Our Itineraries

Day 1 — Norman Island Beginnings & Cave-Light Magic (Tortola → Norman)

Welcome aboard at Village Cay; bags away, welcome cocktail in hand, and an easy first sail to The Bight. You settle in with a swim and a visit to the white sand beach, and maybe a stop at the Willie T. A lazy shower, sunset canapés, and your first starlit dinner on deck set the tone for the week.

Day 2 — Cooper Island Drift & Boutique Ease (Norman → Cooper)

You wake to breakfast on a quiet sea overlooking The Caves, of Treasure Island fame.  After a pre-breakfast snorkel, you enjoy Chef Tara’s breakfast with the cliffs as the backdrop.  After breakfast, Captain Travis heads towards The Indians for a snorkel that rivals all other Virgin Island snorkels.  Once you’ve take in everything the Indians has to offer, RumAway sets sail past Peter Island and slips into Manchioneel Bay. Head into Cistern Point for turtles and schooling tangs, then wander the boardwalk cafés for an espresso or a beach cocktail. Golden-hour paddleboards, a warm breeze, and a chef’s island-supper as anchor lights twinkle ashore.

Day 3 — Marina Cay Hues & Diamond Reef Blue (Cooper → Marina Cay)

A short hop brings you over bright, glassy shallows—perfect for a snorkel at Diamond Reef where hard corals glow and butterflyfish dance. Back aboard, lunch slides into hammock time, followed by a dinghy spin around Great Camanoe’s quiet coves. Champagne at sunset, then a “Taste of the Islands” dinner, unhurried and sky-watched.

Day 4 — North Sound Arrival & Leverick Bay Sundowners (Marina Cay → Virgin Gorda)

You thread the channels into North Sound—sailing’s version of a grand amphitheater. Captain Travis docks the boat at Leverick Bay, and the afternoon is your oyster:  do you want to go check out Saba Rock or lounge over at the Bitter End Yacht Club, where Saturn (RumAway’s favorite Bartender) will whip you up the best margarita in the Virgin Islands?  If sporting is your choice, rent an eFoil surfboard and catch a lesson and fly by the billionaires’ playground that we lovingly refer to as the “North Sound”.  When you tire of the sights, head back aboard RumAway for a scrumptious chef prepared meal, or if you choose, get all dressed up and spend the evening at Saba Rock for an amazing meal and ambiance that you will remember always. 

Day 5 — North Sound Play Day & Saba Rock Chic (Virgin Gorda, second night)

Wake up to the smells of coffee and bacon while Captain Travis arranges a safari truck for the day.  Spend the next few hours being whisked around Virgin Gorda, enjoying the Copper Mine, the world famous Baths, followed by lunch at the incomparable Sugarcane Restaurant.  After lunch and a dip in the pool, head to Savannah Bay for a solitary swim on an isolated beach.  On your way back to Leverick Bay, stop in at Hog Heaven for a quick drink and to take in the best view in the BVI.  When you board the boat, enjoy hors d’oeuvres followed by a luxurious dinner with the view of Leverick Bay in the background.  If it happens to be Friday night, join in the Beach BBQ, followed by an amazing show by the Jumbie dancers, followed up by the fire dancers and finally a DJ and dancing extravaganza by the beach.

Day 6 — Cane Garden Bay Curve & Steel-Drum Sunset (North Sound → Tortola)

A postcard run down Tortola’s north shore lands you in Cane Garden’s crescent of sand. Swim ashore for a rum sampler, play with all the water toys in the afternoon, then watch the hillside lights flicker to life. As the sun sets, barefoot canapés at dusk and a cozy, grill-kissed dinner as the bay settles into a soft sway.

Day 7 — Sandy Cay Postcards & Jost Afterglow (Cane Garden → Great Harbour, JVD)

A sparkling stop at Sandy Cay—powder sand, turquoise frames—before you ease into Great Harbour. Afternoon options: a lazy White Bay float and a classic Painkiller at Soggy Dollar, or a sea-splash hike to the Bubbly Pool when the swell sets it fizzing. Sunset Champagne on deck, then Foxy’s by night or a candlelit private dessert course under the stars.

Day 8 — Disembark (Village Cay, Tortola)

Leisurely breakfast on the return glide, hugs with the crew, and a smooth, late-morning departure. Your BVI week—caves and corals, quiet bays and island nights—packs itself neatly into sun-warmed memories you’ll replay for years.

Day 1 — St. Thomas Arrival, Buck Island Wreck & Christmas Cove

Board RumAway at Yacht Haven Grande for a VIP welcome. Cruise to Buck Island for a guided snorkel over the historic shipwreck, then cross to Christmas Cove—calm, crystal-clear water with starfish gardens. Sunset cocktails and your first Chef Tara dinner onboard.

Day 2 — Hawksnest Bay & Oppenheimer Beach, Private Beach Setup

Sail to Hawksnest Bay (St. John) for vibrant coral right off the beach and a visit to storied Oppenheimer Beach. Your crew sets a private beach club: shade tent, loungers, snorkel gear, and a stocked cooler. Return by tender for hors d’oeuvres, sundowners, and dinner under the stars.

Day 3 — Maho Bay Turtles & Water Toys

Short hop to Maho Bay, famed for green sea turtles (Captain Travis’ favorite—sightings are highly likely when visibility is good). Stroll to Maho Crossroads for casual tiki-style bites, then enjoy paddleboards, kayaks, and water toys behind RumAway. After day-boats depart, the bay turns peaceful and private.

Day 4 — Waterlemon Bay: Hidden Gem & Octopus Snorkel

Waterlemon Bay is car-free and wonderfully quiet. Hike the mangroves to the hilltop ruins known as “The Office” (a local in-the-know spot) and snorkel Waterlemon Cay, where Chef Tara has spotted multiple octopus on a single swim. Expect a tranquil, starlit anchorage with wildlife along the shore.

Day 5 — “The Drop,” Lime Out & Little Lameshur Bay

Kick off with a colorful snorkel at The Drop (schools of reef fish, vibrant structure). Lunch at Lime Out, the floating taco bar—enjoy from lily pads in turquoise water. Afternoon sail to Little Lameshur Bay, a quiet south-shore sanctuary. Optional hike on the Reef Bay Trail to ancient petroglyphs. At night, enjoy Milky Way stargazing—no light pollution, just silence and sky.

Day 6 — Caneel Bay, Honeymoon Beach & Cruz Bay

Downwind sail to Caneel Bay near Honeymoon Beach. Tender to Cruz Bay for boutique shopping and fresh coconut rum drinks at Our Market Smoothies (don’t miss the coconut ice cream). Return for sunset cocktails and a chef’s tasting dinner aboard.

Day 7 — Private Mooring at Pacquereau Bay & Farewell Dinghy Cruise

 Settle in on RumAway’s private mooring at Pacquereau Bay, overlooking a lush waterfall and Frenchman’s Cove. Snorkel, paddle, or relax, then join Captain Travis for a golden-hour dinghy tour through Long Bay. One last, slow Caribbean evening to savor it all.

 Day 8 — Gourmet Breakfast & Noon Departure

 Enjoy a final Chef Tara breakfast before returning to the dock at noon. Your bucket-list USVI luxury yacht charter becomes a lifetime memory—until you’re back on board.

Day 1 — Welcome Aboard in St. Thoma, USVI

Your crew greets you at Cruz Bay with island cocktails and a safety orientation aboard RumAway. Settle in as Captain Travis sails to a nearby St. Thomas anchorage for your first night—often Christmas Cove or Honeymoon Bay, ideal for a sunset swim and Chef Tara’s first Caribbean-inspired dinner.

Day 2 — Crossing to Culebrita: The Spanish Virgin Islands Awaken

Enjoy breakfast under sail as you cross into the Spanish Virgin Islands, a lesser-known paradise often called “the Caribbean before the crowds.” Anchor off Culebrita, home to the island’s historic lighthouse and natural tide pools known as the Jacuzzis. Spend the day snorkeling pristine reefs, lounging on white sand, and exploring trails to panoramic views.

Evening brings sundowners and a starlit dinner in one of the Caribbean’s most peaceful bays.

Day 3 — Culebrita Bliss: Tide Pools & Turtles

A full day to enjoy Culebrita’s untouched beauty. Morning snorkel with turtles near the reef, paddleboard through calm shallows, or hike again to the lighthouse for sunrise photos. The crew sets up a private beach picnic or floating lunch.

As night falls, the absence of light pollution delivers Milky Way stargazing right from the trampoline deck.

Day 4 — Sail to Culebra: Colorful Caribbean Culture

After breakfast, a short sail takes you to Culebra, beloved for its turquoise coves and laid-back island vibe. Drop anchor near Tamarindo Bay or Flamenco Beach, ranked among the world’s best. Snorkel with rays and schools of reef fish, then head ashore to explore Culebra’s charming town, art boutiques, and local eateries.

Dinner onboard features fresh Caribbean flavors paired with tropical cocktails crafted by your crew.

Day 5 — Vieques: Wild Beauty & Horses on the Beach

Set sail to Vieques, the largest and most diverse of the Spanish Virgins. Anchor in a quiet bay surrounded by lush hillsides where wild horses often wander the shoreline. After lunch, snorkel colorful reefs or paddle along mangroves before heading to shore for a guided Bioluminescent Bay tour—a once-in-a-lifetime experience where the water glows with every movement.

Return to RumAway for dessert beneath a glowing night sky.

Day 6 — Hidden Coves of Vieques

Enjoy a slow morning with fresh coffee and Chef Tara’s signature breakfast. Spend the day exploring secluded coves like Sun Bay or Pata Prieta, kayaking through mangroves, or swimming with spotted eagle rays. Afternoon sail westward along Vieques’ dramatic coast.

Your evening onboard features a captain’s dinner and sunset champagne toast to celebrate your voyage.

Day 7 — Arrival at Puerto del Rey Marina, Puerto Rico

Sail into Puerto del Rey Marina—the Caribbean’s largest and most sophisticated yachting hub. Enjoy a farewell brunch on deck while the crew handles customs and docking. Spend the day touring the El Junque National Rainforest and allowing Captain Travis and Chef Tara show you why they adore Puerto Rico. Enjoy dinner and a swim at Captain Travis and Chef Tara’s RumAway’s Retreat - their home across from Puerto Del Rey. You will spend the last night on board RumAway at the dock, and prepare for your departure in comfort.

Day 8 - A final breakfast prepared by the RumAway Chef, and it’s off to the airport, or to enjoy a few more days on Puerto Rico at one of their many hotels and resorts.

7-Night Sample Itinerary (weather & clearance permitting)

Day 1 — Welcome Aboard (Simpson Bay, St. Maarten) → Anguilla’s Rendezvous Bay

Step aboard at Simpson Bay Marina for a VIP welcome and safety-made-simple briefing. We clear out of SXM and enjoy a scenic crossing to Rendezvous Bay, Anguilla—a mile-long sweep of white powder facing Cap Juluca. Swim off the transom, stroll the beach, then savor Chef’s first dinner under the stars at anchor.

Day 2 — Shoal Bay East, Little Bay & Meads Bay Sundowners (Anguilla)

A languid beach-day built for wow-moments. Snorkel Shoal Bay East over pastel reefs, then tender to Little Bay for cliff-perch photos and glass-clear water (optional easy cliff jump). Lunch can be a Sandy Island castaway experience or a chef’s beach picnic. Glide to Meads Bay for an opulent sunset—spa stop or chic beach bar optional—then dinner aboard.

Day 3 — Prickly Pear Cays & Champagne-Blue Water (Anguilla)

Morning sail to the Prickly Pear Cays: sugar-white sand, turtle-spotted shallows, and reef-sheltered snorkeling. Kayaks and paddleboards come out while Chef prepares a grill-lunch on deck. Afternoon siesta, then back to Road Bay (Sandy Ground) or Rendezvous depending on wind—cocktails, stargazing, and Milky Way skies.

Day 4 — Anguilla → Gustavia, St. Barth’s (Shell Beach & Glamour Night)

Clear out of Anguilla and set a stylish course to Gustavia, St. Barth’s. Your crew manages clearance while you explore Shell Beach (perfect for a late-lunch toes-in-the-sand). Browse luxury boutiques, then opt for a Michelin-level dinner ashore or a chef’s tasting menu aboard with harbor lights as your backdrop.

Day 5 — Colombier Bay Nature Reserve & St. Jean Beach Clubs (St. Barth’s)

Wake in Colombier, a pristine, roadless crescent known for sea turtles and calm, cobalt water. Snorkel the point, hike the overlook trail for iconic photos, then slide around the corner to St. Jean. Afternoon is yours: Nikki Beach beats, a chic Eden Rock sundowner, or playful water-toys off the stern. Dinner aboard or tables at a top address—your call.

Day 6 — Gouverneur/Saline Serenity & Gustavia After Dark (St. Barth’s)

Morning swim and breakfast, then a beach-hop to Gouverneur or Saline (taxi from Gustavia)—wild, clean, breathtaking. Return for a lazy lunch onboard, a harbor-side spa visit, or boutique time. Sunset Champagne, then Gustavia by night: wine bars, pastry stops, late-night cafés—or a candlelit private dessert course on deck.

Day 7 — St. Barth’s → Tintamarre/Creole Rock (St-Martin Nature Reserve) → Simpson Bay

A sparkling reach back toward St. Maarten with a snorkel stop at Tintamarre (turtles, sand-plate rays) or Creole Rock off Grand Case (aquarium-calm shallows). Slow lunch underway, then an unhurried glide into Simpson Bay. Final golden-hour dinghy cruise, family photos, and Chef’s farewell dinner beneath a sky full of stars.

Day 8 — Disembark (Simpson Bay Marina, St. Maarten)

Leisurely breakfast, hugs with the crew, and a smooth noon departure. Your bucket-list St. Maarten–Anguilla–St. Barth’s luxury charter becomes a memory you’ll replay for years.