Ocean City → Block Island → Martha’s Vineyard → Nantucket — Northbound New England

The White Marlin Open has taken over Ocean City, and Alyosha is taking advantage of the chaos to slip out of town for a mid-season adventure up the East Coast! This is something Captain Steve has done before — back when the family first purchased Alyosha — and it was fantastic.

This four-day, four-night sailing adventure features an overnight passage north to Block Island, Rhode Island — a windswept gem with dramatic bluffs, pristine beaches, and a charming harbor town. From there, Alyosha hops to Martha’s Vineyard, where you’ll explore the iconic gingerbread cottages of Oak Bluffs and the fishing village of Menemsha. The trip culminates in Nantucket — cobblestone streets, world-class seafood, and the unmistakable feel of old New England maritime culture.

This is a completely different flavor of SAVA — cooler waters, New England charm, and a taste of what makes the East Coast such incredible cruising ground. The overnight sail is a highlight: stars overhead, the boat humming along, and the anticipation of making landfall at a legendary island.

Nantucket → Newport → New York City → Ocean City — Southbound Icons

If the northbound trip is about New England charm, the southbound leg is about iconic East Coast ports and the thrill of sailing into the biggest city in the world. Starting in Nantucket, Alyosha heads south to Newport, Rhode Island — the sailing capital of America, home of legendary regattas, Gilded Age mansions, and a waterfront that has hosted sailors for centuries.

Then comes the showstopper: sailing into New York Harbor. There is nothing quite like approaching the Statue of Liberty and the Manhattan skyline from the water aboard a 50-foot catamaran. Whether it’s a daytime arrival with the city gleaming in the sun or an evening approach with the skyline lit up, this is a moment you will never forget.

From New York, Alyosha sails the Jersey Shore and Delaware coast back to Ocean City, completing a loop that covers some of the most storied waters on the Eastern Seaboard. This trip has a completely different energy from the Caribbean charters — it’s urban, cultural, and packed with contrasts.

Ocean City → Cape May → C&D Canal → Baltimore — Sailing to Charm City

This is a uniquely Mid-Atlantic adventure — sailing up the coast from Ocean City, rounding Cape May at the tip of New Jersey, transiting the Delaware Bay and the historic C&D Canal, and emerging into the beautiful north Chesapeake Bay. The destination: Baltimore’s iconic Inner Harbor.

The sailing is varied and interesting: ocean coastline gives way to the wide Delaware Bay, then the narrow canal, and finally the open Chesapeake. Stops could include Chesapeake City — a charming canal-side town perfect for an evening stroll and dinner — before arriving in Baltimore. The north Chesapeake in September is absolutely delightful: the water stays warm, the nights cool down to perfect sleeping temperatures, and the fall colors are just starting to hint at what’s coming.

Customers booking the entire boat (all three staterooms) can dictate the itinerary; otherwise Captain Steve will consult with each group to find the best route. Sailing to a big city — what a perfect way to enjoy everything that makes our state great!

Annapolis → Ocean City — North Chesapeake & Home

Alyosha departs Annapolis and heads south through the north Chesapeake Bay, cruising past some of the most scenic shoreline on the East Coast before rounding back out to the Atlantic and returning to Ocean City. This is a short but sweet three-day adventure — perfect for someone who wants a taste of the SAVA experience without a full week’s commitment.

The north Chesapeake in late September is spectacular: warm water, crisp fall air, and the early hints of autumn foliage along the shoreline. You’ll sail past historic watermen communities, quiet creeks perfect for a morning paddle, and wide-open stretches of Bay where Alyosha can really stretch her legs under sail. It’s an ideal way to close out the summer season and transition into the big adventures ahead.

Ocean City, MD → Bermuda — The Adventure Begins

This is where it all starts. You’ll join Captain Steve in Ocean City, Maryland, and set out across 660 nautical miles of open Atlantic to the island of Bermuda. This is a true blue-water passage — no land in sight for days, nothing but ocean, sky, stars, and the hum of Alyosha cutting through the swells.

You’ll learn the rhythms of passage-making: standing watch, trimming sails for changing conditions, navigating by the stars at night. You’ll likely spot dolphins riding Alyosha’s bow wave, and the night skies out here are absolutely extraordinary. When Bermuda’s pastel-colored buildings finally appear on the horizon, you’ll feel the kind of accomplishment that only an ocean crossing can deliver.

This is a repositioning leg — priced low to reward those bold enough to make an ocean passage their first SAVA experience. Two staterooms are available for this charter.

Bermuda → US Virgin Islands — Crossing the Deep Blue

After a few days in beautiful Bermuda to provision and explore, Alyosha sets sail south for the US Virgin Islands — 850 nautical miles across some of the deepest water in the Atlantic. This is the longest single passage of the season, and it’s as real as offshore sailing gets.

You’ll spend five days and nights at sea, settling into the watch rotation, cooking meals in the galley while the ocean rolls beneath you, and watching the water temperature slowly climb as you sail into the tropics. The transition is magical — you depart in autumn and arrive in the Caribbean. Trade winds will fill our sails for most of this passage, and the fishing is outstanding along the way.

When the green hills of the Virgin Islands appear on the horizon, you’ll have completed a true ocean crossing that very few people ever experience.

US Virgin Islands → The Grenadines — Island-Hopping South

This is the best of both worlds — a blended experience that combines short ocean passages with stops at some of the Caribbean’s most beautiful islands along the way. You’ll depart the US Virgin Islands and head south through the Lesser Antilles, touching islands that most tourists never see from the water.

Expect two days of open-water sailing interspersed with island stops where you can stretch your legs, snorkel reefs, and sample local cuisine at beachside restaurants. The islands get progressively more remote and unspoiled the further south you go. By the time you reach the Grenadines, you’ll feel like you’ve truly left the beaten path behind.

This charter is ideal for someone who wants the thrill of passage-making but also craves the variety of waking up at a new island every other day.

Grenadines Sailing #1 — Tropical Island Paradise

Welcome to the Grenadines — a chain of impossibly beautiful islands scattered across turquoise Caribbean waters. This is pure island hopping: short, easy sails between anchorages, with zero days of open-ocean passage. You’ll wake each morning to a new view, a new beach, a new adventure.

The itinerary is flexible, but expect to visit places like Bequia, with its charming waterfront and local boat-building tradition; the Tobago Cays, a marine park with world-class snorkeling among sea turtles and reef fish; and Mustique, an exclusive island with gorgeous hiking trails and sunset views. Alyosha anchors in sheltered bays, and your days are yours — snorkel, paddle, explore ashore, or simply relax on the trampolines with a book and a cocktail.

The Grenadines charters are self-provisioned: you decide how much food and drink to bring aboard versus how often you want to eat ashore. This keeps costs down and puts you in control of the experience.

Grenadines Sailing #2 — Sun, Snorkeling & Secluded Bays

Same stunning Grenadines, but no two weeks are ever alike. The captain tailors each trip based on wind, weather, and the group’s interests. Maybe this week it’s a deeper dive into the southern islands — Canouan, Mayreau, and the palm-studded Petit St. Vincent. Maybe it’s a lazy circuit of the Tobago Cays with long afternoons snorkeling the reef.

What stays constant is the vibe: easy sailing, warm water, cold drinks, incredible sunsets, and the kind of connections that happen when a small group shares a boat in paradise. This is what Captain Steve and Lisa discovered was the real magic of chartering — watching people unwind, disconnect from everyday life, and bond over shared adventure.

Grenadines Sailing #3 — A Caribbean Christmas

Spend the holidays the way they were meant to be spent — barefoot on a catamaran in the Caribbean. This is Christmas week in the Grenadines, and there is nowhere on earth quite like it. Imagine Christmas morning anchored in a turquoise bay, a warm breeze replacing the cold back home, snorkeling instead of shoveling snow.

The islands come alive over the holidays with local festivities, live music, and a festive energy that’s totally unique to the Caribbean. And on Alyosha, the crew makes it special — expect a holiday meal, some creative decorating, and the kind of warm, communal celebration that only happens on a boat far from home.

Grenadines Sailing #4 — Ring in the New Year at Sea

End 2026 and welcome 2027 from the deck of a catamaran in one of the most beautiful places on earth. New Year’s Eve in the Grenadines is something else entirely — fireworks over the water, rum punch toasts at midnight, and the satisfaction of knowing you’re starting the new year with an adventure rather than a hangover on the couch.

This charter wraps up our Grenadines season before Alyosha begins her northbound journey through the Caribbean island chain. It’s a bittersweet goodbye to these incredible islands — but there’s so much more ahead.

St. Vincent → St. Lucia — The Pitons Await

Alyosha begins her northbound journey. Sail from St. Vincent to St. Lucia, with its iconic Piton mountains, lush rainforests, and vibrant local culture. A blend of short passages and island exploration.

St. Lucia → Martinique — A French Gem

Cross to Martinique — a French Caribbean gem with world-class cuisine, rum distilleries, and dramatic volcanic landscapes. Experience the unique blend of French and Caribbean culture.

Martinique → Dominica — The Nature Island

Sail to the Nature Island of Dominica — volcanic hot springs, pristine rainforests, and some of the most dramatic scenery in the Caribbean. Dominica is wild, unspoiled, and utterly unique.

Dominica → Guadeloupe — The Butterfly Island

Continue north to Guadeloupe — a butterfly-shaped French archipelago with stunning beaches, tropical forests, and the dramatic La Soufrière volcano. Another taste of French Caribbean culture and cuisine.

Guadeloupe → Antigua — A Sailor’s Paradise

Sail to Antigua — famous for having a different beach for every day of the year. Explore English Harbour, Nelson’s Dockyard, and the island’s incredible sailing heritage.

Antigua → St. Kitts — Historic Colonial Charm

From Antigua to the historic island of St. Kitts — home to Brimstone Hill Fortress, beautiful volcanic beaches, and a charming capital in Basseterre. Rich colonial history meets Caribbean beauty.

St. Kitts → St. Martin — Dual-Nation Delight

Sail to the dual-nation island of St. Martin/St. Maarten. World-class dining on the French side, duty-free shopping on the Dutch side, and beautiful beaches all around.

St. Martin Exploration — Island Hopping Bliss

Spend a full week exploring St. Martin and the surrounding islands — Anguilla, St. Barths, and the hidden coves of the St. Martin coastline. No long passages, just pure island-hopping bliss.

St. Martin → BVI — Legendary Sailing Grounds

Sail south from St. Martin to the British Virgin Islands — legendary sailing grounds with protected anchorages, world-famous beach bars, and crystal-clear waters perfect for snorkeling.

BVI → USVI — Virgin Islands Beauty

Short hop from the British Virgin Islands to the US Virgin Islands. Explore St. Thomas, St. John, and St. Croix — stunning beaches, world-class diving, and a unique blend of Caribbean and American culture.

USVI Exploration — Island Paradise

Spend a week exploring the USVI in depth — snorkeling at Buck Island, hiking in the Virgin Islands National Park on St. John, and enjoying the vibrant nightlife of St. Thomas. Pure relaxation.

USVI → Puerto Rico — Colorful Caribbean Culture

Short hop to Puerto Rico — explore the colorful streets of Old San Juan, the bioluminescent bays, and the rich culture of this Caribbean island. Great food, vibrant nightlife, and Caribbean charm.

Puerto Rico → Turks & Caicos — Ocean Passage Adventure

Ocean passage from Puerto Rico to the Turks & Caicos Islands — 430 nautical miles across open Atlantic. The reward: some of the most stunning turquoise water and pristine beaches anywhere in the world.

Turks & Caicos → Bahamas — Crystal Waters & Blue Banks

Island hop from Turks & Caicos into the Bahamas — through crystal-clear waters over shallow banks that glow every shade of blue and green imaginable. The transition into the Bahamas is like entering another world.

Bahamas Sailing — Exuma Bliss

Five days exploring the Exumas and surrounding Bahamas islands. Crystal-clear water, swimming pigs, nurse sharks at Compass Cay, and the stunning Thunderball Grotto. The Bahamas at their finest.

Bahamas → Florida → Chesapeake Bay — The Journey Home

The grand finale of the SAVA season. Alyosha departs the Bahamas and begins the 1,100 nautical mile journey home to the Chesapeake Bay. This is an epic repositioning voyage — across the Gulf Stream, up the Florida coast, past Cape Hatteras, and into the Chesapeake. Four to five days at sea, with the possibility of coastal stops along the way depending on weather and conditions.

Crossing the Gulf Stream is an experience unto itself — the water temperature changes dramatically, the current can run three to four knots, and the marine life is incredible. You may spot sea turtles, manta rays, and dolphins. As you sail north, you’ll watch the tropics fade and the familiar coastline of the eastern US emerge. Arriving back in the Chesapeake after months in the Caribbean is a powerful feeling — the season complete, the miles logged, the memories made.

This repositioning leg is priced low to reward adventurous sailors who want to be part of the journey. It’s a fitting way to end an incredible season — and to earn your place in the SAVA story.