurants and bars in all price ranges some of which feature live entertainment that doesn't get too wild. Plenty of interesting things to see/do/explore at your leisure.

Fly into St. Thomas then take ferry or short island hopper flight to island.
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Old May 18th, 2016, 08:44 PM
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Anguilla any time May-early August or Mid Nov-mid-December. Beautiful beaches, several different shades of turquoise water and talcum white sands, awesome food, great locals, beach bars and live music. Art galleries, heritage trail, rum tasting, mini-golf. If you want more shopping, gambling , other culture, take a day trip to St Martin/St Maarten (public ferry runs every 30 minutes). Check out CuisinArt, Frangiapani, Rendezvous Bay Hotel. More expensive and beast beach-Cap Juluca. Malliouhana is fully redone. Cheaper and more self catering but on the beach and near great restaurants- Turtle's Nest (beach service from Straw Hat Restaurant), Turtle's Nest. Anacoana is a short walk to beach. Villas range in price also. The island is 3 miles wide, so you are never far from the beach
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Old May 20th, 2016, 04:21 AM
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I've been to 4 of the islands you mention -- St. John once, Virgin Gorda once, Anguilla 20+ times and Bermuda 7 times. My vote is Bermuda. It's beautiful with great beaches, really nice downtown and is very sophisticated. Lots of hotel and restaurant choices. However, there are no car rentals, so you'd need to be comfortable riding motor scooters which are a lot of fun (but be careful on them). The other 3 islands are all great choices too, but based on what you're looking for, I'd go with Bermuda. Very short flight from Newark, Philadelphia or JFK.
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Old May 28th, 2016, 11:13 AM
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The OP does not like all-inclusives. We don't either. That's one reason (of many) that we chose The Buccaneer resort on St Croix.

You can find details at my two threads:

We were upgraded to oceanfront deluxe suites, with patios right at the beach.
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Old May 28th, 2016, 01:49 PM
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And St Thomas isn't known for all-inclusives anyway. Lots of choices for a condo on a beach with easy access to ferries and boat trips to other places.Good snorkeling and easy to get to from Philadelphia and NY/NJ.
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