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If you are staying in Portland, plan on spending time around the Old Port and Commercial Street since it is easy to walk, full of good food, and the waterfront vibe is great. A small rental car also helps if you want a quick coastal drive to places like Cape Elizabeth, and October evenings can feel chilly near the water. For the Boston side, I once used Blue Nile Livery for an early airport pickup and it made the travel day much smoother.

YES!!! "SOME" chairs, not nearly enough for five ships and where can they lay towels down when there are HUNDREDS of people standing??? I'm simply trying to make people aware that although Maho is very exciting beach to be at, there are catches to spending the day!! That's all!!

Enjoy your stay. A trip to the Pitons is worth it (although climbing either one is a major effort); the mud baths are so-so, I was given a free excursion there so I did the trip. I don't know if they offer a boat trip to the Pitons but that would be more fun than a road trip.

Keep you wits about you and your head on a swivel and your dinghy locked as crime on some of the islands is out of control. That said the seas, beaches and islands are very beautiful.
My favorite island it the area is Bequia. Drink at the Whaleboner bar, drinks and service are not very good but where else can you drink from a whale rib bar while sitting on whale vertebra barstools? Walk the waterfront and dine at the Plantation Hotel.
Don't miss a stop in Mustique for a drink at Basils Bar and a fine dinner at the Cotton House. If open, the Firefly Hotel has a wonderful bar with a spectacular view.
The bay on the north end of Mayreau is very nice. Here and everywhere you go ignore the boat "boys" that come out to "assist" and anchor where you feel is best.
In the Grenadines you can and should visit Petit Tabac, it's where Johnny Dep had his rum set ablaze. Take your dinghy through the poorly marked cut in the reef to reach it.
The beach bbq in the Grenadines is fun and picturesque but expect massive amounts of mediocre food.
Just a bit further south is Mopion Island, Petite St. Vincent (whole island seems to be a resort and they charge to land), and Petite Martinique. Petite Martinique is unique as the locals, while dark skinned often consider themselves Scottish. I recommend the Palm Restaurant and Bar, the family that runs it are beyond nice.
Sandy Island off the west coast of Carriacou is a wonderful anchorage with amazing snorkeling.
I really don't care for Union Island but it's a must to clear in and out. Anchor near Happy Island and enjoy it before taking the dinghy into the cool dinghy dock in Clifton Harbor. The "Boat Boys" here are awful.
As someone who has sailed the BVI over a dozen times and really loves it I find the Grenadines more beautiful, more interesting, and more even more fun than the BVI.

Have a great trip! I'll be there on my boat this fall.

The original post is over FOUR AND A HALF YEARS OLD! I think they’ve been by now.😂😂

My dream is a trip to Nazare, Portugal to see its huge waves. Any advice about what else is interesting there in half an hour drive? (gonna rent a car)

Dominica if you like eco-tourism, St. Bart's if you want "French Sophistication" on a small island, Grenada or St. Lucia if you crave a mountainous island with lush tropical feel, Grand Cayman if you desire something more cosmopolitan but flat and arid like Anguilla, or St. Vincent & The Grenadines if you want an experience island hopping similar to the BVI's, Barbados for the reasons mentioned by islandVet88 and perhaps Bonaire if you crave excellent snorkeling and dive sites.

This page lets you check boxes for what you want at a beach and then displays those that match your needs.

https://barbados.org/barbados-beach-guide.htm