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5 Fabulous Sailing Vacations at Points Resorts

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In this month’s installment of “Sail Away,” TPG Contributor (and expert sailor) Shayne Benowitz shares the scoop on five points properties that offer experiences for your inner sailor. Whether it’s a US Sailing Certified course or a luxurious day sail complete with a butler and chilled Champagne, these far-flung adventures will put the wind into your wanderlust.

Sailing on Ruedi Reservoir near Aspen, Colorado.
Sailing on Ruedi Reservoir near Aspen, Colorado

1. The St. Regis Aspen, Colorado

If you thought Aspen’s scenic Rocky Mountains were just for skiing, think again: The The St. Regis Aspen has partnered with Aspen Sailing School for a one-of-a-kind sailing experience, set 9,000 feet above sea level on Ruedi Reservoir. The adventure begins when the St. Regis hands over the keys to a turbo-charged Lexus NX for the scenic, winding drive along the iconic Frying Pan River, where you may spot bald eagles and bighorn sheep.

You’ll meet your instructors and their fleet of 12-foot Sunfish sloops at the pine tree-lined reservoir. While these boats are small and come with no frills, they’re excellent for learning the basics and getting a good feel for how to catch the wind — they’re also a lot of fun! The mountain winds and chilly water temperatures present some unique challenges for even experienced sailors.

Your four-hour lesson (from 12-4 pm) is paired with a picnic lunch (including wine, a lobster BLT, heirloom tomato salad, s’mores cookies, etc.) packed by the St. Regis Aspen’s Executive Chef David Viviano, and served either at a private cove or at the Aspen Yacht Club.

Available during the summer, this package starts at $2,000. Rooms at this SPG Category 7 hotel start at $519 or 30,000 Starpoints per night.

Lovely poolside views of the marina at Scrub Island Resort.
Lovely poolside views of the marina at Scrub Island Resort.

2. Scrub Island Resort, Spa & Marina, British Virgin Islands

On this idyllic private island in the British Virgin Islands (just a mile from Tortola), Scrub Island Resort, Spa & Marina (a Marriott Autograph Collection property recently featured in this list of 5 Small Caribbean Islands with Points Hotels) offers vacations for those who are serious about the sailing lifestyle.

In partnership with the acclaimed Offshore Sailing School (which has locations in New York City and Florida), beginners can take the Learn To Sail course, which leads to US Sailing Certification. These courses can be taken in an intensive three-day setting with full six-hour days that include both classroom and on-the-water coursework. Another option is the more relaxed five-day schedule in half-day sessions, which allows you to more fully enjoy the resort’s tiered pools, spa and fine dining. More advanced sailors can continue their certifications with Bareboat, Live Aboard and Catamaran courses, or you could study navigation, passage making and performance sailing — or simply hit the water for a leisurely sailing lesson.

Packages are priced to include both sailing lessons and accommodations, and can be customized to suit your needs. At this Marriott Rewards Category 9 hotel, rates start at $369 or 45,000 points per night.

The marina at the St. Regis Sanya Yalong Bay.
The marina at the St. Regis Sanya Yalong Bay.

3. The St. Regis Sanya Yalong Bay, China

A glittering resort along China’s Yalong Bay, the The St. Regis Sanya Yalong offers a two-night package that includes eight hours of sailing school each day. Stay the night in the luxurious Empire Suite, start your morning with a Champagne breakfast, and set out into the open sea where you’ll learn the basics of wind direction, tacking, jibing, trimming the sails and knot-tying, all while luxuriating in the South China Sea breeze.

Only available March through December, the package requires a minimum of six people and starts at $1,450 per person, inclusive of your Empire Suite stay. At this SPG Category 6 hotel, rates start at ¥1,478 ($238) or 20,000 Starpoints per night.

Head off on the "Island of the Gods" sailing adventure with the St. Regis Bali.
Set sail on an Island of the Gods adventure with the St. Regis Bali.

4. The St. Regis Bali

For a lavish sailing experience in Bali, set sail aboard a private 52-foot catamaran charter with captain and expert crew for an adventure in Bali’s crystal-blue waters. Spend the morning unwinding at the spa with an Aloe Vera wrap, then climb aboard to either treat the day as a hand’s-on sailing experience or a chance to get some sun on the bow. As you sail across the Badung Strait down the coast to East Bali, your guide will stop at prime spots to reel in giant tuna and mahi mahi; keep your eyes peeled for dolphins as you make your way to Lembongan Island for a picnic lunch prepared on the beach. A St. Regis Butler will accompany the expedition, keeping the chilled Champagne flowing throughout the day.

As you sail back to the The St. Regis Bali, you’ll discover traditional village life, including seaweed farms. When you return, a four-course dinner will be waiting at the resort’s Kayuputi beachfront restaurant. I’m not sure how much you’ll actually learn about sailing on this excursion, but you’ll definitely enjoy a sublime day on the water.

This package starts at $1,788 per night and includes accommodations in a St. Regis Pool Suite and daily breakfast. At this SPG Category 7 hotel, rates start at $520 or 30,000 Starpoints per night.

Offshore Sailing School offers expert sailing instruction in St. Petersburg.
Offshore Sailing School offers expert sailing instruction in St. Petersburg.

5. Hampton Inn & Suites, St. Petersburg, Florida

Picturesque downtown St. Petersburg on Tampa Bay is an ideal setting to learn to sail, with calm, flat waters, warm weather and pretty city views, and Clearwater Beach just a short drive away. The Hampton Inn & Suites, St. Petersburg is conveniently located next to the St. Petersburg Yacht Club in the historic downtown district. They’ve partnered with renowned Offshore Sailing School to offer a variety of sailing courses with the serious sailor in mind. Beginners can take the three- or five-day version of the Learn to Sail Course leading to a US Sailing Certification, or simply get a taste with a single sailing lesson.

Advanced courses in Cruising, Bareboat Charters, Live Aboard and Performance Sailing are also available for those looking to take their sailing to the next level in a convenient Florida setting with expert instruction. Packages are priced to include both sailing lessons and accommodations, and can be customized to suit your needs. The Hampton Inn & Suites is a Hilton HHonors Rewards Category 5 hotel, and rates start at $169 or 30,000 points per night.

What’s your dream sailing excursion?

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