Which Island Should I Choose for My Vacation?

We love to talk tropical travel and we love that you ask our opinion! But, the hardest question for us to answer is actually the one we get asked the most, “Which Island Should I Choose For My Vacation?”

Why is that a tough question? Although we’ve yet to meet an island we don’t like for some reason or another, everyone has such different vacation tastes.  Some want the best beaches, others want shopping or luxurious accommodations or absolute solitude. The best fishing, snorkeling, rum, diving, sailing, hiking, historical sites, foliage…. We’ve been trying to come up with a method to help people select destinations based on different criteria, but decided the best thing to do is what we already do –  show you the islands through our photos and let you know what we’ve enjoyed – then you can see what areas you might be interested in visiting!

Below we’ve listed many of the islands we’ve recently been to and just a few key words of what we’ve really enjoyed about that island. Some are links to articles we’ve written on that destination with additional pictures. There are many additional GREAT things about each of these islands, but here are a few tips to start with.

Ready for a little tropciation? Let’s go to the islands!

Shoal-Bay-(600)-OShoal Bay, Anguilla

(see map)
Stunning, white sand beaches, Shoal Bay, Rendezvous Bay, Dune Preserve, excellent dining, great beach bars (see several in Sandy Ground), Gwen’s Reggae Grill, live music, luxurious accommodations, easy to explore on your own

Many (365 they say!) gorgeous beaches, Half Moon Bay, Dickenson Bay, Shirley Heights, Antiguan Smile Rum Drink, English Harbour Rum

Find a place to get “off the grid”, beautiful white and pink sand beaches, bonefishing and other fishing, snorkeling, peace and quiet, conch, variety of accommodations

Champers - Barbados - OChamper’s Restaurant

Excellent dining, Champers Restaurant, Superb beaches, Crane Beach, Mount Gay Rum Factory Tour

White-Bay-3--OWhite Bay, Jost Van Dyke, British Virgin Islands

British Virgin Islands
(for individual maps of the British Virgin Islands, use the drop-down on the Island Map feature on our home page)

Fantastic sailing destination, secluded and beautiful beaches, Anegada Lobster Dinner on the beach, fantastic beach bars, Jost Van Dyke, White Bay, Willy T, Virgin Gorda, The Baths, Smuggler’s Cove, roti, easy to explore on your own, Sandy Spit, sunsets, Painkillers, Bubbly Pool, snorkeling, floating, Cane Garden Bay, full moon parties, crystal clear water, driving on Tortola, North Sound Virgin Gorda

Dominican-Repub-Golf-1---OCorales Golf Course

Dominican Republic
(see map)
Excellent golf, reasonably priced all-inclusive resorts,
Mamajuana, Coco Loco, long stretches of pretty beaches,
The 3 B’s – Bermudez, Brugal and Barcelo Rums


(see map)
All-Inclusive Resorts, Jerk Seasoning, 7 mile Beach, Floyd’s Pelican Bar, Blue Mountain Coffee, Waterfalls, Appleton Rum and Rum Factory Tour, Bob Marley Nine Mile Tour, Jamaican Smile, red snapper, Dirty Banana

Gustavia-Harbor-O Gustavia Harbour

St. Barthelemy
(see map)
Great place to yacht watch, high end shopping, excellent dining, beautiful beaches, homemade vanilla infused rhums, overlook of Gustavia Harbour, watching planes land on the very short runway!

Orient - Bikini Beach (600)Orient Beach, St. Martin

St. Maarten/St. Martin
(see map)
Gorgeous beaches on both the Dutch and French sides, clothing optional on some French side beaches, nightlife, great beach bars, watch planes land over your head at Sunset Beach Bar, Karakter Beach Bar, Marigot Market, Sarafina’s Bakery, street festivals in Grand Case, duty free shopping, we found it easy to explore on our own, wide range of accommodations, excellent dining options – especially in Grand Case, busy cruise ship stop – but because of that, there are many activities to choose from

Saltwhistle-1-(600)-OSaltwhistle Bay, Mayreau

St. Vincent and the Grenadines
(see map)
Excellent sailing destination, beautiful remote islands, gorgeous quiet beaches, filming location for some parts of the Pirates of the Caribbean,
Sunset Very Strong Rum, Tobago Cays, excellent snorkeling, turtles, clear turquoise blue water, Happy Island, Mopion, a few exquisite resorts, not busy, Petit Tabac

Pier-Pleasure-OPumpkin Bluff Beach, North Caicos

Turks and Caicos
(see map)
Spectacular white sand beaches, quiet and remote, great snorkeling, variety of accommodations, long beach walks, conch shells, sand dollars, cave exploring, Bambarra Rum, da Conch Shack, bonefishing, conch stew, fried conch, exploring secluded cays

Hawksnest-1-(600) Hawksnest Bay, St. John

US Virgin Islands
No passport needed for US citizens going to St. Croix, St. John, St. Thomas – each island has it’s own personality and they’re easy to explore on your own

St. Croix
(see map)
Buck Island, Cruzan Rum Factory To
ur, Cruzan Rum,
Sandy Point Beach and Wildlife Preserve, Cruzan Confusion, Mt. Pellier Domino Club, seaplane from St. Croix to St. Thomas

St. John
(see map)
very beach on St. John, cheeseburgers at Skinny Legs, hiking, snorkeling, exploring the shops, restaurants and bars in Cruz Bay

 St. Thomas (see map)
Megans Bay, the view and banana daiquiris at Mountain Top
, Paradise Point Skyride, Bushwackers at the top, Duffy’s Love Shack, Lindquist Beach, variety of accommodations, Bones Rum

Banana-Daiquiri.-OjpgView of Magens Bay (and a Banana Daiquiri) at Mountaintop, St. Thomas

So – any ideas on where YOU would like to go next?

For even more island posts, be sure to check out our Blog Directory by Island!


Copyright©Rum Therapy Beaches, Bars & More, Tropical Travel Guide, 2014
Pictures and other content may not be re-used without written consent from Rum Therapy, LLC


  1. Dianne jones says:

    Cayman Islands. Grand Cayman especially I would live to help you see and feel what I have for over 70 trips. DJ

    • Dianne – we love the Cayman Islands too! We just haven’t been there recently enough to cover them through our photos and articles. It is HIGH on the list of upcoming trips. We’ll have to ask you for your recommendations when we head back!