Planning a 5 year anniversary trip with my husband. Went to St. John, USVI for our honeymoon and loved it, but want to try something new. Looking for a nice combination of peace/quiet/privacy with easy/short distance access to activities like dining, shopping, cultural spots, etc. Ocean view a must! Was originally thinking Bahamas but haven't been impressed with what I've found so far. Checking into any Caribbean islands. Thanks for your help!
Has anyone ever stayed here: Sheraton Nassau Beach Resort and Casino? Looks pretty nice, price is reasonable and flight schedule is good. Their web site seems to indicate that they are close to downtown, other dining and shopping/activities. If you've been, can you say how hard or easy it was to go off resort to other things if you wanted to? Thanks!
Thoughts on Key West? Where to stay, what to do, etc. Is it worth flying into Miami and doing the overseas highway drive or should we just fly directly into Key West and rent something if we need to get around? Overseas drive looks long and could possible chew up a lot of precious vacation time. Thanks!
Trip Plan Details
- Straight Wharf6 Harbor Sq, Nantucket, MA 02554
- Lola 4115 S Beach St, Nantucket, MA 02554recommended Lola 41Love the setting and the food. A bit of funky manhattan in the relaxed Nantucket setting. Gives you a reason to wear that cute new dress you bought to show of your summer glow. Pan Asian food.
- TOPPER'S Restaurant at the Wauwinet120 Wauwinet Rd, Nantucket, MA 02554recommended TOPPER'S Restaurant at the WauwinetFirst of all, we love this hotel. But if you aren't staying at the hotel it's worth going to their restuarant. Located on the very tip of the island, if you are staying more in town they will pick you ... read moreup on a boat to take you to the restuarant. Come early and enjoy the garden that leads to the sea. Must have the most comfortable lounge chairs ever. The food in the restaurant is good. It is a sophisticated and elegant environment. Fantastic wine menu. I will say, however, we've been to this hotel several times and the last time we stayed there the quality of service had decreased. So, hopefully it's back to being up to snuff. If you cannot make it for dinner, definitely go for brunch. Really yummy food. And the outside seating is lovely.
- The Nantucket Hotel & Resort77 Easton St
- Galley Beach54 Jefferson Ave, Nantucket, MA 02554
recommended Cottages at Boat Basin.Comment.8 months ago . FlagDon Zereski
These cottages on the harbor are very nice and centrally located. The same company that operates the nicest hotels on the island - White Elephant and Wauwinet also runs the boat basin cottages. Check out the Ship's Inn and Cliff Lodge too.
- The Cafe509 Southard Street, Key West, FLrecommended The CafeGreat food. Excellent Veggie Burger Bits, tasty sweet potato fries, and superb portabello mushroom sandwich. Great variety of vegetarian food, and tastes great. Fresh juice menus with a wide variety. ... read moreDecent service. Nothing in Key West, Fl is cheap. And you know what it doesn't have to be. This was well priced as far as I am concerned.
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I just came from Key West like 3 weeks ago. I spend most of my time at Fort Zachary Taylor. Its only $2.50 cents for the whole day, and is the best place to go to take a dip in the water, and the cleanest water from the land side of key west. Also, make sure , I mean make sure you take a boat tour which includes snorkeling, and if you know how to Scuba please research it. As far as musuems go there is an older spanish type architected building Cuba something building, the butter fly museum. If you have emotional attachment you could check out Hemingways House and his many, many cats. I stayed out of Duval street, all people do there is drink, drink, drink - its quite pathetic - as if I couldn't have a drink on my couch all day here in new york city. Key West, however, has great food even for a vegetarian like myself, I am sure all the food there is great.
Also, I recommend flying with Jet Blue to Fort Myers, and then taking the Boat Ferry to Key West going into Keys, and if you want you could do the same route back -Yet, I recommend flying out or the reverse of the above. Do not go into Miami - it sucks - the American Airlines Planes are really freaken old!. Also, Delta has nice planes, yet, if you connect to a shorter distance flight from Atlanta, Georgia - Delta starts using older planes. If you are flying use Jet Blue.
I made a mistake this time, and took the bus shuttle, and took for ever to get there from Miami. On my way out I just flew out. Best is to take the Boat-Ferry, and its cheaper, and enjoy the water. Hope all this helps....
- Captain Tony's Saloon428 Greene Street, Key West, FLrecommended Captain Tony's SaloonOne of the best dive bars anywhere in the world! In the spot of the original Sloppy Joe's bar, which was Hemingway's old hang out, the saloon is owned and operated by one of Key West's colorful town ... read moremascots - Captain Tony. If you've ever heard the Jimmy Buffett song "Last Mango in Paris", it's about the life of Captain Tony. The place is full of character and a dangerous pit stop for anyone trying to stay sober!Arlo Hemphill
My favorite bar in the world. Don't be fooled by Sloppy Joe's - this is the REAL place that Hemingway used to hang out at. The bar's owner is the subject of the Jimmy Buffet song 'Last Mango In Paris' - which, for a travel buff, is reason enough to check the place out.
- Blue Heaven729 Thomas St., Key West, FL 33040recommended Blue HeavenKey West at it's best. Outdoor seating in a tropical garden full of strutting roosters and massive strangler figs. The food is wonderful, the service full of Key West character, and the experience ... read moretruly tropical.Arlo Hemphill
Eat breakfast here!
- National Key Deer Refuge28950 Watson Boulevard, Big Pine Key, FL 33043-6087recommended National Key Deer RefugeOne of my favorite stops on the drive south through the Florida Keys. These little deer were isolated from the mainland for generations, shrinking down to a dwarf version of their mainland cousins. ... read moreThey're cute and very approachable. Sometimes you have to drive around on lonely backroads of Big Pine Key until you find a group of them. But once you do, they're fairly sociable and don't really have fear of humans. Very fun wildlife interaction!Arlo Hemphill
My personal favorite pit-stop on the way to Key West is Big Pine Key to see the tiny key deer. These white tail minis roam the island at will, but sometimes take a little dedication to track down. My advice, drive slowly down the old backcountry roads on the island and eventually these amazing deer will appear. Once found, they are quite approachable, making for perfect wildlife and you photo opportunities!
- The World Famous Tiki Bar84001 Overseas Highway, Islamorada, FLrecommended The World Famous Tiki BarThis place has a reputation much bigger than the bar itself. Apparently, everyone's cousin has had a night here they'd like to forget, but they're friends won't let them. In the day hours, it feels ... read morejust a like a chill tiki hut by the water that happens to pour insanely volatile rum drinks. But once the sun sets... who knows?Arlo Hemphill
Aside from Key West, the most popular party spot in the Keys is Holiday Isle at Islamorada. The Tiki Bar and her sister establishments boast a beautiful sand beach and several pools, and are literally a non-stop party. Beware - you could easily get stuck here if you drink too much!
- Alabama Jacks58000 Card Sound Road, Key Largo, FLrecommended Alabama JacksGrab a beer, order some chow and watch for manatees to swim by in this little secret of the mangroves. Off the beaten trail of the Florida Key's, Alabama Jacks is a remnant of old Florida - the place ... read moreof Jimmy Buffet songs before the strip malls and golf courses. Swing by on a weekend afternoon and, if luck is with you, they'll be some great, local live music playing. The food is good, the brew is better and the hideaway shack environment is beyond charming. Visit now before someone decides to turn this into a Cheesecake Factory.Arlo Hemphill
HipKat - I highly advice flying into Miami and doing the drive. You might want to fly out of Key West, but the drive down is at least half the adventure. This is a stunningly scenic byway with tons of points of interest - and the whole thing will get you riled up for a good time in Key West. When you first get o the Keys - I advise taking the alternate route instead of Route 1. Your first stop will be here - Alabama Jacks - a little piece of pure old Florida in the middle of the mangroves.
recommended La FortunaLa Fortuna is only a few hours from San Jose, the capital city of Costa Rica and anyone with a lust for lava should not miss this destination. Imagine Hawaii - only take out all the bad (loud ... read moretourists, spam, and people you don't want to see wearing grass skirts). The small town of La Fortuna boasts plenty of touristy charms but none greater than the Arenal volcano that entrances all with lush jungle foliage and hypnotic orange-red lava! Stay at a hidden resort, go on a tropical hike, wake up to wild animals with a cup of the world's best coffee, and soak in natural hot springs, ok you get the idea...better start looking for cheap flights. Pura Vida!Paul @TAKEYATHERE
I know you're thinking the Caribbean because it's a quick flight but don't forget to take a look at Central America. Costa Rica is a no stress/easy spot to pick and you can fly direct from NYC. I lived in Costa Rica for a whole summer and loved it. Enjoy the trip no matter where you pick!
commented on this trip
The Sheraton is nice... I stayed there years ago. Very close to shopping and casinos. It is really easy to get around. Make sure you schedule a boat trip to neighboring islands. The hotel can arrange it for you.
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Okay... So i am going to put out another alternative.
Playa Del Carmen! It would be perfect and there are two hotels I love!
Le Reve Hotel and Spa and Mosquito Blue. Both are reasonable, well located, shopping nearby and plenty to do. You fly into Cancun BUT don't have the crazy crowds and DO have the beautiful Caribbean waters. There are also more flight options as every major carrier flies to the area. If you have your heart set on the Caribbean then I can suggest Royal Plantation in Jamaica. It is incredible!! I have stayed there three different times and the service is outstanding! Adult Only and a bit more up front but is All-Inclusive and close to Ocho Rios for shopping, it is the greenest part of the island, surrounded by the Blue Mountains.
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Thanks everyone! I really appreciate all the great suggestions. I'm finding that any place that looks interesting is virtually impossible to get to within a reason amount of time. Many of the islands involve a stop over in Miami, sometimes for 3-4 hours. Any thoughts on places with direct flights from New York? I just wanna get there!! :)
recommended English HarbourOld world charm in a New World paradise port of call. This historical shipping center is now the center of all things luxurious on the island of Antigua. Cruise around the marina or climb up to the ... read morelofty Shirley Heights for a party you will never forget.Arlo Hemphill
Antigua is another great option. This is a truly Caribbean nation that balances is it's culture in fine tune with it's breath-taking beaches and tourist industry. This is a place to not only get away from it all, but to find yourself in something new and unexpected.
recommended Jost Van DykeJost Van Dyke is BVI's hidden treasure. More low key, less developed and relaxed than the other islands, it nevertheless equals or outshines them in terms of raw, natural beauty. There's a number of ... read morelittle tucked-away B&Bs, resorts and such, and just enough hopping night life to keep you from craving a trip to one of the more populous islands. Check it out, it's awesome.Arlo Hemphill
Why go much further than the Virgin Islands when paradise is at your doorstep? Unlike the US Virgin Islands, the British Virgin Islands are uncrowded, low pace and always relaxing. Yet, there's always something fun to do and good shopping/dining/entertainment is never too far away. Perhaps the most idyllic and laid back island is Jost Van Dyke - check it out!
recommended TobagoIts a twin Island state. Tobago is the tourist spot. Lovely beaches, many good resorts and Hotels. wide variety of Cuisine. lots of activities and also some great Eco friendly activities. There are ... read morecoral reefs, nature trails with waterfalls, remnants of some of the oldest forts in the Americas. There are even tours to old operational Cocoa estates.Balram Mahabir
The sister isle is the commercial place 20 minutes by aircraft and by ferry 3hrs. Transport is very cheap and cost of services very reasonable.
recommended BarbadosBarbados is a coral island, On the West Coast of Barbados, coral shore beaches of fine white sand stretch along a blue-green sea. Coral reefs fringe the Barbados shoreline to provide excellent ... read moresnorkeling and Scuba Diving. Along the East Coast a lively surf is blown briskly by the strong and constant trade winds and the waves pound against a rocky shore. A mild and pleasant tropical climate. lots of art, activities, night life, music, history and some of the best restaurants to be found anywhere. Lots of Hotels along the beaches. There are lots of things to do. A night cruise explore the Harrison caves, the undersea floral garden.Balram Mahabir
I have been to most of the Islands in the Caribbean. from Tobago to Antigua Bahamas Margarita. My Favorite list is St. Lucia, Barbados, Tobago, Cayman Islands, Grenada and Antigua. Which is best depends on your needs. They all have there unique charm and pros and cons.recommended BarbadosBarbados, the easternmost island in the Lesser Antilles, might take a little longer to get to than other Caribbean isles, but it's worth the trip. The relatively small island (only 21x14 miles) is ... read morepacked with rich history, beautiful beaches, a lively local culture and an island-wide affinity for rum punch that will keep you swaying with the beat long after you've left. Whether it's dancing to the wee hours at the raucuous Oistins fish fry/outdoor music festival (held every Friday night), stand-up paddleboarding in front of your all-inclusive oceanside resort, watching a polo match at the local fields or hiking through the rural, mountainous east coast, it seems improbable that such a tiny island nation can pack such a heavy punch.Ramona Flume
Hi Kathy! Barbados is my favorite Caribbean island and I think it has the right mix of easy-to-access activities and leisurely privacy that you're looking for....
recommended ProvidencialesI was in Turks and Caicos with my boyfriend and his family for Christmas. Was the perfect combination of beach/activity/romance/chill. Great spot for an anniversary. Will definitely return ( but will ... read moreleave the family at home!)
recommended Tayrona National ParkBeautiful coastal park that gives you a wonderful variety of coastlines ranging from pristine white beaches to rocky and coral coasts. The park also has beautiful jungles with great trails to explore ... read moreit. Check out the ancient ruins of the indigenous Tayrona pueblo, and don't forget to enjoy a beautiful sunset on the beach.Daniel Mason-D'Croz
I would suggest taking a look at Colombia's Caribbean coast. There are great beaches, wonderful colonial cities like Cartagena and Santa Marta that give you access to good dining and night-life. Tayrona is especially beautiful, secluded, and relaxing and is a short distance from Santa Marta
recommended TulumTulum town itself is not much to write home about but its beaches are spectacular--i think they're the best in the Riviera Maya. Plus, the beachfront hotels are mostly bungalow/thatch-roof style--some ... read moresuper high end, others totally basic--but most have a bohemian, laid back vibe to them. All that, about 90 minutes south of Cancun International Airport.Liza Prado
Clearly, Tulum is not on an island but it is the Caribbean and has some of the best beaches in the region. It's also a peaceful and romantic place and is a stone's throw from Maya ruins, diving/snorkeling, and outdoorsy activities in the neighboring Sian Ka'an Biosphere Reserve.....
recommended Grand CaseA quiet little town on the French side, Grand Case is the perfect place to relax on the beach and enjoy all that St. Martin has to offer. Grand Case is less hustle and bustle than Philipsburg or ... read moreMarigot, and you won't get bus loads of beach goers from the cruise ships that you will at Orient Bay. The dining options are diverse, delicious, and abundant with most places being right on the beach so you can take in the beautiful sunsets. And its location makes it easy to explore other parts of the island from Grand Case, that is if you ever feel the need to leave.Gregory
St. Martin is great and this was my favorite little spot on St. Martin.
- Sandals Royal Bahamian Spa Resort & Offshore IslandWest Bay Street, Cable Beach, Nassau | PO Box 39-CB-13005, Nassau 20317, New Providence Islandrecommended Sandals Royal Bahamian Spa Resort & Offshore IslandA luxury vacation spot. All inclusive, adult only. Perfect for weddings, honeymooners or to celebrate anniversary. Have they own private white sand beach and own private island. Amazing activities and ... read moreentertaiment, perfect dining and spa and many many other goodies for you to have a memorable vacation.Sveta Berlyant
They have many Sandals resorts all around Carribeans.
recommended Saint Martin / Sint MaartenI didn't love St. Martin, but I was there as a guidebook author, and had to cover every single square inch of the island, from the loud casinos to the French side beaches. I'd give the French side ... read morefive stars and the Dutch side two stars. I loved the butterfly sanctuary, the peaceful beaches, the incredible restaurants and the cozy hotels of the French side. I hated the mega-resorts, offensive restaurants (seriously, a naked-woman sushi restaurant? really?), cruise ship traffic and depressing nightclub feel of the Dutch side. But, the island is easy to reach, less expensive than neighboring islands, and there is plenty to do overall.Alex L
Stay on the French side and this could be a great anniversary destination. You can also take day trips to St Bart and Saba, two of my favorite islands (but not much to do there besides eat, beach and hike).
recommended St. CroixSt Croix is often overlooked by those who opt for busy St Thomas or tranquil St John, which is all the better for those who realize its charms. The island has something for everyone: outdoor ... read moreactivities like golf, tennis, sailing and even quad biking, all-inclusive resorts or private villas, fine dining to beachfront bars. The former colonial capital of Christiansted has a sleepy charm, and the regenerated waterfront in Frederiksted has plenty of shops and cafes to entertain cruise ship passengers. Hiking opportunities abound and fantastic secluded beaches reward those who make the effort to find them. St Croix is worth considering for your next Caribbean vacationThe Northernist
St Croix is worth looking in to for the reasons I've mentioned above. The island has a different feel than St John; certainly it's more developed but still has areas of seclusion and tranquility. You've got a big range of accomodation options; there are plenty of resorts but private villa/apartment rentals are definitely a possibility too. There are plenty of activities to try and I'm happy to recommend things I've done there depending on your tastes. Some great restaurants and cafes too. Good luck planning your trip!