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You are here: Home / Senior Women Travel / World Travel for Baby Boomers / Caribbean / Explore the Sultry Grenadines in a Sailboat
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Explore the Sultry Grenadines in a Sailboat

by Rebecca Forstadt-Olkowski 15 Comments

Imagine island hopping to unknown paradises that pirates once inhabited, with reggae music wafting through the air as warm breezes blow, and lying on pristine beaches as you laze away the summer. I took a three-week cruise on a 50ft sailboat from St. Vincent and the Grenadines ending on the island of Spice in Grenada.

Find locally-led guided tours in Saint Vincent and the Grenadines, here.

The Grenadines are part of the Windward Islands in the southern end of the Caribbean south of Martinique to Grenada. It’s an area where chocolate cacao beans grow and rainforest fruits are plentiful. Being laid back is the order of the day.

Sailing in the Grenadines allows you to experience island life in a way that cruise ships never do. You can interact with local salty characters and full-time boat dwellers who live where the wind blows them. The stories they can tell in beachfront bars and shanty shacks will amaze you.

Landing in Barbados

Most small islands in the Grenadines don’t accommodate jets so we flew into Barbados and spent the night at the Butterfly Beach Hotel. It’s located in Christ Church, Barbados on Oistin Bay, and was a perfect location to greet the Caribbean.

***Please click on the thumbnails below to view the images below view full-size.

Baby Boomer Travel | Caribbean | Crane Beach Rocks - Barbados
Crane Beach Rocks – Barbados
Baby Boomer Travel | Caribbean | Crane Beach - Barbados
Crane Beach – Barbados
Baby Boomer Travel | Caribbean | Beach - Boats - Barbados
Beach with Boats – Barbados
Baby Boomer Travel | Caribbean | Banks - Barbados
Banks – Barbados
Baby Boomer Travel | Caribbean LRS Lounge and Bar Barbados
LRS Lounge and Bar – Barbados

We were only there for one night but hired a driver who took us to the Sunbury Plantation House built around 1660 to harvest sugar cane and St. John’s Parish Church built in 1645.

Baby Boomer Travel | Caribbean | Sunbury Plantation House - Barbados
Sunbury Plantation House Dining Room Barbados
Baby Boomer Travel | Caribbean | Sunbury Plantation House - Barbados
Sunbury Plantation Barbados
Baby Boomer Travel | Caribbean | St Johns Parish Church - Barbados
St John’s Parish Church – Barbados
Baby Boomer Travel | Caribbean | St Johns Parish Church -Barbados
St John’s Parish church – Barbados

Things to do in Barbados

St. Vincent and the Grenadines

From Barbados, we boarded a puddle jumper to St. Vincent in the Grenadines where we met up with our group who had flown in from various parts of the U.S.  Kingstown, is the capital of St. Vincent and is its bustling hub. We went into town and walked through the busy outdoor market.  

We could see a peaceful but lively protest taking place in the street. Residents were angry at the sitting Prime Minister who they called a dictator. St. Vincent is a parliamentary democracy with the British monarch as head of state.

Baby Boomer Travel | Caribbean | Protest - St Vincent
St. Vincent Protest 2007
Baby Boomer Travel | Caribbean | St Vincent market
St Vincent Market

Immediately upon arriving in St. Vincent, I was affected by the intense Caribbean humidity. My feet swelled up and I could only wear sandals. That didn’t deter us from touring the island and we allowed a local man to lead us on a hike to the Botanical Garden and a tour of the town in exchange for a “tip.”

Goats rule the islands

They are everywhere. Almost everyone in the Grenadines owns a gaggle of goats, sheep, or chickens. You must be careful not to hit them with your car because they wander through towns like tourists. Goat yoga, anyone?

A goat on Union Island in the Grenadines
Goat wandering the streets on Union Island

We were a group of six. Two were part-time sailors and the rest were mere passengers along for the adventure. We rented a 50-foot Beneteau sailboat from Sunsail. It had 4 tiny staterooms below and one in the bow filled with supplies.

Our quarters were tiny and the bed I shared with my partner wasn’t much bigger than a twin. Sailing is like camping, which isn’t something I’m a big fan of. But somehow, the crystal clear azure sea made it bearable.

That night we stayed at the Blue Lagoon Hotel at the Sunsail marina.

The mosquitos started munching on me immediately, even though I wore a strong repellent. I became their favorite host during our trip while everyone else was spared. The next day, as we were sitting at the bar waiting to board our boat, I started feeling weird and was convinced I had Dengue fever. Luckily, the feeling passed and was probably a result of the humidity.

Baby Boomer Travel | Caribbean | St Vincent - St George Cathedral -
St. George Cathedral – St Vincent
Baby Boomer Travel | Caribbean | St Vincent - Botanical Gardens
Botanical Gardens – St Vincent
Baby Boomer Travel | Caribbean | St Vincent - Sunsail Marina
Sunsail Marina – St Vincent
Baby Boomer Travel | Caribbean | St Vincent - Sunsail Marina
Sunsail Marina – St Vincent
Baby Boomer Travel | Caribbean | St Vincent - View Kingstown
View – Kingstown – St Vincent

Things to do in St. Vincent

Bequia

We enjoyed a slightly rough and tumble ride to the island of Bequia. It’s known as “the island of sailors and boats.” I didn’t get seasick but the other woman in our group, a motion picture stuntwoman, had to use the bucket several times.  

As we sailed into Admiralty Bay, we could hear the gentle sounds of reggae music wafting through the air. Bequia is a charming little island with small sea-themed restaurants and colorfully painted shops. We anchored our boat in the bay and took our dinghy to the shore to explore.

Baby Boomer Travel | Caribbean | Bequia
Bequia boats and bay

The next day, we hired a driver who took us on a tour of the island including the Old Hegg Turtle Sanctuary.

Baby Boomer Travel | Caribbean | Bequia - OldHegg Turtle Sanctuary
OldHegg Turtle Sanctuary – Bequia

Sailing life in the Grenadines is relaxed and free-spirited. It’s not unusual to see people, especially the French, jump off their boats buck-naked. If we had known our boat mates better, we may have skinny-dipped too.

Find things to do in Bequia, here.

Mustique

If you’re wondering where Mick Jagger, Kate Moss, Shania Twain, and The Beckhams hang out in their spare time, it’s Mustique. Other residents have included David Bowie, Tommy Hilfiger, Raquel Welsh, and Princess Margaret. This picturesque island is privately owned, making it much different than the other islands in the Grenadines.

The rich and famous own large estates that are secluded and isolated from the paparazzi.  When they aren’t in residence, their homes are rented out to visitors who can afford the high price tags.

Baby Boomer Travel | Caribbean | Mustique - Beach
Beach on Mustique

We anchored at the marina where we could walk directly into the famous Basil’s Bar. It’s a rustic Hemingwayesque establishment operating for over 50 years. It’s known as one of the world’s best beach bars. Make sure to order their rum punch.

As we sipped our cocktails someone invited us to a private reception at The Cotton House, Mustique’s exclusive premiere hotel.

Even though we were shabby from sailing, we happily obliged and proceeded to hobnob with the jet setters, although Mick was nowhere to be found… darn!  

The next day, we hired a local driver (our favorite way to explore new places) and toured the island and beaches. Sadly, we didn’t run into Mick or Shania but had fun anyway.

Baby Boomer Travel | Caribbean | Beach - Mustique
Beach at Mustique
Baby Boomer Travel | Caribbean | Cotton House - Mustique
Lilypond – Cotton House – Mustique
Baby Boomer Travel | Caribbean | House - Mustique
House on Mustique

Find things to do in Mustique, here

Canouan

Did I mention I’m not a good camper?  By the time we arrived at Canouan, I was over having to sleep on the boat. We had to leave the hatch open while we slept to avoid sweltering in the humidity. It never failed that it would rain on our heads several times a night and we’d have to get up and close the hatch until it stopped.

I also wasn’t thrilled with the toilet being in the shower and was dreaming of an air-conditioned hotel. Once we set anchor in Canouan, my partner and I took the dingy and booked a room at the Tamarind Beach Hotel. It was wonderful!  I took a “real” shower, and was a much happier “camper.”

Canouan is a sleepy but stunning island and I wish we could have spent more time there.

Baby Boomer Travel | Caribbean | Canouan
View of Canouan

Find things to do in Canouan, her.

Mayreau

Mayreau is a tiny fishing village and is the smallest inhabited island in the Grenadines with a population of about 300.  A smattering of beachside bars and restaurants can be found in the village and a couple of vendors are onshore.

We landed at Saltwhistle Bay and were invited to join in on a BBQ hosted by Jean’s Seaside Restaurant and Beach Bar under an outdoor canopy. We sat there as it rained, mosquitos and all, and enjoyed a tasty freshly caught fish dinner.

Baby Boomer Travel | Caribbean | Salt Whistle Bay, Mayreau
Salt Whistle Bay – Mayreau
Baby Boomer Travel | Caribbean | Mayreau - BBQ
Mayreau Fisherman – Mayreau
Baby Boomer Travel | Caribbean | Mayreau Beach Bar
Beach Bar – Mayreau
vBaby Boomer Travel | Caribbean | Mayreau - BBQ
Outdoor canopy for BBQ – Mayreau
Baby Boomer Travel | Caribbean | Mayreau - BBQ
Fresh caught fish steaming over the BBQ – Mayreau
Baby Boomer Travel | Caribbean | Mayreau - BBQ
Us eating BBQ – Mayreau

Find things to do in Mayreau here.

Tobago Cays

The Tobago Cays is an archipelago of tiny flat islands surrounded by unbelievably crystal clear sea. It’s a popular snorkeling spot and is mostly uninhabited. Like many of the islands in the Grenadines, we were met by local boat vendors selling bread, ice, art, and other necessities.

We even had two Rastafarians come up to our boat smoking Gangia weed. At Tobago Cays, a tee-shirt vendor named Sydney greeted our boat. He had a deep voice that sounded just like Sebastian in The Little Mermaid. I got a big kick listening to him try to get us to buy his wares.

Most of the boat vendors in the Grenadines are helpful and honest. We took advantage of their services whenever we could.

Baby Boomer Travel | Caribbean | Tabago Cays
Tobago Cays

Tobago Cays is primitive with almost no amenities, but you can hook up with locals who will take you on tours. Scuba diving is said to be spectacular at both Tobago Cays and Mayreau.

Top tips to enjoy Tobago Cays

Union Island

Next was Union Island. It had an internet café that I quickly took advantage of to check in on my kids.

Baby Boomer Travel | Caribbean | Union Island - Anchorage Yacht Club
Anchorage Yacht Club – Union Island
Baby Boomer Travel | Caribbean | Union Island - West Indies Restaurant
West Indies Restaurant – Union Island
Baby Boomer Travel | Caribbean | Union Island - Street sign
Street sign – Union Island
Baby Boomer Travel | Caribbean | Union Island pier
Union Island Pier
Baby Boomer Travel | Caribbean | Union Island - Shoemaker
Union Island shoemaker
Baby Boomer Travel | Caribbean | Union Island - Captain Gourmet Yacht Provisions
Captain Gourmet Yacht Provisions – Union Island

Union Island was originally inhabited by Arawak and Carib Indians before it came into the possession of French and English slave owners. They brought hundreds of Africans to the island. The island has a fascinating history of slave traders, pirates, and mixed cultures.

Most of the people we saw were locals, ex-pats, and foreigners. I bought a stunning handmade turquoise necklace with silver sea symbols from a Frenchwoman who had spent twenty years living on a sailboat in the Caribbean. She finally opened a tiny shop on Union Island.

We stayed overnight at the Anchorage Yacht Club in Clifton Harbor, next to the island’s tiny airport.

Baby Boomer Travel | Caribbean | Union Island - Anchorage Yacht Club
Anchorage Yacht Club – Union Island

Find things to do on Union Island, here.

Carriacou

Before arriving at the island of Grenada, we had to dock at Hillsborough in Carriacou to go through customs. Carriacou is part of the nation of Grenada which is separate from St. Vincent and the Grenadines.

They are all part of the Commonwealth Caribbean. Carriacou is known for having over 100 rum shops. It’s an enchanting and friendly island with many areas of interest. As we did on all the islands we visited, we found a local driver who took us on an island tour.

Baby Boomer Travel | Caribbean | Ades Dream Ltd Carriacou
Ades Dream Ltd – Carriacou

Find things to do on Carriacou here.

Grenada

Grenada was formed from the crater of an underwater volcano and is a stunning and diverse island with gorgeous beaches, small towns, and rainforests. The capital city is St. George’s, which has a deep bay formed by the crater.

The island was originally inhabited by the Arawak and island Caribes and is known as the Isle of Spice. It’s the perfect place to purchase, nutmeg, cacao balls, cinnamon, and other rainforest products.

Baby Boomer Travel | Caribbean | St. George, Grenada - half sunk boat
Half sunk boat – Saint George’s- Grenada
Baby Boomer Travel | Caribbean | St George, Grenada
Saint George’s, Grenada
Baby Boomer Travel | Caribbean | St George, Grenada
Saint George’s, Grenada
Baby Boomer Travel | Caribbean | St. George, Grenada
St. George’s, Grenada
Baby Boomer Travel | Caribbean | St George - Grenada
Saint George’s, Grenada
Grenada - The Grenadines - Caribbean
Saint George’s from Fort Rupert
Baby Boomer Travel | Caribbean | St George, Grenada
Saint George’s and fort – Grenada
Baby Boomer Travel | Caribbean | Fort George - Grenada
Fort George, Grenada
St. George, Grenada
Fort Rupert in Grenada
Baby Boomer Travel | Caribbean | Fort George, Grenada
Fort George, Grenada
Baby Boomer Travel | Caribbean | Church - Grenada
Church in Grenada
Baby Boomer Travel | Caribbean | Grenada - Beach
Grenada Beach – man with coconuts
The Grenadines - Caribbean
Beach in Grenada

You may remember the invasion of Grenada by the U.S. in 1983 when Ronald Reagan was President. Grenada gained independence from Great Britain in 1971 and Eric Gairy became Prime Minister. Maurice Bishop staged a coup in 1979, removed Gairy, and took over.

He was Marxist-Leninist and his party, the People’s Revolutionary Government (PRG) had close ties with Cuba, Nicaragua, and communist bloc countries.  In 1983, there was another coup, this time by members of the same party. Bishop, along with his cabinet members, were executed at Fort George in St. George’s, Grenada.

Baby Boomer Travel | Caribbean | Memorial at Ft George - Grenada
Memorial – Fort George – Grenada

The U.S. became involved when they learned a 10,000-foot airstrip was being constructed on Grenada by Cuban construction workers.  Along with the Regional Security System, they invaded Grenada on Oct 25, 1983, and the pre-revolutionary government came back into power. Grenada is now a stable, peaceful, and safe place to visit.

We arrived on the island after maneuvering through a brief squall. Luckily, our captain knew what he was doing. We spent the night at the Grenada Yacht Club in St. George’s.

The next day we headed out to the True Blue Bay Boutique Resort, near Prickly Bay, where we stayed for the rest of our trip before flying home.  It’s set in an idyllic bay with a marina bar and is charming beyond belief.

Baby Boomer Travel | Caribbean | Grenada - True Blue
True Blue Resort – Grenada
Baby Boomer Travel | Caribbean | Grenada - True Blue
True Blue, Grenada – Tree House Rooms

Our group spent several days exploring the island in a rented car. Highlights included The Belmont Estate’s cacao plantation, the rainforest, several of the island’s gorgeous beaches, and extraordinary restaurants.  It’s no wonder why ex-pats love living there. Life in Grenada is mellow, almost free from hurricanes, has fresh and natural rainforest superfoods, and is not far from Argentina in South America.

Grenada - The Grenadines - Caribbean
Belmont Estate – Chocolate Plantation
Baby Boomer Travel | Caribbean | Grenada - Rain Forest Cacao
Rain forest Cacao – Grenada

Find things to do in Grenada, here.

There’s never enough time

We missed the islands of Palm, PSV, and Martinique because it would have been impossible to do it all in the time we spent there. However, we did pass by the Kick ‘Em Jenny Volcano on the way to Grenada. It’s an active submarine volcano.  I’m glad it didn’t explode while we sailed by.

A few glitches but worth it anyway

On the way to Grenada, we hit a reef in a shallow spot and could have wrecked the boat but didn’t. There was also the day our toilets backed up and it stank to high heaven. Our captain managed to fix it and hopefully, he did it legally.  

I learned nothing about sailing the entire time and sat there like a Princess letting the guys do all of the work. Aside from the mosquitos and living on a boat for 3 weeks, St. Vincent and the Grenadines and Grenada are true paradises and not to be missed.

Baby Boomer Travel | Caribbean | Tee shirt humor - same shit - different island
Tee Shirt Humor – Grenadines

Next time

If we were to do it again, we’d book a Catamaran instead of a regular sailboat because there is more room to move around. Even still, our experience with Sunsail was incredible. They have rental locations all over the world.

During our trip, we ate fish, fish, and more fish. All fresh, and incredible! Oh, and the rum drinks. We drank lots of those too. Yo Ho! Yo Ho! A pirate’s life for me.

Plan to sail anytime soon or have you been on a sailing trip? Please leave a comment below.

Baby Boomer Travel | Caribbean | St Vincent - Grenadines - Grenada
St. Vincent and the Grenadines & Grenada on a Sailboat

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Filed Under: Caribbean, Photo Galleries Tagged With: Baby Boomer Travel, islands, Travel Over 50

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About Rebecca Forstadt-Olkowski

Rebecca Olkowski is a travel/lifestyle blogger and founder of BabyBoomster.com, for active older women over 50. She is a purveyor of all things fun, loves to venture out in the world, is a foodie, and lives in Los Angeles.

Comments

  1. Douglas Knapp says

    September 5, 2017 at 1:37 pm

    A wonderfully told story. Seeing those photos brings back many memories. A wonderful time Rebecca. Unfortunately, our wonderful Captain Tom passed away a couple of years after our trip. Michael & Marian Hofstein live in Atlanta now – Michael wants to return to Los Angeles. Lost touch with Tom’s brother Kevin. Hope all you readers enjoy our 3 week Caribbean trip.

    Reply
    • Rebecca Forstadt-Olkowski says

      September 5, 2017 at 5:16 pm

      Thanks, Doug and you took most of the photos. It was fun remembering our trip and all the fun we had.

      Reply
  2. Haralee says

    September 5, 2017 at 3:31 pm

    I’m no pirate but it sounds like an incredible experience! I never knew there were so many islands in that area.

    Reply
    • Rebecca Forstadt-Olkowski says

      September 5, 2017 at 5:17 pm

      To be honest, we didn’t either. I had never heard of the Grenadines before we went there. I’m ready to do it again.

      Reply
  3. Ellen Dolgen says

    September 5, 2017 at 5:21 pm

    I have never been to Grenada. It looks amazing. Thanks for the travel tips!

    Reply
    • Rebecca Forstadt-Olkowski says

      September 5, 2017 at 5:33 pm

      You may want to plan a trip there someday. It’s an amazing island all by itself and it has an airport.

      Reply
  4. AnnMerle Feldman says

    September 8, 2017 at 9:11 am

    Wow! What an adventure! Good for you. Now these locations are on my lists!

    Reply
    • Rebecca Forstadt-Olkowski says

      September 8, 2017 at 1:25 pm

      I hope you get a chance to go AnnMerle. It’s a fantastic and sometimes overlooked part of the Earth. So beautiful and incredibly mellow.

      Reply
  5. Suzanne Fluhr says

    September 8, 2017 at 8:50 pm

    I get seasick on small boats—combine that with mosquitoes, heat and humidity and the toilet in the shower, and I’m thinking that sail boat might not be a good method of travel for me. OTOH, your itinerary seems like it was wonderful and you were able to visit some smaller places that most of us will never see. PS: In our family, my poor mother was the mosquito magnet. She suffered mightily the year we lived in Mexico when I was growing up.

    Reply
    • Rebecca Forstadt-Olkowski says

      September 10, 2017 at 9:53 am

      It was exciting to visit each small island and see the way the people live there. They were all so friendly. We mosquito magnets feel for your mother’s plight in Mexico.

      Reply
  6. Ania | Snow to Seas says

    September 10, 2017 at 3:35 am

    What an incredible trip and experience! It’s really great to hear that opting for a sailboat trip gave you the opportunity to interact with locals – those are some of the most memorable experiences. I recently went on a small boat trip in Malta and also had the chance to meet and chat with local sailors/fisherman. It was amazing!

    Reply
    • Rebecca Forstadt-Olkowski says

      September 10, 2017 at 9:54 am

      Ania, your trip to Malta sounds like it was incredible. I’ve always wanted to go there. How cool!

      Reply
  7. Penny says

    September 12, 2017 at 7:07 pm

    Now, that’s what I call fun! I really enjoyed reading about all the islands you visited, as well as your time on the boat. I’m sorry those nasty mosquitos caused you so much misery. They can really put a damper on things.

    Reply
  8. Laura Lee Carter says

    November 10, 2017 at 10:34 am

    Nice islands aren’t they? Our honeymoon was a Windjammer cruise to most of the places you visited…So much fun and we didn’t have to deal with mosquitoes at all. We went in January though… One sailing trip we did have bug problems but that was in November.

    Reply
  9. vikash says

    November 19, 2017 at 9:18 pm

    Wow! It looks amazing. Thanks for the travel tips!

    Reply

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