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St. Thomas in 5 Days

Guest post by skelly

Map tips: each color represents a different day. Click a marker to learn more about the spot, and click the star in the map header to save the entire map under Your Places in Google Maps.

We stayed at Bolongo Bay Beach Resort for the entire trip on Saint Thomas (US Virgin Islands) and splurged on the all inclusive package. It was worth every cent.  It’s a smaller, family run resort. While its not as modern or updated as some of the bigger resorts, I preferred it. Smaller meant quieter and less crowded. We never had to race for a beach chair or wait in line for a drink. The staff were all wonderful and accommodating, quick to remember our names and drink orders, call us a cab, help us plan an excursion, or help out in any way. We even met family members of the owners, who sat down to chat with us and tell us about how the resort rebuilt after the hurricanes a few years ago. After a day everyone felt like family, we loved it.

The amenities at the resort were enough to keep us busy. We snorkeled, swam with sea turtles, lounged in hammocks, sea kayaked, explored the corals, bird watched, and even went on a sunset cruise on the Heavenly Days Catamaran, all included with our package. Since food and drinks were included, we also ate at the resort for most of our meals.

Day 1

  • Charlotte Amalie
  • Bolongo Bay

We arrived in Charlotte Amalie and took an open air cab around town. We just enjoyed the breeze and the busy streets and didn’t make any stops except a brief ‘welcome stop’ to taste rum punch and hear our driver give us some history of the island and point out some landmarks.

Day 2

  • Bolongo Bay Beach Resort
  • Anna’s Retreat
  • Tutu Park Mall

After spending the morning on the beach at our resort, we got a cab into the little town of Anne’s Resort and did some shopping at Tutu Park Mall. This wasn’t really a tourist area, a lot of locals shop here for necessities and there really aren’t souvenir shops, but we didn’t mind.

Day 3

  • Bolongo Bay Beach Resort
  • Fort Christian
  • 99 Steps
  • Three Queens Statue
  • Blackbeard’s Castle
  • Charlotte Amalie Overlook
  • Drake’s Seat
  • Mountain Top
  • Charlotte Amalie

We got up and had breakfast at the resort, then asked the concierge to call us a cab. We intended to go up to Mountain top to do some duty free shopping, and then down to Drakes Seat to take in the gorgeous view of Magen’s Bay. Once we told our driver that, he asked very politely if there was anything else we wanted to see. He explained that the fee for the cab up to mountain top would be about $34 – (all of the cabs on St. Thomas operate on a fee per person) and then told us that his other job was as a tour guide, and that he did tours that included Mountain top, plus lots of other things, for $50 – and if we had time and an interest to see more of the island, he’d be happy to take us on the tour that started later that afternoon. We agreed.

The tour ended up being just us and one couple. with only 4 people, we got a really personal experience from our guide. We were picked up in an air conditioned limo van, and our driver Shemari took us to all the places listed above. At each stop he got out and led us around the site, explaining the history and lore of each place, and sometimes telling us stories of his life growing up on the island. He told us about the devastating hurricanes a few years ago and how the island is still trying to rebuild. He took photos for us, provided cold bottled water, told us entertaining stories about pirates, and answered any questions we had.

Unfortunately, Blackbeards castle was still closed from hurricane damage, so we couldn’t go inside it, but we walked around outside of it and took pics while Shemari told us about its history.

At mountain top, we enjoyed a refreshing banana daiquiri while we shopped duty free and took in lovely views of the deck. (Daiquiri included in tour fee)

Once we got back down to Charlotte Amalie, Shemari took us to a shop that belonged to his friend, poured us a complimentary rum punch and gave us a couple hours to shop in the area, pointing us to some great shops to see. After shopping for awhile we went back to the meeting point and he drove us us back to our resort.  This was a wonderful day and we had a blast with Shemari – we ended up being really glad we took the chance on his tour. I can’t compliment this young man enough – all the locals knew him by name, he was the picture of polite professionalism and was very attentive to our comfort and entertainment. The next day, he came back to the resort and dropped off the purchases we had made the day before so that we didn’t have to go back to town and retrieve them! We took his card and will absolutely call him again if we ever return to St. Thomas.

Day 4

  • Bolongo Bay Beach Resort
  • Heavenly Days Catamaran

We spent the morning snorkeling in Bolongo Bay and relaxing on the beach and at the swim up pool bar.

At 5pm we boarded the Heavenly Days Catamaran for a sunset cruise around the island. There were drinks and tapas on board, and the crew pointed out interesting sights on the coasts to us while teaching us the basics of catamaran sailing. It was a blast and we met a lot of interesting people.

The cruise came back after dark and we had a late dinner at the resort.

Day 5

  • Bolongo Bay
  • Greengos Caribbean Cantina

We spent most of our last day relaxing at the resort and exploring the bay. We walked off resort property over to the rocky area of the bay and hunted for seashells, checked out the little creatures in the tide pools, bird watched, etc.

We had lunch at resort and were getting a little tired of the menu, so after some pool time we went into Charlotte Amalie for dinner. our friend Shemari had recommended Greengo’s Cantina so we tried that out. The food was amazing and the atmosphere was even better, and we wandered around some of the little alleyways nearby exploring the shops we hadn’t gone in the day before.

We hung out in town until it started raining and then got a cab back to the resort.

We had such a nice relaxing time. I was worried that staying at an all inclusive resort meant I would miss out on some of the culture of the Island, but it didn’t. We got the best of both worlds by choosing a smaller resort and by going off the property to explore the island. It was also really nice to not have to worry about staying on budget with the cost of each little thing, since it was all prepaid. I would definitely stay at Bolongo again if we went back to St. Thomas.

St Thomas itself is rich in fun history and bright local culture. Having been a popular pirate island, there’s a lot of colorful local lore surrounding many of the top places.

Traveled in March 2019

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