Punta Cana or Cancun

[methodology]

BVI is a bit more remote though. I did a BVI catamaran charter for a week so we sailed around and island hopped every day. Most of the islands only had 1 bar/restaurant. You could definitely spend a week on Virgin Gorda though and book some excursions through the Bitter End YC.

I think USVI is probably cheaper too. You could spend a week on St. Thomas or St. John and not get bored.

Jost Van Dyke has 3 bars that are awesome, Tortola had a ton that’s all you need and I believe the Willie Ts is back

 

[upstater]

I know Greece like the back of my hand, having spent a great deal of time there. I was curious about the comment regarding the ferry system. Most people I know take the hydrofoils/fast ferries. Not the shipping ferries carrying all the cars and bulk goods. Maybe you took a wrong ferry?

As for Santorini, the upper town is packed because cruise lines drop off their hordes 2x a day, but we rented a home for 2 weeks on the cliff below the main town of Oia, and it was quiet as could be. We avoid the cruise ship times which arrive the same time every single day. Otherwise, there're not many people.

Some of the most spectacular Greek islands are totally unknown to American and most worldwide tourists. For instance, Milos. It's an incredible place, and it's mostly full of Greeks and Italians. I still have no idea why people go to islands that don't have nearly the natural beauty of these places.

 

[aburks41]

Jost Van Dyke has 3 bars that are awesome, Tortola had a ton that’s all you need and I believe the Willie Ts is back

Unfortunately we didn't get a chance to go to Jost Van Dyke. We did Beef Island, the Baths & Bitter End/Saba Rock, Salt Island, Peter Island, and Norman Island. I really want to go back there soon.

Jost Van Dyke and Anegada are on my list for the rest of the BVI

 

[Luckyhusky81]

My wife and I just got back from vacation in Belize. It was amazing and the coolest thing is you can go from a tropical beach to the rainforest in about two hours. Everyone is super friendly it is safe and they speak English. They also just lifted some super strict Covid policies and everyone is in a celebratory mood.

 

[methodology]

Unfortunately we didn't get a chance to go to Jost Van Dyke. We did Beef Island, the Baths & Bitter End/Saba Rock, Salt Island, Peter Island, and Norman Island. I really want to go back there soon.

Jost Van Dyke and Anegada are on my list for the rest of the BVI

Beef island is Tortola… Peter island and Norman are limited inhabitants so that makes sense. Jost is the same but soggy dollar and Ivan’s are musts… willie t would usually be off Norman’s not sure where is resides now

Anegada we were snorkeling following some turtles went back to shore and told the rental guy he started laughing and goes the biggest tiger shark was spotted out there last week guess what they eat, turtles

Bvi are great going to Tortola for 4th time this winter for a month of work. I love my job

 

[storrsroars]

Sit by the beach, we don't all golf umfortunately. This will be total relaxation

Then I'd go to St. Thomas. There's literally nothing to do there but sit on the beach and drink. I'm not a beach person, have no desire to go to a beach resort, and know nothing about other Caribbean islands, but I did go to St. Thomas years ago and recall that rum was cheaper than the bottled water.

Or maybe if you want to add snorkeling, Belize (I see LuckyHusky beat me to that suggestion).

 

[storrsroars]

Italy kind of ruins you for anywhere else. It has everything, in abundance.

Nah. Been 3x, and it's beautiful, historic, relaxing, and fun, but I'm not nearly ruined for other places.

 

[DaveHuskiesFan]

I’ve been doing a decent amount of traveling the last few years through credit card Sign Up Bonuses. Making lodging and flights free. Over the last few years I’ve gone to Cancun, Punta Cana, San Juan, Antigua, Miami, Las Vegas, Napa Valley, San Francisco, Charleston, Portland ME, Florence, Venice, Amalfi Coast (Positano and Praiano), and the Maldives. Even flown business class a handful of times on those international flights.

Cancun is fine if you’re looking to just relax, just beware of the sargassum.

Definitely look into redeeming those points if you have them!

 

[8893]

Nah. Been 3x, and it's beautiful, historic, relaxing, and fun, but I'm not nearly ruined for other places.

I said “kind of,” but this reply is on brand for you.

 

[storrsroars]

I said “kind of,” but this reply is on brand for you.

I've always felt that one has to live their brand. Otherwise, it's just hypocrisy

Unfortunately my brand doesn't include "wealthy", so there are far more places I still want to visit than money to get there.

 

[B1GEast]

When are you thinking of going? Is this a summer or winter vacation?

Late summer

 

[UconnFanDC]

Cancun has more to offer based on my experience and preference.

 

[BigErnMcCracken]

If you’re just looking to sit on the beach and crush boat drinks - nothing wrong with that, by the way - then it almost doesn’t matter where you go. Just pick a resort you like.

 

[UConnDad]

If it’s just beach and drinks I suggest St Maarten. Mullet Bay is my favorite beach anywhere. Little beach shack with beers, ribs, and wings. There is a lot more there too if you get rambunctious.

 

[Edward Sargent]

I found both depressing. Live on the Golf of Mexico so why waste money flying to Mexico. DR was also depressing when the rains brought the flotilla of garbage past our beach. Seeing natives protecting their bananas with AK 47s didn’t relax us nor did the banditos we saw at the turn playing golf. The happy massage on the beach was interesting though

 

[methodology]

Late summer

I would look into Aruba or Barbados. Don’t want to risk hurricane hitting you in a the DR or Mexico

 

[bendm]

Europe makes zero sense if you're just looking to relax at the beach/pool in an all inclusive type atmosphere

if one isnt leaving the grounds of the resort then FL makes more sense than mexico too. unless the exchange rate makes it more than worth the difference in flight cost.

 

[ConnHuskBask]

Anywhere else in the Carribbean

I don't know where you stayed but the place where I was in Cancun was crystal clear turquoise water with nothing but soft sand /sandbars for hundreds of feet off the shoreline.

I'm not saying it's the best, but I have a hard time thinking it wasnt good.

 

[mauconnfan]

If it’s just beach and drinks I suggest St Maarten. Mullet Bay is my favorite beach anywhere. Little beach shack with beers, ribs, and wings. There is a lot more there too if you get rambunctious.

Agree on St Maarten but I did hear it’s a shell of itself right now after the hurricanes they were hammered with. In rebuilding mode but could be wrong.

 

[ClifSpliffy]

it's all crapistan. for a puddle jumper, head down to PR.
big flight? Hawaii.
tweener? socal.

 

[methodology]

I don't know where you stayed but the place where I was in Cancun was crystal clear turquoise water with nothing but soft sand /sandbars for hundreds of feet off the shoreline.

I'm not saying it's the best, but I have a hard time thinking it wasnt good.

It’s not the same turquoise waters in the Caribbean (which is better) vs the gulf.

Best water I’ve ever seen is the exumas Bahamas followed by Anguilla

 

[methodology]

it's all crapistan. for a puddle jumper, head down to PR.
big flight? Hawaii.
tweener? socal.

Water temps.

San Diego is 63 degrees

Caribbean is around 78-82 degrees

 

[FfldCntyFan]

If the only concern is sitting on a beach....

 

[HooperScooper]

Late summer

O.K. here's the thing about Punta Cana during that time, it's during their rainy/hurricane season. You're taking a chance late summer. I think that's the wet season for Cancun also. We found that out going to St. Lucia in late October. We happened to hit a good week but the week before we were there and the week after they said was very rainy. They said there were days where it rained all day.

Not a big fan of either Cancun or Punta Cana. If you want to go to the Caribbean during the late summer I suggest Aruba. There's a reason a lot of people go there during the summer. For one it doesn't rain there much so it's always sunny. And it always has a nice breeze from the trade winds so it's not too hot. I was asking someone who lives there and they said the temperature isn't much different between the winter and summer. During the winter the high temperature is 82-83 everyday. During the summer the high is 87 everyday.

Also, there are a lot of great restaurants in Aruba if you're a foodie. Best food I've had in the Caribbean.

The other thing that was nice about visiting Aruba is there really isn't much poverty. Mostly middle class because they make so much money on tourism (80% of their economy). So it's very safe to be out and about there. Nobody ever tried to sell me anything. I went to Jamaica once and I was hounded all vacation. So much so that it was unpleasant.

JetBlue has direct flights there all summer from Boston and JFK. So easy to get to. All the hotels are only about 15-20 minutes from the airport.

The beaches and resorts are great. The only negative is there is no forest or rainforest there because it's so dry. The Atlantic side of the island (east side) is a desert. All the resorts are on the Caribbean side (west side) because the ocean is very calm there.

Let me know if you're interested and I can suggest lots of restaurants and a few resorts to stay at.

 

[husky429]

I know Greece like the back of my hand, having spent a great deal of time there. I was curious about the comment regarding the ferry system. Most people I know take the hydrofoils/fast ferries. Not the shipping ferries carrying all the cars and bulk goods. Maybe you took a wrong ferry?

As for Santorini, the upper town is packed because cruise lines drop off their hordes 2x a day, but we rented a home for 2 weeks on the cliff below the main town of Oia, and it was quiet as could be. We avoid the cruise ship times which arrive the same time every single day. Otherwise, there're not many people.

Some of the most spectacular Greek islands are totally unknown to American and most worldwide tourists. For instance, Milos. It's an incredible place, and it's mostly full of Greeks and Italians. I still have no idea why people go to islands that don't have nearly the natural beauty of these places.

Greek ferries are notoriously awful--including the ones for people. We took high-speed passenger ferries on every trip--2 out of the 3 were awful.